easternshoremdfineproperties.com Search Results

$1,625,000

Welcome to White Barn at Middlespring, a remarkable 8-acre Eastern Shore estate offering the perfect blend of historic charm, modern updates, privacy, and country living. Set at the end of a quarter-mile private drive surrounded by picturesque farmland, this exceptional property features three distinctive structures: a beautifully restored 1824 manor home, a 3-car detached garage with finished bonus space above, and a historic 40' x 63' barn. Additional highlights include a new metal roof, new windows, composite decking, updated kitchens and bathrooms, irrigation for the rear lawn and landscape beds, landscape lighting, and thoughtfully renovated living spaces, creating a truly move-in-ready retreat just minutes from downtown Easton. Built in 1824 on land first patented in 1663, the manor home has been thoughtfully renovated to preserve its historic character while embracing modern comfort. Wide-plank pine floors, original architectural details, and three wood-burning fireplaces create warmth and timeless elegance throughout. At the heart of the home, the beautifully renovated farmhouse kitchen is designed for gathering, featuring a large center island, professional 8-burner range, farmhouse sink, and recently updated fixtures that blend seamlessly with the home's period character. All kitchen and bathroom fixtures throughout the home have been thoughtfully updated within the past three years, offering today's conveniences while preserving the home's historic integrity. A spacious mudroom with utility sink adds everyday functionality, while the newly constructed sunroom addition showcases exposed wood beams and a cozy propane stove, creating the perfect space to relax and enjoy the surrounding landscape in every season. Outside, enjoy peaceful mornings from the composite deck overlooking eight scenic acres. The beautifully maintained rear lawn and landscape beds are serviced by an irrigation system, while landscape lighting highlights the mature trees, historic outbuilding, and walkways, creating an inviting setting well into the evening. Offered fully furnished, the home includes a beautifully curated collection of furnishings and lighting from Restoration Hardware, Arhaus, and Pottery Barn, allowing the next owner to enjoy a seamless transition into the Eastern Shore lifestyle.

3 Beds ⋅ 3 Baths

Welcome to White Barn at Middlespring, a remarkable 8-acre Eastern Shore estate offering the perfect blend of historic charm, modern updates, privacy, and country living. Set at the end of a quarter-mile private drive surrounded by picturesque farmland, this exceptional property features three distinctive structures: a beautifully restored 1824 manor home, a 3-car detached garage with finished bonus space above, and a historic 40' x 63' barn. Additional highlights include a new metal roof, new windows, composite decking, updated kitchens and bathrooms, irrigation for the rear lawn and landscape beds, landscape lighting, and thoughtfully renovated living spaces, creating a truly move-in-ready retreat just minutes from downtown Easton. Built in 1824 on land first patented in 1663, the manor home has been thoughtfully renovated to preserve its historic character while embracing modern comfort. Wide-plank pine floors, original architectural details, and three wood-burning fireplaces create warmth and timeless elegance throughout. At the heart of the home, the beautifully renovated farmhouse kitchen is designed for gathering, featuring a large center island, professional 8-burner range, farmhouse sink, and recently updated fixtures that blend seamlessly with the home's period character. All kitchen and bathroom fixtures throughout the home have been thoughtfully updated within the past three years, offering today's conveniences while preserving the home's historic integrity. A spacious mudroom with utility sink adds everyday functionality, while the newly constructed sunroom addition showcases exposed wood beams and a cozy propane stove, creating the perfect space to relax and enjoy the surrounding landscape in every season. Outside, enjoy peaceful mornings from the composite deck overlooking eight scenic acres. The beautifully maintained rear lawn and landscape beds are serviced by an irrigation system, while landscape lighting highlights the mature trees, historic outbuilding, and walkways, creating an inviting setting well into the evening. Offered fully furnished, the home includes a beautifully curated collection of furnishings and lighting from Restoration Hardware, Arhaus, and Pottery Barn, allowing the next owner to enjoy a seamless transition into the Eastern Shore lifestyle.

32137 Discovery Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$1,095,000

Waterfront, a deeded boat slip, off-street parking, and a single-car garage with additional storage set the stage for this thoughtfully redesigned coastal retreat in the heart of Oxford. Completely renovated from top to bottom, this 3 bedroom, 2.5 bathroom home blends timeless Eastern Shore charm with luxury finishes and exceptional boating amenities. Every detail has been carefully curated, from the new hardwood flooring and fresh paint throughout to the completely remodeled gourmet kitchen featuring high-end appliances, quartz and soapstone countertops, custom cabinetry, and a butler's pantry connecting the kitchen and dining room. The dining room is anchored by a beautiful masonry fireplace with a gas insert, while the custom "Wine Snug" offers built-in wine racks, a wine refrigerator, and handcrafted wrought iron doors. Designed to maximize its setting, the home captures water views from both the front and rear, with sightlines straight through the home to the water. Upstairs, the primary suite opens to a private balcony overlooking the harbor, and the conveniently located second-floor laundry adds everyday functionality. For boating enthusiasts, the property includes a deeded 40’ boat slip accommodating with approximately 5’ MLW. Ideally located just moments from downtown Oxford, you'll enjoy easy access to marinas, the Oxford Ferry, waterfront parks, and local favorites like Doc's Sunset Grille with frequent live music. Whether you're searching for a full-time residence, weekend getaway, or luxury second home, 100 W. Pier Street offers the perfect blend of water views, boating access, modern updates, and the relaxed Eastern Shore lifestyle.

3 Beds ⋅ 3 Baths

Waterfront, a deeded boat slip, off-street parking, and a single-car garage with additional storage set the stage for this thoughtfully redesigned coastal retreat in the heart of Oxford. Completely renovated from top to bottom, this 3 bedroom, 2.5 bathroom home blends timeless Eastern Shore charm with luxury finishes and exceptional boating amenities. Every detail has been carefully curated, from the new hardwood flooring and fresh paint throughout to the completely remodeled gourmet kitchen featuring high-end appliances, quartz and soapstone countertops, custom cabinetry, and a butler's pantry connecting the kitchen and dining room. The dining room is anchored by a beautiful masonry fireplace with a gas insert, while the custom "Wine Snug" offers built-in wine racks, a wine refrigerator, and handcrafted wrought iron doors. Designed to maximize its setting, the home captures water views from both the front and rear, with sightlines straight through the home to the water. Upstairs, the primary suite opens to a private balcony overlooking the harbor, and the conveniently located second-floor laundry adds everyday functionality. For boating enthusiasts, the property includes a deeded 40’ boat slip accommodating with approximately 5’ MLW. Ideally located just moments from downtown Oxford, you'll enjoy easy access to marinas, the Oxford Ferry, waterfront parks, and local favorites like Doc's Sunset Grille with frequent live music. Whether you're searching for a full-time residence, weekend getaway, or luxury second home, 100 W. Pier Street offers the perfect blend of water views, boating access, modern updates, and the relaxed Eastern Shore lifestyle.

100 Pier St W, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$250,000

Welcome to 3759 Rumsey Drive, Trappe, MD, located in the “La Trappe Heights” community; within the town limits of Trappe and connected to public water and sewer. This spacious home offers 4 bedrooms and 2.5 bathrooms, making it an excellent opportunity for buyers looking to add their personal touches. Being sold strictly sold AS-IS! This property is being sold strictly AS IS. The seller will make no repairs or improvements. Buyers are encouraged to conduct any inspections they deem necessary for informational purposes. This is a great opportunity for investors, renovators, or buyers looking to build equity while enjoying the convenience of an in-town location. The main level features a comfortable spacious living area with a wood-burning fireplace, a formal dining area, along with a kitchen/dining combo area as well. A convenient half bath, and access to the rear deck, perfect for relaxing or entertaining. The home also includes an attached one-car garage for parking and additional storage. Upstairs, you'll find all four bedrooms. The primary suite includes a private bathroom with a walk-in shower, while the second full bathroom, located off the hallway, features a tub/shower combination to accommodate family and guests. Outside, enjoy a spacious rear yard complete with a storage shed for lawn equipment, tools, or seasonal items. Please note that the HVAC system provides heating and cooling to the first floor only that was installed six years ago. The hot water tank is two years old. With some TLC this home is truly a gem in the lovely town of Trappe, Maryland.

4 Beds ⋅ 3 Baths

Welcome to 3759 Rumsey Drive, Trappe, MD, located in the “La Trappe Heights” community; within the town limits of Trappe and connected to public water and sewer. This spacious home offers 4 bedrooms and 2.5 bathrooms, making it an excellent opportunity for buyers looking to add their personal touches. Being sold strictly sold AS-IS! This property is being sold strictly AS IS. The seller will make no repairs or improvements. Buyers are encouraged to conduct any inspections they deem necessary for informational purposes. This is a great opportunity for investors, renovators, or buyers looking to build equity while enjoying the convenience of an in-town location. The main level features a comfortable spacious living area with a wood-burning fireplace, a formal dining area, along with a kitchen/dining combo area as well. A convenient half bath, and access to the rear deck, perfect for relaxing or entertaining. The home also includes an attached one-car garage for parking and additional storage. Upstairs, you'll find all four bedrooms. The primary suite includes a private bathroom with a walk-in shower, while the second full bathroom, located off the hallway, features a tub/shower combination to accommodate family and guests. Outside, enjoy a spacious rear yard complete with a storage shed for lawn equipment, tools, or seasonal items. Please note that the HVAC system provides heating and cooling to the first floor only that was installed six years ago. The hot water tank is two years old. With some TLC this home is truly a gem in the lovely town of Trappe, Maryland.

3759 Rumsey Dr, Trappe

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

$5,295,000

First time offering in Morgans Point. Custom built estate designed by architect Lauren Dianich of Atelier 11, this elegant Georgian-style brick and shingle residence offers over 5,200± square feet of thoughtfully designed living space filled with natural light and panoramic water views of the Tred Avon River. Set on 5± acres, the home is crafted for both refined entertaining and private, relaxed waterfront living. The heart of the home is the River Room, surrounded by windows that frame sweeping views of the Tred Avon River. Hardwood floors by Universal Floors in D.C. feature an inlaid compass medallion that points to magnetic north, creating a distinctive focal point. A fireplace anchors the space, with a screened-in porch with its own fireplace just beyond, perfect for enjoying chilly evenings. The chef’s kitchen is equipped with professional-grade appliances including a Wolf range and double wall ovens, Sub-Zero refrigerator, Asko full-size dishwasher, and Fisher & Paykel dishwasher drawers. A large island offers a wine fridge and illuminated display cabinetry, while the butler’s pantry—complete with an additional refrigerator and charming porthole windows framing water views—enhances the home’s functionality. Additionally, a custom-built oval wet bar with a two-drawer Sub-Zero refrigerator offers substantial cabinetry. This space provides a natural gathering point for entertaining. A large mudroom with powder room provides convenience for busy households. Also on the main level are a library with floor-to-ceiling shelving and a wood-burning fireplace, a fitness room with water vistas, a formal half-bath, and a first-floor en-suite bedroom ideal for guests. A dedicated utility entrance allows for discreet service and maintenance without entering the main living spaces. A 25kW standby generator provides reliable backup power for the main residence, offering peace of mind during outages. Upstairs, the primary suite with a gas fireplace serves as a retreat, with its spacious bathroom offering a shower, jetted soaking tub, and two walk-in closets—one with its own half-bath. Additional bedrooms include an upper-level en-suite and family-friendly accommodations, all supported by a conveniently located laundry room. Completing this floor is a private office with a gas fireplace and panoramic river views, offering an inspiring space for work or study. A generously sized, detached three-car garage includes a second-floor guest quarters with a kitchenette, washer and dryer, and en-suite bedroom, where windows capture tranquil water views. Outdoors, enjoy resort-like amenities including a heated pool with a fully retractable cover and a pool pavilion with its own bathroom and outdoor shower. The grounds are beautifully landscaped and designed for relaxation, with serene river views visible from nearly every room of the property. This rare offering seamlessly blends architectural pedigree, modern luxury, and a spectacular setting on the Tred Avon River—an exceptional opportunity to experience Eastern Shore living at its finest.

4 Beds ⋅ 7 Baths

First time offering in Morgans Point. Custom built estate designed by architect Lauren Dianich of Atelier 11, this elegant Georgian-style brick and shingle residence offers over 5,200± square feet of thoughtfully designed living space filled with natural light and panoramic water views of the Tred Avon River. Set on 5± acres, the home is crafted for both refined entertaining and private, relaxed waterfront living. The heart of the home is the River Room, surrounded by windows that frame sweeping views of the Tred Avon River. Hardwood floors by Universal Floors in D.C. feature an inlaid compass medallion that points to magnetic north, creating a distinctive focal point. A fireplace anchors the space, with a screened-in porch with its own fireplace just beyond, perfect for enjoying chilly evenings. The chef’s kitchen is equipped with professional-grade appliances including a Wolf range and double wall ovens, Sub-Zero refrigerator, Asko full-size dishwasher, and Fisher & Paykel dishwasher drawers. A large island offers a wine fridge and illuminated display cabinetry, while the butler’s pantry—complete with an additional refrigerator and charming porthole windows framing water views—enhances the home’s functionality. Additionally, a custom-built oval wet bar with a two-drawer Sub-Zero refrigerator offers substantial cabinetry. This space provides a natural gathering point for entertaining. A large mudroom with powder room provides convenience for busy households. Also on the main level are a library with floor-to-ceiling shelving and a wood-burning fireplace, a fitness room with water vistas, a formal half-bath, and a first-floor en-suite bedroom ideal for guests. A dedicated utility entrance allows for discreet service and maintenance without entering the main living spaces. A 25kW standby generator provides reliable backup power for the main residence, offering peace of mind during outages. Upstairs, the primary suite with a gas fireplace serves as a retreat, with its spacious bathroom offering a shower, jetted soaking tub, and two walk-in closets—one with its own half-bath. Additional bedrooms include an upper-level en-suite and family-friendly accommodations, all supported by a conveniently located laundry room. Completing this floor is a private office with a gas fireplace and panoramic river views, offering an inspiring space for work or study. A generously sized, detached three-car garage includes a second-floor guest quarters with a kitchenette, washer and dryer, and en-suite bedroom, where windows capture tranquil water views. Outdoors, enjoy resort-like amenities including a heated pool with a fully retractable cover and a pool pavilion with its own bathroom and outdoor shower. The grounds are beautifully landscaped and designed for relaxation, with serene river views visible from nearly every room of the property. This rare offering seamlessly blends architectural pedigree, modern luxury, and a spectacular setting on the Tred Avon River—an exceptional opportunity to experience Eastern Shore living at its finest.

5381 Morgans Point Dr, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$849,000

An Exceptional Opportunity! Unexpectedly available once again due solely to a change in the buyers' personal circumstances, this exceptional property is available through no fault of the home. If you missed it the first time, here's your opportunity to own one of the area's most distinctive and beautifully maintained residences. Ideally situated just four miles from the heart of charming St. Michaels, this timeless home offers peaceful country living with easy access to boutique shopping, exceptional dining, marinas, and the Chesapeake Bay lifestyle. Just moments from Claiborne Landing, you'll enjoy convenient public boat access for effortless days on the water, whether your passion is cruising, fishing, crabbing, or simply exploring the beauty of the Chesapeake Bay. Built in the early 1900s and thoughtfully renovated over the past two decades, this remarkable residence seamlessly blends historic character with today's modern conveniences. Situated on a picturesque half-acre lot, the home offers three spacious bedrooms, each with its own private bath, plus the flexibility for a fourth bedroom, home office, or guest suite. Several bedrooms also enjoy access to private balconies, adding to the home's unique charm and appeal. The beautifully updated kitchen features granite countertops, stainless steel appliances, tile flooring, and generous workspace, making it ideal for both everyday living and entertaining. Gleaming hardwood floors flow throughout the home, showcasing its warmth, craftsmanship, and attention to detail. Step outside to enjoy the beautifully landscaped grounds, complete with a charming potting shed and an additional storage building. The true showpiece, however, is the extraordinary 1,500-square-foot attached garage. This impressive two-story space features three oversized garage bays, a dedicated office, and abundant room for multiple vehicles, boats, workshop space, hobbies, collections, and projects of every kind. Whether you're a car enthusiast, woodworker, craftsman, artist, entrepreneur, or someone who simply enjoys tinkering and creating, this exceptional space offers endless possibilities rarely found in a property of this caliber. Rich in history, impeccably maintained, and completely move-in ready, this one-of-a-kind property offers the perfect blend of timeless elegance, modern comfort, and exceptional versatility. Whether you're searching for a full-time residence, a weekend retreat, or a home with unmatched garage and workspace, this remarkable property delivers. Don't miss this exceptional opportunity to make it yours.

3 Beds ⋅ 4 Baths

An Exceptional Opportunity! Unexpectedly available once again due solely to a change in the buyers' personal circumstances, this exceptional property is available through no fault of the home. If you missed it the first time, here's your opportunity to own one of the area's most distinctive and beautifully maintained residences. Ideally situated just four miles from the heart of charming St. Michaels, this timeless home offers peaceful country living with easy access to boutique shopping, exceptional dining, marinas, and the Chesapeake Bay lifestyle. Just moments from Claiborne Landing, you'll enjoy convenient public boat access for effortless days on the water, whether your passion is cruising, fishing, crabbing, or simply exploring the beauty of the Chesapeake Bay. Built in the early 1900s and thoughtfully renovated over the past two decades, this remarkable residence seamlessly blends historic character with today's modern conveniences. Situated on a picturesque half-acre lot, the home offers three spacious bedrooms, each with its own private bath, plus the flexibility for a fourth bedroom, home office, or guest suite. Several bedrooms also enjoy access to private balconies, adding to the home's unique charm and appeal. The beautifully updated kitchen features granite countertops, stainless steel appliances, tile flooring, and generous workspace, making it ideal for both everyday living and entertaining. Gleaming hardwood floors flow throughout the home, showcasing its warmth, craftsmanship, and attention to detail. Step outside to enjoy the beautifully landscaped grounds, complete with a charming potting shed and an additional storage building. The true showpiece, however, is the extraordinary 1,500-square-foot attached garage. This impressive two-story space features three oversized garage bays, a dedicated office, and abundant room for multiple vehicles, boats, workshop space, hobbies, collections, and projects of every kind. Whether you're a car enthusiast, woodworker, craftsman, artist, entrepreneur, or someone who simply enjoys tinkering and creating, this exceptional space offers endless possibilities rarely found in a property of this caliber. Rich in history, impeccably maintained, and completely move-in ready, this one-of-a-kind property offers the perfect blend of timeless elegance, modern comfort, and exceptional versatility. Whether you're searching for a full-time residence, a weekend retreat, or a home with unmatched garage and workspace, this remarkable property delivers. Don't miss this exceptional opportunity to make it yours.

10494 Rich Neck Rd, Claiborne

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

$850,000

Easton Club. This beautiful 3300 sq. ft. home has been almost entirely renovated. Living room, formal dining room, renovated kitchen with Quartz countertops, new appliances and breakfast area, family room with stone gas fireplace, 1st floor primary suite with remodeled bath, laundry room and powder room. Wood flooring throughout 1st floor. 2nd floor offers 3 bedrooms, 2 baths and large media room or 5th bedroom. Exterior features a tiered deck with awning, lawn irrigation system and extensive landscaping. Sited on a .35 acre lot backing to open space on a quiet cul-de-sac. Roof (new 2023). HVAC (new 2022). Community amenities include a pool and tennis/pickleball court. Close to downtown Easton and many amenities. Short distance to the picturesque towns of St. Michaels and Oxford. A must to see!

4 Beds ⋅ 4 Baths

Easton Club. This beautiful 3300 sq. ft. home has been almost entirely renovated. Living room, formal dining room, renovated kitchen with Quartz countertops, new appliances and breakfast area, family room with stone gas fireplace, 1st floor primary suite with remodeled bath, laundry room and powder room. Wood flooring throughout 1st floor. 2nd floor offers 3 bedrooms, 2 baths and large media room or 5th bedroom. Exterior features a tiered deck with awning, lawn irrigation system and extensive landscaping. Sited on a .35 acre lot backing to open space on a quiet cul-de-sac. Roof (new 2023). HVAC (new 2022). Community amenities include a pool and tennis/pickleball court. Close to downtown Easton and many amenities. Short distance to the picturesque towns of St. Michaels and Oxford. A must to see!

28391 Masters Ct, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$2,995,000

Welcome to Holly House – A Rare Waterfront Legacy Estate on the Miles River Holly House presents an extraordinary opportunity to own one of the Upper Miles River’s most captivating waterfront estates. Set gracefully on five spectacular, beautifully landscaped acres, this contemporary French-inspired residence offers approximately 150 feet of private shoreline, panoramic water views, and unforgettable sunsets. Designed for effortless one-level living, the impeccably constructed brick home blends timeless architecture with endless potential. The current residence features a gracious living room, formal dining room, inviting den, spacious kitchen, sunroom, private office, study/optional bedroom, an elegant waterfront primary suite with dual bathrooms and separate walk-in closets, two additional en-suite bedrooms, a powder room, unfinished basement, and an attached two-car garage. Outdoor living is equally impressive. A waterside 8-foot-deep swimming pool, expansive terrace overlooking the Miles River, private 150-foot pier, tennis court, and oversized outbuilding create an exceptional setting for entertaining, recreation, and peaceful waterfront living. Whether you choose to thoughtfully refresh the existing home or create a spectacular new estate, Holly House offers an unmatched canvas to realize your vision. Adding even greater value, the property includes fully approved architectural, structural, and interior design plans for an extraordinary three-story Modern Country French estate. Every detail has been thoughtfully curated to create a truly remarkable waterfront residence featuring: ● Five bedrooms, including a luxurious waterfront primary suite on the first floor ● Four-stop elevator ● Six full baths and two half baths (powder room and dedicated pool bath) ● Five fireplaces ● Grand staircase ● Dramatic vaulted living room ● Glass-enclosed dining room with black iron NanoWall doors opening to breathtaking Miles River views ● Spacious family room seamlessly connected to an entertainer’s dream kitchen ● Bar, butler’s pantry, and separate catering kitchen with silver vault ● Expansive lower level with a temperature-controlled wine cellar, billiards room, home theater, oversized fitness center, full bath with dog wash, and abundant storage ● Covered 440-square-foot vaulted timber patio with an outdoor wood-burning fireplace and television, creating the ultimate year-round outdoor living space The property has also received its long-awaited approval from Talbot County for a new 5-6 bedroom septic system, allowing construction to begin immediately. Fully permitted architectural and structural plans, along with a stunning full-color exterior fly-through video, are included with the sale. For those wishing to personalize the design, the approved plans can be modified to reflect a buyer’s individual style and lifestyle needs. This is more than a home—it’s a once-in-a-generation opportunity to create a landmark waterfront estate in one of the Eastern Shore’s most coveted locations.

3 Beds ⋅ 4 Baths

Welcome to Holly House – A Rare Waterfront Legacy Estate on the Miles River Holly House presents an extraordinary opportunity to own one of the Upper Miles River’s most captivating waterfront estates. Set gracefully on five spectacular, beautifully landscaped acres, this contemporary French-inspired residence offers approximately 150 feet of private shoreline, panoramic water views, and unforgettable sunsets. Designed for effortless one-level living, the impeccably constructed brick home blends timeless architecture with endless potential. The current residence features a gracious living room, formal dining room, inviting den, spacious kitchen, sunroom, private office, study/optional bedroom, an elegant waterfront primary suite with dual bathrooms and separate walk-in closets, two additional en-suite bedrooms, a powder room, unfinished basement, and an attached two-car garage. Outdoor living is equally impressive. A waterside 8-foot-deep swimming pool, expansive terrace overlooking the Miles River, private 150-foot pier, tennis court, and oversized outbuilding create an exceptional setting for entertaining, recreation, and peaceful waterfront living. Whether you choose to thoughtfully refresh the existing home or create a spectacular new estate, Holly House offers an unmatched canvas to realize your vision. Adding even greater value, the property includes fully approved architectural, structural, and interior design plans for an extraordinary three-story Modern Country French estate. Every detail has been thoughtfully curated to create a truly remarkable waterfront residence featuring: ● Five bedrooms, including a luxurious waterfront primary suite on the first floor ● Four-stop elevator ● Six full baths and two half baths (powder room and dedicated pool bath) ● Five fireplaces ● Grand staircase ● Dramatic vaulted living room ● Glass-enclosed dining room with black iron NanoWall doors opening to breathtaking Miles River views ● Spacious family room seamlessly connected to an entertainer’s dream kitchen ● Bar, butler’s pantry, and separate catering kitchen with silver vault ● Expansive lower level with a temperature-controlled wine cellar, billiards room, home theater, oversized fitness center, full bath with dog wash, and abundant storage ● Covered 440-square-foot vaulted timber patio with an outdoor wood-burning fireplace and television, creating the ultimate year-round outdoor living space The property has also received its long-awaited approval from Talbot County for a new 5-6 bedroom septic system, allowing construction to begin immediately. Fully permitted architectural and structural plans, along with a stunning full-color exterior fly-through video, are included with the sale. For those wishing to personalize the design, the approved plans can be modified to reflect a buyer’s individual style and lifestyle needs. This is more than a home—it’s a once-in-a-generation opportunity to create a landmark waterfront estate in one of the Eastern Shore’s most coveted locations.

9338 Bantry Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: chevychase@ttrsir.com

$495,000

Enjoy the ease of one-level living in this well-maintained rancher, built in 2002 and situated on 2+/- acres in the quaint village of Wittman. Offering 1,662+/- sqft, this 3-bedroom, 2-bath home provides comfortable living with plenty of room to enjoy both inside and out. Hardwood flooring welcomes you into the foyer, which opens to a spacious living room. The kitchen features ample cabinetry, generous table space and overlooks the backyard, creating the perfect setting for everyday meals or entertaining. The spacious primary bedroom features a large walk-in closet. A convenient side entry leads to the laundry room and a separate full bath. Outside, the open yard offers endless possibilities with plenty of space for gardening, recreation or simply enjoying the outdoors. The oversized detached garage provides abundant room for vehicles, a workshop, hobbies and additional storage, while the blacktop driveway adds convenience and curb appeal. A recently installed 3-ton HVAC system provides added comfort and peace of mind. Located less than ¾ of a mile from the Wittman boat landing, you'll have easy access to Cummings Creek, the Chesapeake Bay, and surrounding tributaries for boating, fishing, crabbing, kayaking, and waterfront dining. Conveniently situated between Tilghman Island and Historic downtown St. Michaels, this property offers the perfect opportunity to enjoy the relaxed lifestyle and natural beauty of Maryland's Eastern Shore.

3 Beds ⋅ 2 Baths

Enjoy the ease of one-level living in this well-maintained rancher, built in 2002 and situated on 2+/- acres in the quaint village of Wittman. Offering 1,662+/- sqft, this 3-bedroom, 2-bath home provides comfortable living with plenty of room to enjoy both inside and out. Hardwood flooring welcomes you into the foyer, which opens to a spacious living room. The kitchen features ample cabinetry, generous table space and overlooks the backyard, creating the perfect setting for everyday meals or entertaining. The spacious primary bedroom features a large walk-in closet. A convenient side entry leads to the laundry room and a separate full bath. Outside, the open yard offers endless possibilities with plenty of space for gardening, recreation or simply enjoying the outdoors. The oversized detached garage provides abundant room for vehicles, a workshop, hobbies and additional storage, while the blacktop driveway adds convenience and curb appeal. A recently installed 3-ton HVAC system provides added comfort and peace of mind. Located less than ¾ of a mile from the Wittman boat landing, you'll have easy access to Cummings Creek, the Chesapeake Bay, and surrounding tributaries for boating, fishing, crabbing, kayaking, and waterfront dining. Conveniently situated between Tilghman Island and Historic downtown St. Michaels, this property offers the perfect opportunity to enjoy the relaxed lifestyle and natural beauty of Maryland's Eastern Shore.

8658 Cummings Rd, Wittman

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$3,595,000

Perfectly nestled on 4.96± private waterfront acres between Easton and St. Michaels, this extraordinary estate embodies the very best of Eastern Shore living, anchored by rare deep water dockage (6’+ MLW) for the ultimate Chesapeake boating lifestyle. This Royal Oak home’s western exposure offers amazing sunset views across Solitude Creek.This listing also includes a fully prepaid 96-year recorded ground lease on an adjoining 5.48± acre parcel of land -- featuring a picturesque wildflower pasture, a mature 4± acre maple orchard, and charming outbuildings (detached garage and red barn) -- creating unparalleled privacy, beauty, and tranquility. A winding, tree-lined private drive sets the tone for the peaceful retreat that awaits. Inside, panoramic water views fill nearly every room, while the recently updated home blends timeless elegance with warm, inviting comfort. Soaring ceilings, rich hardwood floors, exquisite custom moldings, and expansive living spaces create an atmosphere that is both refined and welcoming. The formal living and dining rooms, each centered around a cozy fireplace, offer inviting spaces for memorable gatherings and celebrations. The light-filled family room features dramatic volume ceilings, oversized windows, a fireplace, and stunning waterfront views that bring the outdoors in. Designed for both everyday living and effortless entertaining, the gourmet kitchen features slate flooring, stainless steel appliances, a walk-in pantry, and a waterside breakfast area where every meal is paired with breathtaking scenery. The luxurious main-level owner’s suite is a private sanctuary with its own fireplace, spectacular water views, dual walk-in closets with custom built-ins, and a spa-inspired bath designed for relaxation. Upstairs, guests and family are comfortably accommodated with a spacious bedroom suite, two additional guest bedrooms, and a versatile bonus room ideal for a home theater, fitness studio, or playroom. Above the oversized, air-conditioned three-car garage, a separate guest retreat with a kitchenette, full bath, and private balcony with beautiful waterfront views offers the perfect space for visiting friends and family. Outdoor living is equally exceptional. A sprawling slate patio, recently added waterside pool, and enclosed porch with vaulted ceilings and flagstone flooring create inviting spaces to relax, entertain, and take in the serene surroundings. Set on a peninsula with more than 1,000 feet of shoreline, the property offers remarkable privacy and endless water views in seemingly every direction. A private deep water pier on Solitude Creek makes boating effortless and permits a memorable arrival by water for your guests. Enoy fishing and crabbing and direct water access to the Choptank River and Chesapeake Bay. Rarely does a property so gracefully combine timeless architecture, resort-style amenities, and one of Talbot County’s most coveted waterfront settings into a place that truly feels like home.

5 Beds ⋅ 6 Baths

Perfectly nestled on 4.96± private waterfront acres between Easton and St. Michaels, this extraordinary estate embodies the very best of Eastern Shore living, anchored by rare deep water dockage (6’+ MLW) for the ultimate Chesapeake boating lifestyle. This Royal Oak home’s western exposure offers amazing sunset views across Solitude Creek.This listing also includes a fully prepaid 96-year recorded ground lease on an adjoining 5.48± acre parcel of land -- featuring a picturesque wildflower pasture, a mature 4± acre maple orchard, and charming outbuildings (detached garage and red barn) -- creating unparalleled privacy, beauty, and tranquility. A winding, tree-lined private drive sets the tone for the peaceful retreat that awaits. Inside, panoramic water views fill nearly every room, while the recently updated home blends timeless elegance with warm, inviting comfort. Soaring ceilings, rich hardwood floors, exquisite custom moldings, and expansive living spaces create an atmosphere that is both refined and welcoming. The formal living and dining rooms, each centered around a cozy fireplace, offer inviting spaces for memorable gatherings and celebrations. The light-filled family room features dramatic volume ceilings, oversized windows, a fireplace, and stunning waterfront views that bring the outdoors in. Designed for both everyday living and effortless entertaining, the gourmet kitchen features slate flooring, stainless steel appliances, a walk-in pantry, and a waterside breakfast area where every meal is paired with breathtaking scenery. The luxurious main-level owner’s suite is a private sanctuary with its own fireplace, spectacular water views, dual walk-in closets with custom built-ins, and a spa-inspired bath designed for relaxation. Upstairs, guests and family are comfortably accommodated with a spacious bedroom suite, two additional guest bedrooms, and a versatile bonus room ideal for a home theater, fitness studio, or playroom. Above the oversized, air-conditioned three-car garage, a separate guest retreat with a kitchenette, full bath, and private balcony with beautiful waterfront views offers the perfect space for visiting friends and family. Outdoor living is equally exceptional. A sprawling slate patio, recently added waterside pool, and enclosed porch with vaulted ceilings and flagstone flooring create inviting spaces to relax, entertain, and take in the serene surroundings. Set on a peninsula with more than 1,000 feet of shoreline, the property offers remarkable privacy and endless water views in seemingly every direction. A private deep water pier on Solitude Creek makes boating effortless and permits a memorable arrival by water for your guests. Enoy fishing and crabbing and direct water access to the Choptank River and Chesapeake Bay. Rarely does a property so gracefully combine timeless architecture, resort-style amenities, and one of Talbot County’s most coveted waterfront settings into a place that truly feels like home.

25610 Chance Farm Ct, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$379,000

This is a Great Opportunity to make this your Forever Home. Great remodel and expansion potential in this Brick home on a large corner lot with Water Views. Home is in need of a Total Renovation. Just off of St. Michaels Rd. looking across to Oak Creek. With nearly 3/4 of an acre and no Flood Zone this is centrally located between Easton and St. Michaels. Property is being offered "As Is" !

3 Beds ⋅ 2 Baths

This is a Great Opportunity to make this your Forever Home. Great remodel and expansion potential in this Brick home on a large corner lot with Water Views. Home is in need of a Total Renovation. Just off of St. Michaels Rd. looking across to Oak Creek. With nearly 3/4 of an acre and no Flood Zone this is centrally located between Easton and St. Michaels. Property is being offered "As Is" !

25911 River Rd, Newcomb

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$1,595,000

Nestled on Peachblossom Creek in Easton is a property that won’t disappoint if you are one who expects the unexpected. From the one-hundred-year-old oak standing sentinel over the tides to the 42 solar panels creating minimal power bills, this “issue free” home is unexpected, if not actually startling. Ideally located along the desirable Oxford Road corridor, the property offers convenient access to both Easton and Oxford while providing a peaceful waterfront setting. Designed for comfortable one-floor living, with a full second floor, you can expect a lifetime of enjoyment. This home offers 4-bedrooms, 3 full baths, beautiful wood floors throughout, 2 sitting/living room areas, a gas fireplace, an office with built ins, an attractive eat-in kitchen, a beautiful waterside sunroom with separate HVAC, and tons of storage space. There’s even a hot tub! A huge attached garage provides abundant room for vehicles, hobbies, and storage. A yard implemented by an expert environmental gardener (an author on the subject) crafts a haven for birds that is less maintenance—and more attractive to neighbors—than the oh, so very common “all lawn” approach. Watch bluebirds and butterflies while you sip your morning coffee on the expansive Azek deck or large paver patio overlooking the water. Smile at lightning bugs flitting about the yard as you watch the stars come out at night in your private back yard retreat. The open floor plan and large windows keep the home full of light and allow endless views of the water. State-of-the-art solar with 2 large Tesla storage batteries, whole house water purification system and zoned HVAC systems make for healthy living, too. A denitrifying septic system - designed for 4-6 bedrooms - helps keep the Bay clean—in fact, this home's low carbon footprint and thoughtfully designed landscape and rain gardens actually help the environment. Several walk-in storage areas, plus huge unfinished space over the garage. An unforeseen property, even if you expect the unexpected. Don't miss this fabulously easy-care, low maintenance home. All the hard work is done - all that's left is to ENJOY!

4 Beds ⋅ 3 Baths

Nestled on Peachblossom Creek in Easton is a property that won’t disappoint if you are one who expects the unexpected. From the one-hundred-year-old oak standing sentinel over the tides to the 42 solar panels creating minimal power bills, this “issue free” home is unexpected, if not actually startling. Ideally located along the desirable Oxford Road corridor, the property offers convenient access to both Easton and Oxford while providing a peaceful waterfront setting. Designed for comfortable one-floor living, with a full second floor, you can expect a lifetime of enjoyment. This home offers 4-bedrooms, 3 full baths, beautiful wood floors throughout, 2 sitting/living room areas, a gas fireplace, an office with built ins, an attractive eat-in kitchen, a beautiful waterside sunroom with separate HVAC, and tons of storage space. There’s even a hot tub! A huge attached garage provides abundant room for vehicles, hobbies, and storage. A yard implemented by an expert environmental gardener (an author on the subject) crafts a haven for birds that is less maintenance—and more attractive to neighbors—than the oh, so very common “all lawn” approach. Watch bluebirds and butterflies while you sip your morning coffee on the expansive Azek deck or large paver patio overlooking the water. Smile at lightning bugs flitting about the yard as you watch the stars come out at night in your private back yard retreat. The open floor plan and large windows keep the home full of light and allow endless views of the water. State-of-the-art solar with 2 large Tesla storage batteries, whole house water purification system and zoned HVAC systems make for healthy living, too. A denitrifying septic system - designed for 4-6 bedrooms - helps keep the Bay clean—in fact, this home's low carbon footprint and thoughtfully designed landscape and rain gardens actually help the environment. Several walk-in storage areas, plus huge unfinished space over the garage. An unforeseen property, even if you expect the unexpected. Don't miss this fabulously easy-care, low maintenance home. All the hard work is done - all that's left is to ENJOY!

28674 Edgemere Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$950,000

*INCOME PRODUCING* Tucked away in the charming Fairbank community on Tilghman Island, this delightful waterfront home captures the very best of Eastern Shore living. Overlooking the serene waters of Blackwalnut Cove with approximately 3’ MLW, the property blends classic cottage character with thoughtful modern enhancements. The original portion of the home reflects its roots as a cozy summer cottage, complete with a charming screened porch perfect for enjoying warm breezes and waterfront views. A connected wing was elevated 10 feet and now features a spacious two-car garage on the main level, offering abundant storage for boats, kayaks, and gear. The rear wing provides exceptional versatility with a private studio apartment—currently a licensed B&B with its own entrance—ideal for guests, rental income, or multigenerational living. Inside the main home, a wood-burning fireplace invites you to curl up on cool days and evenings, while the screened porch becomes the heart of the home during warmer months. With 4 bedrooms and 3 baths, this property offers comfort, flexibility, and the relaxed coastal lifestyle that defines the Eastern Shore. Appointment-only showings. Do not enter the property without an appointment.

4 Beds ⋅ 3 Baths

*INCOME PRODUCING* Tucked away in the charming Fairbank community on Tilghman Island, this delightful waterfront home captures the very best of Eastern Shore living. Overlooking the serene waters of Blackwalnut Cove with approximately 3’ MLW, the property blends classic cottage character with thoughtful modern enhancements. The original portion of the home reflects its roots as a cozy summer cottage, complete with a charming screened porch perfect for enjoying warm breezes and waterfront views. A connected wing was elevated 10 feet and now features a spacious two-car garage on the main level, offering abundant storage for boats, kayaks, and gear. The rear wing provides exceptional versatility with a private studio apartment—currently a licensed B&B with its own entrance—ideal for guests, rental income, or multigenerational living. Inside the main home, a wood-burning fireplace invites you to curl up on cool days and evenings, while the screened porch becomes the heart of the home during warmer months. With 4 bedrooms and 3 baths, this property offers comfort, flexibility, and the relaxed coastal lifestyle that defines the Eastern Shore. Appointment-only showings. Do not enter the property without an appointment.

4938 Fairbank Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact: 4107458060

$1,795,000

A wonderful opportunity to purchase an amazing one story waterfront home on an expansive 2.5 acre lot with western exposure on Broad Creek. Many upgrades have been done to make this a special home to enjoy your life of relaxation and pure enjoyment on the Eastern Shore of Maryland! Mount Pleasant is a very sought after St Michaels neighborhood with close proximity to the downtown historic area of great restaurants, museums and boutiques but no town taxes! You will love the upgraded gourmet kitchen with granite countertops, large center island, soft close cabinetry, broad water views with Samsung stainless steel appliances where you can make your favorite dishes to enjoy. Besides the kitchen, the large Sunroom is my other favorite room of the home with large windows on three sides for panoramic water views to enjoy nature, sunsets and waterfowl along with great access to the wrap around waterside deck through sliding glass doors. I think you will agree when you see it! You will find a bonus of lovely hardwood floors throughout the home and 2 full upgraded bathrooms as well as a double sided wood burning fireplace for the cooler nights on the Shore and we all know that last winter was colder than most so it was very much enjoyed! The property includes a heated workshop for hobbies as well as 2 other sheds for extra storage should you need it but also a screened waterside Gazebo for entertainment, wraparound deck, partially covered front porch and a deeded private dock on Broad Creek with 3+ MLW with multiple slips, a boat lift and a great place to catch some fresh crabs for dinner! What are you waiting for? This could be the one you have been waiting to come on the market!

3 Beds ⋅ 2 Baths

A wonderful opportunity to purchase an amazing one story waterfront home on an expansive 2.5 acre lot with western exposure on Broad Creek. Many upgrades have been done to make this a special home to enjoy your life of relaxation and pure enjoyment on the Eastern Shore of Maryland! Mount Pleasant is a very sought after St Michaels neighborhood with close proximity to the downtown historic area of great restaurants, museums and boutiques but no town taxes! You will love the upgraded gourmet kitchen with granite countertops, large center island, soft close cabinetry, broad water views with Samsung stainless steel appliances where you can make your favorite dishes to enjoy. Besides the kitchen, the large Sunroom is my other favorite room of the home with large windows on three sides for panoramic water views to enjoy nature, sunsets and waterfowl along with great access to the wrap around waterside deck through sliding glass doors. I think you will agree when you see it! You will find a bonus of lovely hardwood floors throughout the home and 2 full upgraded bathrooms as well as a double sided wood burning fireplace for the cooler nights on the Shore and we all know that last winter was colder than most so it was very much enjoyed! The property includes a heated workshop for hobbies as well as 2 other sheds for extra storage should you need it but also a screened waterside Gazebo for entertainment, wraparound deck, partially covered front porch and a deeded private dock on Broad Creek with 3+ MLW with multiple slips, a boat lift and a great place to catch some fresh crabs for dinner! What are you waiting for? This could be the one you have been waiting to come on the market!

23776 Mount Pleasant Landing, Saint Michaels

Listing courtesy of Shore Living Real Estate. Contact: 4102515291

$2,750,000

This stunning waterfront estate is located just minutes from Historic downtown St. Michaels and offers breathtaking views across Leadenham Creek. Set on 47± picturesque acres, the property combines a beautifully renovated main residence, guest house, private dock, waterside pool and expansive open land in one exceptional Eastern Shore offering. Renovated in 2017, the 3,500± sqft brick residence features an open floor plan designed to capture panoramic water views. The spacious kitchen includes quartz countertops, stainless steel appliances, a large center island, beverage bar and dining area. A dramatic waterside family room showcases cathedral ceilings, exposed beam, skylights, a gas fireplace and floor-to-ceiling windows overlooking the creek and surrounding farmland. This stunning home further features a separate living room, waterfront primary suite, three additional bedrooms, a waterside office, an attached oversized two-car garage and so much more. Outdoor amenities include a waterside patio, in-ground waterside pool with extensive hardscaping and a private dock with electric and boat lift providing access to the Chesapeake Bay and its surrounding tributaries. A separate 2,700± sqft guest house with 3-4 bedrooms and 2.5 baths offers flexible accommodations for family, guests or short/long-term rental opportunities. Approximately 42± acres are currently leased to a local farmer, preserving scenic views and agricultural tax advantages. Multiple barns and outbuildings provide endless possibilities for storage, livestock, equipment, hobbies or recreation. For outdoor enthusiasts, the acreage supports abundant wildlife including deer, turkey and geese, while the waterfront setting offers endless opportunities for boating, fishing, kayaking and exploring the Rivers, Creeks and Bay. This is a rare opportunity to own a waterfront estate just minutes from the shops, restaurants and maritime charm of St. Michaels. This is Eastern Shore living at its finest.

4 Beds ⋅ 3 Baths

This stunning waterfront estate is located just minutes from Historic downtown St. Michaels and offers breathtaking views across Leadenham Creek. Set on 47± picturesque acres, the property combines a beautifully renovated main residence, guest house, private dock, waterside pool and expansive open land in one exceptional Eastern Shore offering. Renovated in 2017, the 3,500± sqft brick residence features an open floor plan designed to capture panoramic water views. The spacious kitchen includes quartz countertops, stainless steel appliances, a large center island, beverage bar and dining area. A dramatic waterside family room showcases cathedral ceilings, exposed beam, skylights, a gas fireplace and floor-to-ceiling windows overlooking the creek and surrounding farmland. This stunning home further features a separate living room, waterfront primary suite, three additional bedrooms, a waterside office, an attached oversized two-car garage and so much more. Outdoor amenities include a waterside patio, in-ground waterside pool with extensive hardscaping and a private dock with electric and boat lift providing access to the Chesapeake Bay and its surrounding tributaries. A separate 2,700± sqft guest house with 3-4 bedrooms and 2.5 baths offers flexible accommodations for family, guests or short/long-term rental opportunities. Approximately 42± acres are currently leased to a local farmer, preserving scenic views and agricultural tax advantages. Multiple barns and outbuildings provide endless possibilities for storage, livestock, equipment, hobbies or recreation. For outdoor enthusiasts, the acreage supports abundant wildlife including deer, turkey and geese, while the waterfront setting offers endless opportunities for boating, fishing, kayaking and exploring the Rivers, Creeks and Bay. This is a rare opportunity to own a waterfront estate just minutes from the shops, restaurants and maritime charm of St. Michaels. This is Eastern Shore living at its finest.

7543 Bozman Neavitt Rd, Bozman

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$2,750,000

This stunning waterfront estate is located just minutes from Historic downtown St. Michaels and offers breathtaking views across Leadenham Creek. Set on 47± picturesque acres, the property combines a beautifully renovated main residence, guest house, private dock, waterside pool and expansive open land in one exceptional Eastern Shore offering. Renovated in 2017, the 3,500± sqft brick residence features an open floor plan designed to capture panoramic water views. The spacious kitchen includes quartz countertops, stainless steel appliances, a large center island, beverage bar and dining area. A dramatic waterside family room showcases cathedral ceilings, exposed beam, skylights, a gas fireplace and floor-to-ceiling windows overlooking the creek and surrounding farmland. This stunning home further features a separate living room, waterfront primary suite, three additional bedrooms, a waterside office, an attached oversized two-car garage and so much more. Outdoor amenities include a waterside patio, in-ground waterside pool with extensive hardscaping and a private dock with electric and boat lift providing access to the Chesapeake Bay and its surrounding tributaries. A separate 2,700± sqft guest house with 3-4 bedrooms and 2.5 baths offers flexible accommodations for family, guests or short/long-term rental opportunities. Approximately 42± acres are currently leased to a local farmer, preserving scenic views and agricultural tax advantages. Multiple barns and outbuildings provide endless possibilities for storage, livestock, equipment, hobbies or recreation. For outdoor enthusiasts, the acreage supports abundant wildlife including deer, turkey and geese, while the waterfront setting offers endless opportunities for boating, fishing, kayaking and exploring the Rivers, Creeks and Bay. This is a rare opportunity to own a waterfront estate just minutes from the shops, restaurants and maritime charm of St. Michaels. This is Eastern Shore living at its finest.

4 Beds ⋅ 3 Baths

This stunning waterfront estate is located just minutes from Historic downtown St. Michaels and offers breathtaking views across Leadenham Creek. Set on 47± picturesque acres, the property combines a beautifully renovated main residence, guest house, private dock, waterside pool and expansive open land in one exceptional Eastern Shore offering. Renovated in 2017, the 3,500± sqft brick residence features an open floor plan designed to capture panoramic water views. The spacious kitchen includes quartz countertops, stainless steel appliances, a large center island, beverage bar and dining area. A dramatic waterside family room showcases cathedral ceilings, exposed beam, skylights, a gas fireplace and floor-to-ceiling windows overlooking the creek and surrounding farmland. This stunning home further features a separate living room, waterfront primary suite, three additional bedrooms, a waterside office, an attached oversized two-car garage and so much more. Outdoor amenities include a waterside patio, in-ground waterside pool with extensive hardscaping and a private dock with electric and boat lift providing access to the Chesapeake Bay and its surrounding tributaries. A separate 2,700± sqft guest house with 3-4 bedrooms and 2.5 baths offers flexible accommodations for family, guests or short/long-term rental opportunities. Approximately 42± acres are currently leased to a local farmer, preserving scenic views and agricultural tax advantages. Multiple barns and outbuildings provide endless possibilities for storage, livestock, equipment, hobbies or recreation. For outdoor enthusiasts, the acreage supports abundant wildlife including deer, turkey and geese, while the waterfront setting offers endless opportunities for boating, fishing, kayaking and exploring the Rivers, Creeks and Bay. This is a rare opportunity to own a waterfront estate just minutes from the shops, restaurants and maritime charm of St. Michaels. This is Eastern Shore living at its finest.

7543 Bozman Neavitt Rd, Bozman

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$2,175,000

Discover a serene retreat in the heart of Waverly Island Estates, where a major renovation in 2025 breathes new life into this charming Cape Cod home. Spanning 2.77 acres, this property offers a perfect blend of comfort and nature, featuring 4 spacious bedrooms and 2 full and 2 half bathrooms, ideal for both comfort and relaxation . Step inside to find a beautifully maintained interior with hardwood and ceramic tile flooring, complemented by a cozy fireplace that invites warmth and gatherings. Outside, the allure continues with a personal pool and a stunning view of the Tred Avon River. Enjoy the tranquility of waterfront living with 200 feet of river frontage, complete with a private dock site, perfect for boating, fishing, or simply soaking in the picturesque surroundings. The lot features rip-rap for added stability and a peaceful, no-thru street setting that enhances privacy. With ample parking, including a side-entry garage and driveway space for guests, convenience is at your fingertips. Embrace the lifestyle of riverfront living, where you can kayak, swim, or enjoy a leisurely day on the water. This home is not just a property; it’s a sanctuary waiting for you to create lasting memories. Experience the perfect blend of comfort, nature, and adventure in this exceptional residence. Only a few short miles to downtown Historic Easton, YMCA, shopping and parks.

4 Beds ⋅ 4 Baths

Discover a serene retreat in the heart of Waverly Island Estates, where a major renovation in 2025 breathes new life into this charming Cape Cod home. Spanning 2.77 acres, this property offers a perfect blend of comfort and nature, featuring 4 spacious bedrooms and 2 full and 2 half bathrooms, ideal for both comfort and relaxation . Step inside to find a beautifully maintained interior with hardwood and ceramic tile flooring, complemented by a cozy fireplace that invites warmth and gatherings. Outside, the allure continues with a personal pool and a stunning view of the Tred Avon River. Enjoy the tranquility of waterfront living with 200 feet of river frontage, complete with a private dock site, perfect for boating, fishing, or simply soaking in the picturesque surroundings. The lot features rip-rap for added stability and a peaceful, no-thru street setting that enhances privacy. With ample parking, including a side-entry garage and driveway space for guests, convenience is at your fingertips. Embrace the lifestyle of riverfront living, where you can kayak, swim, or enjoy a leisurely day on the water. This home is not just a property; it’s a sanctuary waiting for you to create lasting memories. Experience the perfect blend of comfort, nature, and adventure in this exceptional residence. Only a few short miles to downtown Historic Easton, YMCA, shopping and parks.

7272 Waverly Island Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$2,495,000

Tucked away on approximately 3 private acres along Plaindealing Creek just off the Tred Avon River, this striking waterfront retreat offers the perfect blend of Mid-Century Modern style, open-concept living, and exceptional Eastern Shore lifestyle amenities. With approximately 5’ MLW, a private dock with boat lift and floating dock, and sweeping water views from nearly every room, this property is designed for effortless waterfront living. The 3-bedroom residence features a desirable main-level primary suite with expansive creek views and direct access to the rear deck. The updated kitchen is a showpiece, centered around a massive U-shaped island with gas cooktop, abundant seating, and seamless flow into the light-filled living spaces. Hardwood flooring runs throughout most of the main level, while soaring ceilings and expansive windows create an airy, open feel that beautifully captures the surrounding waterfront scenery. Upstairs, two additional bedrooms share a full bath, accompanied by an open loft overlooking the foyer and living room — could be used as an office space or sitting area. Outdoor spaces are equally impressive. A sprawling rear deck stretches across the back of the home with access from the primary suite, living room, and kitchen, creating effortless indoor-outdoor living. The in-ground pool, mature landscaping, attached 2-car garage, and detached garage/workshop/storage building complete this exceptional waterfront offering. A rare opportunity to enjoy privacy, boating, and timeless architectural style in one of Talbot County’s most desirable waterfront settings.

3 Beds ⋅ 3 Baths

Tucked away on approximately 3 private acres along Plaindealing Creek just off the Tred Avon River, this striking waterfront retreat offers the perfect blend of Mid-Century Modern style, open-concept living, and exceptional Eastern Shore lifestyle amenities. With approximately 5’ MLW, a private dock with boat lift and floating dock, and sweeping water views from nearly every room, this property is designed for effortless waterfront living. The 3-bedroom residence features a desirable main-level primary suite with expansive creek views and direct access to the rear deck. The updated kitchen is a showpiece, centered around a massive U-shaped island with gas cooktop, abundant seating, and seamless flow into the light-filled living spaces. Hardwood flooring runs throughout most of the main level, while soaring ceilings and expansive windows create an airy, open feel that beautifully captures the surrounding waterfront scenery. Upstairs, two additional bedrooms share a full bath, accompanied by an open loft overlooking the foyer and living room — could be used as an office space or sitting area. Outdoor spaces are equally impressive. A sprawling rear deck stretches across the back of the home with access from the primary suite, living room, and kitchen, creating effortless indoor-outdoor living. The in-ground pool, mature landscaping, attached 2-car garage, and detached garage/workshop/storage building complete this exceptional waterfront offering. A rare opportunity to enjoy privacy, boating, and timeless architectural style in one of Talbot County’s most desirable waterfront settings.

26282 Deep Water Harbor Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$2,475,000

"Tranquil Waters" is a rare Chesapeake Bay waterfront retreat on Tilghman Island, comprehensively renovated to the highest standard and designed to capture panoramic water views from nearly every room. This extraordinary residence blends refined coastal architecture with the relaxed elegance of Eastern Shore living. Dramatic walls of glass, soaring ceilings, and open living spaces flood the home with natural light while framing endless Bay views, spectacular sunrises, and unforgettable sunsets. The fully renovated interior includes a redesigned chef's kitchen, spa-inspired baths, new windows and sliding doors, updated trim and fireplace features, and extensive system upgrades throughout. Exceptional waterfront amenities include expansive Trex decking, deep-water dockage, a heated indoor pool and spa pavilion, and seamless indoor-outdoor living designed for entertaining and year-round enjoyment. Major capital improvements include new HVAC systems, roof replacement, hot water heater, air purification system, decking, windows, doors, and more, offering true turnkey peace of mind. Beyond its appeal as a private waterfront retreat, "Tranquil Waters" has enjoyed a successful luxury vacation rental history, creating an appealing opportunity for buyers seeking both lifestyle and investment potential. Equally suited as a luxury primary residence, waterfront getaway, or private retreat, "Tranquil Waters" delivers the ultimate Eastern Shore lifestyle: water, light, privacy, and complete escape.

7 Beds ⋅ 6 Baths

"Tranquil Waters" is a rare Chesapeake Bay waterfront retreat on Tilghman Island, comprehensively renovated to the highest standard and designed to capture panoramic water views from nearly every room. This extraordinary residence blends refined coastal architecture with the relaxed elegance of Eastern Shore living. Dramatic walls of glass, soaring ceilings, and open living spaces flood the home with natural light while framing endless Bay views, spectacular sunrises, and unforgettable sunsets. The fully renovated interior includes a redesigned chef's kitchen, spa-inspired baths, new windows and sliding doors, updated trim and fireplace features, and extensive system upgrades throughout. Exceptional waterfront amenities include expansive Trex decking, deep-water dockage, a heated indoor pool and spa pavilion, and seamless indoor-outdoor living designed for entertaining and year-round enjoyment. Major capital improvements include new HVAC systems, roof replacement, hot water heater, air purification system, decking, windows, doors, and more, offering true turnkey peace of mind. Beyond its appeal as a private waterfront retreat, "Tranquil Waters" has enjoyed a successful luxury vacation rental history, creating an appealing opportunity for buyers seeking both lifestyle and investment potential. Equally suited as a luxury primary residence, waterfront getaway, or private retreat, "Tranquil Waters" delivers the ultimate Eastern Shore lifestyle: water, light, privacy, and complete escape.

21642 Chicken Point Rd, Tilghman

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

$5,045,000

8051 Leehaven Road is the only property of its kind on the Eastern Shore right now — a custom-built waterfront estate move-in ready, and available today. This is not a project. It is not a renovation waiting to happen. It is +/-4,800 square feet of considered, uncompromising construction sitting on a private waterfront lot with direct access to the Chesapeake Bay, a Gunite saltwater pool with travertine surround, and a new pier fitted with water, electric, lighting, and three lifts — built to the same standard as the home itself. Focus Construction completed it in 2023, and the quality behind the walls matches what you see in front of them: sprayed insulation, a fully conditioned crawlspace, two tankless water heaters, full-house water filtration, and Hardie Plank exterior — every system selected for longevity, not appearance. Inside, the floor plan is generous without being excessive. Two primary suites — one on the main level — give the home the flexibility to accommodate full-time living, weekend retreats, and extended guests alike. The cook's kitchen is built to entertain. The bathrooms have heated floors, step-in showers, and a soaking tub. The living room and first-floor primary suite have motorized power shades. The fireplace anchors the main living space. The bonus room above the two-car garage has its own kitchenette — a private studio, a home office, or self-contained guest quarters, depending on what the next chapter of your life looks like. Every detail has been thought through and verified firsthand. You arrive, you put your bags down, and the Eastern Shore life that brought you here begins — not in six months, not after contractors and decisions and weekends lost to logistics, but the day you close. Easton and St. Michaels are minutes away. Annapolis is fifty minutes. Washington is ninety. Or a private airport is ten minutes away. *By appointment only* *Do not enter the property without an appointment*

4 Beds ⋅ 5 Baths

8051 Leehaven Road is the only property of its kind on the Eastern Shore right now — a custom-built waterfront estate move-in ready, and available today. This is not a project. It is not a renovation waiting to happen. It is +/-4,800 square feet of considered, uncompromising construction sitting on a private waterfront lot with direct access to the Chesapeake Bay, a Gunite saltwater pool with travertine surround, and a new pier fitted with water, electric, lighting, and three lifts — built to the same standard as the home itself. Focus Construction completed it in 2023, and the quality behind the walls matches what you see in front of them: sprayed insulation, a fully conditioned crawlspace, two tankless water heaters, full-house water filtration, and Hardie Plank exterior — every system selected for longevity, not appearance. Inside, the floor plan is generous without being excessive. Two primary suites — one on the main level — give the home the flexibility to accommodate full-time living, weekend retreats, and extended guests alike. The cook's kitchen is built to entertain. The bathrooms have heated floors, step-in showers, and a soaking tub. The living room and first-floor primary suite have motorized power shades. The fireplace anchors the main living space. The bonus room above the two-car garage has its own kitchenette — a private studio, a home office, or self-contained guest quarters, depending on what the next chapter of your life looks like. Every detail has been thought through and verified firsthand. You arrive, you put your bags down, and the Eastern Shore life that brought you here begins — not in six months, not after contractors and decisions and weekends lost to logistics, but the day you close. Easton and St. Michaels are minutes away. Annapolis is fifty minutes. Washington is ninety. Or a private airport is ten minutes away. *By appointment only* *Do not enter the property without an appointment*

8051 Leehaven Rd, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4107458060

$1,295,000

Harris Creek Waterfront. This 3 bedroom, 2 bath well maintained brick one story house is the perfect getaway. Nestled on 1.63+/- acres it is the perfect blend of privacy and community. This home features a large kitchen with several entertaining areas including a cozy living room complete with a fireplace and a large living room that overlooks the huge screen porch and Harris Creek and a gracious waterside paver patio. The water frontage is spectacular complete with additional seating areas on the shoreline to enjoy the river and a dock with 4' MLW with a newer lift. The two car garage has an additional half bath and plenty of room for cars and additional storage. Carpet and paint have just been completed - this is a turnkey house just in time for the season.

3 Beds ⋅ 3 Baths

Harris Creek Waterfront. This 3 bedroom, 2 bath well maintained brick one story house is the perfect getaway. Nestled on 1.63+/- acres it is the perfect blend of privacy and community. This home features a large kitchen with several entertaining areas including a cozy living room complete with a fireplace and a large living room that overlooks the huge screen porch and Harris Creek and a gracious waterside paver patio. The water frontage is spectacular complete with additional seating areas on the shoreline to enjoy the river and a dock with 4' MLW with a newer lift. The two car garage has an additional half bath and plenty of room for cars and additional storage. Carpet and paint have just been completed - this is a turnkey house just in time for the season.

9251 Mallard Point Ct, Mcdaniel

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$6,995,000

Welcome to Deep Neck Farm Lane, a stately waterfront farm overlooking Broad Creek with sweeping west and southwest views that stretch over the Choptank River to the Western Shore. This extraordinary estate captures dramatic sunsets, summer breezes, and shelter from northern winds, all from an unrivaled vantage point. Built in 2006 by a builder for their family, the 8,500± square foot residence provides thoughtful design and enduring craftsmanship. The home was built for hosting and gathering. Seven ensuite bedrooms welcome family and friends, while soaring ceilings, three fireplaces, and a cozy morning room with a wood stove set the tone for gracious living. The turret, perched to catch the last rays of daylight, reminds one that every detail was designed around the water. The accessory structures and outdoor areas for entertaining are well-positioned to capture broad views and an immense water presence. From the waterside deck of the residence to the pool house with bathroom, loft, kitchenette, and outdoor grill, to the riverfront fire pit, the focal point is Broad Creek. The broad water portion of the shoreline is protected with 1,900 feet of stone revetment, and the remaining 2,500 feet of shoreline along Bridge Creek provides a natural setting. The farm has 13 acres under cultivation, with 3.5 acres in pasture. In addition, a 40 x 60 pole barn, featuring a second-floor caretaker apartment, provides ample space for the hobby enthusiast, complete with a workshop and off-season storage.

7 Beds ⋅ 6 Baths

Welcome to Deep Neck Farm Lane, a stately waterfront farm overlooking Broad Creek with sweeping west and southwest views that stretch over the Choptank River to the Western Shore. This extraordinary estate captures dramatic sunsets, summer breezes, and shelter from northern winds, all from an unrivaled vantage point. Built in 2006 by a builder for their family, the 8,500± square foot residence provides thoughtful design and enduring craftsmanship. The home was built for hosting and gathering. Seven ensuite bedrooms welcome family and friends, while soaring ceilings, three fireplaces, and a cozy morning room with a wood stove set the tone for gracious living. The turret, perched to catch the last rays of daylight, reminds one that every detail was designed around the water. The accessory structures and outdoor areas for entertaining are well-positioned to capture broad views and an immense water presence. From the waterside deck of the residence to the pool house with bathroom, loft, kitchenette, and outdoor grill, to the riverfront fire pit, the focal point is Broad Creek. The broad water portion of the shoreline is protected with 1,900 feet of stone revetment, and the remaining 2,500 feet of shoreline along Bridge Creek provides a natural setting. The farm has 13 acres under cultivation, with 3.5 acres in pasture. In addition, a 40 x 60 pole barn, featuring a second-floor caretaker apartment, provides ample space for the hobby enthusiast, complete with a workshop and off-season storage.

24390 Deep Neck Farm Ln, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

$2,995,000

"Cypress Lodge" - Tucked away on a private waterfront lot along the Tred Avon River, this striking contemporary-style residence offers expansive water views, exceptional privacy, and thoughtfully designed indoor-outdoor living. The 3-bedroom, 5-bath home features an open floorplan filled with natural light, highlighted by soaring vaulted cathedral ceilings and clean architectural lines that create a bright, airy feel throughout. Designed to embrace its waterfront setting, the home seamlessly connects spacious living areas with multiple outdoor entertaining spaces overlooking the river. The well-thought-out outdoor living space was designed to fully maximize the property’s incredible waterfront setting, complete with a pool, outdoor fireplace, and covered pavilion overlooking both the pool and the water. Whether hosting guests or enjoying a quiet evening at home, the outdoor spaces offer a seamless extension of the home’s contemporary design and relaxed Eastern Shore lifestyle. Additional exterior amenities include a private dock, private tennis court, and hot tub, all surrounded by mature landscaping and a peaceful setting that enhances the property’s sense of seclusion. Ideally located just outside of Easton, the property provides convenient access to Washington, D.C., Baltimore, and Philadelphia, making it an exceptional full-time residence or weekend getaway within reach of several major metropolitan areas.

3 Beds ⋅ 5 Baths

"Cypress Lodge" - Tucked away on a private waterfront lot along the Tred Avon River, this striking contemporary-style residence offers expansive water views, exceptional privacy, and thoughtfully designed indoor-outdoor living. The 3-bedroom, 5-bath home features an open floorplan filled with natural light, highlighted by soaring vaulted cathedral ceilings and clean architectural lines that create a bright, airy feel throughout. Designed to embrace its waterfront setting, the home seamlessly connects spacious living areas with multiple outdoor entertaining spaces overlooking the river. The well-thought-out outdoor living space was designed to fully maximize the property’s incredible waterfront setting, complete with a pool, outdoor fireplace, and covered pavilion overlooking both the pool and the water. Whether hosting guests or enjoying a quiet evening at home, the outdoor spaces offer a seamless extension of the home’s contemporary design and relaxed Eastern Shore lifestyle. Additional exterior amenities include a private dock, private tennis court, and hot tub, all surrounded by mature landscaping and a peaceful setting that enhances the property’s sense of seclusion. Ideally located just outside of Easton, the property provides convenient access to Washington, D.C., Baltimore, and Philadelphia, making it an exceptional full-time residence or weekend getaway within reach of several major metropolitan areas.

6906 Travelers Rest Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$4,495,000

Experience refined waterfront living in this stunning Lowcountry-style estate, gracefully set on an exceptional waterfront lot among mature Loblolly pines with a coveted southern exposure. Offering sweeping, unobstructed water views, and a rare sense of privacy, the property is bathed in natural light throughout the day, with breathtaking sunrises and and warm, golden reflections in the evening. This 3,800 square foot main residence is complimented by a beautifully appointed 1,200 sq. foot guest cottage, creating an ideal balance of elegance and hospitality. The guest cottage serves as a private retreat, complete with a comfortable living room, galley kitchen, three bedrooms, and a screened porch for quiet relaxation. Inside, timeless craftsmanship defines every space, from reclaimed oak flooring to granite countertops and a meticulously maintained cedar exterior. Outdoors, the lifestyle continues with resort style amenities, including a sparkling in-ground pool, hot tub, firepit and a private 120 foot pier with approximately 7 feet of depth at mean low water- offering effortless access for boating fishing, and enjoying the very best of waterfront living. A rare offering where exceptional land, elegant design, and an unparalleled coastal lifestyle come together.

5 Beds ⋅ 4 Baths

Experience refined waterfront living in this stunning Lowcountry-style estate, gracefully set on an exceptional waterfront lot among mature Loblolly pines with a coveted southern exposure. Offering sweeping, unobstructed water views, and a rare sense of privacy, the property is bathed in natural light throughout the day, with breathtaking sunrises and and warm, golden reflections in the evening. This 3,800 square foot main residence is complimented by a beautifully appointed 1,200 sq. foot guest cottage, creating an ideal balance of elegance and hospitality. The guest cottage serves as a private retreat, complete with a comfortable living room, galley kitchen, three bedrooms, and a screened porch for quiet relaxation. Inside, timeless craftsmanship defines every space, from reclaimed oak flooring to granite countertops and a meticulously maintained cedar exterior. Outdoors, the lifestyle continues with resort style amenities, including a sparkling in-ground pool, hot tub, firepit and a private 120 foot pier with approximately 7 feet of depth at mean low water- offering effortless access for boating fishing, and enjoying the very best of waterfront living. A rare offering where exceptional land, elegant design, and an unparalleled coastal lifestyle come together.

4335 World Farm Rd, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$795,000

Stunning One-Level Luxury Living with Golf Course & Pond Views Perfectly positioned in one of St. Michaels' most desirable communities, this exceptional residence offers effortless one-level living with a private backyard overlooking a tranquil pond and the 4th green of The Links at Perry Cabin. Just minutes from the historic charm, fine dining, boutiques, and waterfront attractions of St. Michaels, residents enjoy exclusive access to a beautiful private waterfront park on the Miles River—a treasured amenity that embodies the best of Eastern Shore living. Meticulously maintained and thoughtfully renovated, this home is truly move-in ready. Recent improvements include a beautifully updated kitchen, renovated bathrooms, fresh interior paint, and a new roof installed in September 2025 featuring 30-year architectural shingles. Additional upgrades and features include: Main HVAC system installed in 2021 with an active service agreement New hot water heater (2024) New dishwasher (2024) Electric vehicle charging station in the garage Invisible pet fence surrounding the yard The serene setting, spectacular views, and extensive updates create a rare opportunity to enjoy a low-maintenance lifestyle in a premier St. Michaels location. Whether relaxing on the patio overlooking the pond and golf course or enjoying the community's private waterfront park, this home offers the perfect blend of luxury, comfort, and convenience. A truly turnkey property where every detail has been thoughtfully updated and impeccably maintained.

4 Beds ⋅ 3 Baths

Stunning One-Level Luxury Living with Golf Course & Pond Views Perfectly positioned in one of St. Michaels' most desirable communities, this exceptional residence offers effortless one-level living with a private backyard overlooking a tranquil pond and the 4th green of The Links at Perry Cabin. Just minutes from the historic charm, fine dining, boutiques, and waterfront attractions of St. Michaels, residents enjoy exclusive access to a beautiful private waterfront park on the Miles River—a treasured amenity that embodies the best of Eastern Shore living. Meticulously maintained and thoughtfully renovated, this home is truly move-in ready. Recent improvements include a beautifully updated kitchen, renovated bathrooms, fresh interior paint, and a new roof installed in September 2025 featuring 30-year architectural shingles. Additional upgrades and features include: Main HVAC system installed in 2021 with an active service agreement New hot water heater (2024) New dishwasher (2024) Electric vehicle charging station in the garage Invisible pet fence surrounding the yard The serene setting, spectacular views, and extensive updates create a rare opportunity to enjoy a low-maintenance lifestyle in a premier St. Michaels location. Whether relaxing on the patio overlooking the pond and golf course or enjoying the community's private waterfront park, this home offers the perfect blend of luxury, comfort, and convenience. A truly turnkey property where every detail has been thoughtfully updated and impeccably maintained.

9359 Martingham, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283

$799,900

Brand new roof just completed! Extremely well maintained Skipton Estates colonial situated on a wooded 2 acre lot which offers loads of privacy and plenty of bird watching. Upon entering this spacious home you are greeted by a bright, open 2 story foyer with hardwood flooring that's open to the office/study and formal dining room. Continuing into the home features a generous family room that has cathedral ceilings and 2nd floor overlook, gas fireplace and is directly located off the kitchen and sunroom. The kitchen which is perfect for entertaining, offers cooktop with wall oven, tile flooring with an island and bar area with seating. Finishing off the 1st floor offers an oversized laundry room with cabinet storage, the primary bedroom with primary bath, tub, separate shower and double vanity and a walk in closet with sitting room. The 2nd floor offers 3 additional bedrooms as well as a spacious bonus room over the garage. The exterior offers private deck with sunroom and primary bedroom access, 3 car garage and utility shed. Situated in the Chapel School District and 10 minutes to Easton or Centreville and 20 minutes to the Bay Bridge.

4 Beds ⋅ 3 Baths

Brand new roof just completed! Extremely well maintained Skipton Estates colonial situated on a wooded 2 acre lot which offers loads of privacy and plenty of bird watching. Upon entering this spacious home you are greeted by a bright, open 2 story foyer with hardwood flooring that's open to the office/study and formal dining room. Continuing into the home features a generous family room that has cathedral ceilings and 2nd floor overlook, gas fireplace and is directly located off the kitchen and sunroom. The kitchen which is perfect for entertaining, offers cooktop with wall oven, tile flooring with an island and bar area with seating. Finishing off the 1st floor offers an oversized laundry room with cabinet storage, the primary bedroom with primary bath, tub, separate shower and double vanity and a walk in closet with sitting room. The 2nd floor offers 3 additional bedrooms as well as a spacious bonus room over the garage. The exterior offers private deck with sunroom and primary bedroom access, 3 car garage and utility shed. Situated in the Chapel School District and 10 minutes to Easton or Centreville and 20 minutes to the Bay Bridge.

29583 Skipton Estates Dr, Cordova

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$3,495,000

Nestled on a sprawling 42-acre estate adjacent to the historic Wye Heights Plantation, this stately 8-bedroom mansion offers an unparalleled blend of elegance, comfort, and tranquility. The grand interior is marked by soaring ceilings and meticulous detailing, with an elevator providing convenient access across multiple levels. The heart of the home is designed for both relaxation and entertaining, featuring a fully finished basement with a cozy pub and kitchenette. A guest apartment over the garage offers additional private quarters, ideal for hosting family or friends. Outside, a picturesque pond with a charming bridge adds to the serene beauty of the grounds, while the enclosed garden sunroom and an additional sunroom off the breakfast area both offer sweeping views of the gardens and pond. Expansive screened-in porches on both the main and upper levels invite you to savor the peaceful surroundings year-round. Whether you're seeking a private retreat or a magnificent estate for entertaining, this exceptional property provides an exquisite lifestyle amid nature and history.

11 Beds ⋅ 11 Baths

Nestled on a sprawling 42-acre estate adjacent to the historic Wye Heights Plantation, this stately 8-bedroom mansion offers an unparalleled blend of elegance, comfort, and tranquility. The grand interior is marked by soaring ceilings and meticulous detailing, with an elevator providing convenient access across multiple levels. The heart of the home is designed for both relaxation and entertaining, featuring a fully finished basement with a cozy pub and kitchenette. A guest apartment over the garage offers additional private quarters, ideal for hosting family or friends. Outside, a picturesque pond with a charming bridge adds to the serene beauty of the grounds, while the enclosed garden sunroom and an additional sunroom off the breakfast area both offer sweeping views of the gardens and pond. Expansive screened-in porches on both the main and upper levels invite you to savor the peaceful surroundings year-round. Whether you're seeking a private retreat or a magnificent estate for entertaining, this exceptional property provides an exquisite lifestyle amid nature and history.

11470 Wye Heights Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$1,995,000

Offered for the first time in over 50 years, this 13+/- acre waterfront property on Broad Creek presents a rare opportunity to own an expansive estate with exceptional shoreline frontage. With more than 960+/- feet of waterfront, the setting provides unobstructed water views and a private pier, offering direct access to the creek and surrounding natural landscape. A tree-lined private driveway leads to the residence, positioned to take full advantage of its waterfront location. The home features 6 bedrooms and 4 full/1 half baths. The main level includes a screened-in porch entry, welcoming foyer, spacious living room with fireplace, formal dining room with a second fireplace, and a flexible study or office with built-in shelving and water views. The updated eat-in kitchen is equipped with granite countertops, a large breakfast bar, gas cooktop, stainless steel appliances, and a spacious pantry. A main-level half bath completes the floor. Both a primary staircase and a secondary staircase provide access to the upper levels. All six bedrooms are located on the second floor. The owner’s suite includes a fireplace, ensuite bath, and access to a front-facing balcony. Front-facing secondary bedrooms also have balcony access. The third level offers additional living space, including a large bonus room, entertainment room, three additional rooms, completed drywall and electrical work, and a full bath with shower. Additional property features include a detached garage with parking and storage, an externally accessed basement for storage, a wide exterior pad suitable for boat or RV storage, hardwood floors, a waterside deck, and a private pier. This property combines acreage, extensive waterfront frontage, and a spacious residence ready for its next owner.

6 Beds ⋅ 5 Baths

Offered for the first time in over 50 years, this 13+/- acre waterfront property on Broad Creek presents a rare opportunity to own an expansive estate with exceptional shoreline frontage. With more than 960+/- feet of waterfront, the setting provides unobstructed water views and a private pier, offering direct access to the creek and surrounding natural landscape. A tree-lined private driveway leads to the residence, positioned to take full advantage of its waterfront location. The home features 6 bedrooms and 4 full/1 half baths. The main level includes a screened-in porch entry, welcoming foyer, spacious living room with fireplace, formal dining room with a second fireplace, and a flexible study or office with built-in shelving and water views. The updated eat-in kitchen is equipped with granite countertops, a large breakfast bar, gas cooktop, stainless steel appliances, and a spacious pantry. A main-level half bath completes the floor. Both a primary staircase and a secondary staircase provide access to the upper levels. All six bedrooms are located on the second floor. The owner’s suite includes a fireplace, ensuite bath, and access to a front-facing balcony. Front-facing secondary bedrooms also have balcony access. The third level offers additional living space, including a large bonus room, entertainment room, three additional rooms, completed drywall and electrical work, and a full bath with shower. Additional property features include a detached garage with parking and storage, an externally accessed basement for storage, a wide exterior pad suitable for boat or RV storage, hardwood floors, a waterside deck, and a private pier. This property combines acreage, extensive waterfront frontage, and a spacious residence ready for its next owner.

7421 Quaker Neck Rd, Bozman

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$6,495,000

Irish Creek Waterfront Estate Set along more than 1,000 +/- feet of pristine, navigable waterfront on Irish Creek, this remarkable 22.14 +/- acre waterfront estate captures the very essence of luxury living on Maryland’s Eastern Shore. Surrounded by sweeping southwest-facing water views and unspoiled natural beauty, the property offers exceptional privacy and scale just minutes from the charming towns of Easton and St. Michaels. Approached by a long, private paved drive, the stately Colonial residence blends timeless architecture with comfortable sophistication, designed for both elegant entertaining and relaxed waterfront living. Inside, refined interiors feature rich hardwood flooring, extensive crown molding, custom built-ins, and four wood-burning fireplaces, creating warm gathering spaces throughout the home. The main level is thoughtfully designed for hosting and everyday living, with gracious formal and informal spaces that flow effortlessly together. A formal dining room, expansive living and family rooms, and a well-appointed kitchen with island and pantry create the perfect setting for gatherings with family and friends. The main-level primary suite offers a peaceful retreat with its own fireplace, walk-in closet, and spa-inspired bath. Upstairs, three additional bedrooms and two full baths comfortably accommodate guests for extended weekends on the Shore. Outdoors, the estate unfolds as a private waterfront retreat designed for unforgettable weekends and celebrations. Spend warm summer days by the Gunite pool and outdoor spa, gather around the built-in fire pit at sunset, or enjoy a friendly match on the bocce court. A tranquil pond and expansive grounds enhance the sense of serenity, while the vaulted three-season porch provides the perfect vantage point for watching boats drift by and taking in the breathtaking evening sunsets over Irish Creek. The property is exceptionally well-suited for hosting, with a charming pool house and a separate two-bedroom guest apartment above the detached four-car side-entry garage—ideal for visiting family, weekend guests, or extended stays. Located in the coveted Royal Oak waterfront community, and within easy reach of Easton, St. Michaels, and the Chesapeake Bay, this extraordinary offering is less than two hours from Washington, D.C., Baltimore, and Philadelphia, making it the perfect luxury retreat for weekend escapes or year-round living on the Eastern Shore. Here, life slows down—boating at sunset, long summer weekends with family and friends, and the timeless beauty of Chesapeake Bay living.

4 Beds ⋅ 5 Baths

Irish Creek Waterfront Estate Set along more than 1,000 +/- feet of pristine, navigable waterfront on Irish Creek, this remarkable 22.14 +/- acre waterfront estate captures the very essence of luxury living on Maryland’s Eastern Shore. Surrounded by sweeping southwest-facing water views and unspoiled natural beauty, the property offers exceptional privacy and scale just minutes from the charming towns of Easton and St. Michaels. Approached by a long, private paved drive, the stately Colonial residence blends timeless architecture with comfortable sophistication, designed for both elegant entertaining and relaxed waterfront living. Inside, refined interiors feature rich hardwood flooring, extensive crown molding, custom built-ins, and four wood-burning fireplaces, creating warm gathering spaces throughout the home. The main level is thoughtfully designed for hosting and everyday living, with gracious formal and informal spaces that flow effortlessly together. A formal dining room, expansive living and family rooms, and a well-appointed kitchen with island and pantry create the perfect setting for gatherings with family and friends. The main-level primary suite offers a peaceful retreat with its own fireplace, walk-in closet, and spa-inspired bath. Upstairs, three additional bedrooms and two full baths comfortably accommodate guests for extended weekends on the Shore. Outdoors, the estate unfolds as a private waterfront retreat designed for unforgettable weekends and celebrations. Spend warm summer days by the Gunite pool and outdoor spa, gather around the built-in fire pit at sunset, or enjoy a friendly match on the bocce court. A tranquil pond and expansive grounds enhance the sense of serenity, while the vaulted three-season porch provides the perfect vantage point for watching boats drift by and taking in the breathtaking evening sunsets over Irish Creek. The property is exceptionally well-suited for hosting, with a charming pool house and a separate two-bedroom guest apartment above the detached four-car side-entry garage—ideal for visiting family, weekend guests, or extended stays. Located in the coveted Royal Oak waterfront community, and within easy reach of Easton, St. Michaels, and the Chesapeake Bay, this extraordinary offering is less than two hours from Washington, D.C., Baltimore, and Philadelphia, making it the perfect luxury retreat for weekend escapes or year-round living on the Eastern Shore. Here, life slows down—boating at sunset, long summer weekends with family and friends, and the timeless beauty of Chesapeake Bay living.

24679 Deep Neck Rd, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$2,495,000

Incredibly rare Cooke’s Hope at Llandaff opportunity featuring nearly 39+/- acres, a 3,800 +/- custom home all 5 minutes of Easton. As you enter “38 Special Acres” you are greeted with views of the farm and pond and you can see why this property is different from all the others. As the driveway curves around you can see the beautiful Abel built home 3 bay detached garage, and pool house. Upon parking you realize that you can not see another house. As you enter the house the quality of construction is evident with high ceilings, wood floors, and view of the incredible pool area and views of Peachblossom Creek. The open floor plan is comfortable and well suited for entertaining, also offering a cozy den and an office that over look the acreage. The primary suite is stunning with an incredible bath with jetted tub and walk-in shower. The custom closet is enormous with built in drawers and automatic lights. Exploring the first floor even more you will find a gracious laundry room that features the coolest dog washing station that you have ever seen with hot and cold water and tile floors this feature alone sets off the house. The entire house is CAT6 wired with a water filtration system and a whole house reverse osmosis system with holding tanks that hold 150 gallons of treated water. Outside the star of the show is the deck and pool area. The concrete pool and separate hot tub that over look the creek are incredible with a pool house that has a changing area and full bath. There is a 2 car attached garage with a 3 bay detached garage with one bay that is fully insulated for that special car you want to keep out of the weather. There are not many places to hunt this close to Easton but with the pond and 20 acre additional wooded parcel there are waterfowl, deer and turkey opportunities right out your back door. The home also features a first floor and pool generator, and RV plug. There are so many unique things about this property it has to be seen to be believed.

4 Beds ⋅ 4 Baths

Incredibly rare Cooke’s Hope at Llandaff opportunity featuring nearly 39+/- acres, a 3,800 +/- custom home all 5 minutes of Easton. As you enter “38 Special Acres” you are greeted with views of the farm and pond and you can see why this property is different from all the others. As the driveway curves around you can see the beautiful Abel built home 3 bay detached garage, and pool house. Upon parking you realize that you can not see another house. As you enter the house the quality of construction is evident with high ceilings, wood floors, and view of the incredible pool area and views of Peachblossom Creek. The open floor plan is comfortable and well suited for entertaining, also offering a cozy den and an office that over look the acreage. The primary suite is stunning with an incredible bath with jetted tub and walk-in shower. The custom closet is enormous with built in drawers and automatic lights. Exploring the first floor even more you will find a gracious laundry room that features the coolest dog washing station that you have ever seen with hot and cold water and tile floors this feature alone sets off the house. The entire house is CAT6 wired with a water filtration system and a whole house reverse osmosis system with holding tanks that hold 150 gallons of treated water. Outside the star of the show is the deck and pool area. The concrete pool and separate hot tub that over look the creek are incredible with a pool house that has a changing area and full bath. There is a 2 car attached garage with a 3 bay detached garage with one bay that is fully insulated for that special car you want to keep out of the weather. There are not many places to hunt this close to Easton but with the pond and 20 acre additional wooded parcel there are waterfowl, deer and turkey opportunities right out your back door. The home also features a first floor and pool generator, and RV plug. There are so many unique things about this property it has to be seen to be believed.

28910 Jennings Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$559,000

Discover this inviting home in The Easton Club along the desirable Oxford Corridor. Photos coming soon. Welcome to a beautifully designed two‑level residence in the sought‑after Easton Club community. Built in 1995, this home blends timeless style with an open, light‑filled layout that offers both comfort and flexibility. The main level features a spacious primary suite with a luxury en suite bath, creating a private retreat. A separate guest wing includes a second bedroom and full bath—ideal for visitors. The living room, home office, and primary suite all open onto a full‑width deck overlooking the property and community grounds, providing a perfect setting for entertaining or quiet outdoor relaxation. Upstairs, a skylit TV room expands your living space, accompanied by a third bedroom, full bath, and climate‑controlled storage. An attached side‑load two‑car garage adds everyday convenience. The Easton Club is a picturesque neighborhood originally designed around a golf course and now reimagined as open green space with cart paths, abundant wildlife, and scenic views along the Tred Avon River. Residents enjoy outstanding amenities including a swimming pool, tennis and pickleball courts, sidewalks, and public water and sewer. This home offers a rare opportunity to enjoy resort‑style living in one of Easton’s most desirable communities, all just minutes from town conveniences.

3 Beds ⋅ 3 Baths

Discover this inviting home in The Easton Club along the desirable Oxford Corridor. Photos coming soon. Welcome to a beautifully designed two‑level residence in the sought‑after Easton Club community. Built in 1995, this home blends timeless style with an open, light‑filled layout that offers both comfort and flexibility. The main level features a spacious primary suite with a luxury en suite bath, creating a private retreat. A separate guest wing includes a second bedroom and full bath—ideal for visitors. The living room, home office, and primary suite all open onto a full‑width deck overlooking the property and community grounds, providing a perfect setting for entertaining or quiet outdoor relaxation. Upstairs, a skylit TV room expands your living space, accompanied by a third bedroom, full bath, and climate‑controlled storage. An attached side‑load two‑car garage adds everyday convenience. The Easton Club is a picturesque neighborhood originally designed around a golf course and now reimagined as open green space with cart paths, abundant wildlife, and scenic views along the Tred Avon River. Residents enjoy outstanding amenities including a swimming pool, tennis and pickleball courts, sidewalks, and public water and sewer. This home offers a rare opportunity to enjoy resort‑style living in one of Easton’s most desirable communities, all just minutes from town conveniences.

28642 Clubhouse Dr, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272