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

$479,000

Nestled in the serene Chapel Woods subdivision, this charming traditional home offers a perfect blend of comfort and functionality. With four spacious bedrooms and two full bathrooms, this residence is designed to meet your needs for both relaxation and entertaining. Step inside to discover a warm and cozy ambiance throughout. Enjoy the tranquility of your surroundings with picturesque views of trees and lush greenery right from your windows. Outside, the expansive 2.13-acre lot provides ample space for outdoor activities or simply enjoying nature. The detached garage offers plenty of room for your vehicles, toys, and tools, as well as additional storage on the second level of the garage. This home is not just a place to live; it's a sanctuary where you can create lasting memories. Experience the perfect blend of comfort, style, and nature in this delightful property.

4 Beds ⋅ 2 Baths

Nestled in the serene Chapel Woods subdivision, this charming traditional home offers a perfect blend of comfort and functionality. With four spacious bedrooms and two full bathrooms, this residence is designed to meet your needs for both relaxation and entertaining. Step inside to discover a warm and cozy ambiance throughout. Enjoy the tranquility of your surroundings with picturesque views of trees and lush greenery right from your windows. Outside, the expansive 2.13-acre lot provides ample space for outdoor activities or simply enjoying nature. The detached garage offers plenty of room for your vehicles, toys, and tools, as well as additional storage on the second level of the garage. This home is not just a place to live; it's a sanctuary where you can create lasting memories. Experience the perfect blend of comfort, style, and nature in this delightful property.

11598 Malvern Ln, Cordova

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$1,250,000

Experience Eastern Shore waterfront living in this charming Chesapeake Bay home, where breathtaking sunset views and a relaxed coastal atmosphere create the perfect setting for everyday living or weekend escapes. Designed to embrace the waterfront lifestyle, the property offers exceptional indoor and outdoor spaces for entertaining family and friends. A brick walkway welcomes you to the inviting front porch and foyer, where hardwood floors flow throughout the home. Recently renovated, the kitchen features white cabinetry, quartz countertops and large windows that fill the space with natural light while overlooking the front yard. The spacious living room is highlighted by a cathedral ceiling and opening to a year-round sunroom surrounded by walls of windows showcasing panoramic views of the Chesapeake Bay. The primary suite features a newly renovated bath with a tile and glass shower. Two guest bedrooms, an office and two additional beautifully renovated full baths occupy the opposite wing of the home, while the second level offers a fourth bedroom with skylights. Outside, you'll find everything needed to enjoy life on the water. The waterside pool with swim deck is complemented by a screened porch, expansive patio, covered seating area and a pool house/bar complete with air conditioning and electric. The private pier provides the perfect spot for fishing, crabbing, or simply taking in the spectacular sunsets, while the rip-rapped shoreline offers lasting shoreline protection. Additional improvements include an attached two-car garage, a storage shed with electric, and a new roof installed in 2025. Situated on high ground outside of the flood zone, this exceptional waterfront property offers direct access to some of the Chesapeake Bay's best fishing, boating, waterfront restaurants and the unforgettable Eastern Shore lifestyle.

4 Beds ⋅ 3 Baths

Experience Eastern Shore waterfront living in this charming Chesapeake Bay home, where breathtaking sunset views and a relaxed coastal atmosphere create the perfect setting for everyday living or weekend escapes. Designed to embrace the waterfront lifestyle, the property offers exceptional indoor and outdoor spaces for entertaining family and friends. A brick walkway welcomes you to the inviting front porch and foyer, where hardwood floors flow throughout the home. Recently renovated, the kitchen features white cabinetry, quartz countertops and large windows that fill the space with natural light while overlooking the front yard. The spacious living room is highlighted by a cathedral ceiling and opening to a year-round sunroom surrounded by walls of windows showcasing panoramic views of the Chesapeake Bay. The primary suite features a newly renovated bath with a tile and glass shower. Two guest bedrooms, an office and two additional beautifully renovated full baths occupy the opposite wing of the home, while the second level offers a fourth bedroom with skylights. Outside, you'll find everything needed to enjoy life on the water. The waterside pool with swim deck is complemented by a screened porch, expansive patio, covered seating area and a pool house/bar complete with air conditioning and electric. The private pier provides the perfect spot for fishing, crabbing, or simply taking in the spectacular sunsets, while the rip-rapped shoreline offers lasting shoreline protection. Additional improvements include an attached two-car garage, a storage shed with electric, and a new roof installed in 2025. Situated on high ground outside of the flood zone, this exceptional waterfront property offers direct access to some of the Chesapeake Bay's best fishing, boating, waterfront restaurants and the unforgettable Eastern Shore lifestyle.

5480 Windward Dr, Tilghman

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

$2,895,000

With sweeping sunset views, this picturesque estate—perfectly situation on a deepwater point with a private dock on Island Creek just off the Choptank River—offers the rare combination of privacy, acreage, and refined Eastern Shore living. Just ten minutes from Easton, Oxford, and Cambridge, the property features an impressive two‑story Tidewater Colonial of approximately 3,500± fsf that includes a first‑floor primary suite with a private library, multiple walk‑in closets, and a beautifully finished bath; two additional bedrooms and full bath upstairs; a guest apartment with separate kitchenette, bedroom and full bath; a large two‑car garage; and a stunning concrete pool framed by expansive stone patios. The current owners thoughtfully reimagined and upgraded the interior, relocating the kitchen to the waterside, expanding and renovating the spacious family room and first‑floor primary suite, adding an exceptional bar/butler’s pantry with custom cabinetry, refrigerator, dishwasher, and icemaker, and creating a central multi-purpose laundry room. Exterior features include low‑maintenance brick and siding, new roof on the renovated waterside, paved drive with ample parking, and an attached two‑car garage with a separate climate‑controlled workout room and half bath. The fully protected, riprapped shoreline spans approximately 665 feet and features a new pier with two deepwater slips (6’+ MLW), electric and water service, plus a separate kayak dock and launch. From any of the property’s many vantage points, enjoy majestic shade trees, mature landscaping, and an ever-changing panorama of natural beauty—imagine watching schools of fish and abundant waterfowl daily—making this an ideal Eastern Shore retreat.

4 Beds ⋅ 5 Baths

With sweeping sunset views, this picturesque estate—perfectly situation on a deepwater point with a private dock on Island Creek just off the Choptank River—offers the rare combination of privacy, acreage, and refined Eastern Shore living. Just ten minutes from Easton, Oxford, and Cambridge, the property features an impressive two‑story Tidewater Colonial of approximately 3,500± fsf that includes a first‑floor primary suite with a private library, multiple walk‑in closets, and a beautifully finished bath; two additional bedrooms and full bath upstairs; a guest apartment with separate kitchenette, bedroom and full bath; a large two‑car garage; and a stunning concrete pool framed by expansive stone patios. The current owners thoughtfully reimagined and upgraded the interior, relocating the kitchen to the waterside, expanding and renovating the spacious family room and first‑floor primary suite, adding an exceptional bar/butler’s pantry with custom cabinetry, refrigerator, dishwasher, and icemaker, and creating a central multi-purpose laundry room. Exterior features include low‑maintenance brick and siding, new roof on the renovated waterside, paved drive with ample parking, and an attached two‑car garage with a separate climate‑controlled workout room and half bath. The fully protected, riprapped shoreline spans approximately 665 feet and features a new pier with two deepwater slips (6’+ MLW), electric and water service, plus a separate kayak dock and launch. From any of the property’s many vantage points, enjoy majestic shade trees, mature landscaping, and an ever-changing panorama of natural beauty—imagine watching schools of fish and abundant waterfowl daily—making this an ideal Eastern Shore retreat.

4440 Baildon Rd, Trappe

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

$369,000

Welcome to 5116 Ocean Gateway, a thoughtfully updated rancher in Trappe offering Eastern Shore charm, comfortable one-level living, 1.5 acres, and an exceptional detached workshop and four-car garage. Conveniently located along Route 50, the property provides easy access to Easton, Cambridge, Oxford, St. Michaels, shopping, dining, waterfront destinations, and everyday conveniences, with Ocean City approximately one hour away. From the moment you arrive, the property makes a memorable impression with its established perennial gardens, expansive landscape, flagpole, security doors, new windows installed in 2022, and a brand-new roof completed in 2026. A 12-by-24 hobby shed with an upper storage level provides even more room for lawn equipment, seasonal items, projects, or recreational gear. Inside, a brand-new, fully insulated 225-square-foot sunroom completed in 2026 expands the home’s living space and creates a bright, inviting place to relax, entertain, or enjoy views of the surrounding property throughout the year. A new whole-house split system installed in 2026 provides energy-efficient heating and air conditioning in addition to the home’s existing baseboard heat. The renovated kitchen combines style, character, and everyday functionality with new cabinetry, granite countertops, a farmhouse sink, recessed lighting, a large island with a Boos Block butcher-block countertop, built-in pot filler, range hood, and a brand-new 36-inch Cosmo gas range. A mudroom, pantry, and butler’s pantry add valuable storage and help keep the home organized. The updated bathroom offers a spa-inspired retreat with a soaking tub, dual-sink vanity, built-in shelving, and a spacious walk-in shower with a built-in bench. The standout feature of this property is the hand-built 24-by-36 heated workshop, barn, and four-car garage. Designed for vehicle access, equipment, hobbies, and serious project space, the building features handcrafted 10-by-10 Ipe wood carriage doors, a rear 8-by-7 roll-up garage door, concrete flooring, a water hookup, high-intensity lighting, 120- and 230-volt receptacles, and 120/230-volt electrical service supported by a 60-amp subpanel. The generous layout provides space for multiple vehicles, boat or RV storage, woodworking equipment, tools, recreational gear, or a dedicated creative workspace. With major improvements, flexible storage, an updated one-level home, a beautiful new sunroom, and a substantial four-car garage and workshop, this unique Trappe property offers a rare combination of comfort, land, character, and utility. Schedule your private tour and experience everything 5116 Ocean Gateway has to offer.

2 Beds ⋅ 1 Baths

Welcome to 5116 Ocean Gateway, a thoughtfully updated rancher in Trappe offering Eastern Shore charm, comfortable one-level living, 1.5 acres, and an exceptional detached workshop and four-car garage. Conveniently located along Route 50, the property provides easy access to Easton, Cambridge, Oxford, St. Michaels, shopping, dining, waterfront destinations, and everyday conveniences, with Ocean City approximately one hour away. From the moment you arrive, the property makes a memorable impression with its established perennial gardens, expansive landscape, flagpole, security doors, new windows installed in 2022, and a brand-new roof completed in 2026. A 12-by-24 hobby shed with an upper storage level provides even more room for lawn equipment, seasonal items, projects, or recreational gear. Inside, a brand-new, fully insulated 225-square-foot sunroom completed in 2026 expands the home’s living space and creates a bright, inviting place to relax, entertain, or enjoy views of the surrounding property throughout the year. A new whole-house split system installed in 2026 provides energy-efficient heating and air conditioning in addition to the home’s existing baseboard heat. The renovated kitchen combines style, character, and everyday functionality with new cabinetry, granite countertops, a farmhouse sink, recessed lighting, a large island with a Boos Block butcher-block countertop, built-in pot filler, range hood, and a brand-new 36-inch Cosmo gas range. A mudroom, pantry, and butler’s pantry add valuable storage and help keep the home organized. The updated bathroom offers a spa-inspired retreat with a soaking tub, dual-sink vanity, built-in shelving, and a spacious walk-in shower with a built-in bench. The standout feature of this property is the hand-built 24-by-36 heated workshop, barn, and four-car garage. Designed for vehicle access, equipment, hobbies, and serious project space, the building features handcrafted 10-by-10 Ipe wood carriage doors, a rear 8-by-7 roll-up garage door, concrete flooring, a water hookup, high-intensity lighting, 120- and 230-volt receptacles, and 120/230-volt electrical service supported by a 60-amp subpanel. The generous layout provides space for multiple vehicles, boat or RV storage, woodworking equipment, tools, recreational gear, or a dedicated creative workspace. With major improvements, flexible storage, an updated one-level home, a beautiful new sunroom, and a substantial four-car garage and workshop, this unique Trappe property offers a rare combination of comfort, land, character, and utility. Schedule your private tour and experience everything 5116 Ocean Gateway has to offer.

5116 Ocean Gateway, Trappe

Listing courtesy of Keller Williams Flagship. Contact:

$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

$1,995,000

Just 4 miles (five minutes) outside the historic town of St. Michaels, MD, this 15-acre property is located in an area of large, private waterfront estates. Over 400 ft. of protected shoreline. Westerly exposure provides Exceptional Sunset Views across the sparkling waters of Harris Creek! 120' x 6' pile-driven pier provides approximately 4' MLW. Sited near the water at the end of a long, tree-lined driveway, you will find an attractive Dutch Colonial-style home. Constructed in 1966, the house features 4 bedrooms (primary downstairs); 2.5 bathrooms; spacious kitchen/dining/family room w/fireplace; formal living room w/fireplace and a glassed waterside "River Room." The 2-zone HVAC system was replaced with new, efficient system(s) in 2024. The house is dated, but perfectly livable. Some new owners will decide to update. Others might decide to demolish and replace with a new home. The 15-acre site and prime location will support a very substantial home. This is a great boating/fishing/crabbing location. Tilghman Island, with its marinas and waterside restaurants, is just a short, scenic boat ride down Harris Creek from the substantial private dock. The open waters of the Choptank River and Chesapeake Bay are just beyond Tilghman Island.

4 Beds ⋅ 3 Baths

Just 4 miles (five minutes) outside the historic town of St. Michaels, MD, this 15-acre property is located in an area of large, private waterfront estates. Over 400 ft. of protected shoreline. Westerly exposure provides Exceptional Sunset Views across the sparkling waters of Harris Creek! 120' x 6' pile-driven pier provides approximately 4' MLW. Sited near the water at the end of a long, tree-lined driveway, you will find an attractive Dutch Colonial-style home. Constructed in 1966, the house features 4 bedrooms (primary downstairs); 2.5 bathrooms; spacious kitchen/dining/family room w/fireplace; formal living room w/fireplace and a glassed waterside "River Room." The 2-zone HVAC system was replaced with new, efficient system(s) in 2024. The house is dated, but perfectly livable. Some new owners will decide to update. Others might decide to demolish and replace with a new home. The 15-acre site and prime location will support a very substantial home. This is a great boating/fishing/crabbing location. Tilghman Island, with its marinas and waterside restaurants, is just a short, scenic boat ride down Harris Creek from the substantial private dock. The open waters of the Choptank River and Chesapeake Bay are just beyond Tilghman Island.

9020 Bozman Neavitt Rd, Saint Michaels

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

$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

$309,600

Tucked away in a quiet setting, this 3 bedroom, 2 full bathroom home has a full, unfinished basement, front deck and a large, detached garage with numerous access doors and areas for storage and/or a workshop. Situated on a 0.34 +/- acre parcel that backs to an established tree line, providing privacy in the back yard. Located approximately 10 miles from Easton, 40 miles from Annapolis, 60 miles from Delaware Beach Resorts and 80 miles from Ocean City, MD. Home was constructed prior to 1978 and may contain lead-based paint. Seller may contribute up to 3% of the buyer’s closing costs. HUD Case #241-818350. Equal Housing Opportunity.

3 Beds ⋅ 2 Baths

Tucked away in a quiet setting, this 3 bedroom, 2 full bathroom home has a full, unfinished basement, front deck and a large, detached garage with numerous access doors and areas for storage and/or a workshop. Situated on a 0.34 +/- acre parcel that backs to an established tree line, providing privacy in the back yard. Located approximately 10 miles from Easton, 40 miles from Annapolis, 60 miles from Delaware Beach Resorts and 80 miles from Ocean City, MD. Home was constructed prior to 1978 and may contain lead-based paint. Seller may contribute up to 3% of the buyer’s closing costs. HUD Case #241-818350. Equal Housing Opportunity.

31154 Hunteman Aly, Cordova

Listing courtesy of Brokers Realty Group, LLC. Contact: 8556872765

$3,495,000

Rare opportunity to acquire a well-appointed home with immense views and convenient proximity to St Michaels. Ideally located by land and sea in Chance Hope Farm on the Miles River at the confluence of Eastern Bay, this stunning, classic eastern shore brick colonial has everything the most decerning buyer needs. This Daffin custom-built home features a generous, main-level primary suite featuring a spa-like bath with heated floors, a large soaking tub and separate shower, and two walk-in closets. The kitchen is a chef’s dream, featuring high-end stainless-steel appliances, a wine cooler, a warming drawer, and a massive island. There are also formal living and dining rooms, two office spaces, a recreation room, and a river room that enjoys views of Eastern Bay and beyond. The park-like lot has 220+/- feet of rip-rapped shoreline, a private pier with 3’ of MLW, lush landscaping, and a waterside deck with an outdoor kitchen.

4 Beds ⋅ 5 Baths

Rare opportunity to acquire a well-appointed home with immense views and convenient proximity to St Michaels. Ideally located by land and sea in Chance Hope Farm on the Miles River at the confluence of Eastern Bay, this stunning, classic eastern shore brick colonial has everything the most decerning buyer needs. This Daffin custom-built home features a generous, main-level primary suite featuring a spa-like bath with heated floors, a large soaking tub and separate shower, and two walk-in closets. The kitchen is a chef’s dream, featuring high-end stainless-steel appliances, a wine cooler, a warming drawer, and a massive island. There are also formal living and dining rooms, two office spaces, a recreation room, and a river room that enjoys views of Eastern Bay and beyond. The park-like lot has 220+/- feet of rip-rapped shoreline, a private pier with 3’ of MLW, lush landscaping, and a waterside deck with an outdoor kitchen.

24678 New Post Rd, Saint Michaels

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

$354,900

🏡 Cute as a button Updated Rancher Easton – 29316 Will Street 🏡 Welcome to this adorable, move-in ready rancher that perfectly blends comfort, functionality, and style! Nestled in a convenient Easton location, this well-maintained home shines with thoughtful updates throughout. Step inside to discover a warm and inviting interior, ideal for everyday living or entertaining. Major improvements include a brand-new roof and newer HVAC system, giving you peace of mind for years to come. Outside, you’ll love the versatility this property offers: Detached garage complete with a private office space— Additional bonus room for storage, hobbies, or flex space Fenced backyard ideal for privacy Lovely patio area ready for outdoor dining and gatherings Whether you're downsizing, starting out, or looking for a low-maintenance retreat, this adorable home checks all the boxes. Don’t miss your opportunity to enjoy easy living with extra space where you need it most! 📍 Conveniently located near all that Easton has to offer—shops, dining, and more!

3 Beds ⋅ 2 Baths

🏡 Cute as a button Updated Rancher Easton – 29316 Will Street 🏡 Welcome to this adorable, move-in ready rancher that perfectly blends comfort, functionality, and style! Nestled in a convenient Easton location, this well-maintained home shines with thoughtful updates throughout. Step inside to discover a warm and inviting interior, ideal for everyday living or entertaining. Major improvements include a brand-new roof and newer HVAC system, giving you peace of mind for years to come. Outside, you’ll love the versatility this property offers: Detached garage complete with a private office space— Additional bonus room for storage, hobbies, or flex space Fenced backyard ideal for privacy Lovely patio area ready for outdoor dining and gatherings Whether you're downsizing, starting out, or looking for a low-maintenance retreat, this adorable home checks all the boxes. Don’t miss your opportunity to enjoy easy living with extra space where you need it most! 📍 Conveniently located near all that Easton has to offer—shops, dining, and more!

29316 Will St, Easton

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$415,000

Welcome Home to a beautifully maintained home tucked away on a quiet cul-de-sac in an established neighborhood conveniently located within minutes of RT50 for easy commuting to Easton, Cambridge or the beach. This spacious 4 Bedroom, 3 Full Bath home offers the flexibility todays buyer's are looking for with a potential 5th main level bedroom thanks to a dining room with closet access and adjacent full bath. Designed for comfortable everyday living and effortless entertaining, the main level features 9 foot ceilings, crown molding and generous living spaces including an open kitchen with island, plenty of cabinets, dining and living area that flows seamlessly for gatherings both large and small. Step outside to a beautiful 17 x 15 screened in porch with ceiling fan to create a perfect spot for morning coffee or quiet evenings overlooking beautifully landscaped, fenced back yard. Upper level you will find a spacious primary suite with 2 separate closets, the primary suite includes a double sink, soaking tub and separate shower. Upper level laundry area is convenient for the 3 additional upper level bedrooms. The added feature of this home is the upper level 23 x 15 Bonus room with vaulted ceilings. Some facts about this home - Upper level A/C is 1 year old, Main level A/C is 2 years old.

4 Beds ⋅ 3 Baths

Welcome Home to a beautifully maintained home tucked away on a quiet cul-de-sac in an established neighborhood conveniently located within minutes of RT50 for easy commuting to Easton, Cambridge or the beach. This spacious 4 Bedroom, 3 Full Bath home offers the flexibility todays buyer's are looking for with a potential 5th main level bedroom thanks to a dining room with closet access and adjacent full bath. Designed for comfortable everyday living and effortless entertaining, the main level features 9 foot ceilings, crown molding and generous living spaces including an open kitchen with island, plenty of cabinets, dining and living area that flows seamlessly for gatherings both large and small. Step outside to a beautiful 17 x 15 screened in porch with ceiling fan to create a perfect spot for morning coffee or quiet evenings overlooking beautifully landscaped, fenced back yard. Upper level you will find a spacious primary suite with 2 separate closets, the primary suite includes a double sink, soaking tub and separate shower. Upper level laundry area is convenient for the 3 additional upper level bedrooms. The added feature of this home is the upper level 23 x 15 Bonus room with vaulted ceilings. Some facts about this home - Upper level A/C is 1 year old, Main level A/C is 2 years old.

3868 Marvel Dr, Trappe

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$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

$2,395,000

Due to personal reasons, BUYER had to withdraw offer--Inspections were "better than good" according to inspector. LOCATION, CHARM, and beautifully RENOVATED!!!Set on 2.32 glorious acres overlooking Dixon Creek, this beautifully and lovingly maintained 1915 residence offers timeless character, refined comfort, and exceptional waterfront living. Original hardwood floors run throughout much of the home, while expansive windows bathe the traditional floor plan in natural light and frame expansive water views from nearly every room. The main level features gracious formal living and dining rooms, a gourmet kitchen with a beautiful center island and top-tier stainless appliances, and a welcoming family room with wood-burning fireplace. Custom built-ins are thoughtfully integrated throughout the home, reflecting quality craftsmanship and attention to detail. Upstairs, the waterside primary suite offers a fireplace, dual walk-in closets and a luxurious ensuite bath with soaking tub and glass-enclosed shower. Two additional guest bedrooms include one with an ensuite bath and another with access to the hall bath. The third level provides a small loft style BR /flexible bonus room, ideal for an office or studio. Outdoor living is equally inviting, with a waterside screened porch, a poolside screened patio with wet bar, and an additional open deck off the dining room—perfect for enjoying the tranquil setting. The beautifully landscaped grounds feature mature trees, lush plantings, and extensive hardscaping, anchored by a gunite pool with expansive deck and surrounding gardens. Additional structures include a charming former icehouse (currently used as a storage shed) and a larger outbuilding once used as tenant quarters. An attached 2-car garage and a full encapsulated basement offer excellent functionality and versatility. With 280 feet of natural shoreline, a private pier with two slips, boat lift, and 3.5–4' MLW, this property captures the essence of Eastern Shore waterfront living. *Roof- 2011, new siding, new boiler, renovated kitchen and baths, redecked pier. -Septic replaced in 2020 and is for 4 bedrooms-owners have plans for proposed first floor primary suite where existing south side porch currently is.

4 Beds ⋅ 4 Baths

Due to personal reasons, BUYER had to withdraw offer--Inspections were "better than good" according to inspector. LOCATION, CHARM, and beautifully RENOVATED!!!Set on 2.32 glorious acres overlooking Dixon Creek, this beautifully and lovingly maintained 1915 residence offers timeless character, refined comfort, and exceptional waterfront living. Original hardwood floors run throughout much of the home, while expansive windows bathe the traditional floor plan in natural light and frame expansive water views from nearly every room. The main level features gracious formal living and dining rooms, a gourmet kitchen with a beautiful center island and top-tier stainless appliances, and a welcoming family room with wood-burning fireplace. Custom built-ins are thoughtfully integrated throughout the home, reflecting quality craftsmanship and attention to detail. Upstairs, the waterside primary suite offers a fireplace, dual walk-in closets and a luxurious ensuite bath with soaking tub and glass-enclosed shower. Two additional guest bedrooms include one with an ensuite bath and another with access to the hall bath. The third level provides a small loft style BR /flexible bonus room, ideal for an office or studio. Outdoor living is equally inviting, with a waterside screened porch, a poolside screened patio with wet bar, and an additional open deck off the dining room—perfect for enjoying the tranquil setting. The beautifully landscaped grounds feature mature trees, lush plantings, and extensive hardscaping, anchored by a gunite pool with expansive deck and surrounding gardens. Additional structures include a charming former icehouse (currently used as a storage shed) and a larger outbuilding once used as tenant quarters. An attached 2-car garage and a full encapsulated basement offer excellent functionality and versatility. With 280 feet of natural shoreline, a private pier with two slips, boat lift, and 3.5–4' MLW, this property captures the essence of Eastern Shore waterfront living. *Roof- 2011, new siding, new boiler, renovated kitchen and baths, redecked pier. -Septic replaced in 2020 and is for 4 bedrooms-owners have plans for proposed first floor primary suite where existing south side porch currently is.

8075 Leehaven Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$3,249,000

Island Creek Estate — rare total privacy, deep water dockage, meaningful architecture, and superb build quality all intersect at this remarkable, truly one-of-a-kind waterfront offering. Set on approximately 6 acres of park-like grounds with 500± feet of shoreline and 6’± MLW, the property offers exceptional water access along the peaceful expanse of Island Creek. The setting is serene and private, with a gracious approach that complements the estate’s architectural presence. Impeccably built with careful attention to detail, the residence offers 4 bedrooms and 3.5 baths within a thoughtfully designed floor plan that maximizes natural light and water views. The living room, kitchen, and dining area flow comfortably together, creating a spacious central gathering area framed by expansive windows overlooking the creek and anchored by a fireplace. The kitchen is generously sized, featuring a substantial island, quality finishes, and an inviting eat-in area suited for both everyday living and entertaining. Outdoor living is equally compelling, with a screened porch overlooking the water and an in-ground pool set against sweeping creek views. The private pier provides deep water dockage, ideal for boating enthusiasts seeking immediate access to the Chesapeake Bay watershed. A finished rec room above the attached garage offers flexible use as a media room, office, or fitness space. In addition to the attached two-car garage, the property features a substantial detached multi-bay garage equipped with a hydraulic vehicle lift, air compressor, and rough-in for a future bath — an exceptional amenity for car collectors, hobbyists, or workshop space. This exceptional Island Creek estate combines craftsmanship, privacy, and premier waterfront living in a setting that is both refined and enduring.

4 Beds ⋅ 4 Baths

Island Creek Estate — rare total privacy, deep water dockage, meaningful architecture, and superb build quality all intersect at this remarkable, truly one-of-a-kind waterfront offering. Set on approximately 6 acres of park-like grounds with 500± feet of shoreline and 6’± MLW, the property offers exceptional water access along the peaceful expanse of Island Creek. The setting is serene and private, with a gracious approach that complements the estate’s architectural presence. Impeccably built with careful attention to detail, the residence offers 4 bedrooms and 3.5 baths within a thoughtfully designed floor plan that maximizes natural light and water views. The living room, kitchen, and dining area flow comfortably together, creating a spacious central gathering area framed by expansive windows overlooking the creek and anchored by a fireplace. The kitchen is generously sized, featuring a substantial island, quality finishes, and an inviting eat-in area suited for both everyday living and entertaining. Outdoor living is equally compelling, with a screened porch overlooking the water and an in-ground pool set against sweeping creek views. The private pier provides deep water dockage, ideal for boating enthusiasts seeking immediate access to the Chesapeake Bay watershed. A finished rec room above the attached garage offers flexible use as a media room, office, or fitness space. In addition to the attached two-car garage, the property features a substantial detached multi-bay garage equipped with a hydraulic vehicle lift, air compressor, and rough-in for a future bath — an exceptional amenity for car collectors, hobbyists, or workshop space. This exceptional Island Creek estate combines craftsmanship, privacy, and premier waterfront living in a setting that is both refined and enduring.

4346 Southside Ln, Trappe

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

$1,195,000

Incredible opportunity to own a circa 1875 home in Oxford's Historic District that has been renovated with a separate 2 bedroom apartment with views of Town Creek. Formerly a Bed and Breakfast, it features 2 first floor bedrooms with 1 and 1/2 baths and 3 second floor bedrooms each with its own full bath. Entire exterior has been newly painted and most of the windows have been replaced. A lovely side garden with a fountain, front porch close to Town Park, and a one and one half car garage with room for a workshop compliment the home. The bright, newly renovated kitchen is the center of the house featuring an alcove with a large kitchen table. It overlooks the side garden. Owner prefers 24 hour notice if possible

5 Beds ⋅ 6 Baths

Incredible opportunity to own a circa 1875 home in Oxford's Historic District that has been renovated with a separate 2 bedroom apartment with views of Town Creek. Formerly a Bed and Breakfast, it features 2 first floor bedrooms with 1 and 1/2 baths and 3 second floor bedrooms each with its own full bath. Entire exterior has been newly painted and most of the windows have been replaced. A lovely side garden with a fountain, front porch close to Town Park, and a one and one half car garage with room for a workshop compliment the home. The bright, newly renovated kitchen is the center of the house featuring an alcove with a large kitchen table. It overlooks the side garden. Owner prefers 24 hour notice if possible

110 N Morris St, Oxford

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

$2,000,000

PRICE IMPROVEMENT.... PRIVATE Estate Living Minutes from Historic St. Michaels... Escape to nearly twenty acres of unspoiled countryside just moments from the charm and waterfront allure of historic St. Michaels. This 4,492-square-foot home offers refined comfort with four bedrooms, two and a half baths, and a gourmet kitchen designed for both everyday living and effortless entertaining. A dedicated space for a future elevator adds thoughtful flexibility for years to come. Outside, the possibilities are as expansive as the land itself- 19.5 private acres with pastures suited for up to eleven Horses, plus a car barn for storage, hobbies, or collections. Agricultural and livestock production also permitted (buyers should confirm specifics with Easton P&Z). Notably, 5.75 wooded acres are enrolled in the DNR's Forest Stewardship Plan, preserving the agricultural tax discount without the requirement to grow crops or house livestock.

4 Beds ⋅ 3 Baths

PRICE IMPROVEMENT.... PRIVATE Estate Living Minutes from Historic St. Michaels... Escape to nearly twenty acres of unspoiled countryside just moments from the charm and waterfront allure of historic St. Michaels. This 4,492-square-foot home offers refined comfort with four bedrooms, two and a half baths, and a gourmet kitchen designed for both everyday living and effortless entertaining. A dedicated space for a future elevator adds thoughtful flexibility for years to come. Outside, the possibilities are as expansive as the land itself- 19.5 private acres with pastures suited for up to eleven Horses, plus a car barn for storage, hobbies, or collections. Agricultural and livestock production also permitted (buyers should confirm specifics with Easton P&Z). Notably, 5.75 wooded acres are enrolled in the DNR's Forest Stewardship Plan, preserving the agricultural tax discount without the requirement to grow crops or house livestock.

7909 Church Neck, Saint Michaels

Listing courtesy of TTR Sotheby's International Realty. Contact:

$925,000

Set on a peaceful two-acre lot in Wye Mills, 28715 Jacks Field Road has been thoughtfully updated from top to bottom, offering the space, functionality, and modern finishes today’s buyers are looking for. This spacious five-bedroom, three-bath home features a newly reimagined interior with new flooring throughout, custom blinds, and a series of high-impact upgrades that elevate both everyday living and entertaining. The kitchen serves as the heart of the home, showcasing brand-new stainless steel appliances, a gas cooktop with downdraft, double ovens, new countertops, and an oversized center island with new cabinetry. Part of the kitchen and dining area has been remodeled to create a more open, connected floor plan, complemented by updated lighting throughout the kitchen, dining area, office, laundry room, and four bedrooms. The primary suite offers a relaxing retreat with heated floors in the master bath and a newly installed walk-in closet organizer. Two additional bathrooms have been completely remodeled, providing fresh, modern finishes throughout the home. Major system upgrades include two brand-new HVAC heat pump systems with new exterior components and a new asphalt driveway, ensuring both comfort and peace of mind. Practical features abound with new laundry room cabinetry, ample storage, and flexible spaces for work, guests, or hobbies. Outside, the property truly shines. A 20’ x 20’ brick-lined patio seamlessly matches the existing covered patio, creating an ideal setting for outdoor entertaining. The expansive backyard is anchored by a 16’–20’ diameter gas fire pit with stone surround, perfect for gatherings under the stars. In addition to the two-car attached garage with walk-up attic storage, the property also includes a two-car detached garage, offering exceptional storage and workspace options. With its generous acreage, extensive updates, and move-in-ready condition, 28715 Jacks Field Road delivers a rare blend of privacy, functionality, and modern comfort in a sought-after Eastern Shore setting.

5 Beds ⋅ 3 Baths

Set on a peaceful two-acre lot in Wye Mills, 28715 Jacks Field Road has been thoughtfully updated from top to bottom, offering the space, functionality, and modern finishes today’s buyers are looking for. This spacious five-bedroom, three-bath home features a newly reimagined interior with new flooring throughout, custom blinds, and a series of high-impact upgrades that elevate both everyday living and entertaining. The kitchen serves as the heart of the home, showcasing brand-new stainless steel appliances, a gas cooktop with downdraft, double ovens, new countertops, and an oversized center island with new cabinetry. Part of the kitchen and dining area has been remodeled to create a more open, connected floor plan, complemented by updated lighting throughout the kitchen, dining area, office, laundry room, and four bedrooms. The primary suite offers a relaxing retreat with heated floors in the master bath and a newly installed walk-in closet organizer. Two additional bathrooms have been completely remodeled, providing fresh, modern finishes throughout the home. Major system upgrades include two brand-new HVAC heat pump systems with new exterior components and a new asphalt driveway, ensuring both comfort and peace of mind. Practical features abound with new laundry room cabinetry, ample storage, and flexible spaces for work, guests, or hobbies. Outside, the property truly shines. A 20’ x 20’ brick-lined patio seamlessly matches the existing covered patio, creating an ideal setting for outdoor entertaining. The expansive backyard is anchored by a 16’–20’ diameter gas fire pit with stone surround, perfect for gatherings under the stars. In addition to the two-car attached garage with walk-up attic storage, the property also includes a two-car detached garage, offering exceptional storage and workspace options. With its generous acreage, extensive updates, and move-in-ready condition, 28715 Jacks Field Road delivers a rare blend of privacy, functionality, and modern comfort in a sought-after Eastern Shore setting.

28715 Jacks Field Rd, Wye Mills

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

$1,685,000

UNIQUE PROPERTY RIGHT OUTSIDE OF HISTORIC ST MICHAELS TOWN LIMITS ACROSS THE LINK AT PERRY CABIN. THIS FABULOUS HOME OFFERS SPACE FOR GATHERINGS WITH FAMILY OR FRIENDS BUT ALSO FEELS COZY FOR EMPTY NESTERS THAT LOVE TO ENTERTAIN. THERE ARE NO RESTRICTIONS THAT PROHIBIT VACATION RENTAL, THERE SHOULD BE SPACE FOR AN INGROUND POOL . ORIGINALLY BUILD IN 1973 THE CURRENT OWNER GUTTED THE HOME, ALL SYSTEMS, ELECTRICAL, WINDOWS, FLOORS ETC ARE NEW- JUST MOVE IN AND ENJOY. FROM NATURAL OAK FLOORS TO MARBLE BATHROOMS, WHITE SPACIOUS KITCHEN WITH GLEAMING GRANITE AND SOAP STONE COUNTERTOPS. EXTENSIVE OUTDOOR LIGHTENING , SPEAKERS, LIGHTENING UNDER THE EVES TURN THIS INTO A MAGICAL PLACE IN THE EVENING. GATHER BY THE HUGE FIREPIT AND ENJOY OUTDOOR LIVING , COOKING AND DINING ON THE VARIOUS PATIOS OR WRAP AROUND DECK. MAINTENANCE EASY MATERIALS HAVE BEEN USED FOR THE DECKING, SIDING AND ROOFING, ATTENTION WAS PAID TO GUTTER SYSTEMS AND GRADING. THE DRIVEWAY IS FRAMED BY BELGIAN COBBLESTONE, STONE COLUMNS GREET YOU WHEN YOU ENTER THE PROPERTY. THIS IS A RARE OPPORTUNITY FOR A TURN KEY PROPERTY IN ST MICHAELS WITHOUT THE TOWN PROPERTY TAXES AND RESTRICTIONS.

5 Beds ⋅ 5 Baths

UNIQUE PROPERTY RIGHT OUTSIDE OF HISTORIC ST MICHAELS TOWN LIMITS ACROSS THE LINK AT PERRY CABIN. THIS FABULOUS HOME OFFERS SPACE FOR GATHERINGS WITH FAMILY OR FRIENDS BUT ALSO FEELS COZY FOR EMPTY NESTERS THAT LOVE TO ENTERTAIN. THERE ARE NO RESTRICTIONS THAT PROHIBIT VACATION RENTAL, THERE SHOULD BE SPACE FOR AN INGROUND POOL . ORIGINALLY BUILD IN 1973 THE CURRENT OWNER GUTTED THE HOME, ALL SYSTEMS, ELECTRICAL, WINDOWS, FLOORS ETC ARE NEW- JUST MOVE IN AND ENJOY. FROM NATURAL OAK FLOORS TO MARBLE BATHROOMS, WHITE SPACIOUS KITCHEN WITH GLEAMING GRANITE AND SOAP STONE COUNTERTOPS. EXTENSIVE OUTDOOR LIGHTENING , SPEAKERS, LIGHTENING UNDER THE EVES TURN THIS INTO A MAGICAL PLACE IN THE EVENING. GATHER BY THE HUGE FIREPIT AND ENJOY OUTDOOR LIVING , COOKING AND DINING ON THE VARIOUS PATIOS OR WRAP AROUND DECK. MAINTENANCE EASY MATERIALS HAVE BEEN USED FOR THE DECKING, SIDING AND ROOFING, ATTENTION WAS PAID TO GUTTER SYSTEMS AND GRADING. THE DRIVEWAY IS FRAMED BY BELGIAN COBBLESTONE, STONE COLUMNS GREET YOU WHEN YOU ENTER THE PROPERTY. THIS IS A RARE OPPORTUNITY FOR A TURN KEY PROPERTY IN ST MICHAELS WITHOUT THE TOWN PROPERTY TAXES AND RESTRICTIONS.

9180 Saint Michaels, Saint Michaels

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

$11,000,000

Presenting "Middleville" (est. 1880), one of the largest waterfront farm and residential estates currently available in the State of Maryland. Spanning over 662 pristine acres in Talbot County, this once-in-a-lifetime landholding features 1.8 miles of shoreline and a world-class infrastructure for luxury living and elite conservation. The Residences & Amenities: The centerpiece of the Estate is the Tidewater Colonial Main Residence, meticulously renovated in 2025. Blending Coastal Charm with modern luxury, the home features: Gourmet Kitchen, equipped with custom cabinetry and top-tier luxury appliances. Waterfront Great Room, an architectural masterpiece with floor-to-ceiling glass offering expansive views of the Chesapeake Bay. Owner’s Wing, a first-floor primary suite featuring dual bathrooms and dual walk-in closets. Refined Finishes: Time-period hardwood flooring throughout, four brick wood-burning fireplaces, and durable HardiePlank siding with a metal roof. Outdoor Living: A tree-lined drive leads to a resort-style grounds featuring a swimming pool, pool house, built-in hot tub, and dedicated pickleball and basketball courts. Estate Infrastructure: 3-car garage, geothermal heating, backup generator, professional hardscaping and multiple barns and storage buildings . Additional Housing: The compound includes three private guest houses and a dedicated caretaker’s residence . The Land & Conservation: Comprised of five distinct parcels, the acreage is a diverse blend of productive agriculture and natural sanctuary. Acreage Breakdown: 390+/- acres of fertile, income-producing cropland and 175+/- acres of mature forest. Waterfowl & Wildlife: A premier destination for sportsmen, the property includes a 7+ acre stocked fishpond/waterfowl holding and six well-fed, water-controlled waterfowl impoundments designed for quality game management. Shoreline & Pier: Over 1,200 feet of shoreline revetment protects the coast. The private pier is equipped with two boat lifts and additional mooring capacity. Middleville is a "turn-key" legacy estate on Maryland’s Eastern Shore, offering a rare fusion of historic significance, 2025 modern luxury, and vast natural resources. In an era where land is the ultimate luxury, this is a unique opportunity to secure one of the region's most significant holdings.

4 Beds ⋅ 5 Baths

Presenting "Middleville" (est. 1880), one of the largest waterfront farm and residential estates currently available in the State of Maryland. Spanning over 662 pristine acres in Talbot County, this once-in-a-lifetime landholding features 1.8 miles of shoreline and a world-class infrastructure for luxury living and elite conservation. The Residences & Amenities: The centerpiece of the Estate is the Tidewater Colonial Main Residence, meticulously renovated in 2025. Blending Coastal Charm with modern luxury, the home features: Gourmet Kitchen, equipped with custom cabinetry and top-tier luxury appliances. Waterfront Great Room, an architectural masterpiece with floor-to-ceiling glass offering expansive views of the Chesapeake Bay. Owner’s Wing, a first-floor primary suite featuring dual bathrooms and dual walk-in closets. Refined Finishes: Time-period hardwood flooring throughout, four brick wood-burning fireplaces, and durable HardiePlank siding with a metal roof. Outdoor Living: A tree-lined drive leads to a resort-style grounds featuring a swimming pool, pool house, built-in hot tub, and dedicated pickleball and basketball courts. Estate Infrastructure: 3-car garage, geothermal heating, backup generator, professional hardscaping and multiple barns and storage buildings . Additional Housing: The compound includes three private guest houses and a dedicated caretaker’s residence . The Land & Conservation: Comprised of five distinct parcels, the acreage is a diverse blend of productive agriculture and natural sanctuary. Acreage Breakdown: 390+/- acres of fertile, income-producing cropland and 175+/- acres of mature forest. Waterfowl & Wildlife: A premier destination for sportsmen, the property includes a 7+ acre stocked fishpond/waterfowl holding and six well-fed, water-controlled waterfowl impoundments designed for quality game management. Shoreline & Pier: Over 1,200 feet of shoreline revetment protects the coast. The private pier is equipped with two boat lifts and additional mooring capacity. Middleville is a "turn-key" legacy estate on Maryland’s Eastern Shore, offering a rare fusion of historic significance, 2025 modern luxury, and vast natural resources. In an era where land is the ultimate luxury, this is a unique opportunity to secure one of the region's most significant holdings.

29245 Howell Point Rd, Trappe

Listing courtesy of Holiday Real Estate. Contact: 4105247700

$575,000

Spacious Colonial in Charlestown Village - Welcome home to this beautifully cared-for Colonial offering 4 bedrooms, 2.5 baths, and over 2,288 sq. ft. of living space (actual square footage exceeds the tax record). The main level features hardwood flooring and a comfortable flow designed for everyday living and entertaining. At the back of the home, the kitchen with stainless steel appliances and granite countertops opens to a breakfast area and a cozy family room with a gas fireplace, all with easy access to the deck and in-ground pool. The main level also includes a formal dining room and a flexible living room/office. Upstairs, a spacious bonus room over the garage offers the perfect hangout space—or could easily serve as the 4th bedroom. Outside, enjoy a fenced backyard, large storage shed, paved driveway, and an attached 2-car garage. Charlestown Village is a sought-after neighborhood featuring lighted streets, sidewalks, and in-town convenience. This home combines space, comfort, and an ideal location. The owners are currently building a new home.

4 Beds ⋅ 3 Baths

Spacious Colonial in Charlestown Village - Welcome home to this beautifully cared-for Colonial offering 4 bedrooms, 2.5 baths, and over 2,288 sq. ft. of living space (actual square footage exceeds the tax record). The main level features hardwood flooring and a comfortable flow designed for everyday living and entertaining. At the back of the home, the kitchen with stainless steel appliances and granite countertops opens to a breakfast area and a cozy family room with a gas fireplace, all with easy access to the deck and in-ground pool. The main level also includes a formal dining room and a flexible living room/office. Upstairs, a spacious bonus room over the garage offers the perfect hangout space—or could easily serve as the 4th bedroom. Outside, enjoy a fenced backyard, large storage shed, paved driveway, and an attached 2-car garage. Charlestown Village is a sought-after neighborhood featuring lighted streets, sidewalks, and in-town convenience. This home combines space, comfort, and an ideal location. The owners are currently building a new home.

316 Spring Dr, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$3,999,900

Swan Point is an exquisite waterfront estate set on approximately 4.5 acres, offering sweeping westerly views across the Tred Avon River. A gated, paved driveway with cobblestone curbs welcomes you to this private retreat. This stately Colonial features 4 bedrooms, 4 full baths, and 3 half baths, thoughtfully designed for both intimate living and grand entertaining. The formal living room, complete with a wood-burning fireplace, opens to a charming three-season porch. A separate formal dining room provides an elegant setting for gatherings. The gourmet kitchen includes a breakfast area and adjoining den with a wood-burning fireplace and 600-year-old heart pine floors that are radiant-heated. A spacious sunroom extends from the kitchen and flows seamlessly onto a brick patio with a built-in grill and is just steps from an inground, heated pool with spa and brick surround. A separate laundry room with powder room, and an attached two-car garage finish off the main level. The partially finished basement offers additional living space with a wood-burning fireplace, full kitchen, and powder room. A private staircase leads to the primary suite, located in its own secluded wing, featuring two walk-in cedar closets and a luxurious bath with soaking tub and separate shower. The main staircase leads to additional bedrooms, including a second primary suite, a third bedroom with hall bath, and a fourth bedroom with a sitting room and en suite bath. Outdoors, a large dock with seating area offers approximately 4’ MLW, water, electric, and two boat lifts. The partially rip-rapped shoreline enhances both beauty and stability. The spacious carriage house includes room for collector cars, an office with gas fireplace and wet bar, a conference room or flex space, and a powder room. A three-car detached garage offers additional storage with a guest apartment above. Equestrian enthusiasts will appreciate the barn with four stalls, office, tack room, and abundant loft storage, along with three paddocks for horses. A workshop with wood stove and powder room provides the perfect space for woodworking or creative pursuits. A second entrance offers convenient access for horse trailers or boats. Swan Point combines timeless elegance, comfort, and versatility—all set against one of the Eastern Shore’s most captivating waterfront backdrops. Easton, Maryland, known as the New Hamptons of the Chesapeake Bay by Forbes Magazine, is conveniently located 1.5 hours from D.C. and Baltimore, and 2 hours from Philadelphia. Just minutes from fine dining, shopping, healthcare, theatres, galleries, museums, golf courses, a country club, a yacht club, and a jet airport.

4 Beds ⋅ 7 Baths

Swan Point is an exquisite waterfront estate set on approximately 4.5 acres, offering sweeping westerly views across the Tred Avon River. A gated, paved driveway with cobblestone curbs welcomes you to this private retreat. This stately Colonial features 4 bedrooms, 4 full baths, and 3 half baths, thoughtfully designed for both intimate living and grand entertaining. The formal living room, complete with a wood-burning fireplace, opens to a charming three-season porch. A separate formal dining room provides an elegant setting for gatherings. The gourmet kitchen includes a breakfast area and adjoining den with a wood-burning fireplace and 600-year-old heart pine floors that are radiant-heated. A spacious sunroom extends from the kitchen and flows seamlessly onto a brick patio with a built-in grill and is just steps from an inground, heated pool with spa and brick surround. A separate laundry room with powder room, and an attached two-car garage finish off the main level. The partially finished basement offers additional living space with a wood-burning fireplace, full kitchen, and powder room. A private staircase leads to the primary suite, located in its own secluded wing, featuring two walk-in cedar closets and a luxurious bath with soaking tub and separate shower. The main staircase leads to additional bedrooms, including a second primary suite, a third bedroom with hall bath, and a fourth bedroom with a sitting room and en suite bath. Outdoors, a large dock with seating area offers approximately 4’ MLW, water, electric, and two boat lifts. The partially rip-rapped shoreline enhances both beauty and stability. The spacious carriage house includes room for collector cars, an office with gas fireplace and wet bar, a conference room or flex space, and a powder room. A three-car detached garage offers additional storage with a guest apartment above. Equestrian enthusiasts will appreciate the barn with four stalls, office, tack room, and abundant loft storage, along with three paddocks for horses. A workshop with wood stove and powder room provides the perfect space for woodworking or creative pursuits. A second entrance offers convenient access for horse trailers or boats. Swan Point combines timeless elegance, comfort, and versatility—all set against one of the Eastern Shore’s most captivating waterfront backdrops. Easton, Maryland, known as the New Hamptons of the Chesapeake Bay by Forbes Magazine, is conveniently located 1.5 hours from D.C. and Baltimore, and 2 hours from Philadelphia. Just minutes from fine dining, shopping, healthcare, theatres, galleries, museums, golf courses, a country club, a yacht club, and a jet airport.

27473 Westpoint Rd, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$729,500

Nestled in the prestigious Cooke's Hope community, this exquisite end-of-row townhouse embodies the perfect blend of elegance and comfort. Built in 2004, this Colonial-style residence boasts a timeless brick façade that invites you into a world of refined living. Spanning 2,819 square feet, this home features three spacious bedrooms and two and a half luxurious bathrooms, designed to cater to your every need. Step inside to discover an open floor plan that seamlessly connects the living and dining areas, adorned with crown moldings and warm bamboo and hardwood flooring. The family room, conveniently located off the kitchen, is perfect for cozy gatherings, enhanced by a stunning gas fireplace with glass doors that create an inviting ambiance. Natural light floods the space through double-pane insulated windows, offering serene views of the lush garden and surrounding trees. The gourmet kitchen is a chef's dream, featuring energy-efficient appliances, including a built-in microwave, self-cleaning oven, and a sleek range hood. The galley-style layout is complemented by a pantry and ample counter space, making meal preparation a delight. Enjoy casual dining in the charming breakfast area, where you can savor your morning coffee while overlooking the tranquil rear yard. Retreat to the master suite, complete with a walk-in closet and a spa-like en-suite bathroom featuring a soaking tub and a walk-in shower. Each additional bedroom offers generous space and comfort, ensuring a restful haven for all. Outside, the property is equally impressive. The 0.14-acre lot adjoins open space and backs to a serene common area, providing a sense of privacy and tranquility. Enjoy leisurely evenings on your patio, surrounded by beautifully landscaped gardens and the gentle rustle of trees. The cul-de-sac location ensures minimal traffic, enhancing the peaceful atmosphere. Additional features include a two-car attached garage with extra storage, a main floor laundry area, and a comprehensive security system for peace of mind. The community offers lawn maintenance, allowing you to spend more time enjoying your luxurious lifestyle. This home is not just a residence; it's a sanctuary that offers an exclusive lifestyle, where every detail has been thoughtfully curated for comfort and elegance. Experience the perfect blend of luxury and warmth in this remarkable property.

3 Beds ⋅ 3 Baths

Nestled in the prestigious Cooke's Hope community, this exquisite end-of-row townhouse embodies the perfect blend of elegance and comfort. Built in 2004, this Colonial-style residence boasts a timeless brick façade that invites you into a world of refined living. Spanning 2,819 square feet, this home features three spacious bedrooms and two and a half luxurious bathrooms, designed to cater to your every need. Step inside to discover an open floor plan that seamlessly connects the living and dining areas, adorned with crown moldings and warm bamboo and hardwood flooring. The family room, conveniently located off the kitchen, is perfect for cozy gatherings, enhanced by a stunning gas fireplace with glass doors that create an inviting ambiance. Natural light floods the space through double-pane insulated windows, offering serene views of the lush garden and surrounding trees. The gourmet kitchen is a chef's dream, featuring energy-efficient appliances, including a built-in microwave, self-cleaning oven, and a sleek range hood. The galley-style layout is complemented by a pantry and ample counter space, making meal preparation a delight. Enjoy casual dining in the charming breakfast area, where you can savor your morning coffee while overlooking the tranquil rear yard. Retreat to the master suite, complete with a walk-in closet and a spa-like en-suite bathroom featuring a soaking tub and a walk-in shower. Each additional bedroom offers generous space and comfort, ensuring a restful haven for all. Outside, the property is equally impressive. The 0.14-acre lot adjoins open space and backs to a serene common area, providing a sense of privacy and tranquility. Enjoy leisurely evenings on your patio, surrounded by beautifully landscaped gardens and the gentle rustle of trees. The cul-de-sac location ensures minimal traffic, enhancing the peaceful atmosphere. Additional features include a two-car attached garage with extra storage, a main floor laundry area, and a comprehensive security system for peace of mind. The community offers lawn maintenance, allowing you to spend more time enjoying your luxurious lifestyle. This home is not just a residence; it's a sanctuary that offers an exclusive lifestyle, where every detail has been thoughtfully curated for comfort and elegance. Experience the perfect blend of luxury and warmth in this remarkable property.

28959 Jasper Ln, Easton

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

$5,000,000

Now offered at an improved price of $5,000,000. Excellent opportunity to own your own private Eastern Shore estate in Royal Oak. Anderby Hall, part of an original 1680 land grant, spans a breathtaking 12+/- acre parcel featuring 3,260’+/- of rip-rapped shoreline. This exceptional property includes a tidal pond, a private cove, and an exclusive island peninsula accessed by bridge. Pass through the gated driveway to discover the main residence: a 3,000+/- sq. ft. Colonial showcasing a great room with a fireplace, charming old pine floors, hand-hewn ceiling beams, and a granite island kitchen. The luxury primary suite features his-and-her closets alongside a second-floor office/den. Nearly every room frames gorgeous, unobstructed views of Irish Creek. Outside, brick walkways lead to a spectacular waterside pool. Boaters will love the private dock offering 5' MLW, located just minutes from the Choptank River. Additional amenities include a 2,600 sq. ft. guest house, tennis courts (easily convertible to pickleball) with a gazebo, a 30x50 detached 3-car garage, an additional 1-car garage with a workshop, new well, and a service shed. Complete with a licensed shoreline and abundant local wildlife (geese, ducks, deer, and turkey), this estate is convenient to Easton and St. Michaels. Experience an unmatched lifestyle of luxury, privacy, and waterfront beauty at an incredible new value.

3 Beds ⋅ 4 Baths

Now offered at an improved price of $5,000,000. Excellent opportunity to own your own private Eastern Shore estate in Royal Oak. Anderby Hall, part of an original 1680 land grant, spans a breathtaking 12+/- acre parcel featuring 3,260’+/- of rip-rapped shoreline. This exceptional property includes a tidal pond, a private cove, and an exclusive island peninsula accessed by bridge. Pass through the gated driveway to discover the main residence: a 3,000+/- sq. ft. Colonial showcasing a great room with a fireplace, charming old pine floors, hand-hewn ceiling beams, and a granite island kitchen. The luxury primary suite features his-and-her closets alongside a second-floor office/den. Nearly every room frames gorgeous, unobstructed views of Irish Creek. Outside, brick walkways lead to a spectacular waterside pool. Boaters will love the private dock offering 5' MLW, located just minutes from the Choptank River. Additional amenities include a 2,600 sq. ft. guest house, tennis courts (easily convertible to pickleball) with a gazebo, a 30x50 detached 3-car garage, an additional 1-car garage with a workshop, new well, and a service shed. Complete with a licensed shoreline and abundant local wildlife (geese, ducks, deer, and turkey), this estate is convenient to Easton and St. Michaels. Experience an unmatched lifestyle of luxury, privacy, and waterfront beauty at an incredible new value.

5499 Anderby Hall Rd, Royal Oak

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$6,800,000

Welcome to this extraordinary waterfront estate, gracefully sited on 6.92 lush, landscaped acres with sweeping views of Leadenham Creek. Designed by architect Alan Meyers, constructed by Ilex Construction, and masterfully styled by interior designer Skip Sroka, this 10,000+/-sq. ft. residence is a showcase of timeless craftsmanship and elevated design. The custom brick exterior is crowned by a new cedar shake roof with copper caps and bands, creating a refined profile that blends seamlessly into the natural surroundings. Double mahogany doors with full-view, artistically designed leaded glass open to a luminous foyer with immediate, breathtaking views of the water. Inside, riff-sawn red oak floors flow through expansive formal and informal living areas. Vaulted ceilings add architectural drama, while curated lighting provides warmth and sophistication throughout. The main level features formal living and dining rooms, a stunning gourmet kitchen, and multiple spaces designed for both relaxation and entertaining. The kitchen is a chef’s dream—equipped with top-tier appliances, a large center island, sitting area with fireplace, and an eat-in dining space. Just off the kitchen, a beautifully crafted screened porch with an octagonal ceiling offers a peaceful, year-round retreat. A walk-in pantry and custom-designed bar enhance both function and hospitality. Also on the main level is a striking private office wrapped in Anigre wood paneling, featuring custom built-ins and a circular backlit ceiling. A separate guest wing includes a spacious family/recreation room with spectacular river views and two guest suites with ensuite baths. The primary suite enjoys its own private wing, with serene water views, a cozy sitting area and fireplace, dual walk-in closets, and an elegant dressing hall. The luxurious, spa-inspired bath includes a soaking tub and glass-enclosed shower, creating a true sanctuary of comfort and privacy. Upstairs, dual wings on opposite sides of the home offer two additional guest suites with ensuite baths, a bonus/music room, and a dedicated fitness room. Five fireplaces handcrafted by Collecio Brothers Stone Masons bring warmth and timeless character throughout the home. Modern systems include geothermal heating and cooling, a new Honeywell HVAC control system, Vantage lighting automation, a fully encapsulated crawlspace, and a Generac generator. In addition to the oversized 3+ car attached garage, a separate detached two-bay garage offers equipment storage, a workshop, and a half bath. Outdoors, the estate is designed for both grand entertaining and quiet waterfront living. Features include an extended waterside patio, beautiful pool house with a fully equipped outdoor kitchen, two dressing rooms, an outdoor shower, and an in-ground pool with heated spa. Over 1,000 feet of riprapped shoreline and a 210-foot private dock with two slips, a floating dock, and 7-foot MLW offer direct access to the Chesapeake Bay. This remarkable estate was built for luxurious living, effortless entertaining, and a deep connection to the natural beauty of Maryland’s Eastern Shore. *Current taxes are based on homestead credit.

5 Beds ⋅ 6 Baths

Welcome to this extraordinary waterfront estate, gracefully sited on 6.92 lush, landscaped acres with sweeping views of Leadenham Creek. Designed by architect Alan Meyers, constructed by Ilex Construction, and masterfully styled by interior designer Skip Sroka, this 10,000+/-sq. ft. residence is a showcase of timeless craftsmanship and elevated design. The custom brick exterior is crowned by a new cedar shake roof with copper caps and bands, creating a refined profile that blends seamlessly into the natural surroundings. Double mahogany doors with full-view, artistically designed leaded glass open to a luminous foyer with immediate, breathtaking views of the water. Inside, riff-sawn red oak floors flow through expansive formal and informal living areas. Vaulted ceilings add architectural drama, while curated lighting provides warmth and sophistication throughout. The main level features formal living and dining rooms, a stunning gourmet kitchen, and multiple spaces designed for both relaxation and entertaining. The kitchen is a chef’s dream—equipped with top-tier appliances, a large center island, sitting area with fireplace, and an eat-in dining space. Just off the kitchen, a beautifully crafted screened porch with an octagonal ceiling offers a peaceful, year-round retreat. A walk-in pantry and custom-designed bar enhance both function and hospitality. Also on the main level is a striking private office wrapped in Anigre wood paneling, featuring custom built-ins and a circular backlit ceiling. A separate guest wing includes a spacious family/recreation room with spectacular river views and two guest suites with ensuite baths. The primary suite enjoys its own private wing, with serene water views, a cozy sitting area and fireplace, dual walk-in closets, and an elegant dressing hall. The luxurious, spa-inspired bath includes a soaking tub and glass-enclosed shower, creating a true sanctuary of comfort and privacy. Upstairs, dual wings on opposite sides of the home offer two additional guest suites with ensuite baths, a bonus/music room, and a dedicated fitness room. Five fireplaces handcrafted by Collecio Brothers Stone Masons bring warmth and timeless character throughout the home. Modern systems include geothermal heating and cooling, a new Honeywell HVAC control system, Vantage lighting automation, a fully encapsulated crawlspace, and a Generac generator. In addition to the oversized 3+ car attached garage, a separate detached two-bay garage offers equipment storage, a workshop, and a half bath. Outdoors, the estate is designed for both grand entertaining and quiet waterfront living. Features include an extended waterside patio, beautiful pool house with a fully equipped outdoor kitchen, two dressing rooms, an outdoor shower, and an in-ground pool with heated spa. Over 1,000 feet of riprapped shoreline and a 210-foot private dock with two slips, a floating dock, and 7-foot MLW offer direct access to the Chesapeake Bay. This remarkable estate was built for luxurious living, effortless entertaining, and a deep connection to the natural beauty of Maryland’s Eastern Shore. *Current taxes are based on homestead credit.

7090 Cooper Point Rd, Bozman

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$8,495,000

NEW PRICE! Located minutes from downtown St. Michaels, “Aqua Vitae” the waters of life, sits on 8.6 private acres on Harris Creek, a Chesapeake Bay tributary. This custom-built offering w/ over 400’ of direct water frontage is comprised of 3 magnificent structures: a grand main residence, guest cottage, & “party barn” all highlighted by a waterside pool, pier w/ 4’ MLW, pine grove, putting green, extensive landscaping & incomparable craftmanship. The 12,000 SF main residence, positioned to prioritize water views, welcomes you via prominent double lead-glass doors & a grand 3-story foyer w/ dual-staircase. The “river room” w/ 2-story octagon copula offers 270◦ views of the property & creek. The TV room w/ 3 exposures & gas-burning fireplace offers double French doors on two sides leading to the wrap-around flagstone patio. The stunning gourmet kitchen is a true chefs dream. Offering oversized island, built-in media/storage cabinet, coffered ceiling, fireplace, 3 sinks, double Subzero fridges w/ freezer drawers, 2 beverage drawers, 3 dishwashers, Wolf microwave & a stainless-steel Lacanche range with 6-burners, pot warmer, warming oven, & 2 ovens. Complimenting the kitchen is a large walk-in pantry w/ dishwasher, sink & extra freezer in hall. Off the kitchen is a covered porch w/ gas fireplace & “ghost’ screens, a perfect spot to enjoy evenings. A large open dining room has 2 custom built-in display cases. The grand salon w/ bay window, gas-fireplace & intricate mantel is reminiscent of Paris. Adjoining the salon is the handsome 2-story curly cherrywood library w/ custom display cases & leaded-glass pocket doors. The adjoining climate-controlled wine room has a wet bar & storage for 750+ bottles. Wood floors flow throughout the entire main level. The main level is completed by an office, powder room & laundry to service the pool, 2 additional powder rooms, elevator to all 4 levels, mud/dog room, rear spiral staircase, guest suite w/ ensuite bathroom, & 2-car attached garage. The 2nd level offers a generous primary suite w/ fireplace & full length terrace overlooking the water. Her wing features dressing room w/ custom built-ins, separate sitting room, & a luxurious bathroom w/ marble tile, separate shower, jetted tub, & vanity. His wing offers an office w/ fireplace, paneled closet leading to separate bathroom w/ shower, travertine stone, & vanity. From his office access the 2nd level of library, open to below. Just off of the primary suite is a bar area/kitchen. 3 additional bedrooms, each w/ ensuite bathroom, and a laundry room complete the 2nd level. The 3rd level offers theater/rec room, play area, bedroom w/ ensuite bathroom, powder room, & ample storage. The lower-level houses utilities, storage, & enough room for an exercise area. The charming guest cottage sits amongst extensive landscaping. The main level offers a full kitchen, dining area, living room, sunroom, large family room, 2 bedrooms w/ shared bathroom, additional guest bathroom, & large entertaining room. Upstairs is a full bedroom w/ ensuite bathroom. The unfinished lower level offers storage. The party barn originally built for boat storage was designed to look like an old Pennsylvania barn w/ 4’ of stone around the base. Flanked by 2 garage wings allowing for 4+ cars & capped w/ a cupola, the shingled-style barn has two large doors on either side of the building that allow for a trailered boat or 4+ more cars. The 2nd level is a loft w/ sleeping/living area w/ full bathroom, plumbed for potential kitchenette, front & rear terraces, & a spiral staircase to a crow’s nest w/ amazing views. There is a full property generator & a dog run w/ kennel just off the rear. Outside enjoy the benefits of beautiful shore living amongst the verdant grounds, mature landscaping & exceptional views. The pier offers 4’ MLW & the shoreline is fully rip-rapped w/ natural plantings.

6 Beds ⋅ 11 Baths

NEW PRICE! Located minutes from downtown St. Michaels, “Aqua Vitae” the waters of life, sits on 8.6 private acres on Harris Creek, a Chesapeake Bay tributary. This custom-built offering w/ over 400’ of direct water frontage is comprised of 3 magnificent structures: a grand main residence, guest cottage, & “party barn” all highlighted by a waterside pool, pier w/ 4’ MLW, pine grove, putting green, extensive landscaping & incomparable craftmanship. The 12,000 SF main residence, positioned to prioritize water views, welcomes you via prominent double lead-glass doors & a grand 3-story foyer w/ dual-staircase. The “river room” w/ 2-story octagon copula offers 270◦ views of the property & creek. The TV room w/ 3 exposures & gas-burning fireplace offers double French doors on two sides leading to the wrap-around flagstone patio. The stunning gourmet kitchen is a true chefs dream. Offering oversized island, built-in media/storage cabinet, coffered ceiling, fireplace, 3 sinks, double Subzero fridges w/ freezer drawers, 2 beverage drawers, 3 dishwashers, Wolf microwave & a stainless-steel Lacanche range with 6-burners, pot warmer, warming oven, & 2 ovens. Complimenting the kitchen is a large walk-in pantry w/ dishwasher, sink & extra freezer in hall. Off the kitchen is a covered porch w/ gas fireplace & “ghost’ screens, a perfect spot to enjoy evenings. A large open dining room has 2 custom built-in display cases. The grand salon w/ bay window, gas-fireplace & intricate mantel is reminiscent of Paris. Adjoining the salon is the handsome 2-story curly cherrywood library w/ custom display cases & leaded-glass pocket doors. The adjoining climate-controlled wine room has a wet bar & storage for 750+ bottles. Wood floors flow throughout the entire main level. The main level is completed by an office, powder room & laundry to service the pool, 2 additional powder rooms, elevator to all 4 levels, mud/dog room, rear spiral staircase, guest suite w/ ensuite bathroom, & 2-car attached garage. The 2nd level offers a generous primary suite w/ fireplace & full length terrace overlooking the water. Her wing features dressing room w/ custom built-ins, separate sitting room, & a luxurious bathroom w/ marble tile, separate shower, jetted tub, & vanity. His wing offers an office w/ fireplace, paneled closet leading to separate bathroom w/ shower, travertine stone, & vanity. From his office access the 2nd level of library, open to below. Just off of the primary suite is a bar area/kitchen. 3 additional bedrooms, each w/ ensuite bathroom, and a laundry room complete the 2nd level. The 3rd level offers theater/rec room, play area, bedroom w/ ensuite bathroom, powder room, & ample storage. The lower-level houses utilities, storage, & enough room for an exercise area. The charming guest cottage sits amongst extensive landscaping. The main level offers a full kitchen, dining area, living room, sunroom, large family room, 2 bedrooms w/ shared bathroom, additional guest bathroom, & large entertaining room. Upstairs is a full bedroom w/ ensuite bathroom. The unfinished lower level offers storage. The party barn originally built for boat storage was designed to look like an old Pennsylvania barn w/ 4’ of stone around the base. Flanked by 2 garage wings allowing for 4+ cars & capped w/ a cupola, the shingled-style barn has two large doors on either side of the building that allow for a trailered boat or 4+ more cars. The 2nd level is a loft w/ sleeping/living area w/ full bathroom, plumbed for potential kitchenette, front & rear terraces, & a spiral staircase to a crow’s nest w/ amazing views. There is a full property generator & a dog run w/ kennel just off the rear. Outside enjoy the benefits of beautiful shore living amongst the verdant grounds, mature landscaping & exceptional views. The pier offers 4’ MLW & the shoreline is fully rip-rapped w/ natural plantings.

8620 Bozman Neavitt, Saint Michaels

Listing courtesy of Washington Fine Properties, LLC. Contact: info@wfp.com

$9,900,000

Situated on one of the finest residential parcels in the country, Ship’s Point, is an estate with few rivals anywhere, at any price. The completely private 13+/- acre estate includes a deep water pier, and 270-degree views at the confluence of Trippe’s Creek and the Tred Avon River. The south-west facing manor house has been meticulously renovated by renowned builder Winchester Construction. A visit is necessary to understand the rarity of the views provided by the nearly one-half mile of shoreline that surrounds this home.

5 Beds ⋅ 6 Baths

Situated on one of the finest residential parcels in the country, Ship’s Point, is an estate with few rivals anywhere, at any price. The completely private 13+/- acre estate includes a deep water pier, and 270-degree views at the confluence of Trippe’s Creek and the Tred Avon River. The south-west facing manor house has been meticulously renovated by renowned builder Winchester Construction. A visit is necessary to understand the rarity of the views provided by the nearly one-half mile of shoreline that surrounds this home.

6010 Shipyard Ln, Easton

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