easternshoremdfineproperties.com Search Results

$1,095,000

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

3 Beds ⋅ 3 Baths

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

100 Pier St W, Oxford

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

$1,595,000

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

4 Beds ⋅ 3 Baths

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

28674 Edgemere Rd, Easton

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

$2,495,000

Timeless Tidewater Colonial-inspired waterfront estate set on 3.5± private acres with 870± feet of shoreline and panoramic water views. A rare offering combining classic architecture, thoughtful upgrades and exceptional outdoor living in one of Talbot County’s most desirable waterfront settings, with a seamless indoor-outdoor flow and water views from nearly every room. Featured in Coastal Living, the residence reflects exceptional design and offers gracious living spaces, including four bedrooms with three updated en-suite baths and three fireplaces. A custom great room with wood-burning fireplace, built-ins and fine wood cabinetry anchors the home, complemented by formal living and dining rooms each with fireplaces. The gourmet custom kitchen includes custom cabinetry, quartz countertops, KitchenAid appliances and dual pantries. Outdoor amenities include a 30,000-gallon pool, expansive lawns, mature trees, irrigation system, partial rip-rapped shoreline and private pier with electric and water. Ideal for boating, kayaking, paddleboarding and waterfront entertaining, this exceptional property offers privacy, comfort and enduring Eastern Shore appeal. Two Osprey nesting platforms convery with the property. Some furniture available under separate contract. Boat Lift sold As Is. Do not come down driveway without an appointment.

4 Beds ⋅ 4 Baths

Timeless Tidewater Colonial-inspired waterfront estate set on 3.5± private acres with 870± feet of shoreline and panoramic water views. A rare offering combining classic architecture, thoughtful upgrades and exceptional outdoor living in one of Talbot County’s most desirable waterfront settings, with a seamless indoor-outdoor flow and water views from nearly every room. Featured in Coastal Living, the residence reflects exceptional design and offers gracious living spaces, including four bedrooms with three updated en-suite baths and three fireplaces. A custom great room with wood-burning fireplace, built-ins and fine wood cabinetry anchors the home, complemented by formal living and dining rooms each with fireplaces. The gourmet custom kitchen includes custom cabinetry, quartz countertops, KitchenAid appliances and dual pantries. Outdoor amenities include a 30,000-gallon pool, expansive lawns, mature trees, irrigation system, partial rip-rapped shoreline and private pier with electric and water. Ideal for boating, kayaking, paddleboarding and waterfront entertaining, this exceptional property offers privacy, comfort and enduring Eastern Shore appeal. Two Osprey nesting platforms convery with the property. Some furniture available under separate contract. Boat Lift sold As Is. Do not come down driveway without an appointment.

3770 Leonard Cove Lane Ln, Trappe

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

$5,995,000

Wilderness Estate- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 47± acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton, Cambridge, and St. Michaels, The Wilderness is sure to please the discerning buyer. Sited among large waterfront estates, The Wilderness enjoys privacy and a commanding presence with old-growth trees, broad southerly views, and deep water. The scope of improvements includes the primary residence, waterside guest cottage, beach house, pool, pier, tennis court, early 20th-century barn, and a host of accessory structures for life on the farm. Visit the virtual tour for an inside look. The main house has great historical significance not only for the original owner’s grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Maryland’s domestic architecture, as noted on two markers from the Maryland Bicentennial Commission and the Maryland Historical Society. The smaller and original of the two brick wings dates from the late 18th century and the larger wing from the early 19th century. The house’s architecture is unusual in that the 19th-century wings telescope up, instead of down, from the original wing. The white brick, black shutters, and historical olive green trim color are a serene palette against the house’s majestic specimen trees around the property, including a gigantic Sycamore that was at one time, the largest of its species in Maryland. The long white gravel drive under the sheltering canopy of mature trees passes by the barn and other outbuildings then curves around the front of the house. Brick steps lead up to the front porch of the early 19th century wing opening into a gracious foyer and stair hall with an elegant elliptical arch that rests on pilasters at the side walls to separate the public from private areas of the house. A French door at the rear of the foyer frames a vista of the lawn and Choptank River. To the side of the foyer are two identical parlors at the front and rear corners of the house. Both rooms have magnificent fireplace mantles and surround; one is a 1740 hand-carved mantel by noted English artisan woodcarver Grinnling Gibbons and the other is a 1780 mantel surrounded by the famous English architect and artisan, Robert Adam. The main floor of the 18th-century wing contains a spacious living room, dining room, original kitchen, and larger kitchen, pantry, two powder rooms, and a stunning sunroom connecting to a terrace along the rear of the house overlooking the Choptank River. Part of this wing was the final addition to the original home. The second floor of the 19th-century wing contains two bedrooms over the two parlors below with fireplaces and walk-in closets and two baths. The 18th-century wing and later addition contain an artist’s studio with cabinetry and sink that has a myriad uses– TV room, arts and crafts room. The primary suite is located at the rear corner of this wing. It has a fireplace flanked by single windows and another window on the rear wall for panoramic views of the mature landscape and the Choptank River. Two baths complete the suite, with one bath off a hall for access from the art studio. Two stairs access the attic level; one in the 18th-century wing leads to two bedrooms and one bath. The main stair in the 19th-century wing leads to a large game room and another cozy bedroom ensuite.

6 Beds ⋅ 6 Baths

Wilderness Estate- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 47± acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton, Cambridge, and St. Michaels, The Wilderness is sure to please the discerning buyer. Sited among large waterfront estates, The Wilderness enjoys privacy and a commanding presence with old-growth trees, broad southerly views, and deep water. The scope of improvements includes the primary residence, waterside guest cottage, beach house, pool, pier, tennis court, early 20th-century barn, and a host of accessory structures for life on the farm. Visit the virtual tour for an inside look. The main house has great historical significance not only for the original owner’s grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Maryland’s domestic architecture, as noted on two markers from the Maryland Bicentennial Commission and the Maryland Historical Society. The smaller and original of the two brick wings dates from the late 18th century and the larger wing from the early 19th century. The house’s architecture is unusual in that the 19th-century wings telescope up, instead of down, from the original wing. The white brick, black shutters, and historical olive green trim color are a serene palette against the house’s majestic specimen trees around the property, including a gigantic Sycamore that was at one time, the largest of its species in Maryland. The long white gravel drive under the sheltering canopy of mature trees passes by the barn and other outbuildings then curves around the front of the house. Brick steps lead up to the front porch of the early 19th century wing opening into a gracious foyer and stair hall with an elegant elliptical arch that rests on pilasters at the side walls to separate the public from private areas of the house. A French door at the rear of the foyer frames a vista of the lawn and Choptank River. To the side of the foyer are two identical parlors at the front and rear corners of the house. Both rooms have magnificent fireplace mantles and surround; one is a 1740 hand-carved mantel by noted English artisan woodcarver Grinnling Gibbons and the other is a 1780 mantel surrounded by the famous English architect and artisan, Robert Adam. The main floor of the 18th-century wing contains a spacious living room, dining room, original kitchen, and larger kitchen, pantry, two powder rooms, and a stunning sunroom connecting to a terrace along the rear of the house overlooking the Choptank River. Part of this wing was the final addition to the original home. The second floor of the 19th-century wing contains two bedrooms over the two parlors below with fireplaces and walk-in closets and two baths. The 18th-century wing and later addition contain an artist’s studio with cabinetry and sink that has a myriad uses– TV room, arts and crafts room. The primary suite is located at the rear corner of this wing. It has a fireplace flanked by single windows and another window on the rear wall for panoramic views of the mature landscape and the Choptank River. Two baths complete the suite, with one bath off a hall for access from the art studio. Two stairs access the attic level; one in the 18th-century wing leads to two bedrooms and one bath. The main stair in the 19th-century wing leads to a large game room and another cozy bedroom ensuite.

27293 Southside Island Creek Rd, Trappe

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

$299,900

Huge price improvement 5/21/26! Welcome to 8186 June Way, #307 in Easton—a move-in ready, spacious and bright three-bedroom end townhome located just one mile from downtown Easton. This beautifully situated unit offers the best location in the townhome section of Waylands, featuring a large backyard bordered by trees and a private side deck off the kitchen/dining area overlooking peaceful greenspace. Inside, you’ll find a well-designed floor plan with a first-floor primary suite, open kitchen with breakfast bar flowing into the dining area, a large living room, and convenient laundry on the main level. Upstairs includes two generously sized bedrooms with plenty of closet space and a full hall bath. Additional highlights include ample storage in the attic, a large detached backyard shed, and crawl space access at the rear of the home. Conveniently located near shopping (Giant, Walmart, and more) and with quick access to Route 50 for commuters.

3 Beds ⋅ 2 Baths

Huge price improvement 5/21/26! Welcome to 8186 June Way, #307 in Easton—a move-in ready, spacious and bright three-bedroom end townhome located just one mile from downtown Easton. This beautifully situated unit offers the best location in the townhome section of Waylands, featuring a large backyard bordered by trees and a private side deck off the kitchen/dining area overlooking peaceful greenspace. Inside, you’ll find a well-designed floor plan with a first-floor primary suite, open kitchen with breakfast bar flowing into the dining area, a large living room, and convenient laundry on the main level. Upstairs includes two generously sized bedrooms with plenty of closet space and a full hall bath. Additional highlights include ample storage in the attic, a large detached backyard shed, and crawl space access at the rear of the home. Conveniently located near shopping (Giant, Walmart, and more) and with quick access to Route 50 for commuters.

8186 June Way Unit #307, Easton

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

$519,000

Barely lived in totally maintenance free rancher on a 3+/- acre lot with broad water views. Freshly painted with new landscaping it is vacant and available for immediate occupancy! Main area has beautiful wood laminate flooring with carpet in all bedrooms. Bonus room to be used as an office/family room, granite counters with wine refrigerator and all nearly new appliances with utility room and washer and dryer. Located at the end of a cul de sac with mature trees and a great water view of Harris Creek and Sherwood landing. A truly unique opportunity!

3 Beds ⋅ 2 Baths

Barely lived in totally maintenance free rancher on a 3+/- acre lot with broad water views. Freshly painted with new landscaping it is vacant and available for immediate occupancy! Main area has beautiful wood laminate flooring with carpet in all bedrooms. Bonus room to be used as an office/family room, granite counters with wine refrigerator and all nearly new appliances with utility room and washer and dryer. Located at the end of a cul de sac with mature trees and a great water view of Harris Creek and Sherwood landing. A truly unique opportunity!

21869 Albie Rd, Sherwood

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

$699,000

Broker and Public Open 4/23 from 10am to Noon! OCCUPANCY PERMIT in hand, move right in! Nestled in the charming town of Easton Maryland, this exquisite new construction offers a perfect blend of modern luxury and traditional elegance. The sixth of Sandy Lane's ten total homes to be built, this design is the first two story that includes a first-floor primary suite with gorgeous en-suite bath and a huge walk-in closet. There are two additional bedrooms up and a 320sf family room, providing a second spacious gathering place for tv watching, reading, homework, pool table, games, the works! It is a thoughtfully designed custom layout providing plenty of space for privacy, relaxation and entertainment. Step inside to discover an inviting open floor plan that seamlessly connects the gourmet kitchen to the dining and living areas. The kitchen as designed is a cook's dream, with an island providing ample workspace and seating for four. The kitchen is equipped with custom cabinetry and elegant countertops as well as stainless appliances. The kitchen island serves as a focal point for gatherings, while recessed lighting and ceiling fans enhance the ambiance throughout the home. The interior is fitted with luxurious vinyl plank flooring and carpeting, creating a warm and comfortable atmosphere. The first-floor primary suite features a huge walk-in closet and a private, beautifully finished bathroom with a custom-tiled shower. Next to the interior entrance to the garage, you will find a convenient, dedicated laundry room and private powder room. Outside, the property is equally impressive. The extensive hardscape and beautifully landscaped front yard create a picturesque setting, with a rear patio and front porch perfect for outdoor entertaining or quiet evenings spent enjoying the neighborhood views. In addition to an encapsulated and climate-controlled crawl space, features include energy-efficient double-pane windows, Certified IECC Energy Efficient insulation (R-49 ceiling, R 21 walls), exterior lighting, and a well-designed gutter system, ensuring both functionality and aesthetic appeal. Whether you are retired, work from home or have a growing family, this flexible floorplan will suit your needs. Parking is a breeze with an attached garage with electric car charger, driveway space for two vehicles, and additional on-street parking available. Located on a cul-de-sac, this home offers a sense of privacy while still being in the heart of downtown, where the vibrant community life of Easton awaits. You can experience the luxury of modern living in a prime downtown Easton location, where every detail has been meticulously crafted to provide comfort and elegance. Don't miss the opportunity to make this stunning residence your own and enjoy the exclusive lifestyle offered on Sandy Lane. Sandy Lane homes are subject to recorded Covenants and Restrictions (attached in docs) but there is no HOA or fees. Developer: Sandy Lane, LLC, MHBR 9512. Builder: Stansbury and Sons Home Improvement Inc., MHBR 8351. BUILDER CONTRACT REQUIRED.

3 Beds ⋅ 3 Baths

Broker and Public Open 4/23 from 10am to Noon! OCCUPANCY PERMIT in hand, move right in! Nestled in the charming town of Easton Maryland, this exquisite new construction offers a perfect blend of modern luxury and traditional elegance. The sixth of Sandy Lane's ten total homes to be built, this design is the first two story that includes a first-floor primary suite with gorgeous en-suite bath and a huge walk-in closet. There are two additional bedrooms up and a 320sf family room, providing a second spacious gathering place for tv watching, reading, homework, pool table, games, the works! It is a thoughtfully designed custom layout providing plenty of space for privacy, relaxation and entertainment. Step inside to discover an inviting open floor plan that seamlessly connects the gourmet kitchen to the dining and living areas. The kitchen as designed is a cook's dream, with an island providing ample workspace and seating for four. The kitchen is equipped with custom cabinetry and elegant countertops as well as stainless appliances. The kitchen island serves as a focal point for gatherings, while recessed lighting and ceiling fans enhance the ambiance throughout the home. The interior is fitted with luxurious vinyl plank flooring and carpeting, creating a warm and comfortable atmosphere. The first-floor primary suite features a huge walk-in closet and a private, beautifully finished bathroom with a custom-tiled shower. Next to the interior entrance to the garage, you will find a convenient, dedicated laundry room and private powder room. Outside, the property is equally impressive. The extensive hardscape and beautifully landscaped front yard create a picturesque setting, with a rear patio and front porch perfect for outdoor entertaining or quiet evenings spent enjoying the neighborhood views. In addition to an encapsulated and climate-controlled crawl space, features include energy-efficient double-pane windows, Certified IECC Energy Efficient insulation (R-49 ceiling, R 21 walls), exterior lighting, and a well-designed gutter system, ensuring both functionality and aesthetic appeal. Whether you are retired, work from home or have a growing family, this flexible floorplan will suit your needs. Parking is a breeze with an attached garage with electric car charger, driveway space for two vehicles, and additional on-street parking available. Located on a cul-de-sac, this home offers a sense of privacy while still being in the heart of downtown, where the vibrant community life of Easton awaits. You can experience the luxury of modern living in a prime downtown Easton location, where every detail has been meticulously crafted to provide comfort and elegance. Don't miss the opportunity to make this stunning residence your own and enjoy the exclusive lifestyle offered on Sandy Lane. Sandy Lane homes are subject to recorded Covenants and Restrictions (attached in docs) but there is no HOA or fees. Developer: Sandy Lane, LLC, MHBR 9512. Builder: Stansbury and Sons Home Improvement Inc., MHBR 8351. BUILDER CONTRACT REQUIRED.

18 Sandy Ln, Easton

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

$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

$1,250,000

Welcome to this exceptional William Poole–designed Tidewater Colonial, gracefully sited on approximately 2.3 acres in the desirable community of Waverly Island Estates, just three miles from the Town of Easton. Offering a refined blend of classic coastal architecture and modern comfort, this property provides a private retreat on Maryland’s Eastern Shore. NEW ROOF and Pool Equipment 2026, HVAC 2019 & 2021. Inside, the home features a well-designed floor plan with abundant natural light and timeless appeal. The open kitchen connects seamlessly to a casual dining and living area highlighted by a vaulted ceiling, creating an inviting space for everyday living and entertaining. Formal living and dining rooms offer elegant settings for gatherings, while the expansive deck, fenced backyard, and in-ground pool extend the living space outdoors. The first-floor primary suite provides convenience and privacy. Upstairs, you’ll find spacious guest suites, a dedicated office, and a flexible family room ideal for work, relaxation, or hobbies. A large walk-up attic offers excellent storage and future expansion potential. Ideally positioned within the Oxford corridor, this home allows easy access to the waterfront town of Oxford and the shopping, dining, and cultural amenities of Easton. Enjoy the best of rural living with proximity to modern conveniences, all within a peaceful and sought-after neighborhood.

4 Beds ⋅ 4 Baths

Welcome to this exceptional William Poole–designed Tidewater Colonial, gracefully sited on approximately 2.3 acres in the desirable community of Waverly Island Estates, just three miles from the Town of Easton. Offering a refined blend of classic coastal architecture and modern comfort, this property provides a private retreat on Maryland’s Eastern Shore. NEW ROOF and Pool Equipment 2026, HVAC 2019 & 2021. Inside, the home features a well-designed floor plan with abundant natural light and timeless appeal. The open kitchen connects seamlessly to a casual dining and living area highlighted by a vaulted ceiling, creating an inviting space for everyday living and entertaining. Formal living and dining rooms offer elegant settings for gatherings, while the expansive deck, fenced backyard, and in-ground pool extend the living space outdoors. The first-floor primary suite provides convenience and privacy. Upstairs, you’ll find spacious guest suites, a dedicated office, and a flexible family room ideal for work, relaxation, or hobbies. A large walk-up attic offers excellent storage and future expansion potential. Ideally positioned within the Oxford corridor, this home allows easy access to the waterfront town of Oxford and the shopping, dining, and cultural amenities of Easton. Enjoy the best of rural living with proximity to modern conveniences, all within a peaceful and sought-after neighborhood.

28028 Playtor Rd, Easton

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

$8,750,000

Wilderness Estate- REVISED OFFERING INCLUDES 5 PARCELS 6.27.25- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 234 acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton, Cambridge, and St. Michaels, The Wilderness is sure to please the discerning buyer. Sited among large waterfront estates, The Wilderness enjoys privacy and a commanding presence with old-growth trees, broad southerly views, and deep water. The scope of improvements includes the primary residence, waterside guest cottage, beach house, pool, pier, tennis court, early 20th-century barn, and a host of accessory structures for life on the farm. Visit the virtual tour for an inside look and appreciation for the scope of this offering. The main house has great historical significance not only for the original owner’s grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Maryland’s domestic architecture, as noted on two markers from the Maryland Bicentennial Commission and the Maryland Historical Society. The smaller and original of the two brick wings dates from the late 18th century and the larger wing from the early 19th century. The house’s architecture is unusual in that the 19th-century wings telescope up, instead of down, from the original wing. The white brick, black shutters, and historical olive green trim color are a serene palette against the house’s majestic specimen trees around the property, including a gigantic Sycamore that is the largest of its species in Maryland. The long white gravel drive under the sheltering canopy of mature trees passes by the barn and other outbuildings then curves around the front of the house. Brick steps lead up to the front porch of the early 19th century wing opening into a gracious foyer and stair hall with an elegant elliptical arch that rests on pilasters at the side walls to separate the public from private areas of the house. A French door at the rear of the foyer frames a vista of the lawn and Choptank River. To the side of the foyer are two identical parlors at the front and rear corners of the house. Both rooms have magnificent fireplace mantles and surround; one is a 1740 hand-carved mantel by noted English artisan woodcarver Grinnling Gibbons and the other is a 1780 mantel surrounded by the famous English architect and artisan, Robert Adam. The main floor of the 18th-century wing contains a spacious living room, dining room, original kitchen, and larger kitchen, pantry, two powder rooms, and a stunning sunroom connecting to a terrace along the rear of the house overlooking the Choptank River. Part of this wing was the final addition to the original home. The second floor of the 19th-century wing contains two bedrooms over the two parlors below with fireplaces and walk-in closets and two baths. The 18th-century wing and later addition contain an artist’s studio with cabinetry and sink that has a myriad uses– TV room, arts and crafts room. The primary suite is located at the rear corner of this wing. It has a fireplace flanked by single windows and another window on the rear wall for panoramic views of the mature landscape and the Choptank River. Two baths complete the suite, with one bath off a hall for access from the art studio. Two stairs access the attic level; one in the 18th-century wing leads to two bedrooms and one bath. The main stair in the 19th-century wing leads to a large game room and another cozy bedroom ensuite. The revised offering of The Wilderness, providing 234 acres comprised of 5 recorded parcels with over 3,000 feet of shoreline is a remarkable opportunity to witness life on the Shore.

6 Beds ⋅ 6 Baths

Wilderness Estate- REVISED OFFERING INCLUDES 5 PARCELS 6.27.25- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 234 acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton, Cambridge, and St. Michaels, The Wilderness is sure to please the discerning buyer. Sited among large waterfront estates, The Wilderness enjoys privacy and a commanding presence with old-growth trees, broad southerly views, and deep water. The scope of improvements includes the primary residence, waterside guest cottage, beach house, pool, pier, tennis court, early 20th-century barn, and a host of accessory structures for life on the farm. Visit the virtual tour for an inside look and appreciation for the scope of this offering. The main house has great historical significance not only for the original owner’s grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Maryland’s domestic architecture, as noted on two markers from the Maryland Bicentennial Commission and the Maryland Historical Society. The smaller and original of the two brick wings dates from the late 18th century and the larger wing from the early 19th century. The house’s architecture is unusual in that the 19th-century wings telescope up, instead of down, from the original wing. The white brick, black shutters, and historical olive green trim color are a serene palette against the house’s majestic specimen trees around the property, including a gigantic Sycamore that is the largest of its species in Maryland. The long white gravel drive under the sheltering canopy of mature trees passes by the barn and other outbuildings then curves around the front of the house. Brick steps lead up to the front porch of the early 19th century wing opening into a gracious foyer and stair hall with an elegant elliptical arch that rests on pilasters at the side walls to separate the public from private areas of the house. A French door at the rear of the foyer frames a vista of the lawn and Choptank River. To the side of the foyer are two identical parlors at the front and rear corners of the house. Both rooms have magnificent fireplace mantles and surround; one is a 1740 hand-carved mantel by noted English artisan woodcarver Grinnling Gibbons and the other is a 1780 mantel surrounded by the famous English architect and artisan, Robert Adam. The main floor of the 18th-century wing contains a spacious living room, dining room, original kitchen, and larger kitchen, pantry, two powder rooms, and a stunning sunroom connecting to a terrace along the rear of the house overlooking the Choptank River. Part of this wing was the final addition to the original home. The second floor of the 19th-century wing contains two bedrooms over the two parlors below with fireplaces and walk-in closets and two baths. The 18th-century wing and later addition contain an artist’s studio with cabinetry and sink that has a myriad uses– TV room, arts and crafts room. The primary suite is located at the rear corner of this wing. It has a fireplace flanked by single windows and another window on the rear wall for panoramic views of the mature landscape and the Choptank River. Two baths complete the suite, with one bath off a hall for access from the art studio. Two stairs access the attic level; one in the 18th-century wing leads to two bedrooms and one bath. The main stair in the 19th-century wing leads to a large game room and another cozy bedroom ensuite. The revised offering of The Wilderness, providing 234 acres comprised of 5 recorded parcels with over 3,000 feet of shoreline is a remarkable opportunity to witness life on the Shore.

27295 Southside Island Creek Rd, Trappe

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