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See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 76+-acre waterfront estate has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

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

$7,900,000

"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. An adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. An adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

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

$5,995,000

See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 76+-acre waterfront estate has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 76+-acre waterfront estate has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

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

$2,995,000

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

3 Beds ⋅ 4 Baths

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

9338 Bantry Rd, Easton

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

$509,000

Chesapeake by Del Webb. Nicely sited for maximum sunshine , this handsome and beautifully cared for two story Wittman model awaits you. Recent upgrades include luxury Vinyl flooring throughout the entire house ( even the stairs ! ) , entire house repainted neutral tones, custom blinds, enhanced lighting and fans, architectural roof, new high quality kitchen appliances including washer/dryer, primary bedroom closet organization, all bathrooms refreshed, fenced rear yard and drywalled/painted garage interior. The layout offers traditional rooms that blend together with attractive sight lines and connectivity. Step outside and find a relaxing brick paver patio with mature privacy plantings and a natural gas Weber Grill connected to town gas service all encompassed within the fenced back yard. This is a great house, move in ready for you! 55+ age-restricted section. Community amenities include Clubhouse with meeting room, exercise rooms, library and game rooms, outdoor pool, tennis/pickleball courts, picnic areas and common grounds, putting green, exercise paths, bocce ball, horse shoes and more. Located close to downtown Easton with fine restaurants and shopping and medical facilities, St. Michaels and Oxford. 1.5 hours to MD/DE beaches. 30 minutes to Bay Bridge.

Chesapeake by Del Webb. Nicely sited for maximum sunshine , this handsome and beautifully cared for two story Wittman model awaits you. Recent upgrades include luxury Vinyl flooring throughout the entire house ( even the stairs ! ) , entire house repainted neutral tones, custom blinds, enhanced lighting and fans, architectural roof, new high quality kitchen appliances including washer/dryer, primary bedroom closet organization, all bathrooms refreshed, fenced rear yard and drywalled/painted garage interior. The layout offers traditional rooms that blend together with attractive sight lines and connectivity. Step outside and find a relaxing brick paver patio with mature privacy plantings and a natural gas Weber Grill connected to town gas service all encompassed within the fenced back yard. This is a great house, move in ready for you! 55+ age-restricted section. Community amenities include Clubhouse with meeting room, exercise rooms, library and game rooms, outdoor pool, tennis/pickleball courts, picnic areas and common grounds, putting green, exercise paths, bocce ball, horse shoes and more. Located close to downtown Easton with fine restaurants and shopping and medical facilities, St. Michaels and Oxford. 1.5 hours to MD/DE beaches. 30 minutes to Bay Bridge.

7432 Karen Ave, Easton

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

$7,800,000

Grafton Manour Estate—A Rare Chesapeake Waterfront Legacy. Embrace the quiet grandeur of Grafton Manour Estate, an 86±-acre peninsula wrapped by approximately 1.5± miles of shoreline with panoramic water views in every direction. Bordered by Briary Cove to the east, Harris Creek to the southeast, and Waterhole Cove to the west, this extraordinary property blends pastoral elegance with true Chesapeake Bay access. Property Highlights: 86± acres with sweeping water vistas, open fields, and meticulously manicured lawns. Varied shoreline: riprap, sandy beaches, and natural grasses. Deep-water pier with 7' MLW, suitable for larger boats and sailboats; direct access to the Chesapeake Bay. Two subdivided, waterfront lots included: Lot 2: 6± acres on Briary Cove (east side), with prior SDA approval for a 4-bedroom home (re-evaluation required). Lot 3: 5.5± acres is located on Waterhole Cove (west side), with prior SDA approval for a 4-bedroom home (re-evaluation required). Historic Lowes Family Cemetery on the west side, dating to the 1700s. Land mix: approximately 60± acres tillable; balance in timber and lawns along the eastern shoreline. Main Residence: Custom-built in 2004, approx. 7,400 sq ft, four en suite bedrooms. Primary suite in the main-floor north wing with private laundry, library, office/workout room, and sunroom. Dramatic great room and dining room with vaulted ceiling, chestnut beams, cedar ceiling, and a raised-hearth stone fireplace. Signature silo feature: 1st and 2nd floors: full baths serving two bedrooms. 3rd floor: window-lined observatory with 360° views across the estate. Wide-plank wood floors milled from the same chestnut as the great room beams. Exceptional craftsmanship throughout; a must-see for discerning buyers. Guest/Farmhouse: Approx. 2,000 sq ft with three bedrooms and one bath. Two wood-burning fireplaces (living room and dining room). Charming and versatile for guests, caretakers, or rental income. Barns and Outbuildings: Large heated barn with concrete floors, three overhead doors, expansive workbench, and open-loft recreation room. Attached a conditioned office/hunters’ lodge with full bath and hookups for laundry and kitchenette. Adjacent irrigated, fenced raised-bed garden; nearby small apple orchard. Additional smaller barn for equipment or livestock. Lifestyle and Possibilities: Ideal for a family compound, equestrian pursuits, or an exclusive retreat. Premier sporting opportunities: shoreline waterfowl, whitetail deer, and turkey. Ample acreage and infrastructure for hobby farming, vineyards, or conservation. A once-in-a-generation opportunity to own an iconic waterfront estate where open water, open sky, and open fields meet. Follow the country road home to the place you belong—Grafton Manour Estate. By appointment only. Do not enter the property by water or land without the listing agent. The property is monitored by camera surveillance 24/7.

4 Beds ⋅ 5 Baths

Grafton Manour Estate—A Rare Chesapeake Waterfront Legacy. Embrace the quiet grandeur of Grafton Manour Estate, an 86±-acre peninsula wrapped by approximately 1.5± miles of shoreline with panoramic water views in every direction. Bordered by Briary Cove to the east, Harris Creek to the southeast, and Waterhole Cove to the west, this extraordinary property blends pastoral elegance with true Chesapeake Bay access. Property Highlights: 86± acres with sweeping water vistas, open fields, and meticulously manicured lawns. Varied shoreline: riprap, sandy beaches, and natural grasses. Deep-water pier with 7' MLW, suitable for larger boats and sailboats; direct access to the Chesapeake Bay. Two subdivided, waterfront lots included: Lot 2: 6± acres on Briary Cove (east side), with prior SDA approval for a 4-bedroom home (re-evaluation required). Lot 3: 5.5± acres is located on Waterhole Cove (west side), with prior SDA approval for a 4-bedroom home (re-evaluation required). Historic Lowes Family Cemetery on the west side, dating to the 1700s. Land mix: approximately 60± acres tillable; balance in timber and lawns along the eastern shoreline. Main Residence: Custom-built in 2004, approx. 7,400 sq ft, four en suite bedrooms. Primary suite in the main-floor north wing with private laundry, library, office/workout room, and sunroom. Dramatic great room and dining room with vaulted ceiling, chestnut beams, cedar ceiling, and a raised-hearth stone fireplace. Signature silo feature: 1st and 2nd floors: full baths serving two bedrooms. 3rd floor: window-lined observatory with 360° views across the estate. Wide-plank wood floors milled from the same chestnut as the great room beams. Exceptional craftsmanship throughout; a must-see for discerning buyers. Guest/Farmhouse: Approx. 2,000 sq ft with three bedrooms and one bath. Two wood-burning fireplaces (living room and dining room). Charming and versatile for guests, caretakers, or rental income. Barns and Outbuildings: Large heated barn with concrete floors, three overhead doors, expansive workbench, and open-loft recreation room. Attached a conditioned office/hunters’ lodge with full bath and hookups for laundry and kitchenette. Adjacent irrigated, fenced raised-bed garden; nearby small apple orchard. Additional smaller barn for equipment or livestock. Lifestyle and Possibilities: Ideal for a family compound, equestrian pursuits, or an exclusive retreat. Premier sporting opportunities: shoreline waterfowl, whitetail deer, and turkey. Ample acreage and infrastructure for hobby farming, vineyards, or conservation. A once-in-a-generation opportunity to own an iconic waterfront estate where open water, open sky, and open fields meet. Follow the country road home to the place you belong—Grafton Manour Estate. By appointment only. Do not enter the property by water or land without the listing agent. The property is monitored by camera surveillance 24/7.

22101 Grafton Manour Ln, Wittman

Listing courtesy of Meredith Fine Properties. Contact: 4107458060

$3,100,000

Set on 28 private acres overlooking Plaindealing Creek along the desirable Easton–St. Michaels corridor, this beautifully remodeled waterfront home offers 4 bedrooms, 4 full baths, and breathtaking panoramic views stretching across to Oxford, the Choptank River, and beyond. Positioned on an exceptional point of land, the property enjoys a rare combination of expansive water vistas, privacy, and direct access to some of the Eastern Shore’s finest boating and sporting waters. A scenic, tree-lined drive leads to the residence, where the water immediately takes center stage. Thoughtfully renovated in 2019, with numerous additional upgrades completed in subsequent years, the home is designed for both relaxed everyday living and effortless entertaining. The main level features a waterside primary suite with an exquisite ensuite bath, along with an additional guest bedroom and adjacent full bath(with sauna). The spacious living room is anchored by a brick fireplace with pellet stove insert, custom built-ins, and sliding doors opening to the waterside patio, creating a seamless connection to the remarkable setting. A well-appointed kitchen with stainless steel appliances and granite countertops adjoins the separate dining room, where spectacular water views provide a memorable backdrop for gatherings. Two other main-level rooms offer flexibility for an office, family room, exercise room, or other living needs, while a generous laundry room with built-ins and a secondary staircase adds everyday convenience. Upstairs are two additional guest bedrooms and two en-suite baths along with an adjoining bonus room ideal for guests or hobbies, and a second staircase. A true sportsman’s paradise, the property offers deep water, excellent fishing, private hunting, and endless opportunities for boating and recreation. The private pier, completed in 2023, features three slips, a boat lift, and a jet ski lift. With approximately 7' MLW, a newly riprapped shoreline, sandy beach, new BAT septic system installed in 2019, and a new roof completed in 2026, this exceptional waterfront retreat is perfectly suited for those seeking the very best of Eastern Shore living. *Approximately 24 acres are enrolled in a Forest Stewardship Plan. * Please do not drive in without an appointment-security monitoring.

4 Beds ⋅ 4 Baths

Set on 28 private acres overlooking Plaindealing Creek along the desirable Easton–St. Michaels corridor, this beautifully remodeled waterfront home offers 4 bedrooms, 4 full baths, and breathtaking panoramic views stretching across to Oxford, the Choptank River, and beyond. Positioned on an exceptional point of land, the property enjoys a rare combination of expansive water vistas, privacy, and direct access to some of the Eastern Shore’s finest boating and sporting waters. A scenic, tree-lined drive leads to the residence, where the water immediately takes center stage. Thoughtfully renovated in 2019, with numerous additional upgrades completed in subsequent years, the home is designed for both relaxed everyday living and effortless entertaining. The main level features a waterside primary suite with an exquisite ensuite bath, along with an additional guest bedroom and adjacent full bath(with sauna). The spacious living room is anchored by a brick fireplace with pellet stove insert, custom built-ins, and sliding doors opening to the waterside patio, creating a seamless connection to the remarkable setting. A well-appointed kitchen with stainless steel appliances and granite countertops adjoins the separate dining room, where spectacular water views provide a memorable backdrop for gatherings. Two other main-level rooms offer flexibility for an office, family room, exercise room, or other living needs, while a generous laundry room with built-ins and a secondary staircase adds everyday convenience. Upstairs are two additional guest bedrooms and two en-suite baths along with an adjoining bonus room ideal for guests or hobbies, and a second staircase. A true sportsman’s paradise, the property offers deep water, excellent fishing, private hunting, and endless opportunities for boating and recreation. The private pier, completed in 2023, features three slips, a boat lift, and a jet ski lift. With approximately 7' MLW, a newly riprapped shoreline, sandy beach, new BAT septic system installed in 2019, and a new roof completed in 2026, this exceptional waterfront retreat is perfectly suited for those seeking the very best of Eastern Shore living. *Approximately 24 acres are enrolled in a Forest Stewardship Plan. * Please do not drive in without an appointment-security monitoring.

26279 Deep Water Harbor Rd, Easton

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

$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!

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

$410,000

Experience authentic Eastern Shore living in this peaceful Chesapeake Bay retreat, located just steps from historic Dogwood Harbour, home to the Skipjacks—the last working commercial sailing fleet in the United States. This charming home features three first-floor bedrooms and a full bath, providing comfortable one-level living for family and guests. The remodeled eat-in kitchen showcases granite countertops and opens to a spacious outdoor deck, perfect for entertaining or relaxing while enjoying the coastal atmosphere. Upstairs, the private primary suite offers a full bath with a spa tub, creating a tranquil retreat. Also on the second level is an expansive open living area complete with a half bath and wet bar, providing exceptional flexibility for entertaining, recreation, a home office, or additional guest accommodations. Recent improvements include a new roof (2026), luxury vinyl plank flooring throughout, a new washer and dryer, a new stove/range, and a new central heating and air conditioning system, offering peace of mind and modern comfort. Combining historic waterfront charm with thoughtful updates, this property presents a rare opportunity to enjoy the best of Chesapeake Bay living, whether as a full-time residence, weekend getaway, or investment property. The owner is a licensed Maryland Real Estate agent.

Experience authentic Eastern Shore living in this peaceful Chesapeake Bay retreat, located just steps from historic Dogwood Harbour, home to the Skipjacks—the last working commercial sailing fleet in the United States. This charming home features three first-floor bedrooms and a full bath, providing comfortable one-level living for family and guests. The remodeled eat-in kitchen showcases granite countertops and opens to a spacious outdoor deck, perfect for entertaining or relaxing while enjoying the coastal atmosphere. Upstairs, the private primary suite offers a full bath with a spa tub, creating a tranquil retreat. Also on the second level is an expansive open living area complete with a half bath and wet bar, providing exceptional flexibility for entertaining, recreation, a home office, or additional guest accommodations. Recent improvements include a new roof (2026), luxury vinyl plank flooring throughout, a new washer and dryer, a new stove/range, and a new central heating and air conditioning system, offering peace of mind and modern comfort. Combining historic waterfront charm with thoughtful updates, this property presents a rare opportunity to enjoy the best of Chesapeake Bay living, whether as a full-time residence, weekend getaway, or investment property. The owner is a licensed Maryland Real Estate agent.

21406 Dogwood Cove Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact: 4107149166

$950,000

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

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

4938 Fairbank Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact: 4107458060

$2,750,000

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

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

7543 Bozman Neavitt Rd, Bozman

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

$2,750,000

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

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

7543 Bozman Neavitt Rd, Bozman

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

$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

$1,295,000

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

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

9251 Mallard Point Ct, Mcdaniel

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

$799,999

Positioned along the picturesque 5th fairway of the prestigious Talbot Country Club, this comprehensively renovated Easton residence blends timeless Eastern Shore charm with elevated modern design. Privately set on beautifully landscaped grounds with sweeping golf course vistas, the property offers refined one-level living in one of Talbot County’s most desirable country club settings. Thoughtfully reimagined from top to bottom, the home showcases a sophisticated, light-filled interior highlighted by white oak hardwood flooring throughout, curated West Elm lighting, custom millwork, and seamless indoor-outdoor flow. A dramatic 15-foot sliding glass door anchors the rear living spaces, opening effortlessly to the expansive terrace and manicured grounds beyond. At the center of the home is a stunning designer kitchen featuring Borghini Gold quartz countertops, custom cabinetry, premium GE Profile appliances, a 36-inch Verona range, beverage refrigeration, floating wood shelving, and an oversized center island designed for both entertaining and everyday living. Kohler faucets and fixtures throughout the home further elevate the carefully curated finish package. The gracious living room is centered around a striking marble fireplace surround with custom built-ins, creating a warm yet sophisticated focal point for gathering and entertaining. The thoughtfully designed floor plan offers generously sized bedrooms, beautifully renovated baths, and a spacious primary suite retreat with a boutique hotel feel. Beyond the cosmetic renovation, the property also benefits from a brand-new septic system and freshly refreshed gravel driveway, providing both style and peace of mind in equal measure. Combining understated luxury, turnkey condition, and premier golf course positioning just minutes from downtown Easton’s celebrated restaurants, boutiques, galleries, and waterfront amenities, this exceptional offering captures the very best of Eastern Shore living.

3 Beds ⋅ 2 Baths

Positioned along the picturesque 5th fairway of the prestigious Talbot Country Club, this comprehensively renovated Easton residence blends timeless Eastern Shore charm with elevated modern design. Privately set on beautifully landscaped grounds with sweeping golf course vistas, the property offers refined one-level living in one of Talbot County’s most desirable country club settings. Thoughtfully reimagined from top to bottom, the home showcases a sophisticated, light-filled interior highlighted by white oak hardwood flooring throughout, curated West Elm lighting, custom millwork, and seamless indoor-outdoor flow. A dramatic 15-foot sliding glass door anchors the rear living spaces, opening effortlessly to the expansive terrace and manicured grounds beyond. At the center of the home is a stunning designer kitchen featuring Borghini Gold quartz countertops, custom cabinetry, premium GE Profile appliances, a 36-inch Verona range, beverage refrigeration, floating wood shelving, and an oversized center island designed for both entertaining and everyday living. Kohler faucets and fixtures throughout the home further elevate the carefully curated finish package. The gracious living room is centered around a striking marble fireplace surround with custom built-ins, creating a warm yet sophisticated focal point for gathering and entertaining. The thoughtfully designed floor plan offers generously sized bedrooms, beautifully renovated baths, and a spacious primary suite retreat with a boutique hotel feel. Beyond the cosmetic renovation, the property also benefits from a brand-new septic system and freshly refreshed gravel driveway, providing both style and peace of mind in equal measure. Combining understated luxury, turnkey condition, and premier golf course positioning just minutes from downtown Easton’s celebrated restaurants, boutiques, galleries, and waterfront amenities, this exceptional offering captures the very best of Eastern Shore living.

6524 Oxford Rd, Easton

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

$6,995,000

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

7 Beds ⋅ 6 Baths

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

24390 Deep Neck Farm Ln, Royal Oak

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

$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

$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

$6,250,000

Set on 31 private acres along the peaceful waters of Hunting Creek, this exceptional Eastern Shore estate combines timeless architecture with modern sophistication. With over 1,000 feet of waterfront and approximately 6 feet of mean low water, the property offers deep-water access, stunning views, and an unmatched sense of privacy. The five-bedroom, five-and-a-half-bath residence has been completely renovated from top to bottom, showcasing impeccable finishes, custom millwork, and thoughtfully designed spaces throughout. Sunlight pours through large windows that frame panoramic views of the creek and surrounding landscape. The home features two luxurious primary suites, each offering a private retreat with refined finishes, spa-inspired baths, and generous closets. Two additional bedrooms share a beautifully designed ensuite bathroom, while a first-floor bunk room with its own bath provides the perfect space for guests. Outside, the saltwater pool overlooks the water, surrounded by manicured lawns and mature trees that extend to the shoreline. A long, tree-lined driveway creates an impressive approach to the home, setting the tone for the peaceful retreat that awaits. Located just minutes by car to Easton and St. Michaels—and even closer by boat—this Hunting Creek estate captures the very best of the Chesapeake Bay lifestyle: elegance, tranquility, and effortless connection to the water.

5 Beds ⋅ 6 Baths

Set on 31 private acres along the peaceful waters of Hunting Creek, this exceptional Eastern Shore estate combines timeless architecture with modern sophistication. With over 1,000 feet of waterfront and approximately 6 feet of mean low water, the property offers deep-water access, stunning views, and an unmatched sense of privacy. The five-bedroom, five-and-a-half-bath residence has been completely renovated from top to bottom, showcasing impeccable finishes, custom millwork, and thoughtfully designed spaces throughout. Sunlight pours through large windows that frame panoramic views of the creek and surrounding landscape. The home features two luxurious primary suites, each offering a private retreat with refined finishes, spa-inspired baths, and generous closets. Two additional bedrooms share a beautifully designed ensuite bathroom, while a first-floor bunk room with its own bath provides the perfect space for guests. Outside, the saltwater pool overlooks the water, surrounded by manicured lawns and mature trees that extend to the shoreline. A long, tree-lined driveway creates an impressive approach to the home, setting the tone for the peaceful retreat that awaits. Located just minutes by car to Easton and St. Michaels—and even closer by boat—this Hunting Creek estate captures the very best of the Chesapeake Bay lifestyle: elegance, tranquility, and effortless connection to the water.

9170 Hunting Creek Ln, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$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

$4,395,000

Irish Tides offers a quintessential Eastern Shore retreat with luxury and style. This beautifully crafted 4-bedroom, 5.5-bath main house provides captivating views of the Miles River from almost every room. The main level has been enhanced with a new HVAC system and ductwork, ensuring comfort and efficiency throughout. Exquisite crown moldings, hardwood floors, and custom built-ins add an inviting elegance. Enjoy formal living and dining areas, chef’s kitchen with an island, quartz countertops, and a scenic waterside dining nook for informal meals. The family room, with its soaring cathedral ceilings and gas fireplace, flows through a light-filled hallway with cozy seating, offering direct views of the river. New roof installed in 2026. The main-level primary suite features a cathedral ceiling, built-ins, and a private patio, while its spa-like en-suite includes abundant natural light, a jetted soaking tub, marble accents, and two generous walk-in closets. The home also features a newly encapsulated basement and crawlspace, ensuring a well- maintained environment year-round. The professionally landscaped grounds set the stage for a well-equipped pool house complete with a guest room, kitchenette, sitting area, and bathroom. The outdoor space also boasts an in-ground pool with a spacious patio, outdoor shower, and grill area. A private pier with a boat lift offers approximately 4' +/- MLW, a 300' +/- shoreline, and a private beach. For added convenience, the main house includes attic storage and a storage shed, while the 3-car detached garage features a bonus room—perfect for an office or rec room—with kitchenette. All of this is just a short drive from Easton’s dining, shopping, and airport access.

4 Beds ⋅ 6 Baths

Irish Tides offers a quintessential Eastern Shore retreat with luxury and style. This beautifully crafted 4-bedroom, 5.5-bath main house provides captivating views of the Miles River from almost every room. The main level has been enhanced with a new HVAC system and ductwork, ensuring comfort and efficiency throughout. Exquisite crown moldings, hardwood floors, and custom built-ins add an inviting elegance. Enjoy formal living and dining areas, chef’s kitchen with an island, quartz countertops, and a scenic waterside dining nook for informal meals. The family room, with its soaring cathedral ceilings and gas fireplace, flows through a light-filled hallway with cozy seating, offering direct views of the river. New roof installed in 2026. The main-level primary suite features a cathedral ceiling, built-ins, and a private patio, while its spa-like en-suite includes abundant natural light, a jetted soaking tub, marble accents, and two generous walk-in closets. The home also features a newly encapsulated basement and crawlspace, ensuring a well- maintained environment year-round. The professionally landscaped grounds set the stage for a well-equipped pool house complete with a guest room, kitchenette, sitting area, and bathroom. The outdoor space also boasts an in-ground pool with a spacious patio, outdoor shower, and grill area. A private pier with a boat lift offers approximately 4' +/- MLW, a 300' +/- shoreline, and a private beach. For added convenience, the main house includes attic storage and a storage shed, while the 3-car detached garage features a bonus room—perfect for an office or rec room—with kitchenette. All of this is just a short drive from Easton’s dining, shopping, and airport access.

27029 Miles River Rd, Easton

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

$1,250,000

A very exciting, well-built (stick built by Mister Construction-1996), open floor plan waterfront home in Oxford. Amazing broad South facing with river views. Three bedrooms on second floor, each with private bath, elevator to 3rd floor, full attic storage, 2 car garage, new roof in 2022, waterside deck, 2 enclosed waterfront sitting rooms, spacious first floor rooms for entertaining! First floor sitting room is large enough to use as 4th bedroom with full bath on first floor.

3 Beds ⋅ 4 Baths

A very exciting, well-built (stick built by Mister Construction-1996), open floor plan waterfront home in Oxford. Amazing broad South facing with river views. Three bedrooms on second floor, each with private bath, elevator to 3rd floor, full attic storage, 2 car garage, new roof in 2022, waterside deck, 2 enclosed waterfront sitting rooms, spacious first floor rooms for entertaining! First floor sitting room is large enough to use as 4th bedroom with full bath on first floor.

115 W Pier St, Oxford

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

$7,900,000

"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. The adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. The adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

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

$2,149,000

NEW PRICE DO NOT MISS THIS ONE Nestled in the highly desirable Drum Point neighborhood of St. Michaels, this exceptional waterfront property offers the perfect blend of privacy, comfort, and Eastern Shore charm. Just minutes from the vibrant heart of town, you'll enjoy easy access to renowned restaurants, boutique shopping, cozy cafés, the Classic Motor Museum, and the Chesapeake Bay Maritime Museum. A former successful vacation rental, this beautifully maintained three-bedroom brick home is designed for effortless living and year-round enjoyment. The open floor plan features rich wood flooring, a striking double-sided fireplace, a renovated kitchen, updated bathrooms, and energy-efficient geothermal HVAC. Water views surround you at every turn. Relax in the shade of mature trees by the shoreline, sway in a hammock with refreshing bay breezes, or spend the day enjoying the property's outstanding outdoor amenities. Entertain guests on the spacious deck complete with an outdoor kitchen and hot tub, gather on the charming stone-walled patio, rinse off in the outdoor shower, and cool off with a swim in the pool. Boaters will appreciate the private dock offering approximately 3 feet MLW, a boat lift, and a boat launch for easy access to the water. A detached two-room studio with a covered porch provides additional flexible space for guests, hobbies, or a private retreat while enjoying spectacular water views. Additional highlights include an encapsulated crawl space and numerous upgrades throughout. This is Eastern Shore living at its finest—a rare opportunity to own a waterfront sanctuary in one of St. Michaels' most sought-after locations.T MICHAELS TUCKED AWAY ON DESIRABLE DRUM POINT NEIGHBORHOOD, MINUTES FROM THE

NEW PRICE DO NOT MISS THIS ONE Nestled in the highly desirable Drum Point neighborhood of St. Michaels, this exceptional waterfront property offers the perfect blend of privacy, comfort, and Eastern Shore charm. Just minutes from the vibrant heart of town, you'll enjoy easy access to renowned restaurants, boutique shopping, cozy cafés, the Classic Motor Museum, and the Chesapeake Bay Maritime Museum. A former successful vacation rental, this beautifully maintained three-bedroom brick home is designed for effortless living and year-round enjoyment. The open floor plan features rich wood flooring, a striking double-sided fireplace, a renovated kitchen, updated bathrooms, and energy-efficient geothermal HVAC. Water views surround you at every turn. Relax in the shade of mature trees by the shoreline, sway in a hammock with refreshing bay breezes, or spend the day enjoying the property's outstanding outdoor amenities. Entertain guests on the spacious deck complete with an outdoor kitchen and hot tub, gather on the charming stone-walled patio, rinse off in the outdoor shower, and cool off with a swim in the pool. Boaters will appreciate the private dock offering approximately 3 feet MLW, a boat lift, and a boat launch for easy access to the water. A detached two-room studio with a covered porch provides additional flexible space for guests, hobbies, or a private retreat while enjoying spectacular water views. Additional highlights include an encapsulated crawl space and numerous upgrades throughout. This is Eastern Shore living at its finest—a rare opportunity to own a waterfront sanctuary in one of St. Michaels' most sought-after locations.T MICHAELS TUCKED AWAY ON DESIRABLE DRUM POINT NEIGHBORHOOD, MINUTES FROM THE

7149 Drum Point, Saint Michaels

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

$475,000

Unique, one-of-a-kind property located in the heart of Tilghman Island, offering unparalleled tranquility and breathtaking water views overlooking Dogwood Harbor. Welcome to your private Eastern Shore retreat! This beautifully updated water-view home captures the essence of coastal living with sweeping views of the harbor and surrounding wildlife. Enjoy stunning sunsets and peaceful mornings from the expansive screened porch or spacious deck—perfect for relaxing or entertaining while taking in the natural beauty of the island. Inside, the home has been thoughtfully updated and features a bright, open living area and a beautifully renovated kitchen designed for both everyday living and gatherings with family and friends. The spacious primary suite offers a private bath and walk-in closet, along with panoramic water views and direct access to the second-story porch/deck with a retractable awning—an ideal place to unwind and enjoy the serene surroundings. Two additional guest bedrooms and a full bath complete the home’s comfortable and functional layout. Additional highlights include a charming screened porch, generous outdoor living spaces, a storage shed, and beautifully landscaped patios and walkways that enhance the home’s inviting coastal atmosphere. Located in the heart of Tilghman Island, this exceptional property offers the perfect opportunity to relax, boat, fish, and explore everything the Eastern Shore lifestyle has to offer.