Refine Search
Map
Sort by
$5,850,000
5 Beds ⋅ 6 Baths ⋅ 22601111 MLS
This 5-bedroom, 5.5-bath, 5,620-square-foot home on 40,000 + square foot lot sits along Chatham's popular walking loop, just steps from Stage Harbor, public town landing and the Yacht Club. Ideal for entertaining or relaxing, it features a large deck, swimming pool and hot tub. Inside, hardwood floors and tall ceilings create a bright, open feel. The kitchen offers granite countertops, generous storage, and space for an 8-seat table by a picture window. The layout includes a family room with fireplace, living room with fireplace, and dining room. There is a finished basement with full bath adding flexibility and function. Upstairs are two ensuite bedrooms, plus three more bedrooms, two additional full baths and dedicated laundry room. You'll also find an office nook and access to a rooftop deck/widow's walk with water views. An attached two-car garage and deeded access to a quiet stretch of Stage Harbor Beach complete the home. Properties like this seldom come on the market.

15 Windy Hill Way, Chatham
$5,850,000
5 Beds ⋅ 6 Baths ⋅ 73495151 MLS
This 5-bedroom, 5.5-bath, 5,620-square-foot home on 40,000 + square foot lot sits along Chatham's popular walking loop, just steps from Stage Harbor, public town landing and the Yacht Club. Ideal for entertaining or relaxing, it features a large deck, swimming pool and hot tub. Inside, hardwood floors and tall ceilings create a bright, open feel. The kitchen offers granite countertops, generous storage, and space for an 8-seat table by a picture window. The layout includes a family room with fireplace, living room with fireplace, and dining room. There is a finished basement with full bath adding flexibility and function. Upstairs are two ensuite bedrooms, plus three more bedrooms, two additional full baths and dedicated laundry room. You'll also find an office nook and access to a rooftop deck/widow's walk with water views. An attached two-car garage and deeded access to a quiet stretch of Stage Harbor Beach complete the home. Properties like this seldom come on the market.

15 Windy Hill Way, Chatham
$5,850,000
5 Beds ⋅ 6 Baths ⋅ 22601111 MLS
This 5-bedroom, 5.5-bath, 5,620-square-foot home on 40,000 + square foot lot sits along Chatham's popular walking loop, just steps from Stage Harbor, public town landing and the Yacht Club. Ideal for entertaining or relaxing, it features a large deck, swimming pool and hot tub. Inside, hardwood floors and tall ceilings create a bright, open feel. The kitchen offers granite countertops, generous storage, and space for an 8-seat table by a picture window. The layout includes a family room with fireplace, living room with fireplace, and dining room. There is a finished basement with full bath adding flexibility and function. Upstairs are two ensuite bedrooms, plus three more bedrooms, two additional full baths and dedicated laundry room. You'll also find an office nook and access to a rooftop deck/widow's walk with water views. An attached two-car garage and deeded access to a quiet stretch of Stage Harbor Beach complete the home. Properties like this seldom come on the market.

15 Windy Hill Way, Chatham
$5,800,000
6 Beds ⋅ 9 Baths ⋅ 73525014 MLS
Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and bourgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation home for a client list that included Lady Diana Spencer. The historic main house has been completely modernized. There are 6 bedrooms spread out over almost 6000 square feet, a detached pool house, swimming pool, and Har-Tru tennis court. Wherever you are in this gracious home you will be blessed with sweeping views of the open fields, stone walls, and horses in the neighboring farm, a scene as if from a painting done in a previous century. Included within the 10 acres is a separate 3.3-acre parcel of land that will accommodate a full-size home. Association located dock on Lake Tashmoo!

31 Lambert's Cove Rd., Tisbury
$5,795,000
3 Beds ⋅ 4 Baths ⋅ 73553944 MLS
Stylish South Beach Retreat With Resort-Style Pool - Ideally located in the heart of Katama near South Beach, this stylish contemporary home offers the perfect blend of beach living and luxury amenities. Vaulted ceilings, a sleek linear fireplace, and a wall of 12-foot glass doors open the main living area to an expansive mahogany deck, creating seamless indoor-outdoor living. The gourmet kitchen, open dining area, and spacious living room are designed for effortless entertaining. The private primary suite features a balcony, two walk-in closets, and a spa-inspired bath. The walkout lower level includes a family room, two guest bedrooms, full bath, and laundry. Outside, enjoy a spectacular gunite pool with spa, waterfall, and fire feature, plus an outdoor cabana with bar, beverage refrigerators, and TV wall, along with a sunken firepit lounge. Offered furnished*, this turnkey Katama property is ideal for personal enjoyment or rental investment.

7 Katama Dr, Edgartown
$5,750,000
5 Beds ⋅ 5 Baths ⋅ 22601572 MLS
Experience refined coastal living in this fully renovated waterfront, water view estate on the Oyster River in Chatham, complete with deeded boat house! Encompassing over 4,000 square feet, this exceptional 5 Bdrm, 4-1/2 bath residence blends timeless elegance & luxurious touches throughout. Soaring cathedral ceilings and thoughtfully designed custom built-ins create a sense of openness and sophistication. A first-floor primary suite offers a private retreat with tranquil water views, private bath & walk-in-closet. Four additional water view bedrooms provide comfort and flexibility for family and guests. A walk-out lower level expands living space with an entertainment room and full bath. Features include new HVAC w/natural gas heat, Central A/C, outside shower, well-irrigation, spacious deck, yard with pool potential, and private stairs to the water. Beautifully sited on 1.83 acres of pastoral grounds, you'll enjoy over 230 feet of frontage on one of the most desirable boating waterways in Chatham, with deep water access to Nantucket Sound. This exceptional property just off the Chatham Loop offers both privacy and a picturesque natural setting only minutes to Town.

70 Judges Way, Chatham
$5,750,000
5 Beds ⋅ 5 Baths ⋅ 73506909 MLS
Experience refined coastal living in this fully renovated waterfront, water view estate on the Oyster River in Chatham. Encompassing over 4,000 sqft, this exceptional 5-bedroom, 4-1/2 bath residence blends timeless elegance & luxurious touches throughout. Soaring cathedral ceilings & thoughtfully designed custom built-ins create a sense of openness and sophistication. A first-floor primary suite offers a private retreat w/tranquil water views, private bath & walk-in-closet. Four additional water view bedrooms provide comfort and flexibility for guests. A walk-out lower level expands living space with an entertainment room and full bath. New HVAC w/natural gas heat, Central A/C, outside shower, well-irrigation, spacious deck, yard with pool potential, and private stairs to the water. Beautifully sited on 1.83 acres of pastoral grounds, you'll enjoy over 230 feet of frontage on one of the most desirable boating waterways in Chatham PLUS deeded rights to a boat house steps away!

70 Judges Way, Chatham
$5,750,000
5 Beds ⋅ 5 Baths ⋅ 22601572 MLS
Experience refined coastal living in this fully renovated waterfront, water view estate on the Oyster River in Chatham, complete with deeded boat house! Encompassing over 4,000 square feet, this exceptional 5 Bdrm, 4-1/2 bath residence blends timeless elegance & luxurious touches throughout. Soaring cathedral ceilings and thoughtfully designed custom built-ins create a sense of openness and sophistication. A first-floor primary suite offers a private retreat with tranquil water views, private bath & walk-in-closet. Four additional water view bedrooms provide comfort and flexibility for family and guests. A walk-out lower level expands living space with an entertainment room and full bath. Features include new HVAC w/natural gas heat, Central A/C, outside shower, well-irrigation, spacious deck, yard with pool potential, and private stairs to the water. Beautifully sited on 1.83 acres of pastoral grounds, you'll enjoy over 230 feet of frontage on one of the most desirable boating waterways in Chatham, with deep water access to Nantucket Sound. This exceptional property just off the Chatham Loop offers both privacy and a picturesque natural setting only minutes to Town.

70 Judges Way, Chatham
$5,650,000
6 Beds ⋅ 6 Baths ⋅ 22602494 MLS
Located within the coveted seaside enclave of Salten Point, this extraordinary custom-built home captures sweeping views of Barnstable Harbor and Sandy Neck Beach. Designed for elegant coastal living, the residence showcases exquisite craftsmanship and materials, including custom mahogany millwork throughout. Dazzling views take center stage immediately upon entering, with an open floor plan lined with walls of windows and French doors that lead to outdoor spaces offering a resort-inspired experience. A covered deck gives way to the breathtaking pool and spa area with a spacious terrace, outdoor kitchen, and fire pit. In the living room, a grand stone fireplace and custom built-ins create a sophisticated gathering space with an adjacent den. The chef's kitchen is ideal for cooking and entertaining on any scale, complete with a marble island, custom cabinetry, and professional-grade appliances including a Sub-Zero refrigerator and Wolf range. Direct access to a screened-in porch provides the perfect setting for al fresco dining. An en suite bedroom completes the first level, providing private quarters for guests. On the second floor, the primary suite features a large balcony with stunning views, a fireplace, and a luxurious bathroom with a walk-in shower and soaking tub. Three additional bedrooms - one en suite and two sharing a Jack-and-Jill bathroom - deliver well-appointed accommodations. A walkout lower level provides a multi-purpose space with built-in bunk beds, a TV area, and a fitness room. Additional highlights include an attached two-car garage and top-of-the-line heating and cooling systems with built-in air purification and dehumidification. This magnificent property is on town sewer, has deeded water access for swimming and kayaking, and is within walking distance of the wonderful restaurants and shops in Barnstable Village.

22 Kent Road, Barnstable
$5,650,000
6 Beds ⋅ 6 Baths ⋅ 73528133 MLS
Located within coveted Salten Point, this custom home captures sweeping views of Barnstable Harbor and Sandy Neck Beach. The open floor plan features mahogany millwork, walls of windows, and a living room with a grand stone fireplace and den. A chef’s kitchen boasts a marble island, Sub-Zero/Wolf appliances, and access to a screened-in dining porch. Outdoor amenities include a covered deck, pool, outdoor kitchen, and fire pit. An en suite guest bedroom completes the main level. Upstairs, the primary suite offers a private balcony, fireplace, and luxury bath with a soaking tub and walk-in shower, alongside three additional bedrooms (one en suite, two sharing a Jack-and-Jill bath). The lower level features built-in bunks, a TV area, and a fitness room. Equipped with a 2-car garage, top-of-the-line HVAC with air purification and dehumidification, and town sewer, the property includes deeded water access for swimming and kayaking, and is walking distance to Barnstable Village.

22 Kent Road, Barnstable
$5,650,000
6 Beds ⋅ 6 Baths ⋅ 22602494 MLS
Located within the coveted seaside enclave of Salten Point, this extraordinary custom-built home captures sweeping views of Barnstable Harbor and Sandy Neck Beach. Designed for elegant coastal living, the residence showcases exquisite craftsmanship and materials, including custom mahogany millwork throughout. Dazzling views take center stage immediately upon entering, with an open floor plan lined with walls of windows and French doors that lead to outdoor spaces offering a resort-inspired experience. A covered deck gives way to the breathtaking pool and spa area with a spacious terrace, outdoor kitchen, and fire pit. In the living room, a grand stone fireplace and custom built-ins create a sophisticated gathering space with an adjacent den. The chef's kitchen is ideal for cooking and entertaining on any scale, complete with a marble island, custom cabinetry, and professional-grade appliances including a Sub-Zero refrigerator and Wolf range. Direct access to a screened-in porch provides the perfect setting for al fresco dining. An en suite bedroom completes the first level, providing private quarters for guests. On the second floor, the primary suite features a large balcony with stunning views, a fireplace, and a luxurious bathroom with a walk-in shower and soaking tub. Three additional bedrooms - one en suite and two sharing a Jack-and-Jill bathroom - deliver well-appointed accommodations. A walkout lower level provides a multi-purpose space with built-in bunk beds, a TV area, and a fitness room. Additional highlights include an attached two-car garage and top-of-the-line heating and cooling systems with built-in air purification and dehumidification. This magnificent property is on town sewer, has deeded water access for swimming and kayaking, and is within walking distance of the wonderful restaurants and shops in Barnstable Village.

22 Kent Road, Barnstable
$5,650,000
5 Beds ⋅ 6 Baths ⋅ 73507096 MLS
Set at the quiet edge of Cohasset Harbor, this shingle-style home offers rare privacy on elevated land surrounded by 20 acres of salt marsh & woodland with sweeping harbor views. Meandering boardwalks lead to small islands, including one with a tidal dock for direct water access. Designed by Sally Weston & fully renovated, the home blends timeless architecture with modern comfort. A dramatic 2 story foyer opens to formal living & dining rooms each with fireplaces. The kitchen features a large island, baking room & banquette seating, flowing into a family room & sunroom filled with natural light. First-floor spaces include a unique octagonal bedroom, mudroom & potting kitchen. Upstairs the primary suite offers a private sitting area & spa-like bath, alongside 3 bedrooms, a loft office & a deck overlooking the harbor. 3rd floor suite adds more living space. Amenities include tennis & bocce courts plus a barn perfect for boat storage, a car collection, indoor sports court & a 1 bedroom apt. Not in flood zone.

1-R Baileys Island Rd, Scituate
$5,500,000
6 Beds ⋅ 7 Baths ⋅ 73492795 MLS
One of Hingham's most admired homes! Landmark colonial with a sweeping front lawn, set elegantly atop a knoll on a 2.2 ACRE lot on a quiet cul de sac, just a stone's throw to downtown Hingham. The current owner has beautifully updated this architecturally significant home to meet the needs of today, while maintaining its original elegance. Gracious 11' ceilings, floor to ceiling windows, front and back staircases and period details throughout. Fabulous recently renovated "wing" off the back of the house with a gorgeous custom kitchen flooded w/natural light OPEN to a large dining area and spacious family room. There are 5 Bedrooms and 3 baths on the second floor including a luxurious primary suite. Opportunity to craft the 3rd floor as you wish. The grounds are EXCEPTIONAL. Expansive lawn, gunite pool with pool/guest house and over an acre of manicured lawn. RARE opportunity for the discerning buyer to acquire this ICONIC home/estate.

187 Main St, Hingham
$5,500,000
4 Beds ⋅ 5 Baths ⋅ 73473408 MLS
Extraordinary and rarely offered, this private estate in the heart of historic Sandwich commands sweeping, panoramic views of Cape Cod Bay from nearly 19 acres of secluded land. A true legacy property, the setting offers unmatched privacy, rolling grounds, and endless possibilities in one of Cape Cod’s most coveted locations. The residence encompasses over 6,000 square feet and is designed to support both refined living and grand-scale entertaining, whether enjoyed as a seasonal retreat or year-round residence. Outdoor living is paramount, with a heated gunite pool, classic farmer’s porch, and widow’s walk serving as exceptional vantage points to take in the ever-changing bay views and coastal horizon. The property also features its own dedicated solar field, enhancing efficiency and sustainability. Rarely does an estate of this magnitude, acreage, and outlook become available—an exceptional opportunity to own a private sanctuary defined by space, serenity, and breathtaking water views

19 Cedarville Road, Sandwich
$5,499,000
4 Beds ⋅ 6 Baths ⋅ 73469087 MLS
Newly Refined with an Updated Design.Spectacular new construction in coveted World’s End by acclaimed design-build team White Oak Home and The Kerr Collective. This coastal residence offers the opportunity to personalize a thoughtfully designed custom home with harbor views and a private setting. Features include a dramatic great room with soaring ceilings, gas fireplace, and French doors to a rear patio for seamless indoor-outdoor living. The chef’s kitchen offers premium appliances, a 10-ft island, separate scullery, and elegant dining room with expansive windows. The first floor includes a bonus room with full bath, formal living room, and office. The second level features a luxurious primary suite with balcony and spa-style bath, three additional bedrooms, family room, and two full baths. Enjoy a 3-car garage, deeded beach rights, and a location steps to World’s End, minutes to Boston.

112 Martins Ln, Hingham
$5,495,000
4 Beds ⋅ 7 Baths ⋅ 22603291 MLS
Introducing an extraordinary new waterfront estate on picturesque Ashumet Pond with a private dock and sandy beach, offering nearly 8,000 square feet of luxury on 1.40 exceptionally private acres. Thoughtfully designed with timeless architecture and impeccable craftsmanship, this custom residence features soaring 30-foot ceilings, dramatic walls of glass, a striking stone fireplace, and breathtaking water views from nearly every room. Outside, enjoy a spectacular pool, fire pit area, expansive patios, lush landscaping, and seamless access to your private beach and dock for swimming, boating, kayaking, or simply taking in the tranquil setting. The chef's kitchen features custom cabinetry, Viking refrigeration, Wolf appliances, a butler's pantry, and a wet bar overlooking the water. Four en-suite bedrooms, dual primary suites, a media room, office, wine cellar, home gym, lower-level kitchen, dual laundry rooms, and smart-home technology complete this remarkable legacy estate.

26 Wheeler Road, Mashpee
$5,495,000
2 Beds ⋅ 3 Baths ⋅ 22503829 MLS
Experience a rare opportunity to own a prime waterfront property in one of Chatham's most sought-after locations. Set on 1.44 acres, this beautifully crafted 2-bedroom, 2.5 bath home offers 1,850 sq ft of refined living space w/commanding panoramic views stretching across Oyster Pond, Oyster River & to Nantucket Sound. This exceptional offering includes a conceptual site plan & video for a future 4-bedroom main house w/swimming pool, allowing you to envision the next chapter of luxury living on Cape Cod. Whether you're looking to enjoy the existing home w/separate post & beam garage w/power & water, or build your dream estate, the possibilities are truly remarkable. Additional to the expansive waterfront, this property boasts access to an adjacent cove down a winding 10-foot path. The current home features wood floors, a 2-car garage, office & generous outdoor living areas. An expansive deck provides the perfect vantage point to take in the ever-changing coastal scenery & sea breezes. Combining timeless Cape Cod charm with a vision for the future, 99 Uncle Alberts Dr is a one-of-a-kind offering on the waterfront, perfect for those seeking privacy & a truly iconic Chatham location.

99 Uncle Alberts Drive Ext, Chatham
$5,495,000
4 Beds ⋅ 7 Baths ⋅ 22603291 MLS
Introducing an extraordinary new waterfront estate on picturesque Ashumet Pond with a private dock and sandy beach, offering nearly 8,000 square feet of luxury on 1.40 exceptionally private acres. Thoughtfully designed with timeless architecture and impeccable craftsmanship, this custom residence features soaring 30-foot ceilings, dramatic walls of glass, a striking stone fireplace, and breathtaking water views from nearly every room. Outside, enjoy a spectacular pool, fire pit area, expansive patios, lush landscaping, and seamless access to your private beach and dock for swimming, boating, kayaking, or simply taking in the tranquil setting. The chef's kitchen features custom cabinetry, Viking refrigeration, Wolf appliances, a butler's pantry, and a wet bar overlooking the water. Four en-suite bedrooms, dual primary suites, a media room, office, wine cellar, home gym, lower-level kitchen, dual laundry rooms, and smart-home technology complete this remarkable legacy estate.

26 Wheeler Road, Mashpee
$5,495,000
4 Beds ⋅ 7 Baths ⋅ 73544553 MLS
Introducing an extraordinary new waterfront estate on picturesque Ashumet Pond with a private dock and sandy beach, offering nearly 8,000 square feet of luxury on 1.40 exceptionally private acres. Thoughtfully designed with timeless architecture and impeccable craftsmanship, this custom residence features soaring 30-foot ceilings, dramatic walls of glass, a striking stone fireplace, and breathtaking water views from nearly every room. Outside, enjoy a spectacular pool, fire pit area, expansive patios, lush landscaping, and seamless access to your private beach and dock for swimming, boating, kayaking, or simply taking in the tranquil setting. The chef's kitchen features custom cabinetry, Viking refrigeration, Wolf appliances, a butler's pantry, and a wet bar overlooking the water. Four en-suite bedrooms, dual primary suites, a media room, office, wine cellar, home gym, lower-level kitchen, dual laundry rooms, and smart-home technology complete this remarkable legacy estate.

26 Wheeler Rd, Mashpee
$5,495,000
5 Beds ⋅ 4 Baths ⋅ 73520860 MLS
Set on 2.5 acres within the coveted Wings Neck community, this extraordinary waterfront estate offers sweeping views of Buzzards Bay amidst total privacy. The five-bedroom home features a sunlit open layout ideally suited for casual living or grand entertaining, with a soaring great room, gourmet kitchen, and dining area with panoramic water views. Indoor and outdoor spaces blend seamlessly, with glass doors leading to an expansive deck overlooking the resort-like swimming pool and Buzzards Bay beyond. Designed for comfort and convenience, the first-floor primary suite boasts unobstructed water views and a sumptuous bathroom. Four additional bedrooms provide ample space for family and friends. A detached boat barn and two-car garage with a home gym above complete this exceptional offering. Residents of Wings Neck Trust enjoy access to two beaches, each with mooring & dinghy slip areas, pickleball & tennis courts, a deep-water dock in the harbor and miles of conservation land.

461 Wings Neck Road, Bourne
$5,495,000
2 Beds ⋅ 3 Baths ⋅ 73419421 MLS
Experience a rare opportunity to own a prime waterfront property in one of Chatham's most sought-after locations. Set on 1.44 acres, this beautifully crafted 2-bedroom, 2.5 bath home offers 1,850 sq ft of refined living space w/commanding panoramic views stretching across Oyster Pond, Oyster River & to Nantucket Sound. This exceptional offering includes a conceptual site plan & video for a future 4-bedroom main house w/swimming pool, allowing you to envision the next chapter of luxury living on Cape Cod. Whether you're looking to enjoy the existing home w/separate post & beam garage w/power & water, or build your dream estate, the possibilities are truly remarkable. Additional to the expansive waterfront, this property boasts access to an adjacent cove down a winding 10-foot path. The current home features wood floors, a 2-car garage, office & generous outdoor living areas. An expansive deck provides the perfect vantage point to take in the ever-changing coastal scenery & sea breezes.

99 Uncle Alberts Drive Ext, Chatham
$5,495,000
2 Beds ⋅ 3 Baths ⋅ 22503829 MLS
Experience a rare opportunity to own a prime waterfront property in one of Chatham's most sought-after locations. Set on 1.44 acres, this beautifully crafted 2-bedroom, 2.5 bath home offers 1,850 sq ft of refined living space w/commanding panoramic views stretching across Oyster Pond, Oyster River & to Nantucket Sound. This exceptional offering includes a conceptual site plan & video for a future 4-bedroom main house w/swimming pool, allowing you to envision the next chapter of luxury living on Cape Cod. Whether you're looking to enjoy the existing home w/separate post & beam garage w/power & water, or build your dream estate, the possibilities are truly remarkable. Additional to the expansive waterfront, this property boasts access to an adjacent cove down a winding 10-foot path. The current home features wood floors, a 2-car garage, office & generous outdoor living areas. An expansive deck provides the perfect vantage point to take in the ever-changing coastal scenery & sea breezes. Combining timeless Cape Cod charm with a vision for the future, 99 Uncle Alberts Dr is a one-of-a-kind offering on the waterfront, perfect for those seeking privacy & a truly iconic Chatham location.

99 Uncle Alberts Drive Ext, Chatham
$5,495,000
4 Beds ⋅ 4 Baths ⋅ 73391055 MLS
Development opportunities! Welcome to your private sanctuary—a breathtaking 5,898 sq. ft. custom contemporary estate nestled on a secluded 13.18-acre compound. In addition to the primary 4-acre lot, the property includes three additional parcels totaling 9.18 acres, offering unmatched privacy, expansion potential, or conservation opportunities. Designed with meticulous attention to detail, this four-bedroom, four-bathroom masterpiece seamlessly blends luxury and comfort. Exquisite custom stonework graces the interior and exterior, lending timeless elegance to the home’s modern aesthetic.Professionally landscaped grounds create a serene outdoor retreat, harmonizing architecture with nature. A spacious three-car garage offers ample storage and convenience, complementing the home’s thoughtful design. Whether hosting grand gatherings or enjoying the tranquility of its surroundings, this exceptional estate offers an unparalleled lifestyle in an extraordinary setting.

32-70 Lazell Street, Hingham
$5,495,000
73391052 MLS
Development opportunities! Welcome to your private sanctuary—a breathtaking 5,898 sq. ft. custom contemporary estate nestled on a secluded 13.18-acre compound. In addition to the primary 4-acre lot, the property includes three additional parcels totaling 9.18 acres, offering unmatched privacy, expansion potential, or conservation opportunities. Designed with meticulous attention to detail, this four-bedroom, four-bathroom masterpiece seamlessly blends luxury and comfort. Exquisite custom stonework graces the interior and exterior, lending timeless elegance to the home’s modern aesthetic.Professionally landscaped grounds create a serene outdoor retreat, harmonizing architecture with nature. A spacious three-car garage offers ample storage and convenience, complementing the home’s thoughtful design. Whether hosting grand gatherings or enjoying the tranquility of its surroundings, this exceptional estate offers an unparalleled lifestyle in an extraordinary setting.

32-70 Lazell Street, Hingham
$5,450,000
5 Beds ⋅ 4 Baths ⋅ 22602292 MLS
Introducing a refined contemporary Chilmark beach house with water views and deeded access to Stonewall Beach on the Atlantic Ocean. The property is set within the storied Stonewall Road and Beach Association - where homes are held for generations and lifelong friendships take root - and offers a true sense of place and continuity. Built by South Mountain Company and thoughtfully renovated and significantly expanded in 2023, the home blends craftsmanship with modern comfort. Enjoy sweeping views of the Atlantic Ocean, Squibnocket Point, and Nomans Land island from both interior living spaces and outdoor vantage points. Designed for multigenerational living, the home offers multiple private zones - including a dedicated media room - allowing for both connection and retreat. This is a rare opportunity to own a meaningful piece of Chilmark--an offering not to be missed.

61 Stonewall Road, Chilmark
$5,450,000
5 Beds ⋅ 4 Baths ⋅ 22602292 MLS
Introducing a refined contemporary Chilmark beach house with water views and deeded access to Stonewall Beach on the Atlantic Ocean. The property is set within the storied Stonewall Road and Beach Association - where homes are held for generations and lifelong friendships take root - and offers a true sense of place and continuity. Built by South Mountain Company and thoughtfully renovated and significantly expanded in 2023, the home blends craftsmanship with modern comfort. Enjoy sweeping views of the Atlantic Ocean, Squibnocket Point, and Nomans Land island from both interior living spaces and outdoor vantage points. Designed for multigenerational living, the home offers multiple private zones - including a dedicated media room - allowing for both connection and retreat. This is a rare opportunity to own a meaningful piece of Chilmark--an offering not to be missed.

61 Stonewall Road, Chilmark
$5,450,000
4 Beds ⋅ 6 Baths ⋅ 73499730 MLS
Refined Vineyard living in The Preserve. Set on a knoll overlooking the pond and sweeping grasslands, this exceptional home blends classic coastal architecture with modern luxury. The expansive great room showcases cathedral ceilings, rich millwork, and abundant natural light, with three sets of French doors opening to a bluestone patio with multiple sitting areas and a heated saltwater pool. The chef’s kitchen flows seamlessly into the dining and living spaces. One wing offers an inviting lounge and a luxurious primary suite with spa-like bath and dressing room, while the opposite wing features three guest bedrooms, each with ensuite baths and walk-in closets. Additional highlights include a proper mudroom and a finished lower level with media room, full bath, and storage. Surrounded by mature landscaping, with easy access to trails, the bike path and Farm Neck Golf Club. The Preserve is a private enclave of luxury homes and is arguably one of Oak Bluffs most exclusive neighborhoods.

8 Paddock Rd, Oak Bluffs
$5,400,000
3 Beds ⋅ 2 Baths ⋅ 73531359 MLS
Rare opportunity in the Seven Gates Farm community of Chilmark. Designed by architects Jane and Christian Langmuir, this exceptional three-bedroom home is set on 5.3 acres of beautifully landscaped grounds. Thoughtfully designed to embrace natural light and its surroundings, the residence blends natural materials with contemporary architectural details.The dramatic great room features a striking fireplace with a glacial stone hearth, while the open kitchen offers custom cabinetry and premium appliances. The primary suite includes two office spaces, a media area, walk-in closet, and spa-inspired bath. A private guest suite features a full bath with soaking tub, and the third bedroom is currently configured as a wellness space with sauna. Additional amenities include an attached two-car garage, owned solar panels, EV charging station, and a six-bedroom septic system.Seven Gates Farm residents enjoy access to private beaches, docks, tennis courts, and more.1000 acres of protected land.

35 South Bowl Rd, Chilmark
$5,350,000
4 Beds ⋅ 5 Baths ⋅ 73495595 MLS
CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this beautifully restored and expanded modern farmhouse offers a seamless blend of timeless Vineyard character and contemporary comfort. The 3-bedroom, 3.5-bath main residence spans approximately 5,400 square feet of thoughtfully designed living space, highlighted by a sun-filled open kitchen and living area anchored by a striking central fireplace—ideal for both everyday living and entertaining. An expansive primary suite wing features a spacious bedroom, full bath, private office, half bath, and dedicated laundry. The second floor offers flexible space for a studio, office, or media room, while a classic three-season room invites relaxed enjoyment of the surrounding landscape and distant winter water views. Perfect for compound living, the property includes a guest house, solar, horse barn, fenced pasture, garage, and historic boat shed. Deeded access to Chilmark Pond and South Shore Beach completes this property.

205 South Rd, Chilmark
$5,295,000
3 Beds ⋅ 7 Baths ⋅ 73496934 MLS
Set along 125 feet of private Lagoon frontage, this beautifully designed home offers over 5,400 sq. ft. of light-filled living space across three levels. High ceilings, skylights, and walls of glass capture sweeping water views, while a decorative stone fireplace anchors the main living area. The chef’s kitchen features stainless appliances, stone counters, custom cabinetry, and a large island, complemented by a wet bar and casual dining area. Three ensuite bedrooms include a primary suite with water views, a sitting area, walk-in closet, pool access, and a spa-like bath. The walk-out lower level offers a game room, media area, kitchenette, wine storage, and bonus room. Outdoors, enjoy a heated pool, spa, bluestone terrace, and direct access to calm waters for swimming, boating, and some of the best steamers, littleneck, and cherry stones on the Island. Offered furnished with strong rental history.

385 Barnes Road, Oak Bluffs

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.