Uppercaperealty.com Search Results

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!

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

$1,095,000

This cheerful sun drenched three-bed & one bath home with cathedral ceilings sits on just over an acre of gently rolling land surrounded by mature pines, oaks and ornamental plantings. Inspired by Norwegian architecture, the current owner designed and built this home in 1999 with his wife who was an artist from Norway. It’s located about a mile to town in one direction and the beach in the other. Many attractive features include hardwood floors and Indian tile throughout, a large inviting mahogany deck off the front of the house overlooking a koi pond, fully owned solar panels that have covered the electrical costs for the past five years, a nitrogen reducing septic system, a full unfinished walkout basement and a large detached shed. This property is deed restricted to year-round housing and is part of the Daggett Ave. Homeowner’s Association which has a ninety-nine-year ground lease agreement.

3 Beds ⋅ 1 Baths ⋅ 73524099 MLS

This cheerful sun drenched three-bed & one bath home with cathedral ceilings sits on just over an acre of gently rolling land surrounded by mature pines, oaks and ornamental plantings. Inspired by Norwegian architecture, the current owner designed and built this home in 1999 with his wife who was an artist from Norway. It’s located about a mile to town in one direction and the beach in the other. Many attractive features include hardwood floors and Indian tile throughout, a large inviting mahogany deck off the front of the house overlooking a koi pond, fully owned solar panels that have covered the electrical costs for the past five years, a nitrogen reducing septic system, a full unfinished walkout basement and a large detached shed. This property is deed restricted to year-round housing and is part of the Daggett Ave. Homeowner’s Association which has a ninety-nine-year ground lease agreement.

299 Daggett Ave Unit A, Tisbury

$45,000,000

A rare offering on the shores of Nashaquitsa Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Set on 4.9 acres with a private 115-foot deep-water dock, this one-of-a-kind compound features striking modern architecture, walls of glass, and panoramic water views throughout. The main residence offers six ensuite bedrooms, including a spectacular first-floor primary suite with dual spa-inspired baths. Dramatic living spaces with soaring cathedral ceilings open to expansive decks and a screened porch overlooking the pond. Exceptional amenities include two chef’s kitchens, a private theater, wine cellar, outdoor shower, and a hilltop writer’s cottage with sweeping views. The pool house is a private wellness retreat with a heated indoor pool, spa, sauna, steam room, cold plunge, guest suite, and retractable glass walls. Additional highlights include a tennis court, boathouse, entertainment barn with gym and recreation space, and a six-car garage.

7 Beds ⋅ 13 Baths ⋅ 73523462 MLS

A rare offering on the shores of Nashaquitsa Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Set on 4.9 acres with a private 115-foot deep-water dock, this one-of-a-kind compound features striking modern architecture, walls of glass, and panoramic water views throughout. The main residence offers six ensuite bedrooms, including a spectacular first-floor primary suite with dual spa-inspired baths. Dramatic living spaces with soaring cathedral ceilings open to expansive decks and a screened porch overlooking the pond. Exceptional amenities include two chef’s kitchens, a private theater, wine cellar, outdoor shower, and a hilltop writer’s cottage with sweeping views. The pool house is a private wellness retreat with a heated indoor pool, spa, sauna, steam room, cold plunge, guest suite, and retractable glass walls. Additional highlights include a tennis court, boathouse, entertainment barn with gym and recreation space, and a six-car garage.

18 Point Inner Way, Chilmark

$2,590,000

Located on a quiet street just minutes from Edgartown Village, this versatile compound offers privacy, flexibility, and close proximity to the Island’s best outdoor amenities. Set on over half an acre, the property includes a main house and detached guest house with separate driveways and mature landscaping.The main home features an open kitchen and dining area, sunken living room, and three bedrooms, plus a finished lower level for added living space. Outdoor highlights include a deck, heated pool, patio, pool house, and outdoor shower.The guest house was built in 2011 and provides additional living space, multiple baths, a garage, and its own private setting. Near conservation land and water access, and just 1.5 miles to town, this property offers strong rental potential and exceptional versatility.

4 Beds ⋅ 8 Baths ⋅ 73523165 MLS

Located on a quiet street just minutes from Edgartown Village, this versatile compound offers privacy, flexibility, and close proximity to the Island’s best outdoor amenities. Set on over half an acre, the property includes a main house and detached guest house with separate driveways and mature landscaping.The main home features an open kitchen and dining area, sunken living room, and three bedrooms, plus a finished lower level for added living space. Outdoor highlights include a deck, heated pool, patio, pool house, and outdoor shower.The guest house was built in 2011 and provides additional living space, multiple baths, a garage, and its own private setting. Near conservation land and water access, and just 1.5 miles to town, this property offers strong rental potential and exceptional versatility.

15 Twenty First St N, Edgartown

$4,600,000

Nestled within the idyllic and highly coveted setting of Farm Neck Golf Club, 15 Tamarack Lane offers a rare opportunity to own a stunning 3.7 acres in one of Martha’s Vineyard’s most exclusive communities. The property enjoys picturesque views over the 7th fairway and 8th tee box, across to Sengekontacket Pond, creating a peaceful backdrop of lush greens and distant water. The historic five-bedroom main residence, along with a separate one-bedroom carriage house, are rich in character and await a thoughtful renovation or reimagining. Ideally located near the clubhouse, restaurant, tennis courts, and pro shop, the property offers easy access to the Farm Neck lifestyle while remaining just minutes from town, the harbor, and ferry terminal. This is an extraordinary chance to secure a property within the esteemed Farm Neck Golf Club community. Included is a highly sought-after Farm Neck Club Stockholder Membership, enhancing both its prestige and value.

6 Beds ⋅ 6 Baths ⋅ 73522816 MLS

Nestled within the idyllic and highly coveted setting of Farm Neck Golf Club, 15 Tamarack Lane offers a rare opportunity to own a stunning 3.7 acres in one of Martha’s Vineyard’s most exclusive communities. The property enjoys picturesque views over the 7th fairway and 8th tee box, across to Sengekontacket Pond, creating a peaceful backdrop of lush greens and distant water. The historic five-bedroom main residence, along with a separate one-bedroom carriage house, are rich in character and await a thoughtful renovation or reimagining. Ideally located near the clubhouse, restaurant, tennis courts, and pro shop, the property offers easy access to the Farm Neck lifestyle while remaining just minutes from town, the harbor, and ferry terminal. This is an extraordinary chance to secure a property within the esteemed Farm Neck Golf Club community. Included is a highly sought-after Farm Neck Club Stockholder Membership, enhancing both its prestige and value.

15 Tamarack Lane, Oak Bluffs

$2,950,000

This classic beach house captures the essence of coastal living with the sound of the Atlantic just beyond. Designed with a reverse-style floor plan to maximize light, the home offers a blend of comfort and Vineyard charm. The main living level is bright and airy, featuring a sun-filled kitchen that opens to a sitting area. Sliders lead to a spacious mahogany deck. This level also includes an additional family room, a generously sized bedroom with access to a private terrace and a full bath. Upstairs, the 3rd floor is dedicated to the primary suite, with vaulted, beamed ceilings and walls of glass that flood the space with natural light. The bath features a glass shower, completing the quiet atmosphere. On the first floor, you’ll find a third bedroom, large bath with laundry, and an additional living area with direct access to a covered porch. Set on a generous 0.7-acre lot, the property includes an outdoor shower. The property also boasts a strong rental history. Please inquire

4 Beds ⋅ 3 Baths ⋅ 73522670 MLS

This classic beach house captures the essence of coastal living with the sound of the Atlantic just beyond. Designed with a reverse-style floor plan to maximize light, the home offers a blend of comfort and Vineyard charm. The main living level is bright and airy, featuring a sun-filled kitchen that opens to a sitting area. Sliders lead to a spacious mahogany deck. This level also includes an additional family room, a generously sized bedroom with access to a private terrace and a full bath. Upstairs, the 3rd floor is dedicated to the primary suite, with vaulted, beamed ceilings and walls of glass that flood the space with natural light. The bath features a glass shower, completing the quiet atmosphere. On the first floor, you’ll find a third bedroom, large bath with laundry, and an additional living area with direct access to a covered porch. Set on a generous 0.7-acre lot, the property includes an outdoor shower. The property also boasts a strong rental history. Please inquire

13 Young Street, Edgartown

$799,000

Located under a mile from the heart of downtown Oak Bluffs, this charming property offers endless potential in a highly convenient location. Set on a level lot, the home is ready for its next chapter — whether as a summer getaway or year-round residence. Enjoy easy access to town, beaches, ferries, restaurants, and shops while creating your own vision in this classic Island setting.

2 Beds ⋅ 1 Baths ⋅ 73522647 MLS

Located under a mile from the heart of downtown Oak Bluffs, this charming property offers endless potential in a highly convenient location. Set on a level lot, the home is ready for its next chapter — whether as a summer getaway or year-round residence. Enjoy easy access to town, beaches, ferries, restaurants, and shops while creating your own vision in this classic Island setting.

19 Perkins Avenue, Oak Bluffs

$6,995,000

Perfectly positioned along the serene shores of Katama Bay, this property offers a front-row seat to nature’s grandeur. Residents will revel in sweeping, 180-degree vistas where the tranquil waters of the bay meet the dramatic horizon of South Beach and the Atlantic Ocean. As you enter the property from Edgartown Bay Road, the home’s timeless architecture and expansive front lawn make an unforgettable first impression. Inside, the home features a bright and airy open-concept layout that seamlessly blends the living, dining, and kitchen areas, all enhanced by the dramatic “big sky, big water” setting. Spanning three levels, the residence offers 4 bedrooms, 3 full bathrooms, and a spacious family room. Nearly every room captures breathtaking water views, creating a true connection to the surrounding coastal landscape. Step outside to the backyard lawn and follow the wooden boardwalk to your own private sandy beach. Whether launching a kayak or paddleboard for a day exploring Katama Bay.

4 Beds ⋅ 3 Baths ⋅ 73520913 MLS

Perfectly positioned along the serene shores of Katama Bay, this property offers a front-row seat to nature’s grandeur. Residents will revel in sweeping, 180-degree vistas where the tranquil waters of the bay meet the dramatic horizon of South Beach and the Atlantic Ocean. As you enter the property from Edgartown Bay Road, the home’s timeless architecture and expansive front lawn make an unforgettable first impression. Inside, the home features a bright and airy open-concept layout that seamlessly blends the living, dining, and kitchen areas, all enhanced by the dramatic “big sky, big water” setting. Spanning three levels, the residence offers 4 bedrooms, 3 full bathrooms, and a spacious family room. Nearly every room captures breathtaking water views, creating a true connection to the surrounding coastal landscape. Step outside to the backyard lawn and follow the wooden boardwalk to your own private sandy beach. Whether launching a kayak or paddleboard for a day exploring Katama Bay.

103 Edgartown Bay Road, Edgartown

$2,195,000

Life on Chappaquiddick has a rhythm all its own — and this exceptional compound is designed to savor every moment of it.Set on three park-like acres of meadows and woodland, two freshly painted log cabin-style homes offer a private world apart. The three-bedroom main house is open and generous, with living spaces that flow seamlessly from inside to out. The two-bedroom guest house is its own considered retreat, complete with covered porch, back deck, and outdoor shower. An oversized garage with loft provides additional space to gather and unwind.A circular drive and pea stone pathways connect the buildings across beautifully layered grounds. Adirondack chairs ring a custom firepit for late nights under the stars; a sauna and cold plunge pool on a bluestone patio create your own personal spa. An enclosed garden, garden shed, and multiple outbuildings complete the setting — your own private park among Martha’s Vineyard most beautiful natural setting.

5 Beds ⋅ 4 Baths ⋅ 73520213 MLS

Life on Chappaquiddick has a rhythm all its own — and this exceptional compound is designed to savor every moment of it.Set on three park-like acres of meadows and woodland, two freshly painted log cabin-style homes offer a private world apart. The three-bedroom main house is open and generous, with living spaces that flow seamlessly from inside to out. The two-bedroom guest house is its own considered retreat, complete with covered porch, back deck, and outdoor shower. An oversized garage with loft provides additional space to gather and unwind.A circular drive and pea stone pathways connect the buildings across beautifully layered grounds. Adirondack chairs ring a custom firepit for late nights under the stars; a sauna and cold plunge pool on a bluestone patio create your own personal spa. An enclosed garden, garden shed, and multiple outbuildings complete the setting — your own private park among Martha’s Vineyard most beautiful natural setting.

7 Pip'n Circle, Edgartown

$2,195,000

This Chilmark 3 bedroom, 2 bath home has been meticulously maintained inside and out. A major addition and reconstruction of the original house was completed in 1991 & included a 22 x 43 addition, The completely new second floor added over 1,500 square feet & the work included new heating, plumbing, electrical, central AC, septic & well! Many nice features include spacious living spaces, a modern kitchen with breakfast bar, open living and dining room with cathedral ceiling, oversized windows & a slider that leads out to a spacious deck. Second floor primary w/ensuite bath, walk-in closet & private deck. Large family room with skylights & built-ins. Two first floor bedrooms w/full bath, basement, wood floors, a whole house generator, Oil FHW heat & new A/C. Privately sited 1.20 acres bordered by stone walls, beautifully landscaped grounds, mature gardens & plantings. Beautiful fruit trees, a garage & shed. The property is gated and entirely enclosed with deer fencing.

3 Beds ⋅ 2 Baths ⋅ 73520138 MLS

This Chilmark 3 bedroom, 2 bath home has been meticulously maintained inside and out. A major addition and reconstruction of the original house was completed in 1991 & included a 22 x 43 addition, The completely new second floor added over 1,500 square feet & the work included new heating, plumbing, electrical, central AC, septic & well! Many nice features include spacious living spaces, a modern kitchen with breakfast bar, open living and dining room with cathedral ceiling, oversized windows & a slider that leads out to a spacious deck. Second floor primary w/ensuite bath, walk-in closet & private deck. Large family room with skylights & built-ins. Two first floor bedrooms w/full bath, basement, wood floors, a whole house generator, Oil FHW heat & new A/C. Privately sited 1.20 acres bordered by stone walls, beautifully landscaped grounds, mature gardens & plantings. Beautiful fruit trees, a garage & shed. The property is gated and entirely enclosed with deer fencing.

26 Bijahs Way, Chilmark

$21,500,000

A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest on Martha’s Vineyard. Originally built in 1835 and masterfully renovated, it blends historic character with refined modern luxury just moments from Edgartown Harbor, dining, and shopping. Spanning two lots, the property features 10 bedrooms and 14 baths, designed for elegant entertaining and everyday living. The main residence showcases oak floors, nickel board walls, premium appliances, and seamless indoor-outdoor flow with a screened patio. The chef’s kitchen includes dual dishwashers, a Miele coffee bar, and wine storage, while a custom bar can convert to a secondary kitchen. Highlights include multiple living areas, en-suite bedrooms, a luxurious primary suite, bunk room, and a finished lower level with media room and wine cellar. Outdoors, a pool, spa, cabana, and carriage house create a private coastal retreat.

10 Beds ⋅ 14 Baths ⋅ 73517157 MLS

A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest on Martha’s Vineyard. Originally built in 1835 and masterfully renovated, it blends historic character with refined modern luxury just moments from Edgartown Harbor, dining, and shopping. Spanning two lots, the property features 10 bedrooms and 14 baths, designed for elegant entertaining and everyday living. The main residence showcases oak floors, nickel board walls, premium appliances, and seamless indoor-outdoor flow with a screened patio. The chef’s kitchen includes dual dishwashers, a Miele coffee bar, and wine storage, while a custom bar can convert to a secondary kitchen. Highlights include multiple living areas, en-suite bedrooms, a luxurious primary suite, bunk room, and a finished lower level with media room and wine cellar. Outdoors, a pool, spa, cabana, and carriage house create a private coastal retreat.

56 North Summer Street, Edgartown

$4,600,000

ONE MILE FROM HISTORIC EDGARTOWN VILLAGE. NEW home with a POOL, and close to SOUTH BEACH. The facade offers a covered porch. The entry foyer presents with an oversized lounge area to the right and a spectacular great room ahead. The great room has a soaring cathedral ceiling and a rear wall of two story windows with a gas fireplace. The great room opens to the dining room with a wall of glass doors overlooking the pool area. The dining room flows into the gourmet kitchen with a seating island. Off the dining and kitchen area is access to the mudroom which has a half bath, pantry, and laundry area. Off the mudroom area is an outdoor shower. The first floor hosts the primary bedroom with a luxurious bathroom. The second floor has three guest rooms and two full bathrooms. The rear yard offers privacy in the 14 x 30 ft. salt water heated pool that is surrounded by bluestone and professional landscape.

4 Beds ⋅ 4 Baths ⋅ 73514104 MLS

ONE MILE FROM HISTORIC EDGARTOWN VILLAGE. NEW home with a POOL, and close to SOUTH BEACH. The facade offers a covered porch. The entry foyer presents with an oversized lounge area to the right and a spectacular great room ahead. The great room has a soaring cathedral ceiling and a rear wall of two story windows with a gas fireplace. The great room opens to the dining room with a wall of glass doors overlooking the pool area. The dining room flows into the gourmet kitchen with a seating island. Off the dining and kitchen area is access to the mudroom which has a half bath, pantry, and laundry area. Off the mudroom area is an outdoor shower. The first floor hosts the primary bedroom with a luxurious bathroom. The second floor has three guest rooms and two full bathrooms. The rear yard offers privacy in the 14 x 30 ft. salt water heated pool that is surrounded by bluestone and professional landscape.

9 Marthas Way, Edgartown

$2,795,000

Tucked off Meetinghouse Way, this 3-acre parcel offers an opportunity to create something lasting on the Vineyard. Open pasture sweeps across the property's core, framed by bordering woodland that lends a sense of privacy without sacrificing the light and openness that makes the setting so appealing. Just under 2.5 miles from the Village and South Beach, the location balances seclusion with easy access to town and the beach. Neighboring Wilson's Landing opens the door to the Edgartown Great Pond, where kayaking, paddleboarding, and quiet days on the water await. With 8 bedrooms possible and the option to add a guest house, the potential here is considerable. This is one of two parcels for sale.

73513671 MLS

Tucked off Meetinghouse Way, this 3-acre parcel offers an opportunity to create something lasting on the Vineyard. Open pasture sweeps across the property's core, framed by bordering woodland that lends a sense of privacy without sacrificing the light and openness that makes the setting so appealing. Just under 2.5 miles from the Village and South Beach, the location balances seclusion with easy access to town and the beach. Neighboring Wilson's Landing opens the door to the Edgartown Great Pond, where kayaking, paddleboarding, and quiet days on the water await. With 8 bedrooms possible and the option to add a guest house, the potential here is considerable. This is one of two parcels for sale.

Lot 4B Browns Farm Lane, Edgartown

$2,795,000

Located off Meetinghouse Way, this 3-acre parcel offers something truly special: room to breathe. Open pasture rolls across the heart of the property, while bordering woodland creates a setting that feels private yet open and airy. The location is less than 2.5 miles from Main Street and South Beach, offering convenient access to both town amenities and the sand and surf of the south shore. Neighboring Wilson’s Landing provides water access to the Edgartown Great Pond for kayaking, paddleboarding, and other activities. With 8 bedrooms possible and the potential to build a guest house, the development options here are many. Whether you envision a family compound, a retreat with room for extended family and friends, or a legacy property designed to be enjoyed for generations, this land provides the canvas. This is one of two parcels for sale.

73513600 MLS

Located off Meetinghouse Way, this 3-acre parcel offers something truly special: room to breathe. Open pasture rolls across the heart of the property, while bordering woodland creates a setting that feels private yet open and airy. The location is less than 2.5 miles from Main Street and South Beach, offering convenient access to both town amenities and the sand and surf of the south shore. Neighboring Wilson’s Landing provides water access to the Edgartown Great Pond for kayaking, paddleboarding, and other activities. With 8 bedrooms possible and the potential to build a guest house, the development options here are many. Whether you envision a family compound, a retreat with room for extended family and friends, or a legacy property designed to be enjoyed for generations, this land provides the canvas. This is one of two parcels for sale.

Lot 4A Browns Farm Lane, Edgartown

$1,695,000

Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha's Vineyard. This fully gut renovated property encompassing 3B/2Ba in total featuring a 2BR/2BA primary home plus a distinctly separate attached 1BR/1BA ADU suite - offering flexible, move-in ready living or investment potential in a prime in-town location. The main residence in the primary showcases a light-filled interior, wood floors, beamwork, and refined finishes throughout. Open living flows to a gourmet kitchen with suede-finish stone counters, Bosch appliances, dining bar, and walk-in pantry. Upstairs offers two spacious bedrooms, a skylit bath with glass and stone shower, and a private balcony. Enjoy multiple outdoor spaces including a covered porch and side deck. The 1b/1ba ADU secondary suite provides a private entrance, parking, and utilities--ideal for guests or rental income. Featuring open living, oak floors, a stylish kitchen with stone counters and Bosch propane oven, plus a bedroom and full bath.

3 Beds ⋅ 3 Baths ⋅ 73511961 MLS

Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha's Vineyard. This fully gut renovated property encompassing 3B/2Ba in total featuring a 2BR/2BA primary home plus a distinctly separate attached 1BR/1BA ADU suite - offering flexible, move-in ready living or investment potential in a prime in-town location. The main residence in the primary showcases a light-filled interior, wood floors, beamwork, and refined finishes throughout. Open living flows to a gourmet kitchen with suede-finish stone counters, Bosch appliances, dining bar, and walk-in pantry. Upstairs offers two spacious bedrooms, a skylit bath with glass and stone shower, and a private balcony. Enjoy multiple outdoor spaces including a covered porch and side deck. The 1b/1ba ADU secondary suite provides a private entrance, parking, and utilities--ideal for guests or rental income. Featuring open living, oak floors, a stylish kitchen with stone counters and Bosch propane oven, plus a bedroom and full bath.

33 Vineyard Ave, Oak Bluffs

$2,195,000

Tucked back from scenic Lake Street, this distinctive home offers privacy and charm on a landscaped 0.7 acre lot with mature trees and a classic stone wall. Inside, rich wood detailing, exposed beams, and high ceilings create a warm, inviting feel. The four-level design provides flexibility and character. The main level features a spacious kitchen with a center island open to the dining area, and a sunken living room with floor-to-ceiling windows overlooking the trees. A large screened porch extends the living space outdoors. Two bedrooms, a full bath, and laundry complete this floor. Upstairs, a dramatic hallway leads to a generous primary suite with a spacious bath and additional laundry. The third level offers a private guest suite with living area and bath. The finished lower level includes added living space, bath, and walkout. Convenient to the public boat landing on Lake Tashmoo, the Lake Street tennis and pickleball courts and just a short distance to Downtown Vineyard Haven.

5 Beds ⋅ 4 Baths ⋅ 73511187 MLS

Tucked back from scenic Lake Street, this distinctive home offers privacy and charm on a landscaped 0.7 acre lot with mature trees and a classic stone wall. Inside, rich wood detailing, exposed beams, and high ceilings create a warm, inviting feel. The four-level design provides flexibility and character. The main level features a spacious kitchen with a center island open to the dining area, and a sunken living room with floor-to-ceiling windows overlooking the trees. A large screened porch extends the living space outdoors. Two bedrooms, a full bath, and laundry complete this floor. Upstairs, a dramatic hallway leads to a generous primary suite with a spacious bath and additional laundry. The third level offers a private guest suite with living area and bath. The finished lower level includes added living space, bath, and walkout. Convenient to the public boat landing on Lake Tashmoo, the Lake Street tennis and pickleball courts and just a short distance to Downtown Vineyard Haven.

159 Lake Street, Tisbury

$2,895,000

Set in a private community, Sweetened Water Farm offers the pastoral charm of Martha's Vineyard's rural up-island, just minutes from the energy of downtown Edgartown. Residents share access to the association's horse barn and common pastures, ideal for keeping horses or other livestock, adding to the farm's authentic agrarian character. This custom-built home is a true Vineyard gem, crafted over time by local artisans and set against sweeping pastoral views. The main house currently offers 3 bedrooms and 2 bathrooms, with the potential to expand to 6 bedrooms, as approved by the Edgartown Board of Health and Building Department. Inside, the home tells its own story: African mahogany millwork in the library, massive fieldstone fireplaces, and a Jotul wood stove . Built to the same exacting standard, the barn and garage include a custom wood-fired sauna and a two-room office on the second floor.

3 Beds ⋅ 2 Baths ⋅ 73511131 MLS

Set in a private community, Sweetened Water Farm offers the pastoral charm of Martha's Vineyard's rural up-island, just minutes from the energy of downtown Edgartown. Residents share access to the association's horse barn and common pastures, ideal for keeping horses or other livestock, adding to the farm's authentic agrarian character. This custom-built home is a true Vineyard gem, crafted over time by local artisans and set against sweeping pastoral views. The main house currently offers 3 bedrooms and 2 bathrooms, with the potential to expand to 6 bedrooms, as approved by the Edgartown Board of Health and Building Department. Inside, the home tells its own story: African mahogany millwork in the library, massive fieldstone fireplaces, and a Jotul wood stove . Built to the same exacting standard, the barn and garage include a custom wood-fired sauna and a two-room office on the second floor.

24 Beetle Swamp Rd, Edgartown

$525,000

A level parcel in a convenient Vineyard Haven location offering ease and opportunity. Set on a no-through street within an established neighborhood, it’s just a short stroll or bike ride to public beach access at the end of Owen Little Way and the town library. Only one mile from the vibrant shops and restaurants of Main Street, and less than two miles from the sandy shores of Lake Tashmoo beach, the setting provides the perfect balance of accessibility and island living. The parcel is not within the Nitrogen Management District, meaning no enhanced septic system is required. A great opportunity to build to suit your needs.

73508644 MLS

A level parcel in a convenient Vineyard Haven location offering ease and opportunity. Set on a no-through street within an established neighborhood, it’s just a short stroll or bike ride to public beach access at the end of Owen Little Way and the town library. Only one mile from the vibrant shops and restaurants of Main Street, and less than two miles from the sandy shores of Lake Tashmoo beach, the setting provides the perfect balance of accessibility and island living. The parcel is not within the Nitrogen Management District, meaning no enhanced septic system is required. A great opportunity to build to suit your needs.

Lot 1 Dolan Avenue, Tisbury

$7,850,000

This classic New England home in Katama offers a refined blend of timeless architecture and modern comfort, set on a spacious, beautifully landscaped lot. The main house features three well-appointed bedrooms, including a light-filled primary suite and inviting guest rooms designed for comfort and privacy. The open-concept living area is ideal for entertaining, highlighted by a cozy fireplace and large windows overlooking the manicured grounds. French doors lead to a deck perfect for outdoor dining and relaxation. A state-of-the-art media room with plush seating and a large screen provides the ultimate space for movie nights or game days, with a wine cellar just steps away. The carriage house includes a three-car garage with a spacious one-bedroom apartment above. Located beside Sheriff’s Meadow Conservation land with public access to Katama Bay, and just minutes to South Beach and downtown Edgartown.

4 Beds ⋅ 6 Baths ⋅ 73504170 MLS

This classic New England home in Katama offers a refined blend of timeless architecture and modern comfort, set on a spacious, beautifully landscaped lot. The main house features three well-appointed bedrooms, including a light-filled primary suite and inviting guest rooms designed for comfort and privacy. The open-concept living area is ideal for entertaining, highlighted by a cozy fireplace and large windows overlooking the manicured grounds. French doors lead to a deck perfect for outdoor dining and relaxation. A state-of-the-art media room with plush seating and a large screen provides the ultimate space for movie nights or game days, with a wine cellar just steps away. The carriage house includes a three-car garage with a spacious one-bedroom apartment above. Located beside Sheriff’s Meadow Conservation land with public access to Katama Bay, and just minutes to South Beach and downtown Edgartown.

24 Katama Bay View Road, Edgartown

$549,000

Rare opportunity to own an office condominium unit at "Beach Road Condominiums". Minutes from the Ferry and Downtown Vineyard Haven, this lower corner unit offers over 460 square feet of space with new windows, heating and cooling, interior and exterior access, with convenient on-site parking. Ideal location for office, retail, wellness, or professional uses. Seller may also offer the space "For Lease". Prime road frontage location with tremendous water views!

4 Baths ⋅ 73503952 MLS

Rare opportunity to own an office condominium unit at "Beach Road Condominiums". Minutes from the Ferry and Downtown Vineyard Haven, this lower corner unit offers over 460 square feet of space with new windows, heating and cooling, interior and exterior access, with convenient on-site parking. Ideal location for office, retail, wellness, or professional uses. Seller may also offer the space "For Lease". Prime road frontage location with tremendous water views!

107 Beach Rd Unit 101, Tisbury

$1,175,000

END UNIT WITH PRIVATE DRIVEWAY IN TASHMOO WOODS. Well-maintained 3BR/3BA condo offering rare privacy, space, and a single-family feel in one of Vineyard Haven’s most desirable communities. End unit with private driveway, one-car garage, and extra storage. Mature plantings, including 24 added trees, enhance the setting. Open layout with granite kitchen and high-end appliances flows to dining area and private deck overlooking woodlands. Living room with wood-burning fireplace. First-floor bedroom and full bath add flexibility. Upstairs, primary suite with soaking tub and separate shower; second bedroom with nearby full bath. Recent updates include new 30-year roof and gutters (April, 2026). Amenities include tennis, heated pool, playground, basketball, private dock on Lake Tashmoo, and beach access, plus full exterior maintenance and landscaping for easy, turnkey living.

3 Beds ⋅ 3 Baths ⋅ 73503832 MLS ⋅ ['Tashmoo Cove'] BLDG.

END UNIT WITH PRIVATE DRIVEWAY IN TASHMOO WOODS. Well-maintained 3BR/3BA condo offering rare privacy, space, and a single-family feel in one of Vineyard Haven’s most desirable communities. End unit with private driveway, one-car garage, and extra storage. Mature plantings, including 24 added trees, enhance the setting. Open layout with granite kitchen and high-end appliances flows to dining area and private deck overlooking woodlands. Living room with wood-burning fireplace. First-floor bedroom and full bath add flexibility. Upstairs, primary suite with soaking tub and separate shower; second bedroom with nearby full bath. Recent updates include new 30-year roof and gutters (April, 2026). Amenities include tennis, heated pool, playground, basketball, private dock on Lake Tashmoo, and beach access, plus full exterior maintenance and landscaping for easy, turnkey living.

261 Sandpiper Lane Unit 12, Tisbury

$5,100,000

A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association on Martha's Vineyard. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build your dream home in this sought-after location. As a homeowner in Farm Neck, you'll enjoy exclusive access to the association’s private dock on Sengekontacket Pond, ideal for kayaking, paddleboarding, and more. This offering also includes a highly coveted stockholder membership to Farm Neck Golf Club, making it a truly unique and valuable investment.

73503350 MLS

A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association on Martha's Vineyard. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build your dream home in this sought-after location. As a homeowner in Farm Neck, you'll enjoy exclusive access to the association’s private dock on Sengekontacket Pond, ideal for kayaking, paddleboarding, and more. This offering also includes a highly coveted stockholder membership to Farm Neck Golf Club, making it a truly unique and valuable investment.

7 Overview Lane, Oak Bluffs

$1,325,000

Set just off North Road, this exceptional parcel offers a rare opportunity to build in a setting rich with natural beauty. Recently subdivided, this land combines privacy, character and thoughtful positioning. The lot is perfectly sited capturing serene woodland views and the natural contours of Middle Line Ridge. A 600ft stonewall lines the western property line, creating a timeless sense of arrival, while the property itself is adorned with beautiful glacial rock formations that add texture and distinction to the landscape. Surrounded by 23 acres of protected land to the southeast, including Roaring Brook Ravine and across Tabor House and along Middle Line for an additional 45+ acres of MV Land Bank ensuring privacy and an unspoiled natural backdrop. Substantial infrastructure work has been completed through clearing and road installation.

73501793 MLS

Set just off North Road, this exceptional parcel offers a rare opportunity to build in a setting rich with natural beauty. Recently subdivided, this land combines privacy, character and thoughtful positioning. The lot is perfectly sited capturing serene woodland views and the natural contours of Middle Line Ridge. A 600ft stonewall lines the western property line, creating a timeless sense of arrival, while the property itself is adorned with beautiful glacial rock formations that add texture and distinction to the landscape. Surrounded by 23 acres of protected land to the southeast, including Roaring Brook Ravine and across Tabor House and along Middle Line for an additional 45+ acres of MV Land Bank ensuring privacy and an unspoiled natural backdrop. Substantial infrastructure work has been completed through clearing and road installation.

0 North 15 Belhaven Way, Chilmark

$1,125,000

Opportunity Abounds - This conforming parcel offers a great opportunity to build with close proximity to Edgartown Village! This adjoining lot offers ability to connect to Town Water and Sewer creating the perfect setting for your custom dream home or next investment. Located just moments from shops, restaurants, parks, and everyday conveniences, this is a chance to enjoy all the benefits of in-town living while building new in a highly desirable neighborhood. NOTE: Being sold as-is; estate rules apply. Sale is subject to probate approval and court confirmation.

73500168 MLS

Opportunity Abounds - This conforming parcel offers a great opportunity to build with close proximity to Edgartown Village! This adjoining lot offers ability to connect to Town Water and Sewer creating the perfect setting for your custom dream home or next investment. Located just moments from shops, restaurants, parks, and everyday conveniences, this is a chance to enjoy all the benefits of in-town living while building new in a highly desirable neighborhood. NOTE: Being sold as-is; estate rules apply. Sale is subject to probate approval and court confirmation.

15 Chapman La, Edgartown

$1,599,000

Waterview Condo in the Heart of Downtown Vineyard Haven. Experience the best of in-town living with this newly built, thoughtfully designed 2-bedroom condo offering beautiful harbor views and luxurious modern finishes. The first level welcomes you with a primary suite featuring a full bath with a tub/shower combination and direct access to a private deck complete with an outdoor shower, perfect after a day at the beach. Also on this level is a comfortable guest bedroom with peaks of the harbor, a stylish full tile bath with a glass-enclosed shower, a cozy living area, and washer/dryer for convenience. Upstairs, cathedral ceilings and a gas fireplace create an inviting open-concept living space. The gourmet kitchen is outfitted with sleek Bosch appliances, a large center island ideal for entertaining, and an adjoining dining area. Enjoy panoramic water views of the harbor, passing ferry boats, and Vineyard Sound from the entire second floor, or step out onto your private deck, perfect f

2 Beds ⋅ 3 Baths ⋅ 73497681 MLS

Waterview Condo in the Heart of Downtown Vineyard Haven. Experience the best of in-town living with this newly built, thoughtfully designed 2-bedroom condo offering beautiful harbor views and luxurious modern finishes. The first level welcomes you with a primary suite featuring a full bath with a tub/shower combination and direct access to a private deck complete with an outdoor shower, perfect after a day at the beach. Also on this level is a comfortable guest bedroom with peaks of the harbor, a stylish full tile bath with a glass-enclosed shower, a cozy living area, and washer/dryer for convenience. Upstairs, cathedral ceilings and a gas fireplace create an inviting open-concept living space. The gourmet kitchen is outfitted with sleek Bosch appliances, a large center island ideal for entertaining, and an adjoining dining area. Enjoy panoramic water views of the harbor, passing ferry boats, and Vineyard Sound from the entire second floor, or step out onto your private deck, perfect f

26 Union Court Unit 7, Tisbury

$550,000

CHAPPAQUIDDICK — Just over one acre in the desirable Calebs Common neighborhood, ideally located near the ferry, beach, and Community Center. Enjoy easy access to beaches, miles of walking trails, and the surrounding conservation land that makes Chappy so special. A wonderful opportunity to create your own island retreat. Per the Board of Health, the lot may support a three-bedroom home with an enhanced system and proper approvals. Also included in the sale is the owner's share of the Calebs Beach Corporation, giving you access to the sandy beach on the outer harbor.

73495792 MLS

CHAPPAQUIDDICK — Just over one acre in the desirable Calebs Common neighborhood, ideally located near the ferry, beach, and Community Center. Enjoy easy access to beaches, miles of walking trails, and the surrounding conservation land that makes Chappy so special. A wonderful opportunity to create your own island retreat. Per the Board of Health, the lot may support a three-bedroom home with an enhanced system and proper approvals. Also included in the sale is the owner's share of the Calebs Beach Corporation, giving you access to the sandy beach on the outer harbor.

23 Calebs Common Lane, Edgartown

$1,575,000

Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with Land Bank-preserved Arrowhead Farm and protected Rodgers Path land on two sides— a setting no existing home can replicate. A naturally flat building envelope crowns the hilltop while the land rolls into a pastoral landscape below. Private without being remote — minutes from Lambert's Cove Beach, West Tisbury village centers, and scenic trails. Architectural plans for a 4-bedroom, 4.5-bath residence & detached garage by Vineyard architect Sullivan & Associates are included. Well installed. Power on-site. Site Plan Review & 6-bedroom Septic Plan approvals in hand. This isn't a compromise. It's everything you wanted, waiting to be built. Very private setting Showing by Appt. only. No DriveBys.

73495787 MLS

Stop Searching. Start Building. You've toured dozens of homes. Nothing feels right. What if your dream home on Martha's Vineyard simply hasn't been built yet? This rare 3.32-acre West Tisbury hilltop is the blank canvas you've been waiting for. Glacial boulders, open pasture, and cathedral oaks with Land Bank-preserved Arrowhead Farm and protected Rodgers Path land on two sides— a setting no existing home can replicate. A naturally flat building envelope crowns the hilltop while the land rolls into a pastoral landscape below. Private without being remote — minutes from Lambert's Cove Beach, West Tisbury village centers, and scenic trails. Architectural plans for a 4-bedroom, 4.5-bath residence & detached garage by Vineyard architect Sullivan & Associates are included. Well installed. Power on-site. Site Plan Review & 6-bedroom Septic Plan approvals in hand. This isn't a compromise. It's everything you wanted, waiting to be built. Very private setting Showing by Appt. only. No DriveBys.

26 Flint Hill Road, West Tisbury

$2,850,000

Nestled on a private 1.7-acre parcel in the Bold Meadow neighborhood, this classic Cape offers a perfect blend of comfort and Vineyard charm. Surrounded by mature woodlands, association land, and State Forest, the property provides a serene retreat just moments from Edgartown. The main level is thoughtfully designed for both relaxation and entertaining, featuring a formal living room with a fireplace and a separate TV/family room. The kitchen includes stainless steel appliances, quartz countertops, and a breakfast bar. An eat-in area opens to a spacious mahogany deck, complete with outdoor seating and beautifully landscaped gardens. The first-floor primary suite features vaulted, beamed ceilings and offers a private retreat with an en-suite bath. An additional bedroom/office and a fully renovated hall bath are also located on this level. Upstairs, 2 guest bedrooms share a full bath, while a loft above the two-car garage provides a flexible bonus space.

4 Beds ⋅ 3 Baths ⋅ 73494371 MLS

Nestled on a private 1.7-acre parcel in the Bold Meadow neighborhood, this classic Cape offers a perfect blend of comfort and Vineyard charm. Surrounded by mature woodlands, association land, and State Forest, the property provides a serene retreat just moments from Edgartown. The main level is thoughtfully designed for both relaxation and entertaining, featuring a formal living room with a fireplace and a separate TV/family room. The kitchen includes stainless steel appliances, quartz countertops, and a breakfast bar. An eat-in area opens to a spacious mahogany deck, complete with outdoor seating and beautifully landscaped gardens. The first-floor primary suite features vaulted, beamed ceilings and offers a private retreat with an en-suite bath. An additional bedroom/office and a fully renovated hall bath are also located on this level. Upstairs, 2 guest bedrooms share a full bath, while a loft above the two-car garage provides a flexible bonus space.

2 Bold Meadow Road, Edgartown

$2,225,000

Experience the ease of summer living in your own Martha’s Vineyard beach house. Perched atop a rise with sweeping views, abundant natural light, and star-filled skies, this furnished, move-in-ready home with four levels of lifestyle. A dramatic 30-foot vaulted foyer leads to a fully renovated chef’s kitchen with Sub-Zero refrigeration, premium stainless appliances, stone counters, and a custom banquette seating 10. The home features a formal dining room, oak floors, a wood-burning stone fireplace featured in Architectural Digest, and a view-facing living room with balcony. The primary suite includes a walk-in closet and en-suite bath with soaking tub and double vanity, plus two additional bedrooms. A spiral staircase leads to a loft lounge with private balcony and two bonus rooms. The walk-out lower level adds flexible space for a gym, office, or lounge. Expansion potential allows up to seven bedrooms, plus guest house, pool, and pool house. $25,000 credit at closing for sewer tie-in.

3 Beds ⋅ 3 Baths ⋅ 73493917 MLS

Experience the ease of summer living in your own Martha’s Vineyard beach house. Perched atop a rise with sweeping views, abundant natural light, and star-filled skies, this furnished, move-in-ready home with four levels of lifestyle. A dramatic 30-foot vaulted foyer leads to a fully renovated chef’s kitchen with Sub-Zero refrigeration, premium stainless appliances, stone counters, and a custom banquette seating 10. The home features a formal dining room, oak floors, a wood-burning stone fireplace featured in Architectural Digest, and a view-facing living room with balcony. The primary suite includes a walk-in closet and en-suite bath with soaking tub and double vanity, plus two additional bedrooms. A spiral staircase leads to a loft lounge with private balcony and two bonus rooms. The walk-out lower level adds flexible space for a gym, office, or lounge. Expansion potential allows up to seven bedrooms, plus guest house, pool, and pool house. $25,000 credit at closing for sewer tie-in.

81 Whalers Walk, Edgartown

$1,395,000

Opportunity Knocks - Located within close proximity to Edgartown Village shops, restaurants, parks, and everyday conveniences, this fixer upper offers the rare chance to renovate in a location that truly shines. This property is full of potential for buyers, investors, or renovators looking to create something special. Bring your vision and transform this property into your signature retreat, while building value in a sought-after location. A fantastic opportunity to customize, restore, and make it your own. NOTE: Being sold as-is; estate rules apply. Sale is subject to probate approval and court confirmation.

3 Beds ⋅ 1 Baths ⋅ 73490019 MLS

Opportunity Knocks - Located within close proximity to Edgartown Village shops, restaurants, parks, and everyday conveniences, this fixer upper offers the rare chance to renovate in a location that truly shines. This property is full of potential for buyers, investors, or renovators looking to create something special. Bring your vision and transform this property into your signature retreat, while building value in a sought-after location. A fantastic opportunity to customize, restore, and make it your own. NOTE: Being sold as-is; estate rules apply. Sale is subject to probate approval and court confirmation.

17 Chapman La, Edgartown