100 houses for sale in 02535

Chockers Ln, Chilmark, Home For Sale
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House · for sale
USD 5,500,000
USD 6,815/sq.ft
New
Chockers Ln, Chilmark, Home For Sale
02535
· 807 sq.ft · 2 Bedrooms · 1 Bath · House
02535 · 807 sq.ft · 2 Bedrooms · 1 Bath · House
Perfectly situated on Nashaquitsa Pond, this charming two-bedroom cottage offers sweeping views of Quitsa and Menemsha Pond from a rare vantage point few properties can match. The cottage includes private beach rights to Short Beach and dock access for a mooring. Inside, hand-painted floors and a warm, unpretentious interior reflect the authentic character of Old Vineyard - a property that has brought multiple families together over generations of summers. For those seeking an authentic connection to the Vineyard's natural beauty and storied past, this is a rare and remarkable find
Perfectly situated on Nashaquitsa Pond, this charming two-bedroom cottage offers sweeping views of Quitsa and Menemsha Pond from a rare vantage point few properties can match. The cottage includes private beach rights to Short Beach and dock access for a mooring. Inside, hand-painted floors and a warm, unpretentious interior reflect the authentic character of Old Vineyard - a property that has brought multiple families together over generations of summers. For those seeking an authentic connection to the Vineyard's natural beauty and storied past, this is a rare and remarkable find
USD 5,500,000
Hammett Ln, Chilmark, Home For Sale
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House · for sale
USD 3,795,000
USD 1,108/sq.ft
New
Hammett Ln, Chilmark, Home For Sale
02535
· 3,423 sq.ft · 3 Bedrooms · 3 Baths · House
· Patio · Garden · Office room · Deck · Fireplace · Equipped kitchen
02535 · 3,423 sq.ft · 3 Bedrooms · 3 Baths · House · Patio · Garden · Office room · Deck · Fireplace · Equipped kitchen
Beautifully designed and built Post and Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher, soapstone counters and a butlers pantry with extra cupboards, shelving and a wine refrigerator. There are sliders that take you to an oversized deck and stairs to a blue stone patio and beautiful gardens. The screened-in porch off the living room steps out to the side yard, patio and outdoor shower. First floor Primary with walk-in closet, access to the deck and a private en-suite bathroom with beautiful tiled steam shower and large soaking tub. Second floor includes a loft with sitting room, 2 spacious bedrooms that share a full bath with shower and office, all with cathedral beamed ceilings. Many nice features throughout include white oak random width floors, marble and til
Beautifully designed and built Post and Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher, soapstone counters and a butlers pantry with extra cupboards, shelving and a wine refrigerator. There are sliders that take you to an oversized deck and stairs to a blue stone patio and beautiful gardens. The screened-in porch off the living room steps out to the side yard, patio and outdoor shower. First floor Primary with walk-in closet, access to the deck and a private en-suite bathroom with beautiful tiled steam shower and large soaking tub. Second floor includes a loft with sitting room, 2 spacious bedrooms that share a full bath with shower and office, all with cathedral beamed ceilings. Many nice features throughout include white oak random width floors, marble and til
USD 3,795,000
Quenames Rd, Chilmark, Home For Sale
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House · for sale
USD 1,125,000
USD 1,259/sq.ft
New
Quenames Rd, Chilmark, Home For Sale
02535
· 893 sq.ft · 2 Bedrooms · 1 Bath · House
· Garden · Equipped kitchen
02535 · 893 sq.ft · 2 Bedrooms · 1 Bath · House · Garden · Equipped kitchen
Set on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and excellent potential. In a sunny clearing among mature trees, the maintained 2-bedroom house features first-floor living, an open kitchen and living area, two spacious bedrooms, a full bath with shower, an enormous three-season screened porch, a large outdoor shower, kitchen gardens, and a potting area with utility sink. Well system updated in 2011. With strong rental income, currently generating $2,500 month to month year-round, and expansion potential, this outstanding value is located close to South Road, West Tisbury's village center, and Chilmark's iconic town beaches Squibnocket and Lucy Vincent. Town records indicate a 4 bedroom septic, passed Title V Inspection in December 2025. #45 is shown as Lot 1-B on a new subdivision not yet reflected on the assessments and public records - approved plans are attached. 47 Quenames Lot 1-B is also available
Set on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and excellent potential. In a sunny clearing among mature trees, the maintained 2-bedroom house features first-floor living, an open kitchen and living area, two spacious bedrooms, a full bath with shower, an enormous three-season screened porch, a large outdoor shower, kitchen gardens, and a potting area with utility sink. Well system updated in 2011. With strong rental income, currently generating $2,500 month to month year-round, and expansion potential, this outstanding value is located close to South Road, West Tisbury's village center, and Chilmark's iconic town beaches Squibnocket and Lucy Vincent. Town records indicate a 4 bedroom septic, passed Title V Inspection in December 2025. #45 is shown as Lot 1-B on a new subdivision not yet reflected on the assessments and public records - approved plans are attached. 47 Quenames Lot 1-B is also available
USD 1,125,000
Bijahs Way, Chilmark, Home For Sale
View photo
House · for sale
USD 2,195,000
USD 875/sq.ft
New
Bijahs Way, Chilmark, Home For Sale
02535
· 2,508 sq.ft · 3 Bedrooms · 2 Baths · House
· Garden · Deck · Equipped kitchen · Air conditioning · Cellar
02535 · 2,508 sq.ft · 3 Bedrooms · 2 Baths · House · Garden · Deck · Equipped kitchen · Air conditioning · Cellar
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 and included a 22 x 43 addition. The completely new second floor added over 1,500 square feet and the work included entirely new heating, plumbing, electrical, central AC, septic and well! Many nice features include spacious living spaces, a modern kitchen with breakfast bar, open living and dining room with cathedral ceiling, oversized windows and a slider that leads out to a spacious deck. There is a second floor primary with ensuite bath, walk-in closet and private deck. Large family room with skylights and built-ins. There are two first floor bedrooms that share a bath, full basement, wood floors, a whole house generator and Oil FHW heat and new A/C. Privately sited 1.20 acres bordered by stone walls, beautifully landscaped grounds, mature gardens and plantings. There are also beautiful fruit trees; peach, pear and app
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 and included a 22 x 43 addition. The completely new second floor added over 1,500 square feet and the work included entirely new heating, plumbing, electrical, central AC, septic and well! Many nice features include spacious living spaces, a modern kitchen with breakfast bar, open living and dining room with cathedral ceiling, oversized windows and a slider that leads out to a spacious deck. There is a second floor primary with ensuite bath, walk-in closet and private deck. Large family room with skylights and built-ins. There are two first floor bedrooms that share a bath, full basement, wood floors, a whole house generator and Oil FHW heat and new A/C. Privately sited 1.20 acres bordered by stone walls, beautifully landscaped grounds, mature gardens and plantings. There are also beautiful fruit trees; peach, pear and app
USD 2,195,000
Quenames Rd, Chilmark, Home For Sale
View photo
House · for sale
USD 1,150,000
USD 1,256/sq.ft
New
Quenames Rd, Chilmark, Home For Sale
02535
· 915 sq.ft · 2 Bedrooms · 1 Bath · House
· Patio · Deck · Equipped kitchen
02535 · 915 sq.ft · 2 Bedrooms · 1 Bath · House · Patio · Deck · Equipped kitchen
On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural woodland setting. With strong rental income, currently generating $2,500 month to month year-round, and expansion opportunities subject to town approvals, the property is conveniently located near South Road, West Tisbury's village center, and Chilmark's iconic Lucy Vincent and Squibnocket Beaches. Passed Title V in December 2025 for 3 Bedrooms. #47 is shown as Lot 1-C on a new subdivision not yet reflected on the assessments and public records - approved survey is attached. 45 Quenames Lot 1-B is also available
On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural woodland setting. With strong rental income, currently generating $2,500 month to month year-round, and expansion opportunities subject to town approvals, the property is conveniently located near South Road, West Tisbury's village center, and Chilmark's iconic Lucy Vincent and Squibnocket Beaches. Passed Title V in December 2025 for 3 Bedrooms. #47 is shown as Lot 1-C on a new subdivision not yet reflected on the assessments and public records - approved survey is attached. 45 Quenames Lot 1-B is also available
USD 1,150,000
Fulling Mill Rd, Chilmark, Home For Sale
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House · for sale
USD 1,995,000
USD 1,041/sq.ft
New
Fulling Mill Rd, Chilmark, Home For Sale
02535
· 1,916 sq.ft · 4 Bedrooms · 3 Baths · House
· Garden · Deck · Equipped kitchen
02535 · 1,916 sq.ft · 4 Bedrooms · 3 Baths · House · Garden · Deck · Equipped kitchen
Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to discover a custom circular staircase with dramatic floor to ceiling windows, leading to the upper living area flooded with natural light from the wall of south-facing windows. The living area with high ceilings and woodstove is a comfortable place to congregate, while the kitchen and open dining areas lend themselves to modern day living. Glass sliding doors open onto a spacious 2nd story deck giving the entire living space an intimate relationship with the outdoors. On the first floor there are three total bedrooms; two bedrooms sharing a full bath plus a primary bedroom with a full bath en-suite.
Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to discover a custom circular staircase with dramatic floor to ceiling windows, leading to the upper living area flooded with natural light from the wall of south-facing windows. The living area with high ceilings and woodstove is a comfortable place to congregate, while the kitchen and open dining areas lend themselves to modern day living. Glass sliding doors open onto a spacious 2nd story deck giving the entire living space an intimate relationship with the outdoors. On the first floor there are three total bedrooms; two bedrooms sharing a full bath plus a primary bedroom with a full bath en-suite.
USD 1,995,000
N Slope Ln, Chilmark, Home For Sale
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House · for sale
USD 1,649,900
USD 1,072/sq.ft
New
N Slope Ln, Chilmark, Home For Sale
02535
· 1,539 sq.ft · 3 Bedrooms · 2 Baths · House
· Office room
02535 · 1,539 sq.ft · 3 Bedrooms · 2 Baths · House · Office room
Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha's Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring comfortable living spaces ideal for year-round living or seasonal enjoyment. With 3 bedrooms and 2 full baths, the layout offers flexibility for family, guests, or a home office. Custom soapstone countertops add to this home's beauty. Expansive outdoor space invites relaxation, exploration, and the potential for future enhancements, all within a serene woodland environment. An increasingly rare opportunity to own a conservation-abutting property on Martha's Vineyard-perfect as a primary residence, vacation home, or long-term investment in one of the island's most desireable natural settings
Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha's Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring comfortable living spaces ideal for year-round living or seasonal enjoyment. With 3 bedrooms and 2 full baths, the layout offers flexibility for family, guests, or a home office. Custom soapstone countertops add to this home's beauty. Expansive outdoor space invites relaxation, exploration, and the potential for future enhancements, all within a serene woodland environment. An increasingly rare opportunity to own a conservation-abutting property on Martha's Vineyard-perfect as a primary residence, vacation home, or long-term investment in one of the island's most desireable natural settings
USD 1,649,900
Wakeman Rd, Chilmark, Home For Sale
View photo
House · for sale
USD 9,875,000
USD 2,628/sq.ft
New
Wakeman Rd, Chilmark, Home For Sale
02535
· 3,757 sq.ft · 6 Bedrooms · 6 Baths · House
· Parking
02535 · 3,757 sq.ft · 6 Bedrooms · 6 Baths · House · Parking
Set in a spectacular water view setting with private beach access, this exceptional coastal compound offers a rare blend of privacy, flexibility, and breathtaking scenery. The property is thoughtfully composed of a beautifully appointed main residence, a separate guest house, an artist's studio, and a detached garage with an additional bedroom above - creating the ideal retreat for extended family, guests, or creative living. Expansive water views are showcased throughout the property, with inviting indoor and outdoor spaces designed to capture the natural beauty of the shoreline. Whether enjoying morning coffee overlooking the water, entertaining on warm summer evenings, or taking a short stroll to the private dock on Chilmark Pond, or boating over to the private sandy Atlantic Ocean beach,every aspect of this property embraces relaxed year-round coastal living. A truly unique offering, this compound presents an extraordinary opportunity to own a multi-generational retreat in an idyll
Set in a spectacular water view setting with private beach access, this exceptional coastal compound offers a rare blend of privacy, flexibility, and breathtaking scenery. The property is thoughtfully composed of a beautifully appointed main residence, a separate guest house, an artist's studio, and a detached garage with an additional bedroom above - creating the ideal retreat for extended family, guests, or creative living. Expansive water views are showcased throughout the property, with inviting indoor and outdoor spaces designed to capture the natural beauty of the shoreline. Whether enjoying morning coffee overlooking the water, entertaining on warm summer evenings, or taking a short stroll to the private dock on Chilmark Pond, or boating over to the private sandy Atlantic Ocean beach,every aspect of this property embraces relaxed year-round coastal living. A truly unique offering, this compound presents an extraordinary opportunity to own a multi-generational retreat in an idyll
USD 9,875,000
Lighthouse Rd, Aquinnah, Home For Sale
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House · for sale
USD 1,499,000
USD 1,046/sq.ft
New
Lighthouse Rd, Aquinnah, Home For Sale
02535
· 1,432 sq.ft · 5 Bedrooms · 2 Baths · House
· Deck · Equipped kitchen
02535 · 1,432 sq.ft · 5 Bedrooms · 2 Baths · House · Deck · Equipped kitchen
Ranch style home and Guest camp situated on 1+/- acre lot. The Main House offers distant views of Lobersterville beach and the Vineyard Sound beyond. Located in the desirable Lighthouse Road area, which offers walkable/close-by beach access and quiet roads. The view can be enjoyed from the Kitchen/Living/Dining as well as the wrap-around deck. Enjoy the open concept main living area, two bedrooms, and a shared bath. Follow the connected deck to the guest camp, which includes three bedrooms and a bathroom with laundry combined. Outdoor shower, storage shed, and the wrap-around deck complete this camp. Make this your family's Aquinnah getaway!
Ranch style home and Guest camp situated on 1+/- acre lot. The Main House offers distant views of Lobersterville beach and the Vineyard Sound beyond. Located in the desirable Lighthouse Road area, which offers walkable/close-by beach access and quiet roads. The view can be enjoyed from the Kitchen/Living/Dining as well as the wrap-around deck. Enjoy the open concept main living area, two bedrooms, and a shared bath. Follow the connected deck to the guest camp, which includes three bedrooms and a bathroom with laundry combined. Outdoor shower, storage shed, and the wrap-around deck complete this camp. Make this your family's Aquinnah getaway!
USD 1,499,000
Putnam Rd, Chilmark, Home For Sale
View photo
House · for sale
USD 4,995,000
USD 2,392/sq.ft
New
Putnam Rd, Chilmark, Home For Sale
02535
· 2,088 sq.ft · 3 Bedrooms · 3 Baths · House
· Deck · Fireplace · Equipped kitchen · Parking
02535 · 2,088 sq.ft · 3 Bedrooms · 3 Baths · House · Deck · Fireplace · Equipped kitchen · Parking
Stylish Chilmark retreat with sweeping water views, private beach, tennis, and walking trails. Set within the coveted Spring Point community, this beautifully renovated island home captures a rare sense of place, with natural beauty, privacy, and effortless indoor-outdoor living. Thoughtfully updated in 2022, the home blends relaxed coastal sophistication with driftwood-colored hardwood floors, a striking stone fireplace, sleek cook's kitchen, custom-tiled baths, and Sonos(R) sound. Large windows and sliding glass doors frame water views and open to private decks, while a spacious screened porch is ideal for morning coffee, summer dining, or entertaining. Landscaped grounds, a paver parking court, charming gazebo, and finished walk-out lower level add comfort and flexibility. Spring Point amenities include 68 acres of common land, ancient walking trails, two tennis courts, and Beck's Beach, a private shoreline with magnificent sunsets from the Elizabeth Islands to Gay Head Lighthouse
Stylish Chilmark retreat with sweeping water views, private beach, tennis, and walking trails. Set within the coveted Spring Point community, this beautifully renovated island home captures a rare sense of place, with natural beauty, privacy, and effortless indoor-outdoor living. Thoughtfully updated in 2022, the home blends relaxed coastal sophistication with driftwood-colored hardwood floors, a striking stone fireplace, sleek cook's kitchen, custom-tiled baths, and Sonos(R) sound. Large windows and sliding glass doors frame water views and open to private decks, while a spacious screened porch is ideal for morning coffee, summer dining, or entertaining. Landscaped grounds, a paver parking court, charming gazebo, and finished walk-out lower level add comfort and flexibility. Spring Point amenities include 68 acres of common land, ancient walking trails, two tennis courts, and Beck's Beach, a private shoreline with magnificent sunsets from the Elizabeth Islands to Gay Head Lighthouse
USD 4,995,000

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