Chilmark, MA Houses for Sale

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  /42

  $4,995,000

  • 3 Beds
  • 2.5 Baths
  • 2,095 Sq Ft

  63 Putnam Rd, Chilmark, MA 02535

  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

  

  Wendy Harman

  Compass

  63 Putnam Rd, Chilmark, MA 02535
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  /27

  $1,699,999

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft

  43 N Slope Ln, Chilmark, MA 02535

  Set on a private 3.5-acre wooded parcel surrounded by conservation land, this 3-bedroom, 2-bath single-family home offers the ultimate Martha’s Vineyard retreat. Nestled among mature trees and protected open space, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully

  

  Barbara O'Hara

  NorthStar Real Estate LLC

  43 N Slope Ln, Chilmark, MA 02535
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  /32

  $2,150,000

  $100K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,522 Sq Ft

  29 Old Nursery Ln, Chilmark, MA 02535

  Modern Cape style home located off Tea Lane could be your special Chilmark retreat. This four bedroom, 2.5 bathroom home needs some updating but is in good condition. Living room with fireplace, dining area and family room provide space for living. Attached two bay garage allows for storage and projects. Wood working area in the basement is a plus. Enjoy the outdoors via the screened porch, large

  Julianna Flanders Flanders Real Estate

  29 Old Nursery Ln, Chilmark, MA 02535
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  /35

  $5,200,000

  • 5 Beds
  • 3.5 Baths
  • 4,044 Sq Ft

  49 Gosnold's Way, Chilmark, MA 02535

  Set high on the north shore with panoramic waterviews of Vineyard Sound and deeded private beach access, this secluded 9.8-acre property occupies a rare setting bordered by conservation land and the Menemsha Hills trail network.The spacious, meticulously maintained residence features a reverse floor plan that accentuates the natural light, soaring ceilings, and breathtaking views. The upper

  Bonnie Pierce Wallace & Co. Sotheby's

  49 Gosnold's Way, Chilmark, MA 02535
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  /33

  $3,600,000

  • 5 Beds
  • 3 Baths
  • 2,701 Sq Ft

  20 James Pond Way, Vineyard Haven, MA 02568

  Tucked away on 4.5 acres off Lambert's Cove Road, this unique property offers privacy and peaceful views to James Pond. A private boardwalk leads to a boathouse with direct access to James Pond, perfect for paddling across to Lambert's Cove and enjoying the nearby James Pond Preserve. The home features a spacious living room with cathedral ceilings and a wood burning fireplace, opening onto a

  Sheila Morse Island Real Estate

  20 James Pond Way, Vineyard Haven, MA 02568
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  /53

  $6,750,000

  • 5 Beds
  • 3.5 Baths
  • 4,050 Sq Ft

  78 Hammett Rd, Chilmark, MA 02535

  This magnificent Spring Point waterfront property, perched 50 ft above sea level and 425 ft back from the North Shore bluff, boasts beautiful views of the Vineyard Sound, Aquinnah coastline and the Elizabeth Islands -- and year dramatic year round sunsets. The property at the end of a well maintained wide dirt road 1 mile from North Rd is SECLUDED and TRANQUIL. It's a SHORT WALK TO THE BEACH,

  Robert Kenney Tea Lane Associates

  78 Hammett Rd, Chilmark, MA 02535
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  /35

  $1,225,000

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  52 Oak Knoll Rd, Vineyard Haven, MA 02568

  Year-round living in the desirable Island Farms Road neighborhood of West Tisbury. This well-built three-bedroom, two-bath home offers a comfortable layout with a first-floor primary bedroom. While ready for your personal updates, it provides a solid foundation to create your forever home. The open kitchen and living area offer a welcoming space for everyday living while the screened porch

  Tina Miller Donnelly + Co.

  52 Oak Knoll Rd, Vineyard Haven, MA 02568
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  /66

  $1,899,000

  $101K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 2,075 Sq Ft

  63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

  Set within the coveted Vineyard Meadow Farms community, this West Tisbury property presents a rare opportunity to own a thoughtfully configured compound in one of the island's most peaceful and sought-after settings. Privately sited on a generous parcel, the property is surrounded by natural beauty and offers a sense of calm that defines up-island living.The three-bedroom main residence is

  Valene Pires The Agency

  63 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
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  /8

  $1,325,000

  $250K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  47 Quenames Rd, Chilmark, MA 02535

  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

  Dawn Bellante Sandpiper Realty, Inc.

  47 Quenames Rd, Chilmark, MA 02535
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  /46

  $6,250,000

  • 5 Beds
  • 2.5 Baths
  • 2,269 Sq Ft

  34 Edys Island Way, Chilmark, MA 02535

  Waterfront house and guest house with a private dock on Menemsha Pond. This location is in the heart of Menemsha, a waterfront enclave within walking distance of this classic Harbor. Built and cared for over four generations by an Island legacy family, this property is unique among Island estates for its combination of privacy yet convenience, seclusion yet expansive views. The property is only a

  Jill Napior Tea Lane Associates

  34 Edys Island Way, Chilmark, MA 02535
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  /42

  $2,250,000

  • 4 Beds
  • 3 Baths
  • 1,918 Sq Ft

  21 & 25 Fulling Mill Rd, Chilmark, MA 02535

  Jessie Holtham Wallace & Co. Sotheby's International Realty

  21 & 25 Fulling Mill Rd, Chilmark, MA 02535
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  /52

  $5,295,000

  • 4 Beds
  • 3 Baths
  • 3,432 Sq Ft

  44 Cencelle St, Chilmark, MA 02535

  This private 17-acre Chilmark estate with ocean views, tucked away in the rolling hills and farmlands of Chilmark, offers sweeping ocean views to the south and a rare sense of seclusion and serenity. At the heart of the property is a striking modern style home, thoughtfully designed to bring the outdoors in. Expansive walls of glass flood the interior with natural light and frame panoramic views

  Meg Bodnar Tea Lane Associates

  44 Cencelle St, Chilmark, MA 02535
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  /53

  $1,700,000

  $145K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,552 Sq Ft

  10 Danls Way, West Tisbury, MA 02575

  Historic West Tisbury farmhouse with detached guest cottage on 1.27 acres in the heart of West Tisbury. Just moments from Alley's General Store, 7a Foods, North Tisbury Village, and a short drive to beaches and both up- and downd Island destinations. This property presents a rare opportunity for a family compound, multi-generational living, or investment with rental income potential. The

  Emma Bryant Studio Realty

  10 Danls Way, West Tisbury, MA 02575
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  /32

  $1,150,000

  $25K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,059 Sq Ft

  4 Rock Pond, West Tisbury, MA 02575

  4 Rock Pond Road offers a rare opportunity to enjoy the best of community-centered living in one of Martha’s Vineyard’s most unique and thoughtfully designed neighborhoods. Located within the Island Cohousing community in West Tisbury, this 4-bedroom, 2-bath home combines warmth, functionality, sustainability, and connection in a peaceful natural setting.Built by South Mountain Company, the

  Trish Lyman Compass | Point B

  4 Rock Pond, West Tisbury, MA 02575
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  /41

  $3,495,000

  • 4 Beds
  • 4 Baths
  • 3,200 Sq Ft

  64 Christiantown Rd, Vineyard Haven, MA 02568

  This stunning 3,200 sq. ft. architectural home features a bright, open layout defined by vaulted ceilings and rich hardwood floors. The gourmet kitchen, appointed with high-end finishes including silestone countertops, flows seamlessly into both a cozy family room and an elegant living room, anchored by a gorgeous dual-sided brick fireplace. With 4 bedrooms, 4 full bathrooms, and 2 dedicated home

  Karen Overtoom Karen M. Overtoom R.E.

  64 Christiantown Rd, Vineyard Haven, MA 02568
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  /31

  $1,150,000

  $25K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,059 Sq Ft

  4 Rock Pond Rd, Vineyard Haven, MA 02568

  4 Rock Pond Road offers a rare opportunity to enjoy the best of community-centered living in one of Martha’s Vineyard’s most unique and thoughtfully designed neighborhoods. Located within the Island Cohousing community in West Tisbury, this 4-bedroom, 2-bath home combines warmth, functionality, sustainability, and connection in a peaceful natural setting.Built by South Mountain Company, the home

  Patricia Lyman Compass

  4 Rock Pond Rd, Vineyard Haven, MA 02568
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  /25

  $7,300,000

  • 5 Beds
  • 5.5 Baths
  • 3,539 Sq Ft

  65 Carl's Way, West Tisbury, MA 02568

  Stylized Private Waterfront Retreat close to townperched along the tranquil shores of the beloved Tisbury Great Pond, this stunning Hutker-designed waterfront home is a seamless blend of coastal elegance and timeless island charm. Designed to capture the essence of Vineyard living, the home features intimate water views, sun-drenched interiors, and carefully curated finishes

  Jill Napior Tea Lane Associates

  65 Carl's Way, West Tisbury, MA 02568
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  /25

  $1,450,000

  $100K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 2,266 Sq Ft

  345 North Rd, Chilmark, MA 02535

  This versatile Chilmark property offers a rare combination of privacy, flexibility, and investment potential. The main residence features 4 bedrooms and 4 bathrooms, complemented by a detached 1-bedroom, 1-bath suite with an attached garage—ideal for guests, extended family, or rental income. Two separate parking areas provide ample space and convenience. Abutting over 200 acres of protected

  Jessica Campbell Flanders Real Estate

  345 North Rd, Chilmark, MA 02535
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  /42

  $5,400,000

  • 3 Beds
  • 2 Baths
  • 2,710 Sq Ft

  35 S Bowl Rd, Chilmark, MA 02535

  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

  Tina Miller Donnelly + Co.

  35 S Bowl Rd, Chilmark, MA 02535
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  /20

  $1,450,000

  • 3 Beds
  • 2 Baths
  • 1,749 Sq Ft

  10 Abels Neck Rd, Chilmark, MA 02535

  Nestled on a beautiful lot in the heart of Chilmark, this charming cottage is framed by mature blueberry bushes just off the deck — a true slice of island life. Perfectly positioned to enjoy the quiet calm of up-island living while remaining close to town, beaches, and all that the Vineyard has to offer. Step inside through sliding glass doors into a cozy living area, where an arched entryway

  Julianna Flanders Flanders Real Estate

  10 Abels Neck Rd, Chilmark, MA 02535
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  /33

  $1,425,000

  $475K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,056 Sq Ft

  20 Brook Hollow Rd, Vineyard Haven, MA 02568

  This spacious custom designed home is well sited to offer maximum privacy in the lush area of Long View. A short bike ride to Lambert's Cove beach, it's also about a 20-minute walk down a quiet private road. The home lays out well for family and extended guests with a roomy living room boasting vaulted ceilings and large windows. The house is designed to have an intimate relationship with the

  Jim Feiner Feiner Real Estate

  20 Brook Hollow Rd, Vineyard Haven, MA 02568
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  /13

  $2,250,000

  $250K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 726 Sq Ft

  18 Allen Farm Rd, Chilmark, MA 02535

  Located in the agricultural heartland of Chilmark one mile from Lucy Vincent Beach this private 2.36 acre property has a charming 1+ bedroom cottage with screened porch. There is a large building zone located between the eighty and one hundred foot contour with exciting architectural options, especially for solar designs. The cottage is offered full furnished with exception of some art and a few

  Patty Kendall Kendall & Kendall

  18 Allen Farm Rd, Chilmark, MA 02535
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  /55

  $5,450,000

  • 5 Beds
  • 4 Baths
  • 3,513 Sq Ft

  61 Stonewall Rd, Chilmark, MA 02535

  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

  Mark Jenkins Wallace & Co. Sotheby's International Realty

  61 Stonewall Rd, Chilmark, MA 02535
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  /78

  $35,000,000

  • 8 Beds
  • 8 Baths
  • 6,841 Sq Ft

  146 Quenames Rd, Chilmark, MA 02535

  Set on 60 acres along one of the most private and unspoiled stretches of Atlantic coastline in Chilmark, this exceptional estate offers a rare combination of scale, privacy, and enduring coastal beauty. With over 800 feet of direct ocean frontage, the property commands expansive views while maintaining a true sense of seclusion, an increasingly scarce offering on Martha’s Vineyard. A gated drive

  Grace Hagerty Grace Hagerty Real Estate Inc

  146 Quenames Rd, Chilmark, MA 02535
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  /34

  $2,195,000

  • 3 Beds
  • 3 Baths
  • 2,363 Sq Ft

  139 Tea Ln, Chilmark, MA 02535

  Tucked away on a quiet country road in a serene Chilmark setting, this beautifully crafted home, built in 2023, offers modern comfort surrounded by natural beauty. The thoughtfully designed main level features an open, light-filled floor plan where the living, dining, kitchen, and family areas flow seamlessly together. A wall of glass doors opens to the outdoors, creating an effortless

  Meg Bodnar Tea Lane Associates

  139 Tea Ln, Chilmark, MA 02535
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  /36

  $1,399,000

  • 4 Beds
  • 2 Baths
  • 1,436 Sq Ft

  145 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

  This coastal contemporary residence is located on a private 1.60-acre lot in West Tisbury, with convenient access to Long Point Wildlife Refuge and access to "Coveted" Lambert's Cove Beach. The home features four bedrooms and two full bathrooms. On the first floor, you'll find two bright bedrooms, a modernized bathroom, and sliders from the living area that lead to a new AZEK deck and enclosed

  Marilyn Moses Ocean Park Realty Inc

  145 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
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  /31

  $2,250,000

  $200K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,918 Sq Ft

  25 Fulling Mill Rd, Chilmark, MA 02535

  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

  Thomas Wallace Wallace & Co. Sotheby's

  25 Fulling Mill Rd, Chilmark, MA 02535
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  /55

  $2,950,000

  • 3 Beds
  • 3 Baths
  • 1,469 Sq Ft

  28 Black Point Rd, Chilmark, MA 02535

  Bright & Airy Black Point Retreat with Private Access to Black Point Beach. Nestled on 5.4 private acres just off Black Point Road in Chilmark, this beautifully maintained retreat offers tranquility and comfort where the sound of the ocean provides a constant backdrop and the shoreline is just moments away. Included with the property is a coveted beach lot (key) to this private south shore beach.

  Michele Moore Island Real Estate

  28 Black Point Rd, Chilmark, MA 02535
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  /65

  $2,550,000

  $649K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 2,618 Sq Ft

  55 Old House Way, West Tisbury, MA 02575

  Lambert’s Cove/West Tisbury- custom-built contemporary farmhouse style. 4 bedrooms & 3 bathrooms in Main & 2 bedrooms & 1 bath Guest Cottage on 3 acres in a private neighborhood. Enter Main house from the covered porch -matching custom arch doors lead you to either the mudroom/laundry room-kitchen entry, or the living room. The kitchen has Mexican tiled floor & granite counters with stainless

  Leslie Graham Anchor Realty of Martha's Vineyard

  55 Old House Way, West Tisbury, MA 02575
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  /31

  $15,400,000

  • 6 Beds
  • 9 Baths
  • 6,967 Sq Ft

  8 Snail Rd, Chilmark, MA 02535

  Horizon House sits atop one of Chilmark's most private and elevated parcels, offering protected and sweeping views of the Atlantic Ocean. Framed by meadow, mature trees, stone walls, and native terrain, the estate holds an extraordinary connection to both land and sea. The 4+ bedroom main house has been thoughtfully reimagined for today's buyer, designed and built by a team of leading architects

  Brian Dougherty Corcoran Property Advisors

  8 Snail Rd, Chilmark, MA 02535
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  /37

  $7,500,000

  $450K PRICE DROP

  • 5 Beds
  • 7 Baths
  • 4,531 Sq Ft

  85 Reservoir Rd, Vineyard Haven, MA 02568

  Nestled within Seven Gates Farm, one of Martha’s Vineyard’s most storied and scenic communities, this 26.5-acre estate features a beautifully renovated farmhouse blending modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property also includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone bench

  Alyssa Halisky Wallace & Co. Sotheby's International Realty

  85 Reservoir Rd, Vineyard Haven, MA 02568
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  /42

  $1,800,000

  • 4 Beds
  • 3 Baths
  • 3,158 Sq Ft

  188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

  House & Guesthouse near Long Point Beach! The Island's coveted south shore is minutes from this charming West Tisbury compound, where the connection to nature is seamless. The main house sits high atop the trees and overlooks a park-like, fenced-in backyard perfect for kids and dogs. The yard also encompasses a sweet garden, storage shed, and outdoor shower. Inside is open with natural light from

  Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

  188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
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  /40

  $1,795,000

  $104K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,061 Sq Ft

  174 Middle Rd, Chilmark, MA 02535

  Nestled in Chilmark, this four-bedroom home blends classic Vineyard charm with modern comfort. The sunlit eat-in kitchen features dual ovens, granite countertops, and custom cherry built-ins, flowing seamlessly to a living room with a Vermont Castings wood stove and access to a covered porch and spacious deck. The first-floor primary suite offers two en-suite baths and two walk-in closets, while

  Sheila Morse Island Real Estate

  174 Middle Rd, Chilmark, MA 02535
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  /29

  $1,550,000

  • 4 Beds
  • 2 Baths
  • 1,757 Sq Ft

  8 Rumpus Ridge Rd, Chilmark, MA 02535

  Escape to your own getaway with mature landscaped gardens and privacy in the heart of Chilmark. Walk to the Chilmark Store, library, Chilmark Community Center, Beetlebung Farm and bank. Access to Chilmark beaches - Lucy Vincent and Squibnocket - and Menemsha Public Beach are a plus.This four bedroom, two bath home has hardwood floors throughout. The living room and eat-in kitchen separate the

  Julianna Flanders Flanders Real Estate

  8 Rumpus Ridge Rd, Chilmark, MA 02535
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  /42

  $3,600,000

  • 6 Beds
  • 6 Baths
  • 4,104 Sq Ft

  12 Brook Hollow Rd, Vineyard Haven, MA 02568

  Just 9/10 of a mile from Lambert's Cove Beach, this beautifully renovated tri-level home offers over 4,000 square feet of thoughtfully designed living space with six bedrooms and six bathrooms. Expanded and extensively updated in 2023, the home provides exceptional flexibility for entertaining and accommodating family and guests.The top-level features an expansive sun deck with water views of

  Rebecca V Conroy Conroy & Company R.E., Inc.

  12 Brook Hollow Rd, Vineyard Haven, MA 02568
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  /40

  $7,000,000

  • 2 Beds
  • 3 Baths
  • 1,550 Sq Ft

  26 Harbor Hill Rd, Chilmark, MA 02535

  Martha's Vineyard has many wonderful properties but only a few are irreplaceable. Menemsha Harbor is authentic and irreplaceable and this property, Topmast, is the highest and most spacious lot with lovely yard and rare privacy. Topmast was designed and built by master craftsmen in 2016 with unusual quality and care and only occupied a few days each year so virtually brand new. Included close by

  Robert Kenney Tea Lane Associates

  26 Harbor Hill Rd, Chilmark, MA 02535
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  /50

  $3,950,000

  $700K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,702 Sq Ft

  7 Black Point Rd, Chilmark, MA 02535

  Laid-back charm meets island character in this one-of-a-kind up-island beach house. Set on 5.5 acres of natural beauty, this four-bedroom, three-bath main house is full of updates, with bright, fun spaces and a relaxed summer-camp vibe. The creative layout on a single level connects sections of the house via breezy walkway, leading to a bedroom wing including a separate family room, off the

  Meg Bodnar Tea Lane Associates

  7 Black Point Rd, Chilmark, MA 02535
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  /35

  $2,650,000

  • 4 Beds
  • 3 Baths
  • 2,967 Sq Ft

  11 By the Woods, Chilmark, MA 02535

  Dreamlike Chilmark retreat on 4.5+/- acres overlooking the Chilmark Pond & Atlantic Ocean beyond. Uniquely designed with European and medieval history in mind. The House has 3 bedrooms, 3 bathrooms, an atrium dining area, a two-story library, a kitchen, and a pantry/wet bar. Charming garden and plantings surround the home.A must-see to appreciate all the special touches throughout the Main

  Julianna Flanders Flanders Real Estate

  11 By the Woods, Chilmark, MA 02535
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  /26

  $2,395,000

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,510 Sq Ft

  26 Bijahs Way, Chilmark, MA 02535

  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

  Brenda Galligan Karen M. Overtoom R.E.

  26 Bijahs Way, Chilmark, MA 02535
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  /28

  $22,950,000

  • 7 Beds
  • 8.5 Baths
  • 8,200 Sq Ft

  60 Bartimus Luce Rd, Vineyard Haven, MA 02568

  This North Shore beachfront estate represents one of the most breathtaking properties in all of New England. The newly built home was created on a 3.3-acre parcel of land, surrounded by specimen trees, rolling grassy meadows and is highly situated on a stable bank overlooking nearly 250 ft of sandy beach. The home, which celebrates and was imagined utilizing the 14 patterns of biophilic design,

  Gerrett Conover Landvest MV

  60 Bartimus Luce Rd, Vineyard Haven, MA 02568

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