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Newest Homes for Sale in Chilmark, MA

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  • 60A Davis Look Rd Unit 46, West Tisbury, MA 02575
    60A Davis Look Rd Unit 46, West Tisbury, MA 02575
    60A Davis Look Rd Unit 46, West Tisbury, MA 02575
    /9

    $1,600,000

    • Land
    • 5.15 Acres
    • $310,680 per Acre

    60A Davis Look Rd Unit 46, West Tisbury, MA 02575

    Over five acres of privacy in one of the Island's most sought-after settings. This 5.15-acre parcel offers a rare opportunity to build a primary residence and accessory structure on old farmland surrounded by large, mature trees. Idyllic stonewalls run along some of the property lines.Large parcel size and building envelope ensures that the character of the neighborhood endures. Adjacent Land

    Julianna Flanders Flanders Real Estate

    60A Davis Look Rd Unit 46, West Tisbury, MA 02575
  • 99 Oak Ln, Vineyard Haven, MA 02568
    99 Oak Ln, Vineyard Haven, MA 02568
    99 Oak Ln, Vineyard Haven, MA 02568
    /30

    $2,200,000

    • 4 Beds
    • 3 Baths
    • 3,771 Sq Ft

    99 Oak Ln, Vineyard Haven, MA 02568

    This enchanting artist-designed property is tucked away on 2.9 private acres in West Tisbury, a thoughtfully composed retreat with pastoral meadows, mature landscaping, and an unmistakable sense of intention and sophisticated taste. The two-bedroom, two-bathroom Main House is complemented by a spacious two-bedroom, one-bathroom Guest Studio with a fireplace, offering a combined 3,771 square feet

    Rose Ryley Wallace & Co. Sotheby's

    99 Oak Ln, Vineyard Haven, MA 02568
  • 0 Cencelle Unit 57 & 56.1 (part of), Chilmark, MA 02535
    0 Cencelle Unit 57 & 56.1 (part of), Chilmark, MA 02535
    0 Cencelle Unit 57 & 56.1 (part of), Chilmark, MA 02535
    /14

    $1,275,000

    • Land
    • 3.91 Acres
    • $326,087 per Acre

    0 Cencelle Unit 57 & 56.1 (part of), Chilmark, MA 02535

    Set amid the rolling farmlands of Chilmark, this beautiful parcel offers an exceptional opportunity to create your own island retreat. Framed by stone walls, wooded surroundings, and open meadow views, the property combines privacy and natural beauty in a serene rural setting with glacial erratics and trails winding throughout. Elevated and peaceful, this is a rare opportunity to build a home

    Meg Bodnar Tea Lane Associates

    0 Cencelle Unit 57 & 56.1 (part of), Chilmark, MA 02535
  • 29 Scotchmans Ln, Vineyard Haven, MA 02568
    29 Scotchmans Ln, Vineyard Haven, MA 02568
    29 Scotchmans Ln, Vineyard Haven, MA 02568
    /16

    $1,350,000

    • 2 Beds
    • 2 Baths
    • 1,996 Sq Ft

    29 Scotchmans Ln, Vineyard Haven, MA 02568

    Discover the charm of West Tisbury with the perfect blend of country living and village convenience. Ideally located just a short stroll from the heart of town, you'll enjoy easy access to all the West Tisbury Village has to offer. Set on a lovely lot, the home features a spacious southeast-facing deck overlooking a sunny yard. Four detached outbuildings. A generous south-facing living room is

    Diana Gilmore Island Real Estate

    29 Scotchmans Ln, Vineyard Haven, MA 02568
  • 220 North Rd, Chilmark, MA 02535
    220 North Rd, Chilmark, MA 02535
    220 North Rd, Chilmark, MA 02535
    /39

    $2,400,000

    • 7 Beds
    • 4 Baths
    • 2,232 Sq Ft

    220 North Rd, Chilmark, MA 02535

    Welcome to 220 North Road, Chilmark, an idyllic, up-island retreat featuring a 4-BR, post-and-beam, main house and 3-BR guest cottage. Set on three private acres, this verdant oasis is surrounded by preserves, walking trails and even an ancient way that leads directly from the property to Middle Line Woods Preserve, and then all the way to Tea Lane Farm. A two-thirds of an acre conservation

    David Lott Vineyard Open House Real Estate

    220 North Rd, Chilmark, MA 02535
  • 174 Middle Rd, Chilmark, MA 02535
    174 Middle Rd, Chilmark, MA 02535
    174 Middle Rd, Chilmark, MA 02535
    /40

    $1,795,000

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

    174 Middle Rd, Chilmark, MA 02535

    Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming

    Sheila Morse Island Real Estate

    174 Middle Rd, Chilmark, MA 02535
  • 150 Field View Ln, Vineyard Haven, MA 02568
    150 Field View Ln, Vineyard Haven, MA 02568
    150 Field View Ln, Vineyard Haven, MA 02568
    /15

    $1,600,000

    • 4 Beds
    • 2.5 Baths
    • 2,334 Sq Ft

    150 Field View Ln, Vineyard Haven, MA 02568

    A pastoral country road leads to this enchanting wood-shingled Cape-style home, offering three bedrooms and a welcoming blend of comfort and charm. The open-concept kitchen flows into a sunken living and dining area, creating an inviting space for everyday living and entertaining. A desirable first-floor bedroom and convenient first-floor laundry add to the home's thoughtful design. Upstairs you

    Sheila Morse Island Real Estate

    150 Field View Ln, Vineyard Haven, MA 02568
  • 23 Flanders Ln, Chilmark, MA 02535
    23 Flanders Ln, Chilmark, MA 02535
    23 Flanders Ln, Chilmark, MA 02535
    /49

    $9,750,000

    • 7 Beds
    • 5 Baths
    • 3,617 Sq Ft

    23 Flanders Ln, Chilmark, MA 02535

    A rare offering of land, history, and sweeping water views — this exceptional 8.7+/- acre estate commands panoramic views of Menemsha Pond and Vineyard Sound from its rolling lawns and open meadows. Property includes parking and access to Menemsha Pond.Whether you're drawn by the storied architecture, the expansive land, or the irreplaceable Vineyard Sound vistas, this is a compound that

    Julianna Flanders Flanders Real Estate

    23 Flanders Ln, Chilmark, MA 02535
  • 25 Brickyard Rd, Chilmark, MA 02535
    25 Brickyard Rd, Chilmark, MA 02535
    25 Brickyard Rd, Chilmark, MA 02535
    /56

    $16,250,000

    • 6 Beds
    • 8 Baths
    • 8,648 Sq Ft

    25 Brickyard Rd, Chilmark, MA 02535

    Perched on an elevated 10.69-acre site off picturesque North Road in Chilmark, this exceptional private compound pairs natural beauty with architectural distinction. Designed by renowned architect Patrick Ahearn and built by Rosbeck Builders, the 7,691-square-foot residence enjoys dramatic views across the Menemsha Hills and Vineyard Sound toward the Elizabeth Islands, with spectacular sunsets.

    Peyton Wallace Studio Realty LLC

    25 Brickyard Rd, Chilmark, MA 02535
  • 3 Bens Way, Chilmark, MA 02535
    3 Bens Way, Chilmark, MA 02535
    3 Bens Way, Chilmark, MA 02535
    /46

    $3,900,000

    • 3 Beds
    • 4 Baths
    • 2,960 Sq Ft

    3 Bens Way, Chilmark, MA 02535

    Sited on 3.94 acres in the North Tabor Farm subdivision, this 3 bedroom, 4 bath farmhouse offers privacy in a quiet, wooded, agricultural setting abutting working pastures. Built in 1995, this home features elegant living room and dining rooms with 12 foot ceilings and large paned windows which flood the rooms with an abundance of natural light. Views are seen to the yard spaces and the heated,

    Russell Maloney Russell Maloney Real Estate

    3 Bens Way, Chilmark, MA 02535
  • 26 Harbor Hill Rd, Chilmark, MA 02535
    26 Harbor Hill Rd, Chilmark, MA 02535
    26 Harbor Hill Rd, Chilmark, MA 02535
    /40

    $7,000,000

    • 2 Beds
    • 3 Baths
    • 2,250 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
  • 21 & 25 Fulling Mill Rd, Chilmark, MA 02535
    21 & 25 Fulling Mill Rd, Chilmark, MA 02535
    21 & 25 Fulling Mill Rd, Chilmark, MA 02535
    /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
  • 16 Red Coat Hill Rd, Vineyard Haven, MA 02568
    16 Red Coat Hill Rd, Vineyard Haven, MA 02568
    16 Red Coat Hill Rd, Vineyard Haven, MA 02568
    /25

    $6,500,000

    • 6 Beds
    • 7 Baths
    • 4,753 Sq Ft

    16 Red Coat Hill Rd, Vineyard Haven, MA 02568

    Private West Tisbury Oasis – Modern Luxury on 4.85 Acres Built by the highly regarded Novo Builds and designed by acclaimed architect Zander Auerbach, this newly constructed estate in the heart of West Tisbury offers the perfect blend of architectural sophistication, privacy, and resort-style amenities. Set on 4.85 acres, the main residence spans 3,806 square feet with an additional unfinished

    Joe & Nicole Holland Vineyard Dream Realty LLC

    16 Red Coat Hill Rd, Vineyard Haven, MA 02568
  • 34 Ebens Ln, Chilmark, MA 02535
    34 Ebens Ln, Chilmark, MA 02535
    34 Ebens Ln, Chilmark, MA 02535
    /8

    $2,725,000

    • Land
    • 7.6 Acres
    • $358,553 per Acre

    34 Ebens Ln, Chilmark, MA 02535

    This rare two-lot offering off Middle Road in Chilmark presents a private sanctuary abutting approximately 50 acres of conservation land. The gently rolling landscape is accented by ancient stone walls and striking glacial boulders, creating a setting of timeless Vineyard character. Ideal for a generational compound or two distinct residences, the property offers both serenity and convenience --

    Peyton Wallace Studio Realty LLC

    34 Ebens Ln, Chilmark, MA 02535
  • 28 Black Point Rd, Chilmark, MA 02535
    28 Black Point Rd, Chilmark, MA 02535
    28 Black Point Rd, Chilmark, MA 02535
    /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
  • 52 Oak Knoll Rd, Vineyard Haven, MA 02568
    52 Oak Knoll Rd, Vineyard Haven, MA 02568
    52 Oak Knoll Rd, Vineyard Haven, MA 02568
    /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
  • 12 Brook Hollow Rd, Vineyard Haven, MA 02568
    12 Brook Hollow Rd, Vineyard Haven, MA 02568
    12 Brook Hollow Rd, Vineyard Haven, MA 02568
    /42

    $3,600,000

    Open Thu 4PM - 6PM
    • 6 Beds
    • 6 Baths
    • 4,100 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. A spa-like backyard features an inviting in-ground pool and hot tub

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

    12 Brook Hollow Rd, Vineyard Haven, MA 02568
  • 30 & 40 Elias Ln, West Tisbury, MA 02575
    30 & 40 Elias Ln, West Tisbury, MA 02575
    30 & 40 Elias Ln, West Tisbury, MA 02575
    /30

    $3,995,000

    • 6 Beds
    • 3.5 Baths
    • 3,070 Sq Ft

    30 & 40 Elias Ln, West Tisbury, MA 02575

    A beautiful pastoral, private family compound in West Tisbury, on 7.5 glorious acres of meadow comprised of two parcels, offers a rare opportunity. Elias Lane is a quiet country road tucked behind Misty Meadows and just minutes from West Tisbury village. The property features a lovingly maintained 4 BDR main house with a well appointed kitchen, recent sun porch addition an elegant Lew French

    Elissa Lash Tea Lane Associates

    30 & 40 Elias Ln, West Tisbury, MA 02575
  • 132 South Rd, Chilmark, MA 02535
    132 South Rd, Chilmark, MA 02535
    132 South Rd, Chilmark, MA 02535
    /34

    $1,600,000

    • 3 Beds
    • 3 Baths
    • 2,155 Sq Ft

    132 South Rd, Chilmark, MA 02535

    Nestled on a private, 1.9-acre lot along historic South Road in Chilmark, this charming New England retreat offers an exceptional sense of tranquility and classic Martha's Vineyard living. Built in 1950, Vineyard Home offers 2 bedrooms and 2 full bathrooms great light, cozy additional living spaces and fireplace. Multiple patios and gardens seamlessly connecting the living spaces to the

    Lisa Da Silva Compass

    132 South Rd, Chilmark, MA 02535
  • 96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    96 Hammett Ln, Chilmark, MA 02535
    /37

    $3,795,000

    • 3 Beds
    • 4 Baths
    • 3,426 Sq Ft

    96 Hammett Ln, Chilmark, MA 02535

    Beautifully designed and built Post & 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

    Brenda Galligan Karen M. Overtoom R.E.

    96 Hammett Ln, Chilmark, MA 02535
  • 42 Field View Ln Unit 79, West Tisbury, MA 02575
    42 Field View Ln Unit 79, West Tisbury, MA 02575
    42 Field View Ln Unit 79, West Tisbury, MA 02575
    /19

    $799,000

    • Land
    • 2.1 Acres
    • $380,476 per Acre

    42 Field View Ln Unit 79, West Tisbury, MA 02575

    Nestled among the open fields of West Tisbury, this beautiful building parcel offers apeaceful, bucolic setting with endless potential. An eclectic artists' camp graces theproperty, creating a unique sense of character and inspiration. Meandering walking trailswind through a diverse landscape of pine, oak, and beech trees, inviting you to exploreand enjoy the natural surroundings.

    kyle Neyer Tea Lane Associates

    42 Field View Ln Unit 79, West Tisbury, MA 02575
  • 131 Pond View Farm Rd Unit 1-7, West Tisbury, MA 02575
    131 Pond View Farm Rd Unit 1-7, West Tisbury, MA 02575
    131 Pond View Farm Rd Unit 1-7, West Tisbury, MA 02575
    /6

    $3,750,000

    • Land
    • 3.6 Acres
    • $1,041,667 per Acre

    131 Pond View Farm Rd Unit 1-7, West Tisbury, MA 02575

    Set on a picturesque peninsula along Tisbury Great Pond, this exceptional pondfront parcel offers a rare opportunity to own a piece of Martha's Vineyard's rural landscape. Currently used for equestrian activities, the expansive open acreage is nestled in one of the Island's most beautiful and unspoiled settings, evoking West Tisbury's rich agricultural heritage. This property is a blank slate,

    Meg Bodnar Tea Lane Associates

    131 Pond View Farm Rd Unit 1-7, West Tisbury, MA 02575
  • 64 Christiantown Rd, Vineyard Haven, MA 02568
    64 Christiantown Rd, Vineyard Haven, MA 02568
    64 Christiantown Rd, Vineyard Haven, MA 02568
    /39

    $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
  • 8 Rumpus Ridge Rd, Chilmark, MA 02535
    8 Rumpus Ridge Rd, Chilmark, MA 02535
    8 Rumpus Ridge Rd, Chilmark, MA 02535
    /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
  • 139 Tea Ln, Chilmark, MA 02535
    139 Tea Ln, Chilmark, MA 02535
    139 Tea Ln, Chilmark, MA 02535
    /34

    $2,095,000

    $100K PRICE DROP
    • 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
  • 23 Onkokemmy Rd Unit 12, West Tisbury, MA 02557
    23 Onkokemmy Rd Unit 12, West Tisbury, MA 02557
    23 Onkokemmy Rd Unit 12, West Tisbury, MA 02557
    /9

    $1,200,000

    • Land
    • 3.42 Acres
    • $350,877 per Acre

    23 Onkokemmy Rd Unit 12, West Tisbury, MA 02557

    Just beyond the Great White Oak and down scenic Rogers Path, this pastoral West Tisbury parcel offers nearly 3.5 acres of privacy and natural beauty. Moments from the village center yet tucked into a peaceful landscape, the property presents an opportunity to create a custom Vineyard compound. As you traverse your own grove of majestic oak trees, the landscape opens to an idyllic pasture dotted

    Katherine Donahue Sandpiper Realty

    23 Onkokemmy Rd Unit 12, West Tisbury, MA 02557
  • 23 Onkokemmy Rd, West Tisbury, MA 02557
    23 Onkokemmy Rd, West Tisbury, MA 02557
    23 Onkokemmy Rd, West Tisbury, MA 02557
    /9

    $1,200,000

    • Land
    • 3.42 Acres
    • $350,877 per Acre

    23 Onkokemmy Rd, West Tisbury, MA 02557

    Just beyond the Great White Oak and down scenic Rogers Path, this pastoral West Tisbury parcel offers nearly 3.5 acres of privacy and natural beauty. Moments from the village center yet tucked into a peaceful landscape, the property presents an opportunity to create a custom Vineyard compound. As you traverse your own grove of majestic oak trees, the landscape opens to an idyllic pasture dotted

    Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    23 Onkokemmy Rd, West Tisbury, MA 02557
  • 8 Snail Rd, Chilmark, MA 02535
    8 Snail Rd, Chilmark, MA 02535
    8 Snail Rd, Chilmark, MA 02535
    /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
  • 53 Stoney Hill Rd, Vineyard Haven, MA 02568
    53 Stoney Hill Rd, Vineyard Haven, MA 02568
    53 Stoney Hill Rd, Vineyard Haven, MA 02568
    /38

    $3,099,000

    $100K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,082 Sq Ft

    53 Stoney Hill Rd, Vineyard Haven, MA 02568

    This custom-built Martha’s Vineyard residence blends timeless elegance with contemporary luxury, offering exclusive access to Lambert’s Cove Beach.At its heart is a chef’s kitchen with bespoke cabinetry, honed Carrara marble, Wolf and Sub-Zero appliances, Miele dishwasher, and Hudson Valley lighting. An adjacent custom bar features Dolomite Italian granite, ideal for entertaining.The home boasts

    Jennifer B. DaSilva Compass

    53 Stoney Hill Rd, Vineyard Haven, MA 02568
  • 145 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    145 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    145 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
    /36

    $1,349,000

    $50K PRICE DROP
    • 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
  • 49 Gosnolds Way, Chilmark, MA 02535
    49 Gosnolds Way, Chilmark, MA 02535
    49 Gosnolds Way, Chilmark, MA 02535
    /32

    $5,200,000

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

    49 Gosnolds Way, Chilmark, MA 02535

    Set high on the north shore with panoramic views of Vineyard Sound and deeded private beach access, this secluded 9.8-acre estate enjoys a rare setting abutting conservation land and the Menemsha Hills trail network. The meticulously maintained residence features a reverse floor plan designed to maximize natural light, soaring ceilings, and stunning water views. The upper level offers an

    Bonnie Pierce Wallace & Co. Sotheby's International Realty

    49 Gosnolds Way, Chilmark, MA 02535
  • 4 Rock Pond, West Tisbury, MA 02575
    4 Rock Pond, West Tisbury, MA 02575
    4 Rock Pond, West Tisbury, MA 02575
    /32

    $1,140,000

    $35K 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
  • 188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
    /50

    $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 just 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 vegetable garden, a storage shed, and outdoor shower. Inside is open with

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

    188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
  • 49 Gosnold's Way, Chilmark, MA 02535
    49 Gosnold's Way, Chilmark, MA 02535
    49 Gosnold's Way, Chilmark, MA 02535
    /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
  • 35 S Bowl Rd, Chilmark, MA 02535
    35 S Bowl Rd, Chilmark, MA 02535
    35 S Bowl Rd, Chilmark, MA 02535
    /42

    $4,995,000

    $405K PRICE DROP
    • 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
  • 15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535
    15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535
    15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535
    /11

    $1,250,000

    • Land
    • 1.9 Acres
    • $657,895 per Acre

    15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535

    Nestled in a bucolic setting moments from the iconic Menemsha fishing village, this beautiful and fully engineered parcel is approved for a 6BR home. One of the few remaining Menemsha buildable lots makes this a rare opportunity. With room for a pool with a special permit!Surrounded by ancient stone walls on three sides and mature trees, the land has stunning sunset skies, lovely pastoral

    Jill Napior Tea Lane Associates

    15 Menemsha Inn Rd Unit 9, Chilmark, MA 02535
  • 4 Rock Pond Rd, Vineyard Haven, MA 02568
    4 Rock Pond Rd, Vineyard Haven, MA 02568
    4 Rock Pond Rd, Vineyard Haven, MA 02568
    /31

    $1,140,000

    $35K 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
  • 100 Gosnolds Way, Chilmark, MA 02535
    100 Gosnolds Way, Chilmark, MA 02535
    100 Gosnolds Way, Chilmark, MA 02535
    /46

    $3,400,000

    • 4 Beds
    • 2.5 Baths
    • 2,383 Sq Ft

    100 Gosnolds Way, Chilmark, MA 02535

    Well designed and maintained home, situated on 5 acres in a private, desirable neighborhood. Open floor plan with high ceilings that allows a lot of great light into house. The screened in porch is perfect for family dinners or relaxing. Nice water views of Vineyard Sound & the Elizabeth Islands. Short walk to the Brickyard Beach on the North Shore, rights are included with property, where you

    Julianna Flanders Flanders Real Estate

    100 Gosnolds Way, Chilmark, MA 02535
  • 20 James Pond Way, Vineyard Haven, MA 02568
    20 James Pond Way, Vineyard Haven, MA 02568
    20 James Pond Way, Vineyard Haven, MA 02568
    /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
  • 6 Wakeman Rd, Chilmark, MA 02535
    6 Wakeman Rd, Chilmark, MA 02535
    6 Wakeman Rd, Chilmark, MA 02535
    /53

    $9,875,000

    • 6 Beds
    • 5.5 Baths
    • 3,758 Sq Ft

    6 Wakeman Rd, Chilmark, MA 02535

    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

    Jill Napior Tea Lane Associates

    6 Wakeman Rd, Chilmark, MA 02535

Showing Results 1 - 40, Page 1 of 3

Massachusetts Dukes County

Newest Listings for Sale in Chilmark, MA

Frequently Asked Questions

What are the most popular zip codes in Chilmark, MA?
The most popular zip codes in Chilmark, MA include 02535, 02568, 02575, 02539 and 02536.
What are the most popular neighborhoods near Chilmark, MA?
The most popular neighborhoods near Chilmark, MA are Chilmark, West Tisbury, Edgartown, Vineyard Haven and Oak Bluffs.
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