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$2,250,000
4 Beds ⋅ 3 Baths ⋅ 73555055 MLS

21 & 25 Fulling Mill Road, Chilmark

Listing courtesy of Listing Agent: Jessica Holtham from Listing Office: Wallace & Co. Sotheby's International Realty.
$3,795,000
3 Beds ⋅ 4 Baths ⋅ 73545525 MLS
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 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 tile.

96 Hammett Ln, Chilmark

Listing courtesy of Listing Agent: Brenda Galligan from Listing Office: Karen M. Overtoom R.E..
$15,400,000
6 Beds ⋅ 9 Baths ⋅ 73538291 MLS
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 and artisans. Grounded in its natural setting, the architecture features dramatic design elements and walls of glass to connect seamlessly with the idyllic landscape. An infinity-edge pool overlooks the pastoral ocean horizon that defines Chilmark, while a screened porch and large outdoor living areas extend the home into its surroundings. A separate 2-bedroom guest house and additional 5.6 acre lot provide flexibility for expansion and subdivision, while a private path to Chilmark Pond allows for deeded access to South Beach. Horizon House is a pleasure to show, by appointment only.

8 Snail Road, Chilmark

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.
$5,200,000
5 Beds ⋅ 4 Baths ⋅ 73534187 MLS
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 open-concept kitchen, dining, and living area, a private primary suite, office, screened porch, and expansive decks. Thoughtfully appointed with air conditioning, a whole-house generator, integrated sound system, and outdoor lighting. The grounds include a tennis court, landscaped gardens with a water feature, and several acres of open meadow surrounded by mature woodland, ensuring exceptional privacy with no visible neighboring homes. Ample room exists for a pool, and the parcel may offer subdivision potential. Ownership includes rights to Brickyard Beach.

49 Gosnolds Way, Chilmark

Listing courtesy of Listing Agent: Bonnie Pierce from Listing Office: Wallace & Co. Sotheby's International Realty.
$4,995,000
3 Beds ⋅ 2 Baths ⋅ 73531359 MLS
Rare opportunity in the Seven Gates Farm community of Chilmark. Designed by architects Jane and Christian Langmuir, this exceptional three-bedroom home is set on 5.3 acres of beautifully landscaped grounds. Thoughtfully designed to embrace natural light and its surroundings, the residence blends natural materials with contemporary architectural details.The dramatic great room features a striking fireplace with a glacial stone hearth, while the open kitchen offers custom cabinetry and premium appliances. The primary suite includes two office spaces, a media area, walk-in closet, and spa-inspired bath. A private guest suite features a full bath with soaking tub, and the third bedroom is currently configured as a wellness space with sauna. Additional amenities include an attached two-car garage, owned solar panels, EV charging station, and a six-bedroom septic system.Seven Gates Farm residents enjoy access to private beaches, docks, tennis courts, and more.1000 acres of protected land.

35 South Bowl Rd, Chilmark

Listing courtesy of Listing Agent: Tina Miller from Listing Office: Donnelly + Co..
$45,000,000
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

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.
$2,395,000
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

Listing courtesy of Listing Agent: Brenda Galligan from Listing Office: Karen M. Overtoom R.E..

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