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 of open pastures, ancient stone walls, woodlands, and the Atlantic beyond. The four-bedroom residence features an open-concept layout that seamlessly connects indoor living spaces to a full-length deck—perfect for entertaining or simply soaking in the peaceful surroundings. Recent updates include new kitchen appliances and a high-efficiency heat pump system with central air conditioning. A true highlight of this property is the land itself. There is an extensive network of trails winding throughout the property, leading through meadows and forest, past streams, a large pond and striking glacial erratics. This property has an extraordinary sense of place and feels like a private piece of up-island history—rich in character, natural beauty, and possibility. Six-bedroom septic installed. Abutting 3.9-acre building parcel available.

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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 primary bedroom. The expansive screened porch effectively doubles the living room, offering an enchanting area for relaxation or gatherings. Tucked just beyond the main house is a versatile barn with its own half bath, currently set up as a rec room and gym, great for guests and entertaining. There are three outdoor showers, full insulation and mini-splits throughout for heat and A/C. The yard is expansive and private, with room to dream—gardens, a pool, or just wide-open space to roam. Best part of all, ownership at Black Point Beach is included, so you can easily bike, stroll or drive down the quiet dirt road for daily visits to the ocean! Approved eight-bedroom septic plan included.

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Magical waterfront Quitsa pond cottage with private dock will change your life living on the water. Every day is special when you have an intimate relationship with Quitsa Pond. Calm, safe and breathtaking, adventure is out the doorstep and the sunsets.... Designed with the setting in mind this sublime piece of architecture has wonderful spaces, fantastic detail and so much packed into a smaller home. Landscape design by Edwina von Gal accentuates the simplistic beauty of this property. A rare and unique inspirational built-in art installation by Andy Goldsworthy adorns the northeastern wall of the living room. A fireplace created with slate roof tiles unlike any other is built into the southwest wall. Custom Will Parry windows and doors throughout with giant floor to ceiling glass doors that slide wide to join the inside and outside of the home bringing the natural beauty of the area into the house. Step outside and onto your private dock with power and water where you can keep 3 boats, one up to 30 feet long. Walk down your boat ramp into the warm waters of the pond for a swim, kayak or paddleboard adventure. A custom staircase influenced by Frank LLoyd Wright has built-in book cases and metal work by artisan Whit Hanschka which brings you to the upper floor where there are 3 bedrooms and 2 baths. 2 of the bedrooms open out onto a small deck overlooking the pond and all have views of the water. This home is cozy with radiant floor heat under the tile floor and AC for the hot steamy summer nights. This house is one of a kind.

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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, saltwater, 50x25x12 in-ground Pebble-Tek pool and pool house. There is an eat in kitchen with ample cabinetry and leathered granite countertops. Doors open onto the rear deck for outdoor entertaining. A guest bedroom, full bath, laundry and hallway lined with built in shelves are found on this level. Two dedicated office spaces—one on each level—provide exceptional flexibility. The upper office offers a vaulted ceiling with exposed beams, wide plank flooring, large windows, and sliding glass doors and sleeping loft. The lower office includes cork flooring, built in bookcases, large windows, a full bath, sauna, gym area, a wine closet and a cedar closet. The 22' x 18' primary bedroom includes a spacious bath with a wood framed soaking tub and steam shower. A guest bedroom with ensuite bath completes the upper level. Other features of this home and property include solar panels for net-zero living, radiant heated bathrooms and dining room, central air conditioning, wood flooring, gas fireplace, fenced vegetable garden, and a 4-bedroom septic system supporting future expansion. A separate artist/writing/garden studio, “The Bunkie,” sits at the end of the gravel drive and is equipped with heat and air conditioning for year round use.

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This 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 tiled baths, incredible workmanship throughout with an eye for style. warmth and comfort. There is also a generous laundry room with wash sink. The fully finished walkout basement includes a great room, finished utility room with a dog bath, workshop and a full bath with shower. Beautifully landscaped grounds with multiple perennial beds , vegetable gardens and surrounding stone retaining walls. Privately sited on 4.80 acres.

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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 can enjoy swimming and watching beautiful sunsets. There is also a 1 car garage with a work space.

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A place of serenity tucked in the woods of Chilmark. Beautifully designed & constructed home which was completely renovated in 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media room with Sonos Music System, and Lutron Radio RA Switching System (can be smartphone controlled) Radiant heat in mudroom, and all bathrooms (except 1/2 bath in basement) to keep cozy in the cooler months, and a heat pump system with Boiler back up. Six bedroom septic. Close proximity to North Road and Middle Road. Beautiful home with a lot of attention to details. sq. footage is Approx.

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Bright & Airy Black Point Retreat with Deeded Beach Lot 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 backdrop and the shoreline is just moments away. Included with the property is a coveted beach lot (key) to this private south shore beach. Thoughtfully designed, the home has a welcoming entry that opens into a light-filled open floor plan that flows seamlessly onto a screened porch and expansive sun deck, creating an ideal setting for indoor-outdoor living and entertaining. The upper level features a serene primary suite with peeks at the water and a private bath. The lower level offers a second bedroom, full bath, and additional living space. The unique layout provides comfort and privacy for family and guests. A substantial detached garage is complemented with a finished guest suite on the second floor with a bedroom and full bath, creating an ideal space for visitors or extended family. Numerous improvements made over the years allow for the property to be enjoyed immediately. Perfectly suited for peaceful island living, the expansive 5.4-acre parcel should allow for future expansion and exceptional flexibility. This serene property offers long-term value in one of Chilmark's most desirable locations.

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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 — just minutes from Lucy Vincent and Squibnocket beaches, and the historic fishing village of Menemsha. Engineering for wells and home sites is complete and utilities are on site. Architectural plans by Morgan Studio for a multi-home compound with a swimming pool and accessory structures are available for review upon request.

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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 House, Guest Camp, and Garage.

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Rare opportunity to build on Chilmark's south shore. This 1.4 acre parcel should allow for new construction of 3,100 square feet and 24 feet in height, by right, with building department approval. Views to the Atlantic Ocean and Chilmark Pond can be seen from the second floor. This parcel comes with a dock on the pond which provides access to a beautiful barrier beach on the Atlantic. Well in place, buyer responsible for new septic system. Fire destroyed house in 2020. See old and new views in document attached.

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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 buffer runs along the length of the back of the property for further privacy. Just across North Road from the ancient way is the walking entrance to Great Rock Bight. If you enjoy the splendid rural nature of upisland Chilmark, then this is your place. MAIN HOUSE: The rich wooden interior radiates warmth and relaxation and is enhanced by the living room's floor-to-cathedral-ceiling natural stone fireplace. A large deck wraps around nearly half the house, giving you treehouse-like views and a magical setting for outdoor entertaining. GUEST COTTAGE: This intimate log-home is a separate getaway, hidden by a clutch of tall trees nearly 100 yards away from the main house which creates highly protected privacy. Flowers and herb gardens surround its sunny deck, creating a peaceful nook for reading and relaxation. A detached bedroom is like a honeymoon retreat that guests will love. A new, 3BR septic system was just installed (July 2026). EACH HOUSE HAS its own septic system and well, making them truly separate and independent. There's room for a swimming pool. Leave the congestion of down-island comfortably behind, while enjoying easy recreation access to public lands and beaches (Lucy Vincent, Squibnocket), sailing on Quitsa & Menemsha ponds, and proximity to Menemsha and the Chilmark Store, community center and famed Chilmark Tavern. ASK ABOUT partial Seller financing. Also, ASK ABOUT about Seller lease-back of the Guest Cottage which could significantly reduce the purchase price.

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