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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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 and potential for a guest house with proper town permitting after 5 years.

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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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This Chilmark home is one-of-a-kind - a warm, charming hideaway set on 4.4 spectacular acres just off North Road. At the top of a shady driveway you are met by stone walls so typical of Chilmark from a bygone era. You enter a courtyard through cedar gates where you find beautifully tended flower beds. The porch is the ideal location for you to enjoy the private, peaceful courtyard. Immediately upon entering the home you captivated by the warm ambience. The main living spaces and primary bedroom suite all showcase views of a sweeping meadow punctuated by granite boulders and stately oaks. In addition to the primary bedroom suite and additional sleeping spaces on the main level, there is a large finished lower level with private entrance - ideal for accommodating your guests. Back upstairs and across the courtyard, there is an unfinished structure with screened porch begging to be converted into a bunkhouse for the kids, if not a studio or office. There are two garage spaces for cars or boats. Visitors are encouraged to walk the grounds and enjoy the private nooks and crannies of this magical piece of land. The property is less than 2 miles to Menemsha Village and Beach, 1 mile to the north shore beach at Great Rock Bight, and a 3-mile drive to parking at Lucy Vincent Beach.

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Enjoy the carefree ease of Mid Century Modern architecture in this pristine classic, filled with sunshine and treetop views. Located on a quiet hilltop in Chilmark and offered turn-key furnished, this simple but elegant summer home features four bedrooms, three baths, with original details and design. Its open all-on-one-floor layout with large glass panel doors and windows throughout lead to a sun-drenched deck, heated in-ground plunge pool, and grassy lawn. Includes a well-equipped kitchen, large living room with wood burning fireplace, a dining area overlooking the pool and yard, air conditioning, cable television and internet and a distant sense of the ocean. The home sleeps 8 comfortably, with two ensuite bedrooms (king and queen), an additional queen room, and a twin room perfect for guests or little ones. Outdoors you will find an inground, 4-foot-deep heated pool including pool side furniture, umbrellas, hammock, outdoor shower, and a gas barbecue. Step across the road to the Land Bank’s Fulling Mill and Ocean View Farm Preserves with stunning ocean views and 20+ acres of walking trails. As a Chilmark resident you will enjoy the beautiful beaches of Lucy Vincent and Squibnocket. This property has a strong rental history with rates ranging to $13,000 weekly. Easy to show, easy to love. Please call listing broker.

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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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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. Total square footage represents house (1,400 sq. ft.) and guest house (518 sq. ft.). A shared six (6) bedroom septic system services both houses.

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Rare Chilmark compound with beach access, barn, horse stalls, and fenced pasture on 1.6 acres. Set just over the West Tisbury line, this restored 1885 farmhouse offers a compelling blend of authentic Vineyard character, modern comfort, and access to Chilmark’s coveted south shore beaches, including Lucy Vincent and Squibnocket. The property unfolds as a small country compound with a distinctly pastoral sensibility. A classic barn, two run-in horse stalls, a fenced field, and a coop support equestrian pursuits or a small gentleman’s farm—an increasingly uncommon offering in Chilmark at this price point. The open acreage invites outdoor living, from summer entertaining and gardening to quiet enjoyment of the surrounding landscape and privacy. Inside, the home balances antique charm with thoughtful updates. Four bedrooms and three full baths include two main-level bedrooms and two second-floor en-suite guest rooms, creating a comfortable and flexible layout for hosting family and friends. Living spaces are warm and inviting, with a masonry double fireplace, preserved period details, and an updated kitchen and baths. Recent improvements include HVAC, windows, insulation, and a five-bedroom septic system, offering flexibility for future expansion and barn renovation. Located steps from West Tisbury village, Alleys General Store, the library, the Yoga Barn, the Grange Hall and nearby conservation trails, the setting combines convenience with the privacy and natural beauty that define Chilmark. A distinctive Vineyard offering with uncommon versatility—equally suited as a summer retreat, year-round residence, or small-scale farmstead.

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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 apple! The property is gated and entirely enclosed with deer fencing. There is also a storage shed and a detached garage. Easy access to Menemsha, Chilmark Store and Chilmark Beaches. Outdoor surveillance system on premises, audio and video.

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