Waterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilmark Pond, this exceptional waterfront residence offers rare privacy, refined design, generous water views and easy pond access. Thoughtfully renovated in 2018, the home blends contemporary sophistication with the beauty of its natural environment. A private dock on the property provides direct pond access. The beautifully manicured path, leads from the house to the dock, where you can launch across the pond to your own private South Shore beach lot, included in this sale. Of course the new owner also has access to iconic Lucy Vincent and Squibnocket beaches. The property is surrounded by over seven acres of abutting conservation land. The grounds are meticulously designed, with mature landscaping and gardens that feel both timeless and intentional. This is more than a residence. It's the key to embracing the Chilmark lifestyle defined by privacy, water access, and understated elegance.

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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, either Great Rock Bight or Spring Point's 1 mile private beach. With Spring Point's 90 acres of common land, along with this exclusive community's private & quiet paths along the bluff and in the woods, it's like LIVING IN A NATURE PRESERVE. The 211 acre Menemsha Hills Reservation is nearby. The house itself, designed by the Nantucket architect Ray Pohl and Boston landscape architect, Skip Burck, majors in LIVABILITY. Along with the three shaded ocean-facing exterior rooms, the house has three set-apart bedroom wings. Five of the house's 8 rooms qualify as "wings of light," meaning windows on three sides. The house was "built to last" by the highly regarded builder, Heikki Soikkeli. The Lew French floor-to-ceiling FIELD-STONE FIREPLACE and CHIMNEY are WORKS OF ART.The house is MOVE-IN-Condition. What sets this house apart is its combination of many highly desirable features - architectural, practical and beautiful - which is what makes it so difficult for the owners, who built the house, to part with it.

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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 short walk to the Menemsha harbor, beach, boutique galleries, and fresh seafood restaurants—from the daily catch from local fish markets to the fine dining of the Home Port. To the Southeast, watch Menemsha Pond ebb and flow around sandy islands with 120 degrees of unobstructed view. To the Northwest, elevated rooms look out over the sunset on Menemsha Harbor. A secluded lawn is partially shaded by healthy blue spruce and bordered by an ancient stone wall. The dock traverses the estuary into a private cove opening. The property has a permit to extend the dock access from the property to 64’. This is a significant dock that can accommodate a power boat, sailboat, and multiple kayaks and paddleboards. Docks are no longer permitted on Menemsha Pond, making this an incredible opportunity for a waterfront house and guest house with a dock. This is a secure environment surrounded by water on three sides. The home is well built with quality hardwood floors, doors, and trim. The wood-burning fireplace has custom-built cabinetry and trim. Both the house and guest house are flooded with natural light due to the southern orientation. The property is set up for year-round water through the Menemsha Water Company, and a new 5-bedroom Title-5 compliant septic is installed. Unique remodeling and expansion ideas included in photos have been designed by Sullivan and Associates. The potential here is exciting compared with other waterfront island properties due to the existing height, large attic with views, and a lower walkout level with tremendous natural light, which together allow for valuable future living square footage. You are welcome to continue the legacy of this extraordinary real estate.

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Set on three beautifully landscaped acres, this exceptional six-bedroom property offers a seamless blend of modern farmhouse design and timeless Vineyard appeal. The estate features a five-bedroom, five and a half bathroom main residence, along with a one-bedroom guest suite above a two-car barn and 16' x 40' swimming pool. This thoughtfully designed post and beam main home was featured in Country Home magazine, and showcases wide-plank satin-finished oak flooring, soaring ceilings, custom cable rail staircases, and a striking double sided propane fireplace that anchors the living spaces. A screened porch extends the living area outdoors, offering both dining and lounge areas centered around another beautiful wood burning fireplace. A finished lower level adds additional square footage with a TV area plus pool and ping pong and a large utility space for laundry and storage. Outdoors, the elegance continues with climbing roses, classic stone walls, and a sweeping lawn that leads to the swimming pool and a traditional two car barn. Above the barn, a charming one-bedroom, one-bath suite provides a private retreat for guests. It's rare to find a home like this in Chilmark, combining a superior quality finished home with scale and style. All in a versatile setting - convenient to down-island while enjoying access to Chilmark’s coveted beaches and amenities.

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Perfectly situated on Nashaquitsa Pond, this charming two-bedroom cottage offers sweeping views of Quitsa and Menemsha Pond from a rare vantage point few properties can match. The cottage includes private beach rights to Short Beach and dock access for a mooring. Inside, hand-painted floors and a warm, unpretentious interior reflect the authentic character of Old Vineyard — a property that has brought multiple families together over generations of summers. For those seeking an authentic connection to the Vineyard's natural beauty and storied past, this is a rare and remarkable find.

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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 significantly expanded in 2023, the home blends craftsmanship with modern comfort. Enjoy sweeping views of the Atlantic Ocean, Squibnocket Point, and Nomans Land island from both interior living spaces and outdoor vantage points. Designed for multigenerational living, the home offers multiple private zones - including a dedicated media room - allowing for both connection and retreat. This is a rare opportunity to own a meaningful piece of Chilmark—an offering not to be missed.

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Rare opportunity in the Seven Gates Farm community of Chilmark. Designed by acclaimed architects Jane & Christian Langmuir, this exceptional home is nestled on 5.3 acres of beautifully landscaped grounds. Thoughtfully designed to embrace warmth, natural light, and its surrounding environment, the three-bedroom residence seamlessly blends natural elements with contemporary architectural details. The dramatic great room is anchored by a striking fireplace with a glacial stone hearth. The open kitchen is complemented by custom-crafted cabinetry and top-tier appliances. The primary suite includes two separate office spaces and a media space, a walk-in closet, and a spa-inspired bathroom. A private guest suite offers a full bath with a soaking tub, providing comfort and privacy for visitors. The third bedroom is currently configured as a gym and wellness space, complete with a sauna. The lower level includes an attached two-car garage. Designed with sustainability and ease of ownership in mind, the property features owned solar panels, an electric vehicle charging station, and a six-bedroom septic system, offering flexibility for future expansion. The striking entrance is highlighted by a beautiful stone patio and tranquil water feature. Surrounded by iconic stone walls, mature trees, the property offers a rare connection to the natural beauty of the Island. Residents of Seven Gates Farm enjoy access to 3 private beaches on Vineyard Sound, two docks, two tennis courts, and more than 1,000 acres of protected land—including vast open fields, woodlands, ponds and miles of walking trails. This is an extraordinary blend of privacy, community, and stewardship. A boat mooring can be transferred with the property. 2% fee paid to Seven Gates Farm at Closing. MV Land Bank fee is additional.

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CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this Modern Chilmark Farmhouse home has been thoughtfully restored and expanded, offering a serene blend of timeless character and modern comfort. The main residence features 3 bedrooms and 3.5 baths, within approximately 5,400 square feet of gracious living space. The sunny, light-filled main house showcases an open kitchen and living area anchored by a striking central fireplace—ideal for both everyday year-round living and entertaining. An expanded primary suite wing includes a spacious primary bedroom, full bath, bright office, half bath, and dedicated laundry. A second-story space offers flexibility as an art studio, office, or media room. A classic three-season living room invites relaxed enjoyment of the surrounding landscape, including distant winter waterviews. Well-suited for compound living, the property is perfect for the equestrian and includes a guest house, horse barn, fenced pastureland, garage, and an old boat shed—providing exceptional flexibility for family, guests, and a wide range of outdoor pursuits. Deeded access to Chilmark Pond and South Shore Beach offers a rare opportunity to enjoy swimming, kayaking, and some of the Island’s most beautiful and unspoiled coastline. This property has a seven-bedroom septic, full solar, and abuts acres of conservation land. Ideally located in the heart of Chilmark, the property is just minutes from Alley’s Store, Lucy Vincent Beach, Chilmark Tavern, Beetlebung Farm, the Chilmark Store, and more—perfectly capturing the essence of the Chilmark lifestyle and the very best of Vineyard living.

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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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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 level includes an open-concept kitchen, dining, and living area, along with a private primary suite and dedicated office space. There is a large open deck and a screened porch in this level, as well as a deck off the primary bedroom suite. Thoughtfully designed for both everyday living and entertaining, the home includes amenities such as air conditioning, whole-house generator, integrated sound system, outdoor lighting, and more. Outside, the grounds are equally impressive, featuring a tennis court, landscaped gardens with a water feature, and a large open meadow spanning several acres, all surrounded by mature woodland for exceptional privacy. No neighboring homes are visible from the property. There is ample room to add a swimming pool, and the parcel may offer subdivision opportunities. Ownership also includes rights to Brickyard Beach.

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STYLISH CHILMARK RETREAT WITH SWEEPING WATER VIEWS, PRIVATE BEACH, TENNIS, AND WALKING TRAILS. Set within the coveted Spring Point community, this beautifully renovated island retreat captures an unmistakable sense of place, where sweeping water views, natural beauty, and effortless indoor-outdoor living define the experience. Thoughtfully updated in 2022 under the direction of a talented architect/design-build team, the home blends relaxed coastal sophistication with warm, organic finishes, including driftwood-colored hardwood floors, a striking stone fireplace with a rough-hewn wood beam mantel, a sleek cook’s kitchen, custom-tiled bathrooms with distinctive design panache, and an integrated Sonos® sound system. Designed to embrace its spectacular setting, every room is framed by large windows and sliding glass doors that open to private decks with water views, creating a seamless connection to the outdoors. A spacious screened porch at the front of the house serves as the perfect gathering hub for morning coffee, quiet afternoons, summer dining, or easy entertaining. Surrounding the home, a handsome paver parking court and gorgeous, meticulously landscaped grounds enhance the property’s serene, retreat-like feel, while a charming gazebo offers a picturesque spot for relaxing, quiet meditation, or simply taking in the Island setting. The fully finished walk-out lower level offers flexible bonus living space, ideal for guests, recreation, media, or future expansion potential. Set within Spring Point’s 68 acres of common land, community amenities include three miles of ancient walking trails traversing old stone walls, two tennis courts, and Beck’s Beach, a three-quarter-mile stretch of private shoreline known for magnificent sunsets and views extending from the Elizabeth Islands all the way to the Gay Head Lighthouse. Located moments from Menemsha, Great Rock Bight, the Chilmark Flea Market, and other Up-Island favorites, this special Spring Point property offers a rare combination of privacy, natural beauty, community amenities, and timeless Vineyard appeal.

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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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