Chilmark Real Estate

MLS Number 42442

• Residential
• Mls Status Active
• Bedrooms 6
• Bathroom 6
• Acreage 9.5

Experience the ultimate luxury lifestyle at this exquisite Martha's Vineyard estate, set on 9.5 acres in two adjoining parcels. Situated in a private location with commanding views of the Atlantic Ocean and Chilmark Pond, the property offers safety and serenity, perched on an elevated site well above the flood zone. The main house and guest house sit on 4-acres, while 0 Wooton Bassett Road is a 5.5-acre lot with an established building envelope, designed to offer water views without obstructing the vistas from the existing home. Together, these properties ensure unparalleled privacy and the potential to create a larger compound in the future. Chilmark House, designed by Seattle-based architect Rick Sundberg and constructed by master builder Andrew Flake, blends contemporary amenities with Vineyard themes to create a unique living experience. An enormous boulder, deposited by a receding glacier, sits strikingly close to the home’s entrance. Inside, tall ceilings, oak flooring, and walls of glass flood the space with natural light and showcase panoramic ocean views. The modern kitchen is a chef's dream, featuring cherry cabinets, granite countertops, and top-tier appliances from Sub-Zero, Miele, Wolf, and Scotsman. The home also includes a screened porch with high ceilings, perfect for dining and relaxing, just off the kitchen and deck. The primary suite offers access to a private study with a fireplace, two baths, a deck, and heated floors. The second wing features three guest bedrooms, two baths, and a dressing room. The heated infinity pool, surrounded by elegant terraces, offers stunning ocean views. Outdoor features include a large kitchen garden, fruit trees, and a half-basketball court. A detached 3-bay garage and additional parking complement the main house, while a two-bedroom cottage provides guests their own private retreat. The estate includes private south shore beach rights, accessible by boat from Chilmark Pond. This one-of-a-kind property, where the Obamas have chosen to vacation, epitomizes luxury living. All furniture, artwork, and gym equipment are available for purchase. Don't miss the opportunity to own this extraordinary estate.

Listed by Compass | The O'Hanlon Group

MLS Number 40007

• Residential
• Mls Status Active
• Bedrooms 4
• Bathroom 4.5
• Acreage 3.3

Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore. Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within a reasonable distance from essential amenities and entertainment options. Whether you're looking for a year-round residence or a vacation getaway, this waterfront home in Squibnocket is an idyllic sanctuary to create unforgettable memories with family and friends.

Listed by Wallace & Co. Sotheby's

MLS Number 42085

• Residential
• Mls Status Active
• Bedrooms 6
• Bathroom 6
• Acreage 4

Experience the ultimate luxury lifestyle at this exquisite Martha's Vineyard estate. Situated in a private location with commanding views of the Atlantic Ocean and Chilmark Pond, the property offers safety and serenity, perched on an elevated site well above the flood zone. Chilmark House, designed by Seattle-based architect Rick Sundberg and constructed by master builder Andrew Flake, seamlessly blends contemporary amenities with Vineyard themes to create a truly unique living experience. As you approach the front door, you'll notice an enormous boulder, deposited by a receding glacier, sitting just inches away from the home – a striking natural feature. Upon entering, you're greeted by tall ceilings, oak flooring, and an abundance of natural light. Your eye will be immediately drawn to the walls of glass showcasing panoramic ocean views. The modern kitchen is a chef's dream, featuring cherry cabinets, granite countertops, and high-end appliances from Sub Zero, Miele, Wolf, and Scotsman. The property includes a wonderful screened porch with high ceilings, ideal for dining and relaxing, just off the kitchen and deck. The primary suite is a luxurious retreat, offering access to a private study with fireplace, two lavish baths, a deck, and heated floors throughout. The second wing of the house features three spacious guest bedrooms, two baths, and a dressing room. The heated infinity pool, a centerpiece of the home, offers elegant terrace views of the ocean. Outdoor features also include a large kitchen garden, fruit trees, and a half-basketball court. A detached 3-bay garage and additional parking complete the main house setup. Additionally, a two-bedroom cottage provides guests with a private retreat of their own. Chilmark House includes private south shore beach rights, accessible by boat from Chilmark Pond. This one-of-a-kind property, where the Obamas have vacationed, epitomizes luxury living. For a seamless transaction, all furniture, artwork, and gym equipment are available for purchase. Adjacent 5.5 acre lot is available as well – call for details. Don't miss the opportunity to own this extraordinary estate.

Listed by Compass | The O'Hanlon Group

MLS Number 41941

• Residential
• Mls Status Active
• Bedrooms 6
• Bathroom 5.5
• Acreage 4.5

CHILMARK SOUTH SHORE WATER VIEWS. This Squibnocket gem is a Hutker Architect-designed family compound on 4.5 acres. With captivating water views in every direction, this home is the perfect launch pad for the ultimate up-Island lifestyle. Grab your surf or paddle board and head down the path to Squibnocket Beach for a morning surf or swim. Pack the cooler with lunch from the Chilmark Store for a day at Lucy Vincent Beach or on the boat. Pick up some local oysters and lobster rolls in Menemsha and then head home to enjoy a perfect summer sunset on the patio overlooking Menemsha Pond and the Elizabeth Islands. The home is pristine and private with many unique features that make it the perfect place from which to enjoy all that up-Island has to offer. The chef's kitchen and dining area are serene, bright, and functional. The main floor living spaces feature unparalleled Chilmark panoramas with views of South Shore beaches, Quitsa and Menemsha Ponds, and the Vineyard Sound. A stately wood-burning stone fireplace centers the living room which overlooks the expansive lap pool and stone patio area with dining space for outdoor enjoyment. The stunning main house has 4 bedrooms and 3 1/2 baths. The primary bedroom, on the main level, has its own fireplace, ensuite bathroom, walk-in closet, and direct access to the outdoor shower. This rare up-Island property also includes a secluded guest house with a well-appointed kitchen, two ensuite bedrooms, and a spacious living area with wood burning fireplace. A one-car garage on the property is a plus for storing all of your Island toys such as surfboards, beach gear, and the Island car. This Chilmark retreat also features deeded access for small boat pick-up and drop-off on Menemsha Pond, just across the way. Close to the Chilmark General store, Chilmark Tavern, Beetlebung Farm Stand, and the Chilmark Community Center for your convenience. However you like to spend your days, at the beach, by the pool, grilling with a crowd, or curled up with a good book in front of the fire, you can do it all at this one-of-a-kind Chilmark property. The co-listing agent is related to the Seller.

Listed by Compass | Point B

MLS Number 42383

• Land
• Mls Status Active
• Acreage 5.3

This rare, unparalleled building opportunity sits on Squibnocket Farm, one of the island’s most private and spectacular locations. Squibnocket Farm consists of approximately 500 acres of forever-protected conservation land, with private access to over 2 miles of beautiful dunes and sandy beach. The 5-acre building site overlooks stone walled conservation fields and beyond to the island’s South Shore. The building envelope has been thoughtfully planned to maximize privacy, views, and to enjoy the pristine natural beauty that Squibnocket Farm affords.

Listed by Landvest MV

MLS Number 42061

• Residential
• Mls Status Active
• Bedrooms 5
• Bathroom 3.5
• Acreage 5.6

This waterfront 4 bedroom 2.5 bath quality custom home and detached 1 bedroom, 1 bath guest studio are sited on 5.6 pristine acres. Enjoy spectacular water views and magnificent sunsets from almost every room as well as from the stone terrace, screened porch and the primary bedroom balcony. This is a finely crafted home with many wonderful details including salvaged heart pine floors and beautiful old beams. A large building envelope allows room for expansion should a new owner desire. Relax amidst the gardens, expansive lawn and mature trees as you take in the beauty around you or go for a leisurely stroll to Menemsha Village. A short path leads to 340 feet of private waterfront on the Vineyard Sound where one can swim peacefully in the calm waters.

Listed by Tea Lane Associates

MLS Number 42074

• Residential
• Mls Status Active
• Bedrooms 5
• Bathroom 4.5
• Acreage 5.6

Walk to a private beach and enjoy the beautifully manicured gardens and landscape of this well-loved and privately situated home! Custom designed with a charming Vineyard feel and tasteful interior design. Water view from a gourmet kitchen and formal dining area. Large open living room and spacious bedrooms. Large deck with exceptional views of the North shore and Elizabeth Island's A large enclosed sun porch off the kitchen to enjoy meals and family time and is adjoined by a breakfast nook. Three (3) Bedrooms are located on the upper level. The primary bedroom is complete with a balcony to enjoy sunrises and sunsets. The 4th bedroom is on the first floor next to a full bathroom. The basement is a finished area with an additional living area. The septic system has been upgraded to allow for six bedrooms.

Listed by Flanders Real Estate

MLS Number 40699

• Residential
• Mls Status Active
• Bedrooms 7
• Bathroom 6
• Acreage 3

Martha's Vineyard has many fine waterfront properties but only a handful of exceptional ones. The Lee Family Compound is an exceptional 3 acre waterfront property with breathtaking unobstructed pond views from an elevated secure location, 750+ ft of pond frontage, 48 ft dock with separate mooring for easy access to Menemsha Pond and Vineyard Sound and privacy without an abutter in view - all compliment the spacious 5 bedroom 5 bath comfortable well built main house and well sited 2 bedroom 1 bath contemporary guest house. The stunning views are everywhere so 14 of the 16 rooms in both houses enjoy grand pond views. Because of the elevation -- the sunsets, moonrises, and stargazing are some of the most remarkable the island has to offer. The two home compound can house 18 comfortably and is perfect for year-round family events. Come launch your canoe, kayak or paddle board from spring to fall; swim, clam or sail from private sandy beach off the point all summer long; sunbathe on your private dock or 3 decks or on the terraced lawn overhanging the cove; and enjoy seasonal holidays by a roaring fire with extended family and loved ones. This compound is proof that a picture is worth a 1,000 words.(see Video Aerial Tour)

Listed by Tea Lane Associates

MLS Number 42003

• Residential
• Mls Status Active
• Bedrooms 5
• Bathroom 3
• Acreage 3

Nestled along the beautiful and tranquil shoreline of Tisbury Great Pond and surrounded by a stunning natural environment of water, sand and sky, this is an unparallelled beach house experience on the south shore of Chilmark. The five-bedroom home consists of a three-bedroom main house connected by walkways to a two-bedroom guest wing with studio space above, all with spectacular water views including from ground floor. The yard surrounding the house is a meadow like setting with an easy grassy path out to the sandy pond shoreline. Play on the pond with paddleboards, kayaks, small motor boats and sailboats, and quickly cross over to the ocean beach. Although little ones love to stay on the pond shoreline at the house to explore and swim in these safe calm waters. The existing buildings and six-bedroom septic await your vision. Abutting conservation land on two sides. Access to Chilmark beaches as well. This is a rare offering with the combination of water frontage on the pond, proximity to the ocean, conforming acreage and panoramic views. Create your own private sanctuary for your family in this wild and beautiful, natural setting.

Listed by Tea Lane Associates

MLS Number 42197

• Residential
• Mls Status Active
• Bedrooms 5
• Bathroom 3.5
• Acreage 9.8

Perched high on the north shore with sweeping views of the Vineyard Sound, this expansive and private property is surrounded by Menemsha Hills conservation land and trails and offers broad water views, even from ground floor of house. The house is large and well maintained with an upside down floor plan allowing for high ceilings and bright spaces in the open plan kitchen/dining/living room, as well as the primary bedroom suite and office on this upper level. This is a great house for entertaining and offers A/C, screened porch, generator, music system, outdoor lighting and other perks. The exterior space features a tennis court, beautiful gardens with water feature, and a cleared meadow, which is several acres in size, surrounded by woodlands. No other houses can be seen from here. A pool is possible and there is plenty of space for this addition. Subdivision potential. Includes Brickyard Beach rights.

Listed by Tea Lane Associates