Chilmark Properties for Sale
Address: 18 Point Inner Way | Town: Chilmark | Link ID: 44498
Price: $45,000,000 | Status: Active
A rare offering on the shores of Menemsha Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Thoughtfully designed with striking modern architecture, walls of glass, and seamless indoor-outdoor living, this one-of-a-kind compound captures breathtaking water ... Click here for more details
Address: 146 Quenames Road | Town: Chilmark | Link ID: 44353
Price: $32,500,000 | Status: Active
Set on 60 acres along one of the most private and unspoiled stretches of Atlantic coastline in Chilmark, this exceptional estate offers a rare combination of scale, privacy, and enduring coastal beauty. With over 800 feet of direct ocean frontage, the property commands expansive views while maintain... Click here for more details
Address: 25 Brickyard Road | Town: Chilmark | Link ID: 44796
Price: $16,250,000 | Status: Active
Perched on an elevated 10.69-acre site just off picturesque North Road in Chilmark, this exceptional private compound brings together natural beauty and architectural distinction. Designed by renowned architect Patrick Ahearn, the residence enjoys dramatic views across the Menemsha Hills and Vineyar... Click here for more details
Address: 0, 36, 38 Black Point Road | Town: Chilmark | Link ID: 43569
Price: $16,000,000 | Status: Active
Forty six extraordinary acres on Black Point Pond with easy access to Black Point sandy ocean beach. Magical expansive views of meadows, pond and ocean. This estate-sized property abuts 140 acres of Sheriff’s Meadow conservation land, offering exceptional privacy. A simple 1041 square foot two bed... Click here for more details
Address: 0, 36, 38 Black Point Road | Town: Chilmark | Link ID: 44495
Price: $16,000,000 | Status: Active
Forty six extraordinary acres on Black Point Pond with easy access to Black Point sandy ocean beach. Magical expansive views of meadows, pond and ocean. This estate-sized property abuts 140 acres of Sheriff's Meadow conservation land, offering exceptional privacy. A simple 1041 square foot two be... Click here for more details
Address: 8 Snail Road | Town: Chilmark | Link ID: 44568
Price: $15,400,000 | Status: Active
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 ... Click here for more details
Address: 64 Squibnocket Farm Road | Town: Chilmark | Link ID: 40007
Price: $14,500,000 | Status: Active
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 an... Click here for more details
Address: 16 Shotnaigher Lane | Town: Chilmark | Link ID: 43060
Price: $10,950,000 | Status: Active
New to market this completely renovated water view home is located in a private enclave of upscale homes fronting on Squibnocket Pond in Chilmark. There are 360 degree views from this 3.6 acre hilltop site offering views of the pond, Atlantic Ocean and north to Menemsha Pond and the Vineyard Sound... Click here for more details
Address: 6 Wakeman Road | Town: Chilmark | Link ID: 44509
Price: $9,875,000 | Status: Active
Set in a spectacular water view setting with private beach access, this exceptional coastal compound offers a rare blend of privacy, flexibility, and breathtaking scenery. The property is thoughtfully composed of a beautifully appointed main residence, a separate guest house, an artist’s studio, a... Click here for more details
Address: 23 Flanders Lane | Town: Chilmark | Link ID: 44823
Price: $9,750,000 | Status: Active
A rare offering of land, history, and sweeping water views — this exceptional 8.7+/- acre estate commands panoramic views of Menemsha Pond and Vineyard Sound from its rolling lawns and open meadows. Property includes parking and access to Menemsha Pond. Whether you're drawn by the storied architec... Click here for more details
Address: 1 Clam Point Cove Road | Town: Chilmark | Link ID: 44970
Price: $7,900,000 | Status: Active
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 f... Click here for more details
Address: 78 Hammett Road | Town: Chilmark | Link ID: 44277
Price: $6,750,000 | Status: Active
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 maintai... Click here for more details
Address: 34 Edys Island Way | Town: Chilmark | Link ID: 44243
Price: $6,250,000 | Status: Active
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 fo... Click here for more details
Address: 17 Chockers Lane | Town: Chilmark | Link ID: 44310
Price: $5,500,000 | Status: Active
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 w... Click here for more details
Address: 8 Wauwompauque Trail | Town: Chilmark | Link ID: 44596
Price: $5,300,000 | Status: Active
Abels Hill opportunity! Coastal living at its finest in this contemporary Abels Hill retreat, where south-facing ocean views and exceptional amenities define the lifestyle. Situated within one of Chilmark's most sought-after communities, the property enjoys exclusive access to the Atlantic Ocean, Ch... Click here for more details
Address: 49 Gosnolds Way | Town: Chilmark | Link ID: 44546
Price: $5,200,000 | Status: Active
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 floo... Click here for more details
Address: 35 South Bowl Road | Town: Chilmark | Link ID: 44534
Price: $4,995,000 | Status: Active
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 th... Click here for more details
Address: 63 Putnam Road | Town: Chilmark | Link ID: 44461
Price: $4,995,000 | Status: Pending
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 ... Click here for more details
Address: 44 Cencelle | Town: Chilmark | Link ID: 44272
Price: $4,975,000 | Status: Active
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 out... Click here for more details
Address: 131 State Road | Town: Chilmark | Link ID: 44554
Price: $3,950,000 | Status: Active
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 s... Click here for more details
Address: 7 Black Point Road | Town: Chilmark | Link ID: 43929
Price: $3,950,000 | Status: Pending
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 ... Click here for more details
Address: 3 Ben's Way | Town: Chilmark | Link ID: 44616
Price: $3,900,000 | Status: Active
Sited on 3.94 acres in the North Tabor Farm subdivision, this flexible 3-4 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... Click here for more details
Address: 96 Hammett Lane | Town: Chilmark | Link ID: 43534
Price: $3,795,000 | Status: Active
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,... Click here for more details
Address: 100 Gosnolds Way | Town: Chilmark | Link ID: 44473
Price: $3,300,000 | Status: Active
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... Click here for more details
Address: 27 Clambelly Road | Town: Chilmark | Link ID: 44318
Price: $3,295,000 | Status: Active
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. ... Click here for more details
Address: 31 Tower Lane and 34 Ebens Lane | Town: Chilmark | Link ID: 43935
Price: $2,725,000 | Status: Active
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 gene... Click here for more details
Address: 11 By The Woods | Town: Chilmark | Link ID: 44451
Price: $2,650,000 | Status: Active
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 plan... Click here for more details
Address: 2 Other House Road | Town: Chilmark | Link ID: 42602
Price: $2,500,000 | Status: Active
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... Click here for more details
Address: 16 South Road | Town: Chilmark | Link ID: 44181
Price: $2,395,000 | Status: Pending
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, includin... Click here for more details
Address: 26 Bijahs Way | Town: Chilmark | Link ID: 44171
Price: $2,195,000 | Status: Active
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 heati... Click here for more details
Address: 220 North Road | Town: Chilmark | Link ID: 44663
Price: $2,195,000 | Status: Active
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 Lin... Click here for more details
Address: 220 North Road | Town: Chilmark | Link ID: 44814
Price: $2,195,000 | Status: Active
A wonderfully private, peaceful aerie in Chilmark on 3 acres (with a Guest House), featuring a spacious, high, secluded, wrap-around Deck off of the Living Room and Dining Room. The house is built into the side of a hill which allows more light and 2 areas to be considered "ground level." There is a... Click here for more details
Address: 29 Old Nursery Lane | Town: Chilmark | Link ID: 43568
Price: $2,150,000 | Status: Active
Modern Cape style home located off Tea Lane could be your special Chilmark retreat. This four bedroom, 2.5 bathroom home needs some updating but is in good condition. Living room with fireplace, dining area and family room provide space for living. Attached two bay garage allows for storage and proj... Click here for more details
Address: 25 Fulling Mill Road | Town: Chilmark | Link ID: 43014
Price: $1,995,000 | Status: Active
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... Click here for more details
Address: 0 High Mark | Town: Chilmark | Link ID: 44445
Price: $1,900,000 | Status: Active
A rare opportunity to build a private retreat awaits at this 15 acre land parcel centrally located in Chilmark. Once part of the High Mark estate, the property features groves of mature trees planted more than 100 years ago, creating a wondrous, secluded and private setting rarely found anywhere on ... Click here for more details
Address: 43 North Slope Lane | Town: Chilmark | Link ID: 44067
Price: $1,649,000 | Status: Active
Set on a private 3.5-acre wooded parcel surrounded by conservation land, this 3-bedroom, 2-bath single-family home offers the ultimate Martha’s Vineyard retreat. Nestled among mature trees and protected open space, the property provides exceptional privacy and a peaceful natural setting, while rem... Click here for more details
Address: 8 Rumpus Ridge | Town: Chilmark | Link ID: 44657
Price: $1,550,000 | Status: Active
Escape to your own getaway with mature landscaped gardens and privacy in the heart of Chilmark. Walk to the Chilmark Store, library, Chilmark Community Center, Beetlebung Farm and bank. Access to Chilmark beaches - Lucy Vincent and Squibnocket - and Menemsha Public Beach are a plus. This four bedroo... Click here for more details
Address: 10 Abels Neck Road | Town: Chilmark | Link ID: 44418
Price: $1,450,000 | Status: Pending
Nestled on a beautiful lot in the heart of Chilmark, this charming cottage is framed by mature blueberry bushes just off the deck — a true slice of island life. Perfectly positioned to enjoy the quiet calm of up-island living while remaining close to town, beaches, and all that the Vineyard has to... Click here for more details
Address: 34 Ebens Lane | Town: Chilmark | Link ID: 40477
Price: $1,449,000 | Status: Pending
Settled high on a peaceful ridge this 3.9-acre property is being offered with a long-term lease for 2.5 acres of prime restricted agricultural farmland abutting the property and the Tiasquam River. With the river running along the edge of the property this area is ideal for growing flowers, vegetabl... Click here for more details
Address: 345 North Road | Town: Chilmark | Link ID: 44126
Price: $1,375,000 | Status: Active
This versatile Chilmark property offers a rare combination of privacy, flexibility, and investment potential. The main residence features 4 bedrooms and 4 bathrooms, complemented by a detached 1-bedroom, 1-bath suite with an attached garage—ideal for guests, extended family, or rental income. Two ... Click here for more details
Address: 0 North Road/15 Belhaven Way | Town: Chilmark | Link ID: 44325
Price: $1,325,000 | Status: Active
Set just off North Road, this exceptional parcel offers a rare opportunity to build in a setting rich with natural beauty. Recently subdivided, this land combines privacy, character and thoughtful positioning. The lot is perfectly sited capturing serene woodland views and the natural contours of Mi... Click here for more details
Address: 15 Menemsha Inn Road | Town: Chilmark | Link ID: 44504
Price: $1,250,000 | Status: Active
Nestled in a bucolic setting moments from the iconic Menemsha fishing village, this beautiful and fully engineered parcel is approved for a 6BR home. One of the few remaining Menemsha buildable lots makes this a rare opportunity. With room for a pool with a special permit! Surrounded by ancient sto... Click here for more details
Address: 37 Bijahs Way | Town: Chilmark | Link ID: 43069
Price: $1,245,000 | Status: Active
FRESHLY BRUSH CUT and EASY to WALK! This quiet and lovely four-and-a-half-acre lot in Chilmark is READY-TO-BUILD. The land has a gentle rise, bounded on one side by an old stone wall. The land features graceful trees and a distant water view is possible from a second floor. The lot has been staked, ... Click here for more details
Address: 47 Quenames Road | Town: Chilmark | Link ID: 43984
Price: $1,150,000 | Status: Active
On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A ... Click here for more details
Address: 45 Quenames Road | Town: Chilmark | Link ID: 43983
Price: $1,125,000 | Status: Active
Set on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and excellent potential. In a sunny clearing among mature trees, the maintained 2-bedroom house features first-floor living, an open kitchen and living area, two bedrooms, a full bath with shower, an enormous three... Click here for more details