Chilmark Properties for Sale
Address: 18 Point Inner Way | Town: Chilmark | Link ID: 44498
Price: $45,000,000
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: $35,000,000
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: 0, 36, 38 Black Point Road | Town: Chilmark | Link ID: 43569
Price: $16,000,000
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
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
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
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: 18 Spruce Gate Road | Town: Chilmark | Link ID: 43244
Price: $12,500,000
Welcome to an extraordinary ocean view coastal sanctuary set within the exclusive gates of Squibnocket Farm, a 450+ acre private community with access to over 2 miles of oceanfront, 1.5 miles of pond frontage, and 300+ acres of conservation land. Set on a peaceful, pastoral landscape abutting 17 acr... Click here for more details
Address: 16 Shotnaigher Lane | Town: Chilmark | Link ID: 43060
Price: $10,950,000
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
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: 308 South Road | Town: Chilmark | Link ID: 43955
Price: $7,350,000
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 t... Click here for more details
Address: 78 Hammett Road | Town: Chilmark | Link ID: 44277
Price: $6,750,000
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
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
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: 61 Stonewall Road | Town: Chilmark | Link ID: 44449
Price: $5,450,000
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 tr... Click here for more details
Address: 35 South Bowl Road | Town: Chilmark | Link ID: 44534
Price: $5,400,000
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: 205 South Road | Town: Chilmark | Link ID: 44028
Price: $5,350,000
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 s... Click here for more details
Address: 44 Cencelle | Town: Chilmark | Link ID: 44272
Price: $5,295,000
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: 49 Gosnolds Way | Town: Chilmark | Link ID: 44546
Price: $5,200,000
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: 63 Putnam Road | Town: Chilmark | Link ID: 44461
Price: $4,995,000
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: 7 Black Point Road | Town: Chilmark | Link ID: 43929
Price: $4,650,000
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: 131 State Road | Town: Chilmark | Link ID: 44554
Price: $4,350,000
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: 96 Hammett Lane | Town: Chilmark | Link ID: 43534
Price: $3,795,000
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: $3,400,000
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
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: 300 North Road/18 Belhaven Way | Town: Chilmark | Link ID: 44545
Price: $2,995,000
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 bed... Click here for more details
Address: 6 Trails End | Town: Chilmark | Link ID: 43845
Price: $2,900,000
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 desig... Click here for more details
Address: 31 Tower Lane and 34 Ebens Lane | Town: Chilmark | Link ID: 43935
Price: $2,725,000
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
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
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
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: 25 Fulling Mill Road | Town: Chilmark | Link ID: 43014
Price: $2,395,000
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: 26 Bijahs Way | Town: Chilmark | Link ID: 44171
Price: $2,395,000
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: 18 Allen Farm Road | Town: Chilmark | Link ID: 44362
Price: $2,250,000
Located in the agricultural heartland of Chilmark one mile from Lucy Vincent Beach this private 2.36 acre property has a charming 1+ bedroom cottage with screened porch. There is a large building zone located between the eighty and one hundred foot contour with exciting architectural options, espec... Click here for more details
Address: 29 Old Nursery Lane | Town: Chilmark | Link ID: 43568
Price: $2,250,000
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: 139 Tea Lane | Town: Chilmark | Link ID: 44548
Price: $2,195,000
Tucked away on a quiet country road in a serene Chilmark setting, this beautifully crafted home, built in 2023, offers modern comfort surrounded by natural beauty. The thoughtfully designed main level features an open, light-filled floor plan where the living, dining, kitchen, and family areas flow ... Click here for more details
Address: 0 High Mark | Town: Chilmark | Link ID: 44445
Price: $1,900,000
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: 174 Middle Road | Town: Chilmark | Link ID: 43364
Price: $1,795,000
Nestled in Chilmark, this four-bedroom home blends classic Vineyard charm with modern comfort. The sunlit eat-in kitchen features dual ovens, granite countertops, and custom cherry built-ins, flowing seamlessly to a living room with a Vermont Castings wood stove and access to a covered porch and spa... Click here for more details
Address: 43 North Slope Lane | Town: Chilmark | Link ID: 44067
Price: $1,699,999
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: 132 South RD | Town: Chilmark | Link ID: 44681
Price: $1,600,000
Nestled on a private, 1.9-acre lot along historic South Road in Chilmark, this charming New England retreat offers an exceptional sense of tranquility and classic Martha's Vineyard living. Built in 1950, Vineyard Home offers 2 bedrooms and 2 full bathrooms great light, cozy additional living spaces ... Click here for more details
Address: 46 Tiercel Lane | Town: Chilmark | Link ID: 43869
Price: $1,550,000
Nestled on a serene 3.32-acre parcel between North Road and Tabor House in Chilmark, this property blends privacy, charm, and great potential. A sweet 2 bedroom guest house—beautifully maintained and offering excellent rental income—sits amid rolling stone walls and mature trees, creating a peac... Click here for more details
Address: 8 Rumpus Ridge | Town: Chilmark | Link ID: 44657
Price: $1,550,000
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: 47 Quenames Road | Town: Chilmark | Link ID: 43984
Price: $1,495,000
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: $1,495,000
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
Address: 10 Abels Neck Road | Town: Chilmark | Link ID: 44418
Price: $1,450,000
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: 345 North Road | Town: Chilmark | Link ID: 44126
Price: $1,450,000
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
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: 37 Bijahs Way | Town: Chilmark | Link ID: 43069
Price: $1,295,000
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, including a proposed home site at th... Click here for more details
Address: 15 Menemsha Inn Road | Town: Chilmark | Link ID: 44504
Price: $1,250,000
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