Stylish Chilmark retreat with sweeping water views, private beach, tennis, and walking trails. Set within the coveted Spring Point community, this beautifully renovated island home captures a rare sense of place, with natural beauty, privacy, and effortless indoor-outdoor living. Thoughtfully updated in 2022, the home blends relaxed coastal sophistication with driftwood-colored hardwood floors, a striking stone fireplace, sleek cook’s kitchen, custom-tiled baths, and Sonos® sound. Large windows and sliding glass doors frame water views and open to private decks, while a spacious screened porch is ideal for morning coffee, summer dining, or entertaining. Landscaped grounds, a paver parking court, charming gazebo, and finished walk-out lower level add comfort and flexibility. Spring Point amenities include 68 acres of common land, ancient walking trails, two tennis courts, and Beck’s Beach, a private shoreline with magnificent sunsets from the Elizabeth Islands to Gay Head Lighthouse.
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 been thoughtfully reimagined for today's buyer, designed and built by a team of leading architects and artisans. Grounded in its natural setting, the architecture features dramatic design elements and walls of glass to connect seamlessly with the idyllic landscape. An infinity-edge pool overlooks the pastoral ocean horizon that defines Chilmark, while a screened porch and large outdoor living areas extend the home into its surroundings. A separate 2-bedroom guest house and additional 5.6 acre lot provide flexibility for expansion and subdivision, while a private path to Chilmark Pond allows for deeded access to South Beach. Horizon House is a pleasure to show, by appointment only.
Set high on the north shore with panoramic views of Vineyard Sound and deeded private beach access, this secluded 9.8-acre estate enjoys a rare setting abutting conservation land and the Menemsha Hills trail network. The meticulously maintained residence features a reverse floor plan designed to maximize natural light, soaring ceilings, and stunning water views. The upper level offers an open-concept kitchen, dining, and living area, a private primary suite, office, screened porch, and expansive decks. Thoughtfully appointed with air conditioning, a whole-house generator, integrated sound system, and outdoor lighting. The grounds include a tennis court, landscaped gardens with a water feature, and several acres of open meadow surrounded by mature woodland, ensuring exceptional privacy with no visible neighboring homes. Ample room exists for a pool, and the parcel may offer subdivision potential. Ownership includes rights to Brickyard Beach.
Tucked away on 4.4 spectacular acres just off North Road, this one-of-a-kind Chilmark retreat blends timeless Vineyard charm with exceptional privacy. A shaded driveway leads to classic stone walls and cedar gates opening into a beautifully landscaped courtyard. The inviting porch overlooks lush gardens, creating a peaceful outdoor sanctuary. Inside, warm, light-filled living spaces and the primary suite enjoy sweeping meadow views framed by granite boulders and stately oaks. The main level offers additional sleeping accommodations, while a spacious finished lower level with a private entrance provides ideal guest quarters. Across the courtyard, an unfinished outbuilding with a screened porch offers exciting potential as a bunkhouse, studio, or office. Two garage bays accommodate cars or boats. Ideally located less than 2 miles from Menemsha Village and Beach, 1 mile from Great Rock Bight, and just 3 miles from Lucy Vincent Beach.
Rare opportunity in the Seven Gates Farm community of Chilmark. Designed by architects Jane and Christian Langmuir, this exceptional three-bedroom home is set on 5.3 acres of beautifully landscaped grounds. Thoughtfully designed to embrace natural light and its surroundings, the residence blends natural materials with contemporary architectural details.The dramatic great room features a striking fireplace with a glacial stone hearth, while the open kitchen offers custom cabinetry and premium appliances. The primary suite includes two office spaces, a media area, walk-in closet, and spa-inspired bath. A private guest suite features a full bath with soaking tub, and the third bedroom is currently configured as a wellness space with sauna. Additional amenities include an attached two-car garage, owned solar panels, EV charging station, and a six-bedroom septic system.Seven Gates Farm residents enjoy access to private beaches, docks, tennis courts, and more.1000 acres of protected land.
A rare offering on the shores of Nashaquitsa Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Set on 4.9 acres with a private 115-foot deep-water dock, this one-of-a-kind compound features striking modern architecture, walls of glass, and panoramic water views throughout. The main residence offers six ensuite bedrooms, including a spectacular first-floor primary suite with dual spa-inspired baths. Dramatic living spaces with soaring cathedral ceilings open to expansive decks and a screened porch overlooking the pond. Exceptional amenities include two chef’s kitchens, a private theater, wine cellar, outdoor shower, and a hilltop writer’s cottage with sweeping views. The pool house is a private wellness retreat with a heated indoor pool, spa, sauna, steam room, cold plunge, guest suite, and retractable glass walls. Additional highlights include a tennis court, boathouse, entertainment barn with gym and recreation space, and a six-car garage.
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 & included a 22 x 43 addition, The completely new second floor added over 1,500 square feet & the work included new heating, plumbing, electrical, central AC, septic & well! Many nice features include spacious living spaces, a modern kitchen with breakfast bar, open living and dining room with cathedral ceiling, oversized windows & a slider that leads out to a spacious deck. Second floor primary w/ensuite bath, walk-in closet & private deck. Large family room with skylights & built-ins. Two first floor bedrooms w/full bath, basement, wood floors, a whole house generator, Oil FHW heat & new A/C. Privately sited 1.20 acres bordered by stone walls, beautifully landscaped grounds, mature gardens & plantings. Beautiful fruit trees, a garage & shed. The property is gated and entirely enclosed with deer fencing.
Welcome to an extraordinary coastal retreat within the exclusive gates of Squibnocket Farm, a 450+ acre private community offering access to over two miles of oceanfront, pond frontage, and conservation land. Designed and built by Soikkeli & Company, this elegant home blends timeless New England farmhouse architecture with refined modern luxury. The chef’s kitchen features soapstone countertops, custom cabinetry, premium appliances, and a walk-in pantry. Spacious living areas and a serene primary suite capture breathtaking Atlantic Ocean views. Additional bedrooms occupy a separate wing for added privacy. Outdoors, organic landscaping, historic stone walls, colorful gardens, fenced pasture, and expansive decks create a peaceful setting for entertaining or stargazing. Ownership includes exclusive access to scenic trails, pond launches, and a private beach. Smart features include Nest thermostats and a HEOS sound system, completing this exceptional Vineyard lifestyle to treasure always.
CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this beautifully restored and expanded modern farmhouse offers a seamless blend of timeless Vineyard character and contemporary comfort. The 3-bedroom, 3.5-bath main residence spans approximately 5,400 square feet of thoughtfully designed living space, highlighted by a sun-filled open kitchen and living area anchored by a striking central fireplace—ideal for both everyday living and entertaining. An expansive primary suite wing features a spacious bedroom, full bath, private office, half bath, and dedicated laundry. The second floor offers flexible space for a studio, office, or media room, while a classic three-season room invites relaxed enjoyment of the surrounding landscape and distant winter water views. Perfect for compound living, the property includes a guest house, solar, horse barn, fenced pasture, garage, and historic boat shed. Deeded access to Chilmark Pond and South Shore Beach completes this property.
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.
Courtesy: William Raveis Real Estate & Home Services
508-487-4005
Luxurious New Construction in Provincetown Experience modern coastal living in these brand-new, stand-alone 2BR/2.5BA townhouse style condominiums just a short walk from the center of town. Each home features sun-filled interiors with wide-plank engineered hardwood floors, Pella windows, and sleek porcelain-tiled ensuite baths. The gourmet kitchen boasts high-end Thor appliances and custom cabinetry, blending luxury and function.Enjoy professionally landscaped grounds with irrigation, private outdoor space, and two dedicated parking spots. Durable hardie board and batten siding, high efficiency heat pumps with air conditioning and meticulous craftsmanship make these homes as efficient as they are beautiful.Ideally located near beaches, shops, and restaurants, 29 Cemetery Road offers the perfect mix of tranquility and convenience -- a rare new-construction opportunity in Provincetown's most desirable setting.Experience a new chapter of Provincetown living--modern, elegant, and entirely your own.
Courtesy: William Raveis Real Estate & Home Services
508-487-4005
Luxurious New Construction in Provincetown Experience modern coastal living in these brand-new, stand-alone 2BR/2.5BA townhouse style condominiums just a short walk from the center of town. Each home features sun-filled interiors with wide-plank engineered hardwood floors, Pella windows, and sleek porcelain-tiled ensuite baths. The gourmet kitchen boasts high-end Thor appliances and custom cabinetry, blending luxury and function.Enjoy professionally landscaped grounds with irrigation, private outdoor space, and two dedicated parking spots. Durable hardie board and batten siding, high efficiency heat pumps with air conditioning and meticulous craftsmanship make these homes as efficient as they are beautiful.Ideally located near beaches, shops, and restaurants, 29 Cemetery Road offers the perfect mix of tranquility and convenience -- a rare new-construction opportunity in Provincetown's most desirable setting.Experience a new chapter of Provincetown living--modern, elegant, and entirely your own.
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 new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural woodland setting. With strong rental income, currently generating $2,500 month to month year-round, and expansion opportunities subject to town approvals, the property is conveniently located near South Road, West Tisbury's village center, and Chilmark's iconic Lucy Vincent and Squibnocket Beaches. Passed Title V in December 2025 for 3 Bedrooms. #47 is shown as Lot 1-C on a new subdivision not yet reflected on the assessments and public records - approved survey is attached. 45 Quenames Lot 1-B is also available.
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 spacious bedrooms, a full bath with shower, an enormous three-season screened porch, a large outdoor shower, kitchen gardens, and a potting area with utility sink. Well system updated in 2011. With strong rental income, currently generating $2,500 month to month year-round, and expansion potential, this outstanding value is located close to South Road, West Tisbury's village center, and Chilmark's iconic town beaches Squibnocket and Lucy Vincent. Town records indicate a 4 bedroom septic, passed Title V Inspection in December 2025. #45 is shown as Lot 1-B on a new subdivision not yet reflected on the assessments and public records - approved plans are attached. 47 Quenames Lot 1-B is also available.
Courtesy: Sandpiper Realty Inc
508-627-3737
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 new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural woodland setting. With strong rental income, currently generating $2,500 month to month year-round, and expansion opportunities subject to town approvals, the property is conveniently located near South Road, West Tisbury's village center, and Chilmark's iconic Lucy Vincent and Squibnocket Beaches. Passed Title V in December 2025 for 3 Bedrooms. #47 is shown as Lot 1-C on a new subdivision not yet reflected on the assessments and public records - approved survey is attached. 45 Quenames Lot 1-B is also available.
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 peaceful woodland setting. Recent updates include a new roof, siding, and HVAC system, ensuring comfort and ease for seasonal and year-round living. The land offers room to grow, with exciting expansion possibilities subject to town approvals. Whether you envision a quiet island retreat, an investment opportunity, or a future compound, this Chilmark gem offers endless possibilities and timeless Vineyard appeal.**abutting 4.28 acre parcel is also for sale, please inquire***
Courtesy: Island Real Estate
508-693-4800
Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming living room, anchored by a pristine Vermont Castings wood stove, opens seamlessly to a covered porch and spacious deck--perfect for morning coffee or evening gatherings. The spacious first-floor primary suite provides a private retreat with two en-suite baths and two walk-in closets. Upstairs, you'll find two bedrooms with beautiful wood floors, built-in drawers, and cabinets that add both charm and functionality to the rooms. These bedrooms share a hall bath, making the second floor an ideal space for family or guests. A generous bonus room above the garage offers flexible space for a home office, gym, or additional sleeping quarters. A separate studio on the property adds further versatility. The private backyardfeaturing a naturally shaded stone bench and trees perfectly placed for a hammockoffers a peaceful retreat. An outdoor shower provides the ideal post-beach rinse or a refreshing start to the day. Additional highlights include a garage and a full, unfinished basement, and a new generator. You will enjoy access to Lucy Vincent Beach and other up-island locations including a quick ride to the center of both Chilmark and West Tisbury. Well-maintained through the years and in close proximity to everything Chilmark has to offer, this property is an exceptional findwhether you're looking for a year-round home, seasonal getaway, or investment opportunity.
Courtesy: Wallace & Co. Sotheby's International Realty
508-627-3313
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. 2 miles to Lucy Vincent beach
Chilmark is located in Massachusetts. Chilmark, Massachusetts has a population of 1,460. Chilmark is less family-centric than the surrounding county with 10.23% of the households containing married families with children. The county average for households married with children is 27.66%.
The median household income in Chilmark, Massachusetts is $104,716. The median household income for the surrounding county is $77,392 compared to the national median of $69,021. The median age of people living in Chilmark is 53.5 years.
The average high temperature in July is 80.1 degrees, with an average low temperature in January of 22.6 degrees. The average rainfall is approximately 47.3 inches per year, with 30.1 inches of snow per year.
