Blackpoint Beach is an exquisite destination for beach walking, swimming, and access to Blackpoint Pond, which leads to the Tisbury Great Pond. Miles of sandy beach east and west with easy access via a boardwalk to the beach. Grassy parking, private gated beach access on the south shore of Chilmark. Blackpoint is a less common offering. This is a great time of year to include this in your summer or year-round living. This is not a buildable property, strictly beach and pond access only

Handsome, large level parcel of land in Chilmark! Bounds are in, lot lines are flagged and brush cut, as well as a bit of the lot interior so that you can appreciate the size and orientation of the parcel. 6-Bedroom septic design has been approved and well will be installed soon. Quenames Road is off South Road, a short hop to West Tisbury village center with Alley's General Store, the Town's fabulous library, 7A takeout, and movies and performances at the Grange; while your Chilmark address affords access to the Town's Lucy Vincent and Squibnocket Beaches! *Lot Subdivision is too new for the land to have been separately assessed. This is the 3 acre southerly portion of what had been identified as 45 Quenames Road.

This quiet and lovely four-and-a-half-acre lot in Chilmark is set on 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 the highest elevation. There are so many outstanding possibilities for a future Buyer to build their dream home on this special piece of land. Peaceful and private, this area is next door to 184 acres of conservation land at Waskosim's Rock Reservation, with miles of walking trails. A 4-bedroom septic has been designed by Sourati Engineering which could be expanded. A guest house is also possible with proper permitting. Natural heritage approval is in process. The lot is part of the Association tennis allowing a future owner access and usage of the community tennis courts. Chilmark residents enjoy the ocean beaches of Lucy Vincent, Squibnocket, and Vineyard Sound beach featuring the celebrated sunsets at Menemsha. *NOTE: Architect Peter Breese designed an elegant potential 4-bedroom home on this land for the current owner that she is willing to share with a Buyer.

Abutting hundreds of acres of conservation land and walking trails leading to the second-highest point on Martha's Vineyard with views of the Elizabeth Islands, this classically-styled house with detached guest quarters offers 5 total bedrooms and 4 full baths plus an outdoor shower. The primary bedroom suite is a generous size and has its own small deck that overlooks the charming front yard. The property feels quintessentially Chilmark with ancient stone walls and mature plantings. The detached guest quarters features a spacious bedroom, full bath, kitchenette eating area, and a garage. Menemsha Hills Reservation is your backyard - 211 acres described by its Trustees as follows: "Menemsha Hills was shaped by thousands of years of glacial advance and retreat. Today an array of mini-environments comprise a rugged, pleasant landscape: low wetlands, woodland groves leading to a hilltop, wind-blasted coastal plains, a rocky ocean edge, and 308-foot Prospect Hill." Not to mention - Menemsha sunsets are a short distance away!

Tucked away in a prime location just off Middle Road is this bright modern home offering the perfect blend of comfort and style. The main level features a large bedroom or first-floor office and a full bath, while the upper floor boasts two additional bedrooms and a beautifully appointed bathroom with a steam shower and double vanity. The open concept living and dining areas flow effortlessly into the kitchen and porch, creating an inviting space ideal for entertaining. The kitchen is neat, functional, and well-equipped. On cooler days, enjoy the warmth of a propane stove in the living room. Step outside to enjoy outdoor life at its best, with a private southwest-facing deck and a spacious, screened-in porch. The property is beautifully landscaped, featuring mature gardens and tasteful granite stonework - complete with a firepit for peaceful evenings. A convenient walk-out basement provides easy access to additional storage space. Nature lovers will appreciate the nearby Fulling Mill Brook Land Bank property, offering nearly 50 acres of scenic trails perfect for hiking and biking. Lucy Vincent Beach is just a short drive or bike ride away, making it easy to enjoy the coast. With great rental potential, this home also presents an excellent investment opportunity. Conveniently located near Chilmark Center and Alley’s General Store, this property offers both privacy and easy access to local amenities. Seller is working on new title V septic for three bedrooms.

Premier Build-Ready Lot with Private Beach Access Get to know Stonewall Association, one of Chilmark’s most sought-after enclaves on the South Shore. This sunny, build-ready parcel offers a rare opportunity to own land with deeded private access to Stonewall Beach—a beloved destination for swimming, surfing, excellent fishing and summer memories. Set on beautifully contoured land with southern exposure, the property is fully engineered and approved, offering the potential for a main residence, an 800 sq ft guest house , plus a detached bedroom and other accessory structures as allowed by Chilmark zoning. Enjoy proximity to Chilmark Town Center, Nashaquitsa Pond boat landing, and Menemsha Harbor, while tucked away in a quiet, nature-rich setting. The southern facing topography is ideal for incorporating a walk-out lower level, perfect for expanding your living space while maximizing natural light . A custom build/design package is available to simplify your development process and bring your dream island retreat to life. Stop trying to find your perfect home and build just what you want!

South shore beachy living in Stonewall Association with private parking and access to a lovely swim and surf beach in a beloved area of Chilmark. There are second floor water views over Squibnocket Point and the Atlantic Ocean. This lot is fully engineered and ready to be built on! Single-family dwelling, plus a detached bedroom and accessory buildings, permitted according to the Chilmark bylaws. Great location in Chilmark, close to the Nashaquitsa town boat landing, Chilmark Town Center, and Menemsha. A dream location for Chilmark lovers. The lot offers interesting topography allowing for a lower-level walk-out basement facing south for maximum sunlight and additional living square footage. A rare opportunity in Chilmark to own land in Chilmark in this association. Build/design package for a new owner will allow for ease in the development process. Why keep looking for your perfect home, build exactly what you want and start your Vineyard life just as you imagined. This location is known for excellent surfing and fishing, walk right to your own beach and enjoy all of the outdoor activity that Stonewall offers.

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.

Beautifully sited on 3.4 acres, this distinctive Chilmark home offers a rare blend of privacy, comfort, and expansive living space, ideal for entertaining, both inside and outside. From the welcoming foyer, step into the dramatic vaulted living room, where wood-paneled ceilings, a gas fireplace, and abundant natural light create a warm and inviting atmosphere. French doors open seamlessly to an expansive deck, extending the living space outdoors. Adjacent to the living area, the dining room and well-appointed kitchen flow effortlessly into a fabulous screened porch—perfect for al fresco dining or relaxing in any weather. A cozy den and full bath are thoughtfully tucked off the entrance for additional flexibility. Beyond the kitchen, a spacious mudroom with a separate entrance leads to an outdoor shower and a generous laundry room with built-ins and a sink, offering exceptional functionality for island living. The primary suite is a private wing on the main level, featuring a large walk-in closet, a full bath, and a striking double-sided stone gas fireplace that connects the bedroom to an adjoining office or den with a shiplap ceiling. With direct access to a wrap-around deck, this space is truly the crown jewel of the home. Upstairs, you’ll find a large bedroom with a private deck, access to a shared full bath, and two additional bedrooms. The full-length basement, offering over 2,200 square feet, and a detached two-car garage provide ample space for storage, hobbies, or future customization. With a 5-bedroom septic in place, there is room for expansion. Just moments from the Great Rock Bight Preserve, Menemsha, and Chilmark’s renowned beaches, this exceptional property captures the essence of up-Island living—private, serene, and quintessentially Chilmark.

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 a dock on the pond which provides access to a beautiful barrier beach on the Atlantic. Well in place, buyer responsible for new septic system.

Designed by renowned architect Araldo Cossutta as his personal retreat, the estate is made up of 5 dwellings providing a rare opportunity with pre existing density. One of the most stunning approaches from Middle Road thru your 8 acres of agriculturally conserved land. In need of renovation, the options are endless. Create a family compound, B+B/Inn, Farm, much needed housing or other ideas. Priced for sale "As Is". Showings to begin Saturday March 15th.

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 plantings surround the home. A must-see to appreciate all the special touches throughout the Main House, Guest Camp, and Garage. Option to buy shares of abutting conservation land for an additional fee, please inquire.

Located on a private lane along North Road in the heart of Chilmark, this hilltop four bedroom home was perfectly sited to enjoy fantastic water views of Vineyard Sound toward the Elizabeth Islands. Built in 1983 and lived in seasonally, this home has been meticulously cared for. There is a new forced air HVAC system, and recently upgraded electrical. In addition, there are three working wood-burning fireplaces, and the roof, windows, exterior doors, decking and siding have all been replaced within the last 10 years. The interior layout is ideally suited to taking in the views and spectacular sunsets, with an open kitchen, dining and living room that connect to a spacious deck and screened porch. The primary suite also connects to the deck and has views to the water. Guest bedrooms are on the ground floor and are privately set. The land is generous and beautifully landscaped, with a half basketball court carved in along the drive up to the house. Located just a short drive or bike ride to Menemsha and all town beaches, the setting is private, convenient and quintessentially Chilmark.

The Salt Shack merges historic preservation with modern updates in Menemsha. Designed by husband-and-wife luxury boutique design firm, Morgan Studio, the renovation of this 100-year-old ocean view cottage preserves its charm and historical integrity while incorporating contemporary design elements to enhance both comfort and aesthetics. Nestled behind Menemsha Pond, the cottage boasts a prime location for watching incredible sunsets over the pond to the ocean beyond and strolling into town for beach-going, fishing, boating, shopping, and dining. The layout and flow of the spaces feature captivating views from many vantages, and all new windows enhance natural light and views. The refined palette and materials reflect the natural surroundings and match the experience of Menemsha living. With modern forced air cooling and heating and a fully insulated structure, the property can be enjoyed year-round. Additionally, the ground level suite is the ideal complement to the two upper floors, providing a private retreat for family and friends. A turnkey ocean-view offering, the Salt Shack presents a rare opportunity to enjoy a stunning escape to the authentic fishing village of Menemsha.

Tucked away in the heart of Chilmark, this nearly 3-acre property blends rustic Vineyard charm with unique creative potential. Chilmark was a very special place for the former owner, American artist Thomas Hart Benton, who summered on the Island for 50 years. Professor and Art Historian, Erika Doss, said “the years he spent in Chilmark honed the artistic style and subjects that led to his celebrated reputation as a leading American scene painter.” You can feel this history when you step inside. Anchored by a classic 1973 home and a classic shingle 1950s artist’s studio, the property is a rare find offering character, privacy, and pastoral beauty. The main house features an updated kitchen, a great room with vaulted ceilings and fireplace, a sitting room with a beach stone fireplace, 2 bedrooms and 2 baths. The oversized screened porch is the perfect spot to end the day. Once outside, the 14x20 pool and hot tub are surrounded by mature plantings, a stone patio and pergola. Nearby, the wisteria-covered patio provides yet another area to enjoy the surroundings. Next door, the detached studio with a full bath —originally built as a creative sanctuary in the 1950s—offers inspiring space for art, writing, or guest accommodations. Rolling hills and stone walls frame the landscape, evoking the casual elegance of old Chilmark. Whether you’re looking to restore, refresh or expand, this property is full of potential in a tranquil up-Island location. *The abutting parcel with two cottages was also part of the Benton family and are available for purchase.

This private and serene 2.36 acre property is located one mile from Lucy Vincent Beach. There is a large building envelope located between the eighty and one hundred foot contour with exciting architectural options. The land has open woodlands, a small pasture and a fenced garden area. A charming cottage on the property is offered fully furnished and has everything you need to enjoy your stays in Chilmark as you design your house of the future. Broker has ownership interest. Call for appointment preferably 48 hours in advance since there might be guests staying at the cottage. TENANTS IN COTTAGE. PLEASE GIVE US 48 HOURS NOTICE FOR SHOWINGS PLEASE AND NO DRIVEBYS!

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, brick patio and outside shower. There is a large building zone located between the eighty and one hundred foot contour with exciting architectural options, especially for solar designs. The cottage is offered fully furnished, with exception of some art and a few other items (to be listed prior to accepted offer), and has everything you need to enjoy your summers in Chilmark as you plan for your future. The property has a 4-bedroom septic system. Broker has ownership interest. TENANTS IN COTTAGE; PLEASE GIVE US 48 HOURS' NOTICE FOR SHOWINGS PLEASE AND NO DRIVEBYS.

11 Greenhouse Lane...an incredible opportunity to own in this sought after private enclave with deeded private south shore beach and pond access close by...this charming vintage cape enjoys views over wetlands out to the Atlantic beyond! Three bedrooms, two baths, living room with fireplace, dining area, updated kitchen, screened porch and outside shower. The owners have taken full advantage of this beautiful site, with a patio for entertaining and a dipping pool. A spacious shed has great storage for kayaks, paddle boards, surfboards and much more. Beautifully landscaped and ready for you to enjoy summer in Chilmark with additional beach access to Lucy Vincent and Squibnocket. An added bonus is the 240v ChargePoint at the driveway.

Nestled in the heart of Chilmark, this 12.5-acre property offers two charming dwellings, each with 3 bedrooms, set in a landscape of privacy and timeless Vineyard character. Built in 1950 and 1963 for American artist, Thomas Hart Benton, the homes were lovingly created as a compound for friends and family to return to year after year. Tucked down a quiet driveway, the two share a special legacy with the neighboring property at its end. Each house reflects the simple beauty of its era, open living spaces, and a relaxed, unpretentious spirit. Whether you choose to update, preserve, or reimagine, these homes are rich with potential with ample space for expansion. The land is natural, wooded, sloping and steeped in Chilmark’s rural charm. This is a unique opportunity to own a multi-home compound with a 50-year family history. *The house with pool, studio and garage at the end of the road, also owned by the Benton family, is also available for sale.

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. Short walk to the Brickyard Beach on the North Shore, rights are included with property, where you can enjoy swimming and watching beautiful sunsets. There is also a 1 car garage with a work space.

Make your own Chilmark dream come true! 12.6 +/- acres of prime land allows you to create your own family compound or Island Farm. Enjoy the peacefulness of the Chilmark with room to expand. Two separate buildable lots provides you unique options. The Main house has three bedrooms, three bathrooms, two studies, multiple living spaces and a large three-car garage

Magical waterfront Quitsa pond cottage with private dock. This home has the most spectacular views including sunsets and an intimate relationship with the charming and timeless waterfront at Quitsa Pond. Designed with the setting in mind this sublime piece of architecture has wonderful spaces, fantastic detail and so much packed into a smaller home. Landscape design by Edwina von Gal accentuates the simplistic beauty of this propery. A unique and inspirational built-in art installation by Andy Goldsworthy adorns the northeastern wall of the living room. A fireplace created with slate roof tiles unlike any other is built into the southwest wall. Custom Will Parry windows and doors throughout with giant floor to ceiling glass doors that slide wide to join the inside and outside of the home bringing the natural beauty of the area into the house. Step outside and onto your private dock with power and water, or walk down your boat ramp into the warm waters of the pond for a swim, kayak or paddleboard adventure. A custom staircase influenced by Frank LLoyd Wright has built-in book cases and metal work by artisan Whit Hanschka which brings you to the upper floor where there are 3 bedrooms and 2 baths. 2 of the bedrooms open out onto a small deck overlooking the pond and all have views of the water. This home is cozy with radiant floor heat under the tile floor

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.

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.

Wonderful elevated Chilmark north shore 3.8 acre secure waterfront property with dramatic year round sunset water views to the Gay Head Lighthouse and Elizabeth Islands. The Vineyard Sound expanse enjoys peaceful sailing, fishing and other boating activity to enhance the ocean splendor. The 5 bedroom 3 1/2 bath 4,050 sq ft home is literally in move-in condition. Architect designed and built by Heikki Soikkeli, the house is light filled with 140 windows so every room has windows on 3 of the 4 sides. The house has 3 self contained bedroom wings and a stunning Lew French fireplace and chimney. The property sits on a private 48 ft elevated 425 ft setback site in the highly desirable Spring Point community -- 48 homeowners on 330 acres with 90 acres of common land, 2 tennis courts and 5 miles of quiet paths and pretty well maintained country dirt roads -- with the finest north shore bluff path along a 1 mile stunning private sandy beach abutting the dreamy Great Rock Bight Beach Cove next to the 200 acre Menemsha Hills Reservation. The house is a short walk on a grassy canopied path to the beach. The living room, primary bedroom and kitchen have grand water views.

This exceptionally elegant and tranquil home in Seven Gates Farm combines contemporary architectural design with timeless high-end features for Vineyard casual, nature-inspired living. Extraordinary and rare, this move-in ready three-bedroom home with six-bedroom septic system sits on an oversized 5.3-acre parcel in Chilmark. This thoughtful layout has an easy flow, soothing tones with cypress wood paneling and accents, and combines open living spaces with separate, more secluded areas such as the TV/media room, private multi-room primary suite and private guest wing. The great room features floor to ceiling walls of windows creating a transfer of light and air from both sides of the space. The primary suite includes a separate office space, expansive walk-through closet, an architectural feature wall defining the sleeping space, beautiful bathroom of wood and glass, and access to the outdoors. Upstairs you'll find an expansive bedroom currently used as a gym and office, a cedar closet room and a large unfinished space for potential expansion. The airy guest bedroom wing is found off the entryway and includes French doors for access to the yard, built-in ceiling curtain tracks and art hanging ledges, and a full bathroom with soaking tub. The interior seamlessly blends into the exterior spaces. The artistic stonework of the front yard patio and water feature lead beyond to gardens, lawn and a trail through the wooded areas of the property. This property is part of Seven Gates Farm and enjoys the benefits of miles of coastline including three distinct beaches and two docks, 1000 acres of common land with trails weaving throughout, two tennis courts and a lovely community of neighbors. Note: 2% fee to Seven Gates Farm at closing in addition to purchase price and Land Bank fee.

An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The original section of this 3000 sq ft home dates from the late 1700s and is on Chilmark's register of historic homes, but it has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to detail, and very good taste. In addition to the beautifully renovated home there is a very large enclosed garden, pickleball court, and a wind turbine that produces large amounts of energy. SHOWINGS START JUNE 20th.

This spectacular and bright modern american farmhouse is perfectly sited to capture the varied scenic beauty that surrounds the farm. Built in 2021 with great attention to detail and materials, this home was created around gatherings and community with ample space for the extended family. The land has been lovingly curated into a place which can grow, generate and support those who want to have the best qualities of an island existance, minimize their impact and enjoy the literal fruits of life. The home has an 81 panel solar production system, granting it producer status and producing a surplus of energy that far surpasses the use. There are fruit orchards around the property that include fig, plum, apple, blueberry, cherry and more. (see addendum) The property achieved status as a Certified Organic Farm (USDA). The fantastic kitchen is designed for the serious chef with a huge 4 x 9 foot center island made of honed granite and a 48 gas range, subzero fridge and bosch dishwasher. The great room has a floor to ceiling rumford designed stone fireplace with cathedral ceilings, reclaimed antique beams, and a great floor plan that still maintains a sense of intimacy. Great mudroom with tons of built in that opens into the garage and the laundry room. Generator fed by 500 gallon buried propane tank provides security if weather goes bad. This is a really wonderful house and must be seen.

Commercial certified organic farm set in the hills of Chilmark. This wonderful small scale farm has been lovingly created and grows a variety of high value fruits and vegtables which are sold to local businsses and restaurants. The land has been lovingly curated into a place which can grow, generate and support those who want to have the best qualities of an island existance, minimize their impact and enjoy the literal fruits of life. Lots of opportunity to expand the commercial operation with value added products. There are fruit orchards around the property that include fig, plum, apple, blueberry, cherry and more. (see addendum) The property achieved status as a Certified Organic Farm (USDA) which is renewed annually. There is a rainwater catchment system to supplement watering with over 7500 gallons of capacity. In addition there is a spectacular and bright modern american farmhouse perfectly sited to capture the varied scenic beauty that surrounds the farm. Built in 2021 with great attention to detail and materials, this home was created around gatherings and community with ample space for the extended family. The home has an 81 panel solar production system, granting it producer status and producing a surplus of energy that far surpasses the use. The fantastic kitchen is designed for the serious chef with a huge 4 x 9 foot center island made of honed granite and a 48 gas range, subzero fridge and bosch dishwasher. The great room has a floor to ceiling rumford designed stone fireplace with cathedral ceilings, reclaimed antique beams, and a great floor plan that still maintains a sense of intimacy. Great mudroom with tons of built in that opens into the garage and the laundry room. Generator fed by 500 gallon buried propane tank provides security if weather goes bad. This is a really wonderful house and must be seen.

This private 21-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 three-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. Crisscrossed with well-maintained trails, it invites exploration through meadows, forest, streams, and even a tranquil pond. With subdivision potential and an extraordinary sense of place, this cherished family estate feels like a private piece of up-island history—rich in character, natural beauty, and possibility.

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 and seclusion yet expansive views. 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. To the south, the dock traverses the estuary into a private cove opening up to the main pond and the ocean. A secure environment surrounded by water on three sides. 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. Southern orientation provides sun all-day to both the house and the guest house. Year-round water and new 5-bedroom Title-5 compliant septic. Unique remodeling and expansion options compared with other waterfront Island property due to the existing height, large attic with views, and a lower level with tremendous natural light allowing for valuable future living square footage. You are welcome to continue the legacy of this extraordinary real estate.

Commanding Pondfront Retreat with Private Dock and South Shore Views. This exceptional Chilmark residence offers an unparalleled blend of privacy, elegance, and modern comfort. An original Tom Tate build, and renovated in 2018, the home exudes contemporary sophistication while embracing its serene natural surroundings. A private dock on Chilmark Pond provides direct access to the water, inviting you to enjoy peaceful mornings and breathtaking sunsets over the shimmering South Shore. Just follow the most gorgeous manicured pathway, an iconic vineyard staple, to your own private dock and launch across the pond to your private south shore beach lot. The property is enveloped by more than 7 acres of abutting conservation land, ensuring a tranquil and secluded setting. The grounds are a masterpiece, featuring meticulously designed gardens that enhance the property’s timeless allure. The expansive first floor makes entertaining a breeze with wide open living spaces, and also allows for quiet work to take place in the private office. The ground level floor features more relaxed living space and wet bar with access out to the gorgeous back yard and path to the pond. The second floor is dedicated entirely to a luxurious primary suite with two private bathrooms—a sanctuary that boasts expansive water views and refined finishes. This is more than a home; it’s a lifestyle defined by elegance, comfort, and beauty. Separate guest house property also available, please inquire.

Spectacular views from one of the most sought after private enclaves on Chilmark's South Shore. This lovely home was built to take advantage of this magical location. Just steps to the shared dock on the shores of Upper Chilmark Pond and minutes to the extraordinary deeded Atlantic Beach front. The homeowners worked with world renowned architects, Crissman & Solomon, along with revolutionary landscape designers, Wolfgang Oehme and James van Sweden, to create a home that fits perfectly into the lovingly curated landscape with native plants that are a joy to behold whatever the season. The open living, dining, kitchen area overlooks the glorious gardens and lawn sloping down to Upper Chilmark Pond, over to the barrier beach, Atlantic Ocean, Squibnocket Point and Noman's Land beyond. Two additional living areas complement the three bedrooms and three baths allowing areas to enjoy the views from the privacy of each bedroom wing. The home has two offices, a studio and laundry room. The basement and one car garage have ample storage. There is a detached bedroom with full bath and separate living area for guests, as well as a shared dock on the pond and a spectacular sandy beach away from the crowds in a world of its own, just a short trip across the pond from this beautiful home. This is rare offering on Chilmark's south side, available for the first time in almost 40 years! Definitely a must see...this could be the one you have been waiting for...please call for a guided tour to experience the magic of this very special location!

Set on 5.6 acres of pristine land, this custom-built 4-bedroom, 2.5-bath main residence, with a detached 1-bedroom, 1-bath guest studio, offers unparalleled privacy, natural surroundings and sweeping views of Vineyard Sound. Nearly every room captures breathtaking water views and unforgettable sunsets, best enjoyed from the expansive stone terrace, screened porch, or the private balcony off the primary suite. Craftsmanship and character define this finely constructed home, featuring salvaged heart pine floors, reclaimed beams, and other thoughtfully curated details throughout. A generous building envelope allows ample room for expansion, making this property a lasting investment as well as a beautiful home. Surrounded by mature trees, lush gardens, and open lawn, this is a place of quiet beauty and natural elegance. A short stroll through the grounds leads to 340 feet of private waterfront—perfect for peaceful swims and tranquil moments on the shore. Enjoy the nearby charm of Menemsha Village, a leisurely walk away.

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.

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 acres of preserved land, this stately home was designed and built by Soikkeli & Company, one of the island’s premier luxury builders. Inspired by traditional New England farmhouse architecture, the exterior features cedar shingles, multiple gables, and timeless charm. At the heart of the home is a stunning chef’s kitchen with soapstone countertops, a custom farm sink, high-end appliances, and a walk-in pantry. Two living rooms flank the kitchen, while the first-floor primary suite occupies the sunny southern end of the house offering luxurious comfort and ocean views. Four additional bedrooms and a two-car garage sit in a separate wing. Smart features include Nest thermostats and a HEOS sound system. Outdoors, the organic landscaping showcases historic stone walls, colorful gardens, and a manicured lawn, all complemented by nearly 3 acres of fenced pasture. Enjoy outdoor living from the expansive back deck or the screened porch with stone fireplace, both perfect for stargazing or enjoying the breathtaking Atlantic Ocean views. Squibnocket Farm ownership includes exclusive access to scenic trails, pond launches, and a private beach with some of the Martha’s Vineyard’s most pristine dunes and shoreline. This is more than a home, it’s a lifestyle.

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. Sunrise and Sunset! This home, completely renovated in 2022 features a state of the art gourmet kitchen, adjacent butler's pantry & vast open living area with wood burning fireplace, mellow wood floors and breathtaking views out every window. Four large bedrooms, three bathrooms plus a powder room. Primary suite bathroom features an independent tub and steam shower. Fully heated, insulated and air conditioned this home is four season living. Walking paths to pond access for kayaking, swimming and boating & association tennis court. This property is protected by a Trustees of Reservation Deed of Conservation Easement.

This exceptional Martha's Vineyard estate promises unmatched privacy and breathtaking views of the Atlantic Ocean and Chilmark Pond. Masterfully designed by acclaimed architect Rick Sundberg and built by renowned island builder Andrew Flake, this three-parcel property seamlessly blends modern sophistication with the timeless charm of the Vineyard. Upon entering, you are greeted by soaring ceilings and rich oak floors that flood the space with natural light. Expansive glass walls open up to sweeping oceanviews over Chilmark Pond creating a seamless connection between the indoors and the stunning landscape. The chef's kitchen is a true standout, featuring custom cherry cabinetry, luxurious granite countertops, and top-tier appliances from Sub-Zero, Miele and Wolf. The primary suite offers a private study with a cozy fireplace, two spa-like baths, and a spacious deck with ocean views. Heated floors throughout add an extra layer of comfort. Outdoors, a spacious screened porch and heated infinity pool overlooks the ocean and a beautifully landscaped terrace. The property also boasts a large kitchen garden, fruit trees, and a half-basketball court. A detached three-bay garage and a charming two-bedroom guest cottage provide plenty of room for family and friends. To complete this extraordinary offering, private access to a secluded south shore beach, accessible by boat from Chilmark Pond, ensures a truly exclusive lifestyle.

A 1930s-built home that has been remarkably updated to retain its historic charm while incorporating sophisticated and modern amenities. The house overlooks the Chilmark Great Pond and the Atlantic Ocean beyond. The Main House includes 3 bedrooms, 3 beautifully renovated bathrooms, a walk-in closet, a Pantry, a Library/Media room, a full basement, Outdoor showers, and a screened-in porch. The property includes a 2-bedroom Guest house, a Garage with a bedroom & bathroom above, a studio, and landscaped gardens. The property has had a pool designed, and there is walking access to the Chilmark Great Pond from the house.

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.