Escape the crowds at Lucy Vincent and Squibnocket and take advantage of this very rare opportunity to own a private, 17 member, Atlantic Ocean beach lot at Thumb Cove (abuts Hancock Beach). Included in the sale of this property is a deeded .2 acres of sandy beach, a deeded parking spot at Chilmark Pond and the right to launch boats from a dock in the pond. Sail, kayak, row, swim(!) or motor across the pond to one of Chilmark's best beaches. Chilmark Pond is the perfect spot for swimming for children, learning to sail and crabbing. Dock space provided for one electric skiff boat and one small sail boat. Storage racks provided for kayaks and row boats. Parking for Thumb Cove is located just one-tenth of a mile off South Road. Call today for a guided tour! Note: This is not a buildable lot, no structures of any kind permitted on the beach or in the parking lot.

Ready to build, private, 4.3 acres in Chilmark located just off of North Road and minutes from the iconic fishing village of Menemsha. This parcel comes equipped with a well, 4 bedroom septic system, electricity and cable all in place for seamless development. There is an existing garden house that can be repurposed as a construction site shed and perhaps later an ADU. The lot has recently been brush cut and cleared. Building envelope has been identified and mapped.

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.

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.

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 backyard—featuring a naturally shaded stone bench and trees perfectly placed for a hammock—offers 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 find—whether you're looking for a year-round home, seasonal getaway, or investment opportunity.

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. Photo of exteriors and plans available. Stop trying to find your perfect home and build just what you want!

Set on three acres of natural beauty, this tranquil up-island compound offers a timeless Vineyard retreat with a post-and-beam main house, private guest studio, and oversized barn-style garage—all surrounded by stone walls, serene gardens, and the glacial boulders that define the Chilmark landscape. The main residence showcases an open floor plan filled with natural light, wide-plank floors, and vaulted ceilings across three levels. A chef’s kitchen with Viking gas range, pantry, and center island flows seamlessly into the living and dining areas, anchored by a fieldstone fireplace and French doors that open to a sunny deck and brick patio for effortless indoor-outdoor living. The first-floor primary suite includes custom closets and an elegant bath featuring artisanal tile, slate floors, and a deep soaking tub. Brick patios and winding garden paths extend the living space outdoors, inviting quiet enjoyment of landscaped grounds and wooded trails. The partially finished walk-out lower level, with its own private entrance and custom stonework, offers flexible bonus space for work or play. Completing the property is a 576 sq. ft. detached guest suite with loft, full bath, and deck—perfect for guests, work, or creative pursuits—along with an oversized two-car garage with a spacious loft above. As a Chilmark resident, you’ll enjoy access to the coveted Lucy Vincent Beach—making this property a rare opportunity to own a distinctive and serene Vineyard escape.

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.

Where Vineyard history meets pastoral beauty.Classic, lovingly restored 1800’s Chilmark farmhouse with multiple outbuildings, which includes a large barn with second floor loft, a run-in barn with two horse stalls, both overlook an expansive, pastoral fenced pasture for horses to run or field games to be played. This historic farmhouse home offers four bedrooms, three baths and has been updated to include modern bathrooms and an upscale kitchen, while remaining respectful to the charm and integrity of the antique home. The inviting spaces offer a masonry wood burning fireplace in the dining/living area, a second lounge area off of the front foyer, and a period stairway leading to the second floor. This is a home with a heart. The location is as stellar as its setting. It is blocks from the historic West Tisbury Village, just over the Chilmark line which includes Chilmark South Shore Beach access to Lucy Vincent and Squibnocket. Close to the Yoga Barn, Alleys, West Tisbury library, and nearby hiking trails to Quansoo. Major improvements include new HVAC systems, windows, insulation, kitchen and bathrooms. There is a 5 bedroom septic system in place for expansion opportunities. Come experience the joy of this home and all the property offers.

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. Fire destroyed house in 2020. See old and new views in document attached.

Designed by the famous mid century architect Andrew Geller, this contemporary home is situated at the top of the parcel with ocean views and a glimpse of Chilmark pond. There is ample open space to accommodate family and friends and overlooks the large meadow which follows the stone wall to South Road. Access to walking trails, and Lucy Vincent Beach is a short distance away.

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.

Winding tree lined driveway off North Rd brings you to this commanding, custom designed residence built by a top tier island builder. This home is set on over 4 private acres of rolling meadows and big sky views. Main living space is all on one level which includes primary bedroom with en-suite bath, large living area with fireplace, bright sunroom or second living room, custom kitchen and two additional bedrooms with full bath. The finished walk-out lower level is an additional 1700 square feet offering a studio suite with full bathroom and separate entrance. Two outbuildings consist of a second garage and an unfinished cottage style building that has amazing potential for detached bedroom or guest suite.

Step into timeless mid-century modern style and comfort in this single-level, 4-bedroom, 3-bathroom home located in the heart of Chilmark. This home features an open layout with large glass panel doors that lead to a sun-drenched deck, heated in-ground pool, and grassy lawn. This home is offered completely furnished with a well-equipped kitchen, large living room with wood burning fireplace, dining area overlooking the pool and yard, air conditioning, and cable television and internet and a distant peek at the ocean. The home sleeps 8 comfortably, with two ensuite bedrooms (king and queen), an additional queen room, and a twin room perfect for guests or little ones. Outdoors you will find an inground, 4-foot-deep heated pool including pool side furniture, umbrellas, hammock, outdoor shower, and a gas barbecue. Step across the road to the Land Bank’s Fulling Mill Preserve and theOcean View Farm Preserve with stunning Atlantic views and 20+ acres of walking trails. As a Chilmark resident you will enjoy the beautiful beaches of Lucy Vincent and Squibnocket. This property has a strong rental history with rates ranging to $13,000 weekly. Easy to show, please call listing broker.

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. DISCLOSURE: Fireplace is not working. There is very limited chance for expansion, no bedrooms can be added and the premises are not heated.

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.

A place of serenity tucked in the woods of Chilmark. Complete renovation 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. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media room with Sonos Music System, and Lutron Radio RA Switching System (can be smartphone controlled) Radiant heat in mudroom, and all bathrooms (except 1/2 bath in basement) to keep cozy in the cooler months, and a heat pump system with Boiler back up. Six bedroom septic. Close proximity to North Road and Middle Road. Beautiful home with a lot of attention to details. sq. footage is Approx.

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

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, Boshe dishwasher soapstone counters and a butlers pantry with extra cupboards, shelving and a wine refrigerator. There are sliders that take you to an oversized deck and stairs to a blue stone patio and beautiful gardens. The screened-in porch off the living room steps out to the side yard, patio and outdoor shower. First floor Primary with walk-in closet, access to the deck and a private en-suite bathroom with beautiful tiled steam shower and large soaking tub. Second floor includes a loft with sitting room, 2 spacious bedrooms that share a full bath with shower and office, all with cathedral beamed ceilings. Many nice features throughout include white oak random width floors, marble and tiled baths, incredible workmanship throughout with an eye for style. warmth and comfort. There is also a generous laundry room with wash sink. The fully finished walkout basement includes a great room, finished utility room with a dog bath, workshop and a full bath with shower. Beautifully landscaped grounds with multiple perennial beds , vegetable gardens and surrounding stone retaining walls. Privately sited on 4.80 acres and potential for a guest house with proper town permitting after 5 years.

CHILMARK BLISS – A Refined Retreat- 15 Old Farm Road, where elegance meets tranquility. Set on over 3 acres of private, manicured grounds, this exceptional Chilmark residence was thoughtfully reimagined in 2020 by architect Peter Breese and expertly built by Doug Best. A beautifully designed hardscape welcomes you, a serene pond, and the gentle murmur of a babbling stream—an introduction to the home’s atmosphere of relaxing sophistication. Step inside to a dramatic open-concept kitchen and living space, where high-end appliances, luxurious stone countertops, and a custom stone fireplace come together to create the heart of the home—ideal for both intimate gatherings and inspired culinary adventures. A spacious pantry off the kitchen, offering extra prep space, leads to a lovely screened porch for summer nights. The first floor features a sunny, bright primary suite that opens to its private deck overlooking the lush landscape. A formal foyer leads to a cozy library and media room. Upstairs is a private guest bedroom and a full bathroom. A breezeway deck—perfect for enjoying morning coffee—leads to a third bedroom suite featuring another exquisite stone fireplace, and a lounge area that provides warmth and privacy for visitors and a full bathroom. There is a large barn door opening to a private patio. The versatile lower level adds yet another layer of functionality, featuring ample dry storage and a bright bonus room that is ideal for a gym, yoga studio, media lounge, or overflow space. This space opens to a verdant backyard, blending beauty with practicality, complete with a fenced flower garden and a charming post-and-beam artist studio with electricity and a basement. The property was designed with a pool in mind. There is also a 5-bedroom septic for expansion possibilities. Enjoy everything Chilmark has to offer, including access to Lucy Vincent and Squibnocket Beach.

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

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 historic house 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.

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.

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.

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.

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.

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.