Chilmark Properties for Sale

Address: 64 Squibnocket Farm Road Town: Chilmark Link ID: 40007

Price: $16,500,000

Property Description:
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

Property description and photographs provided by listing agent: Wallace & Co. Sotheby's

Address: 8 Snail Road Town: Chilmark Link ID: 43118

Price: $14,000,000

Property Description:
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 sophis... Click here for more details

Property description and photographs provided by listing agent: Wallace & Co. Sotheby's

Address: 6 Wakeman Road Town: Chilmark Link ID: 43347

Price: $14,000,000

Property Description:
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,... Click here for more details

Property description and photographs provided by listing agent: Flanders Real Estate

Address: 16 Shotnaigher Lane Town: Chilmark Link ID: 43060

Price: $12,750,000

Property Description:
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

Property description and photographs provided by listing agent: Conroy & Company R.E., Inc.

Address: 18 Spruce Gate Road Town: Chilmark Link ID: 43244

Price: $12,500,000

Property Description:
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 ac... Click here for more details

Property description and photographs provided by listing agent: Wallace & Co. Sotheby's

Address: 25 Osprey Lane Town: Chilmark Link ID: 43313

Price: $7,975,000

Property Description:
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 ... Click here for more details

Property description and photographs provided by listing agent: Hancock Real Estate

Address: 308 South Road Town: Chilmark Link ID: 43117

Price: $7,950,000

Property Description:
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 n... Click here for more details

Property description and photographs provided by listing agent: Sandpiper Realty

Address: 34 Edys Island Way Town: Chilmark Link ID: 42401

Price: $7,450,000

Property Description:
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... Click here for more details

Property description and photographs provided by listing agent: Tea Lane Associates

Address: 44 Cencelle Town: Chilmark Link ID: 43318

Price: $6,750,000

Property Description:
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 out... Click here for more details

Property description and photographs provided by listing agent: Tea Lane Associates

Address: 60 Meetinghouse Road Town: Chilmark Link ID: 43350

Price: $6,490,000

Property Description:
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 ... Click here for more details

Property description and photographs provided by listing agent: Feiner Real Estate

Address: 60 Meetinghouse Road Town: Chilmark Link ID: 43446

Price: $6,490,000

Property Description:
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, generat... Click here for more details

Property description and photographs provided by listing agent: Feiner Real Estate

Address: 35 South Bowl Road Town: Chilmark Link ID: 43145

Price: $6,000,000

Property Description:
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... Click here for more details

Property description and photographs provided by listing agent: Tea Lane Associates

Address: 78 Hammett Road Town: Chilmark Link ID: 43055

Price: $5,975,000

Property Description:
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 bedro... Click here for more details

Property description and photographs provided by listing agent: Tea Lane Associates

Address: 124, 116, 122 Old Farm Road Town: Chilmark Link ID: 43300

Price: $5,450,000

Property Description:
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... Click here for more details

Property description and photographs provided by listing agent: Wallace & Co. Sotheby's

Address: 49 Gosnolds Way Town: Chilmark Link ID: 43016

Price: $5,295,000

Property Description:
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 ... Click here for more details

Property description and photographs provided by listing agent: Tea Lane Associates

Address: 146 Quansoo Road Town: Chilmark Link ID: 43144

Price: $4,850,000

Property Description:
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 ... Click here for more details

Property description and photographs provided by listing agent: Tea Lane Associates

Address: 15 Old Farm Road Town: Chilmark Link ID: 42807

Price: $4,825,000

Property Description:
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 hards... Click here for more details

Property description and photographs provided by listing agent: Compass | Point B

Address: 131 State Road Town: Chilmark Link ID: 43232

Price: $4,350,000

Property Description:
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, fant... Click here for more details

Property description and photographs provided by listing agent: Feiner Real Estate

Address: 88 & 90 Quenames Road Town: Chilmark Link ID: 43258

Price: $3,600,000

Property Description:
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, ... Click here for more details

Property description and photographs provided by listing agent: Flanders Real Estate

Address: 100 Gosnolds Way Town: Chilmark Link ID: 41875

Price: $3,500,000

Property Description:
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

Property description and photographs provided by listing agent: Flanders Real Estate

Address: 19-A Old Woods Road Town: Chilmark Link ID: 43319

Price: $3,400,000

Property Description:
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 ... Click here for more details

Property description and photographs provided by listing agent: Landvest MV

Address: 11 Greenhouse Lane Town: Chilmark Link ID: 41656

Price: $3,350,000

Property Description:
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 ... Click here for more details

Property description and photographs provided by listing agent: Hancock Real Estate

Address: 300 North Road Town: Chilmark Link ID: 42989

Price: $3,250,000

Property Description:
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 b... Click here for more details

Property description and photographs provided by listing agent: Conroy & Company R.E., Inc.

Address: 10 Molly's Way Town: Chilmark Link ID: 42953

Price: $2,950,000

Property Description:
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 t... Click here for more details

Property description and photographs provided by listing agent: Studio Realty

Address: 19-C Old Woods Road Town: Chilmark Link ID: 43314

Price: $2,950,000

Property Description:
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 Dos... Click here for more details

Property description and photographs provided by listing agent: Landvest MV

Address: 18 Allen Farm Road Town: Chilmark Link ID: 43372

Price: $2,950,000

Property Description:
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... Click here for more details

Property description and photographs provided by listing agent: Kendall & Kendall

Address: 18 Allen Farm Road Town: Chilmark Link ID: 42477

Price: $2,950,000

Property Description:
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 exci... Click here for more details

Property description and photographs provided by listing agent: Kendall & Kendall

Address: 31 North Slope Lane Town: Chilmark Link ID: 43097

Price: $2,895,000

Property Description:
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 forc... Click here for more details

Property description and photographs provided by listing agent: Studio Realty

Address: 11 By The Woods Town: Chilmark Link ID: 43266

Price: $2,850,000

Property Description:
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

Property description and photographs provided by listing agent: Flanders Real Estate

Address: 0, 27 & 30 Tower Lane Town: Chilmark Link ID: 42752

Price: $2,699,000

Property Description:
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 opt... Click here for more details

Property description and photographs provided by listing agent: Byrne & Company Real Estate

Address: 2 Other House Road Town: Chilmark Link ID: 42602

Price: $2,500,000

Property Description:
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

Property description and photographs provided by listing agent: Russell Maloney Real Estate

Address: 16 South Road Town: Chilmark Link ID: 43515

Price: $2,500,000

Property Description:
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 game... Click here for more details

Property description and photographs provided by listing agent: Vineyard Village Realty

Address: 9 Beetlebung Grove Way Town: Chilmark Link ID: 42643

Price: $2,495,000

Property Description:
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... Click here for more details

Property description and photographs provided by listing agent: Donnelly + Co

Address: 25 Fulling Mill Road Town: Chilmark Link ID: 43014

Price: $2,450,000

Property Description:
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

Property description and photographs provided by listing agent: Wallace & Co. Sotheby's

Address: 32 Stonewall Road Town: Chilmark Link ID: 43373

Price: $2,100,000

Property Description:
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 dwe... Click here for more details

Property description and photographs provided by listing agent: Tea Lane Associates

Address: 4 Cedar Lane Town: Chilmark Link ID: 43390

Price: $1,985,000

Property Description:
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 swimm... Click here for more details

Property description and photographs provided by listing agent: Tea Lane Associates

Address: 174 Middle Road Town: Chilmark Link ID: 43364

Price: $1,899,000

Property Description:
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, ... Click here for more details

Property description and photographs provided by listing agent: Island Real Estate

Address: 3 Fulling Mill Road Town: Chilmark Link ID: 41666

Price: $1,875,000

Property Description:
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 wi... Click here for more details

Property description and photographs provided by listing agent: Tea Lane Associates

Address: 345 North Road Town: Chilmark Link ID: 42920

Price: $1,625,000

Property Description:
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 bed... Click here for more details

Property description and photographs provided by listing agent: Wallace & Co. Sotheby's

Address: 37 Bijahs Way Town: Chilmark Link ID: 43069

Price: $1,325,000

Property Description:
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. T... Click here for more details

Property description and photographs provided by listing agent: Tea Lane Associates

Address: 00 Quenames Road Town: Chilmark Link ID: 43216

Price: $995,000

Property Description:
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 of... Click here for more details

Property description and photographs provided by listing agent: Feiner Real Estate

Address: 0 Blackpoint Key Town: Chilmark Link ID: 43139

Price: $415,000

Property Description:
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.... Click here for more details

Property description and photographs provided by listing agent: Tea Lane Associates