Chilmark Properties for Sale

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

Price: $14,500,000

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

Price: $10,950,000

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: 308 South Road Town: Chilmark Link ID: 43955

Price: $7,350,000

Property Description:
Waterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilmark Pond, this exceptional waterfront residence offers rare privacy, refined design, generous water views and easy pond access. Thoughtfully renovated in 2018, the home blends contemporary sophistication with t... Click here for more details

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

Address: 96 Hammett Lane Town: Chilmark Link ID: 43534

Price: $3,995,000

Property Description:
This beautifully designed and built Post & Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator,... Click here for more details

Property description and photographs provided by listing agent: Karen M. Overtoom R.E.

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

Price: $3,950,000

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 historic house has been expanded with new additions to create a thoroughly modern residence that ne... Click here for more details

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

Address: 6 Trails End Town: Chilmark Link ID: 43845

Price: $3,200,000

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

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

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

Price: $2,995,000

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: 31 Tower Lane and 34 Ebens Lane Town: Chilmark Link ID: 43935

Price: $2,725,000

Property Description:
This rare two-lot offering off Middle Road in Chilmark presents a private sanctuary abutting approximately 50 acres of conservation land. The gently rolling landscape is accented by ancient stone walls and striking glacial boulders, creating a setting of timeless Vineyard character. Ideal for a gene... Click here for more details

Property description and photographs provided by listing agent: Studio Realty

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

Price: $2,395,000

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: 174 Middle Road Town: Chilmark Link ID: 43364

Price: $1,895,000

Property Description:
Nestled in Chilmark, this four-bedroom home blends classic Vineyard charm with modern comfort. The sunlit eat-in kitchen features dual ovens, granite countertops, and custom cherry built-ins, flowing seamlessly to a living room with a Vermont Castings wood stove and access to a covered porch and spa... Click here for more details

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

Address: 43 North Slope Lane Town: Chilmark Link ID: 44067

Price: $1,799,999

Property Description:
Set on a private 3.5-acre wooded parcel surrounded by conservation land, this 3-bedroom, 2-bath single-family home offers the ultimate Martha’s Vineyard retreat. Nestled among mature trees and protected open space, the property provides exceptional privacy and a peaceful natural setting, while rem... Click here for more details

Property description and photographs provided by listing agent: NorthStar Real Estate LLC

Address: 46 Tiercel Lane Town: Chilmark Link ID: 43869

Price: $1,650,000

Property Description:
Nestled on a serene 3.32-acre parcel between North Road and Tabor House in Chilmark, this property blends privacy, charm, and great potential. A sweet 2 bedroom guest house—beautifully maintained and offering excellent rental income—sits amid rolling stone walls and mature trees, creating a peac... Click here for more details

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

Address: 45 Quenames Road Town: Chilmark Link ID: 43983

Price: $1,575,000

Property Description:
Set on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and excellent potential. In a sunny clearing among mature trees, the maintained 2-bedroom house features first-floor living, an open kitchen and living area, two spacious bedrooms, a full bath with shower, an enorm... Click here for more details

Property description and photographs provided by listing agent: Sandpiper Realty

Address: 47 Quenames Road Town: Chilmark Link ID: 43984

Price: $1,575,000

Property Description:
On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A ... Click here for more details

Property description and photographs provided by listing agent: Sandpiper Realty

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

Price: $1,295,000

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