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

Price: $4,950,000

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: 15 Old Farm Road Town: Chilmark Link ID: 43649

Price: $4,250,000

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: Donnelly + Co

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: 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: 27 Clambelly Road Town: Chilmark Link ID: 43567

Price: $3,500,000

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

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

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: 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: 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: 5 Oceanview Farm Road Town: Chilmark Link ID: 43540

Price: $2,675,000

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

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

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: 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: 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: $1,895,000

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: 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: 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

Address: 99 Cygnet Way Town: Chilmark Link ID: 43837

Price: $400,000

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

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