Chilmark Properties for Sale

Address: 95 Stonewall Road Town: Chilmark Link ID: 34135

Price: $13,500,000

Property Description:
Paradise is located at the magical intersection of the Atlantic Ocean and Stonewall Pond. A true seaside retreat, this 4-acre property with main house and guesthouse welcomes you to an enchanted life. Massive sliding glass doors that showcase truly unparalleled views grace nearly every room. Interi... Click here for more details

Property description and photos provided by listing broker Wallace and Co. Sotheby's.

Address: 277 North Road Town: Chilmark Link ID: 32237

Price: $12,500,000

Property Description:
With a sweeping entrance through an expansive farm field, walking and riding trails, woodlands, pond, beach access, and total privacy, this feels like one of the exclusive home associations on the island, but this is yours all unto your own. Almost 70 acres of storied history, seclusion and a mile o... Click here for more details

Property description and photos provided by listing broker Tea Lane Associates.

Address: 138 and 140 State Road Town: Chilmark Link ID: 33559

Price: $10,300,000

Property Description:
Spectacular 3 home waterfront Chilmark estate on 5.4 acres with private dock on Stonewall Pond. Breathtaking one-of-a-kind views across Stonewall Pond out to the Atlantic from all 3 homes as well as stunning views of Quitsa Pond. Each of the homes is charming and beautifully maintained, with its o... Click here for more details

Property description and photos provided by listing broker Tea Lane Associates.

Address: 22 Quitsa Lane Town: Chilmark Link ID: 34036

Price: $9,995,000

Property Description:
Spectacular and charming; this cottage style home and guest annex is located in one of the most picturesque parts of Martha's Vineyard. This home is full of character with access to private beach just steps from the home and unforgettable ocean views from nearly every vantage point on the property. ... Click here for more details

Property description and photos provided by listing broker Flanders Real Estate.

Address: 100 Beach Plum Lane Town: Chilmark Link ID: 35399

Price: $8,500,000

Property Description:
Travel up a short winding, gravel drive and arrive at a compound of shingle-clad seaside cottages positioned to take advantage of the commanding views of Vineyard Sound and the village of Menemsha. This property, once featured on the cover of Architectural Digest, dates to the 1930's and was loving... Click here for more details

Property description and photos provided by listing broker Russell Maloney Real Estate.

Address: 1 Azalea Lane Town: Chilmark Link ID: 34126

Price: $8,250,000

Property Description:
Rarest of the rare - Ocean-view Chilmark home with swimming pool, 440 feet of private ocean beach, and big, beauteous ocean views. The house is being completely renovated and price shown is for the completed product. Note that the images shown are of the house BEFORE renovation. Detached garage.

Property description and photos provided by listing broker Wallace and Co. Sotheby's.

Address: 135 State Road Town: Chilmark Link ID: 19770

Price: $5,750,000

Property Description:
Located on the edge of Quitsa Pond, this four bedroom home is perfect for summering on the Vineyard. Views from nearly every room of this home over Quitsa and Menemsha Pond. With extremely desirable dock space included, this property has two full private docks and one floating dock only steps from y... Click here for more details

Property description and photos provided by listing broker Flanders Real Estate.

Address: 138 and 138B State Road Town: Chilmark Link ID: 34994

Price: $5,500,000

Property Description:
An amazing Chilmark waterfront property that sits between Stonewall and Nashaquitsa ponds just past Hariffs Bridge. A 3 bedroom main house and 2 bedroom guest house occupy 4 acres of private natural land, and include access to Stonewall pond and Stonewall beach. The "Lenom" property has been in th... Click here for more details

Property description and photos provided by listing broker Tea Lane Associates.

Address: 11 Azalea Lane Town: Chilmark Link ID: 30618

Price: $5,200,000

Property Description:
With 425 ft of private ocean beach, this offering deserves its reputation as the "ultimate beach house". The 5-bedroom home has been completely renovated to the highest specifications with a focus on bold contemporary choices to take advantage of the views and setting. The beach stairs provide acces... Click here for more details

Property description and photos provided by listing broker Wallace and Co. Sotheby's.

Address: 140 State Road Town: Chilmark Link ID: 33561

Price: $4,800,000

Property Description:
Spectacular waterfront property with private dock on Stonewall Pond. Breathtaking one-of-a kind views across Stonewall Pond out to the Atlantic Ocean as well as stunning views of Quitsa Pond. This magical property is known as the "Lorca" home because the current owners purchased it in 1972 from the... Click here for more details

Property description and photos provided by listing broker Tea Lane Associates.

Address: 21 Squibnocket Road Town: Chilmark Link ID: 33963

Price: $4,375,000

Property Description:
Perched above and just steps from beloved Squibnocket Beach and Pond, this idyllic beach house has amazing views of the Atlantic and shoreline out to Squibnocket Point. It has been fully renovated with many tasteful, modern enhancements and sustainably-sourced materials, and yet retains some of the... Click here for more details

Property description and photos provided by listing broker Tea Lane Associates.

Address: 137 Quansoo Road Town: Chilmark Link ID: 35095

Price: $3,700,000

Property Description:
This rare Chilmark waterfront setting is on three acres of graceful land featuring a light-filled home with an intelligent one level layout. Kayak from the private pond front beach to the Atlantic, or enjoy paddle boarding, shell fishing and the sunset right in your front yard. The current home i... Click here for more details

Property description and photos provided by listing broker Tea Lane Associates.

Address: 15 Lake Road Town: Chilmark Link ID: 25297

Price: $3,000,000

Property Description:
Endless Atlantic Ocean views, Squibnocket Pond, rolling hillsides, dramatic vistas, centuries old stone walls, gravel roads... these are just some of the features of this extraordinary property new to market for the first time in nearly fifty five years. This architect designed modern Cape Cod home ... Click here for more details

Property description and photos provided by listing broker Russell Maloney Real Estate.

Address: 11 Howell Lane Town: Chilmark Link ID: 35123

Price: $2,795,000

Property Description:
This property exudes fine craftsmanship and a well rounded experience with pool, privacy and Menemsha Pond access nearby. Located in the Flanders Lane area near Menemsha, this post and beam home was built with only the best materials - red oak timberframe, quarter sawn red oak floors, radiant heat, ... Click here for more details

Property description and photos provided by listing broker Tea Lane Associates.

Address: 13 Deerpath Lane Town: Chilmark Link ID: 34278

Price: $2,650,000

Property Description:
This impeccably built home is set on 3 private acres off of Old Farm Road in Chilmark. Open and light, the 4 bedroom house has an intelligent design that works well for quiet time or company. Upon entering one appreciates the sizable spaces that connect the living room, dining area, well appointed... Click here for more details

Property description and photos provided by listing broker Tea Lane Associates.

Address: 17 Chowder Kettle Lane Town: Chilmark Link ID: 19789

Price: $2,450,000

Property Description:
Menemsha -- one of the most desirable locations on the Island. It is an easy walk to the village for a fish sandwich and a swim at the beach from this sweetly located property. Set at the end of a private cul-de-sac, this remodeled beach themed, sea view cottage oozes with charm. Three bedrooms an... Click here for more details

Property description and photos provided by listing broker Kendall and Kendall.

Address: 18 Henry Hough Lane Town: Chilmark Link ID: 34988

Price: $2,350,000

Property Description:
A Large commanding residence set hilltop off Middle road with outstanding water views of the Atlantic and glimpses of Chilmark Pond. Inviting common room with cathedral ceilings, fireplace and gourmet kitchen seamlessly flows to the screened porch and lounging deck. Each wing of the house is compris... Click here for more details

Property description and photos provided by listing broker Conroy and Company R.E., Inc..

Address: 61 Stonewall Road Town: Chilmark Link ID: 34058

Price: $2,175,000

Property Description:
Stonewall Association, one of the premier waterfront neighborhoods in Chilmark, is the location of this brilliant renovation. A wall of beautiful windows across the entire length of the house, white tile and light hardwood floors, create a delightful and stylish home. The renovation, completed this ... Click here for more details

Property description and photos provided by listing broker Wallace and Co. Sotheby's.

Address: 20 Tennis Lane Town: Chilmark Link ID: 34314

Price: $1,995,000

Property Description:
A thoughtfully appointed contemporary home in the center of Chilmark with 4 bedrooms and three and a half bathrooms all of which are newly renovated. This home has great entertaining spaces in and out. The large living room has a cathedral ceiling and a modern fireplace which is the focal point, th... Click here for more details

Property description and photos provided by listing broker Tea Lane Associates.

Address: 55 Bijahs Way Town: Chilmark Link ID: 35387

Price: $1,975,000

Property Description:
55 Bijah's Way is a custom designed post and beam home built by well-known and respected island builder Heikki Soikkeli. Sited on 3 private acres, this home features 5 bedrooms, 4 1/2 baths, screened porch, 2 decks, fireplace, generator, and an attached two car garage. Native plantings, sweeping la... Click here for more details

Property description and photos provided by listing broker Russell Maloney Real Estate.

Address: 28 Black Point Road Town: Chilmark Link ID: 35279

Price: $1,975,000

Property Description:
Bright and airy retreat on Black Point complete with key to Black Point Beach. Set on 5.4 acres off Black Point Road in Chilmark, this charming cottage brings an immediate feeling of peace and levity. One can hear the ocean and walk, ride or drive to Black Point Beach as a key to this private south ... Click here for more details

Property description and photos provided by listing broker Tea Lane Associates.

Address: 11 Homeward Way Town: Chilmark Link ID: 34559

Price: $1,975,000

Property Description:
Vintage cape-style home, originally built in 1941 by renowned Chilmark builder, Roger Allen. This charming house was created using Chimark stones. A five bedroom home situated on a beautiful private 6.78 acre lot off North Road close to Menemsha. This extraordinary property abuts acres of Land Bank ... Click here for more details

Property description and photos provided by listing broker Hancock Real Estate.

Address: 114 Middle Road Town: Chilmark Link ID: 33858

Price: $1,875,000

Property Description:
MOTIVATED SELLER! New price and BRAND NEW PAVED entrance to driveway. This masterfully-crafted home completed in 2014 was built with the highest quality materials, finishes, and mechanics. There is custom paneling, mill work, and cabinetry gracing each and every room. Start with the open concept flo... Click here for more details

Property description and photos provided by listing broker Viewpoints.

Address: 15 Doctors Creek Path Town: Chilmark Link ID: 34870

Price: $1,800,000

Property Description:
You can "see for miles and miles and miles and miles" from this uniquely located Chilmark cottage. 180 degree water views looking easterly over Chilmark Pond, to the Barrier Beach and beyond and westerly over the Atlantic to Nomans Land. Simply Stunning! Colorful Sunsets! Includes a deeded beach ... Click here for more details

Property description and photos provided by listing broker RE/MAX on Island.

Address: 68 Meeting House Road Town: Chilmark Link ID: 35318

Price: $1,725,000

Property Description:
Lovely four bedroom on six acres of rolling hills and meadow. Portion of land held in conservation, Open floor plan with a large screened in porch. New Windows installed in 2019.

Property description and photos provided by listing broker Flanders Real Estate.

Address: 2 Rockrose Path Town: Chilmark Link ID: 35538

Price: $1,695,000

Property Description:
This four bedroom, three bath home with ocean views and a private, south shore beach, is located on Rockrose Path off of Meetinghouse Road in Chilmark. This heated, year round house is sited on one and a half acres in a private setting with a large front yard and easy to care for landscaping. The o... Click here for more details

Property description and photos provided by listing broker Russell Maloney Real Estate.

Address: 16 Trails End Town: Chilmark Link ID: 34723

Price: $1,550,000

Property Description:
One of the unique aspects of this hilltop home is it's location at the top of a rise where it captures the stunning water views looking westerly over the Atlantic to Squibnocket point and the amazing sunsets. Connect with nature within the abutting Land Bank preserve. Several favorite vantage point... Click here for more details

Property description and photos provided by listing broker Conroy and Company R.E., Inc..

Address: 0 Middle Coomb Town: Chilmark Link ID: 31201

Price: $1,550,000

Property Description:
OLD FIELD COMMUNITY, IN THE QUANSOO AREA OF THE TISBURY GREAT POND IN CHILMARK. 3 PRIVATE WOODED ACRES WITH POND VIEW OF THIS SMALL WATERFRONT ASSOCIATION COMMUNITY. LAND INCLUDES MULTIPLE DEEDED ACCESS TO BOTH THE GREAT POND BEACH AND ATLANTIC OCEAN DUNES BY BOAT. UNTOUCHED AREA OF LOWER CHILMARK... Click here for more details

Property description and photos provided by listing broker Suzanne Lanzone and Associates LLC.

Address: 7 Middle Coomb Town: Chilmark Link ID: 31000

Price: $1,550,000

Property Description:
Private 3-acre wooded parcel on Middle Coomb Pond. Pond views and within walking distance to Tisbury Great Pond and Middle Coomb. Part of the Old Fields Community, ownership includes association common land and two deeded accesses to Tisbury Great Pond with some of the best clamming, fishing... Click here for more details

Property description and photos provided by listing broker Conroy and Company R.E., Inc..

Address: 8B Clambelly Road Town: Chilmark Link ID: 34950

Price: $1,275,000

Property Description:
CHARMING IN CHILMARK - WITH FULLY PERMITTED COMMERCIAL KITCHEN! Nestled among the rolling hills of Chilmark, this expanded Cape welcomes those who wish to retreat to its magical comfort. The thoughtful design captures the southern light traversing the first floor living area as the day unfolds. The ... Click here for more details

Property description and photos provided by listing broker Point B Realty LLC.

Address: 22 Larsen Lane Town: Chilmark Link ID: 34809

Price: $1,199,000

Property Description:
Unique opportunity to enjoy the Vineyard the way it use to be on this lovely country lane just steps from the Homeport and Menemsha Pond. Nestled in among vintage cottages this charming, fully renovated home offers all of the amenities buyers are looking for in an expanded Cape with three floors for... Click here for more details

Property description and photos provided by listing broker Kelleher R.E..

Address: 40 Wintergreen Way Town: Chilmark Link ID: 35506

Price: $1,100,000

Property Description:
Charming Chilmark getaway on 3 acres tucked off Middle Road. As you enter you are immediately aware that this home is built with quality and integrity throughout. Built by South Mountain, the home features an open floor plan, high ceilings with wood detail, gorgeous brick fireplace, a wall of slidin... Click here for more details

Property description and photos provided by listing broker Wallace and Co. Sotheby's.

Address: 252 Middle Road Town: Chilmark Link ID: 35294

Price: $1,060,000

Property Description:
House and guest house on a hilltop sanctuary. The mid-century modern main house designed by Ronald Gourley offers open-living space with a glorious wall of windows that bring in dramatic light throughout the day. Main house has a first floor en suite master with private office space. Two upstairs... Click here for more details

Property description and photos provided by listing broker Feiner Real Estate.

Address: 4 Peases Point Way Town: Chilmark Link ID: 30444

Price: $949,000

Property Description:
Located down an idyllic country lane, this beautiful 3 bedroom home offers an inviting open floor plan with cathedral beamed ceilings perfect for entering summer family and friends. Renovated in 2004, updates include a new kitchen with granite counters and new appliances, updated bathrooms, new roof... Click here for more details

Property description and photos provided by listing broker Kelleher R.E..

Address: 3 Catherines Way Town: Chilmark Link ID: 30329

Price: $925,000

Property Description:
A lovely traditional farmhouse with great history located just a short distance from Chilmark Center. This well maintained home boasts beautiful perennial gardens, and well manicured landscapes. A spacious interior provides the first floor with 2 separate large living areas, a large formal dining ro... Click here for more details

Property description and photos provided by listing broker Flanders Real Estate.

Address: 31 Tea Lane Town: Chilmark Link ID: 35400

Price: $875,000

Property Description:
A beautiful site located in the hills of Chilmark right off historic Tea Lane. Convenient to both Chilmark and West Tisbury town centers and the beaches. Surrounded by stone walls and bordering by conservation land, this 5-acre lot is accented by ancient trees and fertile blue berry bushes. To start... Click here for more details

Property description and photos provided by listing broker Conroy and Company R.E., Inc..

Address: 345 North Road Town: Chilmark Link ID: 35429

Price: $855,000

Property Description:
This classic Chilmark home offers 4 bedrooms, 3 fireplaces, 4 full baths plus outdoor shower on a lovely parcel with stonewalls and mature plantings. The living room and kitchen each have fireplaces, and the dining room has a fireplace and a bay window. Additionally, there's a detached studio with... Click here for more details

Property description and photos provided by listing broker Tea Lane Associates.

Address: 26 Kenasaoome Way Town: Chilmark Link ID: 33069

Price: $799,000

Property Description:
CHILMARK - Abutting 90 + acres of Conservation Land, this gem of a property has so much to offer, with tons of potential! Located in the lovely Quansoo area, on 3.2 acres of level and wooded land. Currently, a two bedroom, two story home, with an open floor plan and a large wrap around mahogany de... Click here for more details

Property description and photos provided by listing broker Alisan Lohan-Conway Properties.

Address: 34 High Meadow Lane Town: Chilmark Link ID: 28497

Price: $799,000

Property Description:
This four acre building lot off Old Farm Road offers an open, sunny building site on a knoll with waterviews of the Elizabeth Island and wooded land for another structure, a barn or walking trails on your own land, plus another view of a pond. This rural Chilmark neighborhood off Old Farm Road abut... Click here for more details

Property description and photos provided by listing broker Tea Lane Associates.

Address: 508 North Road Town: Chilmark Link ID: 32266

Price: $750,000

Property Description:
Historically known as the Cooper Gallery, this endearing icon of Menemsha has remained in the same family for years. A 3 bedroom cottage with a wonderful location, centrally located to all things Menemsha has to offer. Large Kitchen space with dining space, spacious living room, full bathroom and a ... Click here for more details

Property description and photos provided by listing broker Flanders Real Estate.

Address: 1 Swans Way Town: Chilmark Link ID: 33545

Price: $745,000

Property Description:
Designed for the utmost in individual privacy, this truly charming home is comprised of three "pods". The central pod houses living/dining room with brick hearth; immaculate kitchen with windows onto the screened porch that let you serve directly onto a dining bar with stools; a roomy bedroom with a... Click here for more details

Property description and photos provided by listing broker Karen M. Overtoom R.E..

Address: 1 Crowberry Lane Town: Chilmark Link ID: 33477

Price: $725,000

Property Description:
4.32 rolling acres with stone walls. Deeded walking access to north shore beach. 4-bedroom septic, well, and electric power are all installed. Natural Heritage work has already been completed and permit is in hand. The access and building site was recently brush-cut for easy access.

Property description and photos provided by listing broker Wallace and Co. Sotheby's.

Address: 33R North Road Town: Chilmark Link ID: 33959

Price: $720,000

Property Description:
Cozy cottage with lots of windows and light set in a very quiet area far off North Road abutting Seven Gates. Lot offers a lovely back and side yard perfect for entertaining. Stone wall border creates a wonderful, rural Chilmark feel yet the lot is just minutes back down to West Tisbury and still of... Click here for more details

Property description and photos provided by listing broker Kelleher R.E..

Address: 10 Rumpus Ridge Town: Chilmark Link ID: 33533

Price: $700,000

Property Description:
Close to Chilmark Center, this three bedroom, two bathroom home is pleasantly sited on a quiet lane.It is ready for a new owner to repair and refurbish it for the next chapter!

Property description and photos provided by listing broker Flanders Real Estate.

Address: 11 High Meadow Town: Chilmark Link ID: 34844

Price: $699,000

Property Description:
Three acre vacant lot with second story waterviews abutting conservation land. Enjoy pastoral and pond views along with beautifully restored stone walls from your building site. Lot is fully engineered with well and utilities in place with rights to nearby tennis courts. Just bring your plans.

Property description and photos provided by listing broker Compass.

Address: 11 High Meadow Town: Chilmark Link ID: 17138

Price: $699,000

Property Description:
This private three acre lot enjoys North shore waterviews, substantial building envelope, privacy from abutting Waskosim's Rock Reservation, beautiful stonewalls, and pondviews. This is a rare offering of one of only a few lots in an area of pastoral and ecologically protected land in Chilmark. Full... Click here for more details

Property description and photos provided by listing broker Tea Lane Associates.

Address: 15 High Meadow Road-Lot 36 Town: Chilmark Link ID: 35344

Price: $675,000

Property Description:
This beautiful four acre lot in Chilmark is set on a gentle rise with vistas overlooking meadow and woodlands. The building site is open and filled with light. Peaceful and private, this lot abuts 184 acres of conservation land (Waskosim's Rock Reservation) with miles of walking trails. Old growth ... Click here for more details

Property description and photos provided by listing broker Tea Lane Associates.

Address: 96 Hammett Lane Town: Chilmark Link ID: 29872

Price: $659,000

Property Description:
A beautiful 4.2-acre piece of land at the top of Hammett Lane. This is a very special spot with gently undulating woodlands punctuated by lichen-covered boulders. The property can support 6 bedrooms, based upon perk test results. In addition to site work by Sourati Engineering, all NHESP work has be... Click here for more details

Property description and photos provided by listing broker Wallace and Co. Sotheby's.

Address: 12 North Slope Lane Town: Chilmark Link ID: 35012

Price: $645,000

Property Description:
Newly subdivided lot offering 3 acres with main house and guest house potential. Well located close to Menemsha on a sweet private street. Lovely topography and old stone walls. Soil testing complete and well installed with a submersible pump.

Property description and photos provided by listing broker Tea Lane Associates.

Address: Lot 1A Bartlett Woods Town: Chilmark Link ID: 34839

Price: $645,000

Property Description:
Nicely wooded and gently sloping vacant parcel with several choice building sites to choose from. Well is installed and electricity and cable are to the site.

Property description and photos provided by listing broker Compass.

Address: 46 South Ridge Road Town: Chilmark Link ID: 27720

Price: $629,000

Property Description:
Lovely rolling land with dramatic sunsets and sweeping vistas of the Chilmark north shore. Located in the desirable Meetinghouse Road Association which combines wonderful privacy, convenient Chilmark location and many fine homes. South Ridge Rd is an ideal location for endless miles of biking and ... Click here for more details

Property description and photos provided by listing broker Tea Lane Associates.

Address: 46 South Ridge Road Town: Chilmark Link ID: 23680

Price: $629,000

Property Description:
A stunning large building lot on the crest of a long knoll,overlooking the Tiasquam River Valley.Gently rolling terrain and a mix of deciduous ,evergreen and and hardwood trees at the end of a cul de sac Perfect location for your up- island dream house in the heart of the country.Accessible from e... Click here for more details

Property description and photos provided by listing broker Feiner Real Estate.

Address: 102 Kings Highway Town: Chilmark Link ID: 34519

Price: $547,000

Property Description:
Wonderful wooded parcel in a private area. Gently sloped parcel has the well installed and septic design is completed for six bedrooms. A great location for your new home!

Property description and photos provided by listing broker Flanders Real Estate.

Address: 98 Kings Highway Town: Chilmark Link ID: 34926

Price: $535,000

Property Description:
A smart opportunity to own a lovely 2.2 acre south facing parcel off South Road. There is an approved 6 bedroom septic design and access to power allowing for an easy property to develop. Birdsong, glacial boulders and nature all around. Cleared paths and site and easy to show A well located pri... Click here for more details

Property description and photos provided by listing broker Tea Lane Associates.

Address: 0 Eliot Avenue Town: Chilmark Link ID: 33176

Price: $165,000

Property Description:
Enjoy access to lovely stonewall Beach, south shore Atlantic beach with great swimming and fishing! - not a buildable lot.

Property description and photos provided by listing broker Flanders Real Estate.

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