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Homes for sale in Chilmark Massachusetts

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$19,125,000 9.5 acres 6 Beds | 7 Baths | 6967 sqft
8 Snail Road, Chilmark, MA 02535 - Dukes County

9.5 acres Chilmark, MA

Majestically perched 120 feet above the Atlantic Ocean, the magnificent Chilmark House is an award-winning triumph of design and execution. A presidential paradise, this estate served as the 2013 summer White House. A comfortable yet luxurious seaside retreat that celebrates panoramic ocean views of Martha's Vineyard South Shore and Chilmark Pond. This home features gracious skylights, huge windows, soaring ceilings and wonderful detail in both design and materials. Heated infinity pool, half-basketball court, large screened porch and outdoor terraces provide a breezy and beautiful venue for all. This secluded residence and 2 bedroom guest cottage sit on 9.5 acres of wooded hillside and includes three private Atlantic Ocean beach lots acces
$10,500,000 3.5 acres 6 Beds | 5 Baths | 2488 sqft
22 Quitsa Lane, Chilmark, MA 02535 - Dukes County

3.5 acres Chilmark, MA

Cliff Cottage enjoys one of the most picturesque settings and water-views on Martha's Vineyard. Originally built in 1850 and painstakingly remodeled by the current owner's, along with one of the Islands finest builders to reflect today's life style and amenities. The recently constructed detached studio with over 1,400 sq' offers 2 additional bedrooms with water-views along with an office and a garage. An association stairway leads to your private sandy beach on the south shore, additionally, there is deeded access to Menemsha Pond a short walk away.
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$2,495,000 8.5 acres
0-0 Wequobsque Road, Chilmark, MA 02535 - Dukes County

8.5 acres Chilmark, MA

Enjoy 530 of private beach that can only be described as one of the worlds best! *.5 acres of wooded land fronting on the Atlantic near the world famous Lucy Vincent Beach. Build your dream house for generations to enjoy or a summer camp for ease of ownership.
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$2,475,000 4.7 acres 3 Beds | 3 Baths | 3466 sqft
4 Old North Road, Chilmark, MA 02535 - Dukes County

4.7 acres Chilmark, MA

This property offers a fresh interpretation of Chilmark style: relaxed, very cool and ineffably sophisticated. Located on a private 4.7-acre parcel, the house and guest house are less than a mile to Chilmark center. The lot is beautifully developed and landscaped with well chosen plantings, a whimsical vegetable garden, and a sprawling yard with meadow beyond. The guest house will delight you with its country charm and is tucked away from the main house. An artisanal home built by a design/build/landscape couple with an impressive body of work.
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$2,095,000 7.2 acres 5 Beds | 4 Baths | 5000 sqft
85 Quenames Road, Chilmark, MA 02535 - Dukes County

7.2 acres Chilmark, MA

A remarkable property with 5,000 sq. ft. of living space set on over 7 park-like acres. Enjoy access to the beautiful beaches of Chilmark and the convenience of down island amenities with the Quansoo location. The home boasts 5 bedrooms including master suites on the first and second levels and a terrific floor plan that creates an environment that is comfortable and conducive for family living and entertaining guests. A must see for the Vineyard buyer seeking a sizable home with vast acreage enabling the creation of a future compound with guest house and pool.
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$1,600,000 7.5 acres 3 Beds | 3 Baths | 2075 sqft
72 North Blueberry Ridge Lane, Chilmark, MA 02535 - Dukes County

7.5 acres Chilmark, MA

Recently renovated contemporary style home in an inviting setting with water and vista views of the sound and north shore. Professional landscaping with privacy sitting high on a unique site.This home is in great shape with sophisticated touches and updated systems and is being offered turn-key with all furnishings along with a 2001 Jeep Cherokee.
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$1,575,000 5 acres 5 Beds | 4 Baths | 5191 sqft
320 Middle Road, Chilmark, MA 02535 - Dukes County

5 acres Chilmark, MA

Located on picturesque Middle Road in Chilmark, this property has all the right components for your perfect Vineyard residence. The land: 5-acres of gently sloping meadow with distant water views to the south. The main house: Expansive sweep of living room, dining area and beautiful kitchen. 5-bedroom and 4.5 baths. Serene views over a vast lawn to water view vistas. The pool: indoor, 20'x40' with glass doors along south wall. The guest house: privately situated 2-bedroom/1-bath guesthouse. The barn: let your imagination go wild. A horse, a rec room, an artist studio.? You'll want to make your own aesthetic changes to this property, but you'll have all the basic ingredients you need. With many recent improvements, a must see! The guest hou
$1,575,000 5 acres 7 Beds | 5 Baths | 5191 sqft
320 Middle Road, Chilmark, MA 02535 - Dukes County

5 acres Chilmark, MA

Located on picturesque Middle Road in Chilmark, this property has all the right components for your perfect Vineyard residence. The land: 5-acres of gently sloping meadow with distant water views to the south. The main house: Expansive sweep of living room, dining area and beautiful kitchen. 5-bedroom and 4.5 baths. Serene views over a vast lawn to water view vistas. The pool: indoor, 20'x40' with glass doors along south wall. The guest house: privately situated 2-bedroom/1-bath guesthouse. The barn: let your imagination go wild. A horse, a rec room, an artist studio.? You'll want to make your own aesthetic changes to this property, but you'll have all the basic ingredients you need. With many recent improvements, a must see!
$1,375,000 3.5 acres 4 Beds | 3 Baths | 1372 sqft
7 Clambelly Road, Chilmark, MA 02535 - Dukes County

3.5 acres Chilmark, MA

The true meaning of R&R is embodied at this fabulous property. Rustic, in tune with nature, comfortably big enough but not too big, easy to live in without much fuss. When you are engaged in your daily tasks the vision of this property is the carrot that gets you to the end of the week. The open living space with stone fireplace and expansive deck looks out to the tree tops and water view beyond. Two bedrooms and two baths on the same level makes it easy to retire after drowsing off with a good book. The adjacent bedrooms over the garage provide great overflow. Open the house in the spring and close it in late fall, taking advantage of the changing seasonal vistas and the worries of a year round house; the ultimate vacation retreat.
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$750,000 4.3 acres
96 Hammett Lane, Chilmark, MA 02535 - Dukes County

4.3 acres Chilmark, MA

Gently rolling hills and wooded surroundings add to the allure of this 4.3 acre parcel tucked away at the end of Hambett's Lane in Chilmark. The large, corner lot provides a tranquil setting for building an inviting Vineyard home. Property could support 6 bedrooms, based upon perk test results.