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Chilmark, Massachusetts: Country Homes, Houses, and Rural Real Estate

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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
$8,900,000 8.3 acres 7 Beds | 8 Baths | 5240 sqft
72 Cobbs Hill Road, Chilmark, MA 02535 - Dukes County

8.3 acres Chilmark, MA

Travel a short distance down a scenic road past charming fields and country gates to arrive at a beautiful home with unique architectural details and stunning water and farm views. Designed by Richard Bertman of CBT Architects from Boston and built by John Early Builders, this quality built and impeccably maintained home features 6 bedrooms, 6.5 bathrooms, gourmet kitchen,a guest house, private dock, generator, and custom woodwork throughout. With ample space to entertain, the great room and screened in porch are perfectly suited to appreciate the Great Pond setting. Enjoy swimming, kayaking, shellfishing and boating to the sandy south shore beaches nearby.
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$3,500,000 3.5 acres 4 Beds | 4 Baths | 2728 sqft
27 Tilton Road, Chilmark, MA 02535 - Dukes County

3.5 acres Chilmark, MA

Expansive water views of Vineyard Sound and the Elizabeth Islands can be enjoyed from almost every room of this serene and very private Spring Point Estate. Located on the North side of Martha's Vineyard, this secluded 3.5 acre property is lined with a beautiful stone wall and offers exceptional privacy. Designed to provide extended family and friends a perfect place to come together, this property includes a main house, guest house, garage and studio. Recently updated, the light and airy main house has a relaxed contemporary feel with high ceilings, large windows and interesting ceiling lines. Privately sited on the property is a spacious 1 bedroom guest house with gourmet kitchen, living room with fireplace and walkout view deck, dining r
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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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$2,300,000 5.5 acres 4 Beds | 3 Baths | 2157 sqft
7 Black Point Road, Chilmark, MA 02535 - Dukes County

5.5 acres Chilmark, MA

Beautiful Chilmark, architect designed contemporary on 5.5 private acres at Black Point, PRIVATE BEACH LOT (VALUE $297,000) at Black Point Beach on the south shore included. in offering price. This simple and elegant 4 bedroom, 2.5 bath home boasts 2 open and light filled living areas, 3 outdoor showers, deck & patio. Potential for future pool and guest house. Main living area features vaulted ceiling in the living & dining areas with 2 walls of sliding doors that allow for a close connection to the beauty of the Chilmark landscape. Adjacent to the kitchen is the pantry & laundry. Master BR with full bath & private outdoor shower. Across the covered walk way you will find 2BR's with a shared full bath private outdoor shower. Adjacent & co
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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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$1,795,000 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
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$1,795,000 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
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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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$1,380,000 3.2 acres 5 Beds | 3 Baths | 2784 sqft
36 Wintergreen Way, Chilmark, MA 02535 - Dukes County

3.2 acres Chilmark, MA

Pool and tennis are appealing amenities at this home located on an attractive, very private lot off picturesque Middle Rd. The house is an early John Abrams design/build. The main room is wonderfully uplifting with its soaring cathedral ceilings. The exposed beams, painted white, contribute much to the room's aesthetic. This area is an open-concept floor plan with large living room merging into dining and kitchen areas. A screened porch adjacent to an open deck provides the perfect combination of outdoor living areas. Three bedrooms and three baths. This property is a must see is this price range.
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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.