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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
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$10,500,000 3.5 acres 3 Beds | 3 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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$4,950,000 8 acres 5 Beds | 3 Baths | 2511 sqft
1 Azalea Lane, Chilmark, MA 02535 - Dukes County

8 acres Chilmark, MA

Experience extraordinary waterfront living on one of the finest private beaches along Chilmark's south shore. Mesmerizing water views can be enjoyed from almost every room including the living and dining areas, master bedroom, guest bedrooms, and more. The south facing deck & pool area were designed to capture the essence of the ocean while maintaining absolute privacy. Meticulously landscaped from the driveway entrance to the cliff's edge walking path. An association tennis court is shared with 3 other properties. With a permit to build stairs to the beach, this property now has private direct beach access.
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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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$2,170,000 6.6 acres 4 Beds | 3 Baths | 2801 sqft
128 Old Farm Road, Chilmark, MA 02535 - Dukes County

6.6 acres Chilmark, MA

An artistic Up-Island retreat set on 6.6 acres, made up of two adjoining parcels, abutting conservation land. This exquisite, light filled four bedroom contemporary Craftsman house was built by the South Mountain Company, known for their quality craftsmanship, attention to detail and environmentally conscious design, use of reclaimed materials, and energy efficient and sustainable systems. The home offers 3650 square feet of indoor living space, including; two basements, an expansive, open concept first floor, plenty of space for guests and entertaining, and a lovely screened porch as well as a detached bedroom/studio next door. The property has lush landscaping, old stonewalls, fruit trees, a large fenced garden, a rolling lawn, and per
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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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$1,675,000 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.