Chilmark Classified Ad Listings

170 Barnes Rd. Solid Cape-style home located one block from Sailing Camp Park and Medeiros Cove offering water access to the Lagoon and one mile to all the excitement that downtown Oak Bluffs has to offer. The first floor offers a spacious eat in kitchen that is open to the dining room. A full bathroom with laundry, a den with French-doors that leads to the living room with a slider opening out...

22 Bridge Ln. Tucked away on over 3 private, wooded acres just off Lambert's Cove Road, this elegantly renovated estate seamlessly blends classic West Tisbury charm with sophisticated modern living. The expansive main residence is designed for entertaining family and friends, featuring a light-filled great room with dramatic stone fireplace, an intimate den, chef's kitchen, and a gracious livin...

38 Fire Tower Rd. The Tower Hill land, once known as the Dancing Hills, is considered by many a sacred Island space. Standing on the ridge top, you're at one of the highest points on Martha's Vineyard. This 3.01 acre parcel looks out over the trees of Red Farm and the dramatic blue expanse of Vineyard Sound. It's easy to understand why this property is so special. There's a generous designated ...

16 Shotnaigher Ln. 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. Sunrise and Sunset! This home, completely renovated in 2022 features a state o...

111 Old Herring Creek Rd. Surrounded by hundreds of acres of conservation-minded land, this private 4.3-acre parcel presents a rare opportunity to create a truly exceptional architectural masterpiece. Perched atop a high ridge, a three-bedroom home currently exists that commands panoramic water views across the Elizabeth Islands and Lamberts Cove. A gently winding walking path leads approximate...

68 Pond View Dr. Create your ideal island retreat on this exceptional 1.068-acre parcel in Oak Bluffs. This desirable homesite comes with approved plans for a six-bedroom septic system, saving valuable time and expense as you begin the building process. The property also includes a topographic/boundary survey and soil test, providing a strong foundation for planning and development. Subject to ...

PRICE REDUCTION! Presenting the 2002 Sea Ray 340 Sundancer, equipped with powerful 8.1L V-drives and boasting a history of meticulous maintenance and upgrades. This vessel is turn-key and ready for your adventures. Repowered in 2021/2022, it has been continually enhanced and well-maintained, complete with extensive service records. Notable Features & Upgrades include: - Spacious cockpit featuri...

21 Island Inn Rd Unit 38G. Welcome to Unit 38G at the Island Inn, offering resort-style living in an exceptional Oak Bluffs location just steps from the beach. This desirable ground-floor end unit features a large glass slider opening to the patio, with stairs leading to the heated outdoor pool just a few feet away. Accommodating up to six guests, the unit features one bedroom with a queen bed,...

4 Windy Wt Way # 143. THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! The 3.3 acre private setting is most picturesque with its positioning in private Upper Makonikey , the long circular driveway , its grassy lawn, and rolling landscape fields. Only a short distance away is over 3,000 feet of PRIVATE sandy association Beaches , directly below , with two nearby parking lot access-ways. Nestled onto ...

60A Davis Look Rd. Over five acres of privacy in one of the Island's most sought-after settings. This 5.15-acre parcel offers a rare opportunity to build a primary residence and accessory structure on old farmland surrounded by large, mature trees. Idyllic stonewalls run along some of the property lines. Large parcel size and building envelope ensures that the character of the neighborhood endu...

45 Quenames Rd. Set on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and excellent potential. In a sunny clearing among mature trees, the maintained 2-bedroom house features first-floor living, an open kitchen and living area, two spacious bedrooms, a full bath with shower, an enormous three-season screened porch, a large outdoor shower, kitchen gardens, and a p...

Sailaway Ln Lot 7. Discover the epitome of Coastal Charm in this exquisite New Construction farmhouse-style home. Nestled in the new subdivision of Sea Salt Estates, this stunning 4-bedroom, 3.5-bathroom home with 2 car garage offers the perfect blend of modern comfort and classic Cape Cod elegance. Featuring spacious open-concept living bathed in natural light, ideal for entertaining family an...

18 Point Inner Way. A rare offering on the shores of Nashaquitsa Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Set on 4.9 acres with a private 115-foot deep-water dock, this one-of-a-kind compound features striking modern architecture, walls of glass, and panoramic water views throughout. The main residence offers six ensuite bedrooms, including a ...

314 Maravista Ave. Enjoy the best of Cape Cod living in this charming three-bedroom, two bath ranch, nestled in the desirable Maravista neighborhood. Enter into the spacious sun-filled living room and enjoy views of both Little Pond and Great Pond. The inviting living room, dining area, and kitchen feature cathedral ceilings and wood floors, an ideal space for entertaining. The primary bedroom ...

25 Muskegat Rd. Located in one of Falmouth's most desirable coastal neighborhoods, less than two miles from Menauhant Beach, this 3-bedroom, 2.5-bath home offers endless potential. The flexible floor plan features a sought-after first-floor bedroom, spacious living areas, and a walk-out basement ready for future expansion, recreation, or storage. Enjoy peaceful pond views and a natural setting ...

95 Daggett Ave. Centrally located at the top of Daggett Avenue, just blocks from the harbor and town beach, sits this charming turn of the century Cape. The covered porch graces the front of the home welcoming friends and family. Light spills into the living room that stretches across the front of the house featuring vintage architectural details and the warm patina of newly refinished Carolina...

19 Lake Ch Rd # 220. THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. Sweeping views of Squibnocket Pond, Dunes, the South Shore, Nomans Land, to sunsets over Aquinnah. A great family getaway with access to Chilmark's famed Lucy Vincent and Squibnocket Beaches as well as a private association beach in Aquinnah. Roomy and inviting, this house offers 5 five bedrooms all with ...

16 Red Coat Hill Rd. Private West Tisbury Oasis - Modern Luxury on 4.85 Acres Built by the highly regarded Novo Builds and designed by acclaimed architect Zander Auerbach, this newly constructed estate in the heart of West Tisbury offers the perfect blend of architectural sophistication, privacy, and resort-style amenities. Set on 4.85 acres, the main residence spans 3,806 square feet with an a...

533 Woods Hole Rd Unit E101. Introducing the E Building at Lighthouse Station, Woods Hole's premier 55+ coastal community, with completion anticipated in late fall. Designed for effortless single level living, this beautifully appointed condo offers approximately 1,565 square feet, two bedrooms, and 2 1/2 baths. The heart of the residence is an inviting open concept family room and kitchen feat...

3 Viber Ln. Live, work, and create in this beautifully remodeled, move-in-ready 3-bedroom, 2-bath Cape Cod home. Offering over 2,400 sq. ft. of living space on a 22,000+ sq. ft. level lot with a rolling lawn, this property combines versatility with exceptional peace of mind.The unique19' x 23' studio/office, with separate entrance, adds exceptional flexibility for a home-based business, profess...