Chilmark Classified Ad Listings

6 Hollow Way. Single Family Home for sale in Edgartown, MA for $3,950,000 with 5 bedrooms and 4 full baths, 1 half bath. This 4,125 square foot home was built in 1985 on a lot size of 0.93.. Welcome home to this meticulously renovated Martha's Vineyard property, where coastal elegance meets effortless indoor-outdoor living. Offered fully furnished, "turn-key" ready and spanning over 4,100 squar...

4 Garrett Way. Tucked into a quiet corner of Chappaquiddick, with protected views of Nantucket Sound and abutting the Pocha Pond Reservation and miles of endless hiking trails, this beautifully crafted custom home offers a rare combination of privacy, natural beauty, and effortless island living. The home is defined by a sense of casual elegance, with dramatic soaring ceilings and a striking pr...

424 Grand Ave. Breathe in the salt air at 424 Grand Ave and relax into this iconic setting. This inviting 1560 square foot single-family residence, constructed in 1950 has been lovingly maintained, seamlessly blending classic charm with the comfort of old Cape Cod. The living room has sweeping views of Vineyard Sound and features a fireplace that anchors the space, complemented by a warm wood c...

49 The Boulevard. Two side by side cottages built in 1945 Directly Pondfront on Sengekontacket with 180 degree views over the pond out to the Causeway, State Beach, Nantucket Sound and beyond. A rare opportunity to own this classic waterfront property on Sengekontacket Pond, offering sweeping 180 degree views across the pond and salt marsh toward the Causeway, the iconic Jaws bridge, State Beac...

96 S Summer St. Located in the heart of Edgartown Village, this exceptional turnkey home offers timeless New England architecture, modern luxury, and an unbeatable in-town lifestyle. Built by a renowned Island builder, the thoughtfully designed residence features beautifully finished living spaces, four bedrooms, four full baths, and a powder room. The chef's kitchen opens to inviting living an...

331 Grand Ave. Single Family Home for sale in Falmouth, MA for $2,250,000 with 5 bedrooms and 2 full baths. This 2,232 square foot home was built in 1912 on a lot size of 0.09.. Set high on a bluff in the heart of Falmouth Heights, this bright and inviting five-bedroom ocean view retreat captures extraordinary 180-degree views across Vineyard Sound toward Martha's Vineyard and Nantucket Sound. ...

2 Old Pocha Rd. Tucked away down a quiet country road, this one-of-a-kind Chappaquiddick retreat invites you to exhale the moment you arrive. With no visible neighbors and the sounds of nature all around, the property offers a rare sense of privacy, peace, and timeless island charm. Built in an era when homes were crafted with artistry and intention, this distinctive post-and-beam residence ble...

38 Fells Rd Unit 0. Tucked away in the privacy of the woods sits this lovely 4-bedroom, 2-full-bath single-family home. Inside, enjoy a full kitchen featuring a gas stove, central air conditioning, and convenient main-level laundry. The welcoming living room with large windows has peaceful views overlooking the surrounding woods. Located directly across from Spohr Gardens, you have scenic walki...

28 Avalon Dr. Single Family Home for sale in Falmouth, MA for $600,000 with 3 bedrooms and 1 full bath. This 888 square foot home was built in 1956 on a lot size of 0.27.. Enjoy the opportunity to own a turnkey Cape Cod getaway with a solid vacation rental history! This furnished 3-bedroom home offers comfortable single-level living, central A/C, and a convenient location near neighborhood beac...

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Condition: Used, VIN: 1G1YY32G115133466, Mileage: 30300, Engine: 5.7L V8 16V, Drivetrain: RWD, Exterior Color: Black, Interior Color: Black, Seller Notes: 2001 Chevrolet Corvette Convertible For Sale in Falmouth, Massachusetts 02540 Want an astonishing experience? Take a look at this 2001 Chevrolet Corvette Convertible. This is the most attractive sports car on the road. It is stylish, fun, pro...

205 Meetinghouse Way. Privately nestled amid sweeping gardens and lush natural landscaping, this 3-bedroom, 3-bath home offers the perfect blend of timeless design and refined contemporary living. Thoughtfully curated interiors feature an open-concept living area, a large kitchen with Viking cooktop, Fisher and Paykel dishwasher and quartz countertops, inviting dining spaces, and comfortable ga...

76 Washque Ave. This stunning reverse-contemporary four-bedroom custom home is perfectly situated in one of Chappaquiddick's most sought-after locations. Designed with an expansive open-concept floor plan, the airy and inviting living area flows seamlessly onto a generous wraparound deck, where sweeping, bird's-eye views capture the natural beauty that surrounds you. Thoughtfully renovated, the...

286 Grand Ave Unit 4. NOTICE OF INTENDED PRIVATE SALE: Offers due by July 7, 2026. Inquire for complete bidding details. Unit 4 is an oversized one bedroom with an ideal layout for living with an ocean breeze at all times! Amongst the most cherished properties in Falmouth Heights, The Casino Wharf Residences offer timeless connection to Vineyard Sound and the best of Cape Cod living. The beachf...

89F R Lillie Rd. Located on 0.46 acres of private woodland in Woods Hole, this home offers a welcoming retreat with warmth, character and charm. This inviting 3 bedroom, 2 full bath Cape features 1,226sqft of living space, with mini-splits throughout for heating and air-conditioning. It includes a pine-paneled living room with wood-burning fireplace -perfect for cozy evenings. An adjacent dinin...

1 Mariners Way Unit A. A standout commercial offering in Edgartown, combining striking contemporary design with exceptional flexibility. Located just outside the historic district and just shy of 2,000 square feet, this commercial condominium offers a beautifully finished, thoughtfully designed interior that feels anything but ordinary. Soaring ceilings, polished concrete floors, dramatic black...

19 Llewellyn Way. Perfectly situated just moments from the bike path, Edgartown Village, and South Beach, this exceptional Edgartown compound offers the best of Vineyard living. The main house is filled with warmth and character, featuring soaring ceilings, exposed beams, and an inviting open living area centered around a custom stone fireplace. Thoughtfully designed and perfectly sited for pri...

131 N Water St Unit 62. LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 62 at 131 N. Water Street is a beautifully appointed 865+/- sq. ft., second-floor condominium featuring 2 bedrooms and 2 baths in the heart of Edgartown. This fully managed, turnkey residence offers effortless Vineyard ownership with access to the Harbor View Hotel's renowned amenities ...

28 Avalon Drive. Single Family Home for sale in East Falmouth, MA for $600,000 with 3 bedrooms and 1 full bath. This 888 square foot home was built in 1956 on a lot size of 0.27.. Enjoy the opportunity to own a turnkey Cape Cod getaway with a solid vacation rental history! This furnished 3-bedroom home offers comfortable single-level living, central A/C, and a convenient location near neighborh...

12 Avalon Dr. Single Family Home for sale in Falmouth, MA for $625,000 with 2 bedrooms and 1 full bath, 1 half bath. This 1,080 square foot home was built in 1981 on a lot size of 0.18.. Turnkey with Established Rental History! This inviting home is an excellent opportunity for a year-round residence, vacation retreat, or investment property. Successfully operated as a vacation rental for sever...