Chilmark Classified Ad Listings

6 Wakeman Rd. Set in a spectacular water view setting with private beach access, this exceptional coastal compound offers a rare blend of privacy, flexibility, and breathtaking scenery. The property is thoughtfully composed of a beautifully appointed main residence, a separate guest house, an artist's studio, and a detached garage with an additional bedroom above - creating the ideal retreat fo...

99 The Boulevard. Welcome to a beautifully renovated custom contemporary colonial located just 1/3 mile from the Sengekontacket Pond boat landing. Perfect for kayaking, paddle boarding, and coastal living, this builder-owned home seamlessly blends classic Vineyard charm with modern luxury. The bright, open-concept main floor features a wood-burning fireplace, custom kitchen, and direct access t...

61 Canonicus Ave. Location, location, location: This 1999 home with all the comforts of the 21st Century is nestled on a landscaped lot within mellow surroundings. And yet... it's located within mere moments of town, beach, bike path, bus line, parks, recreation, Farm Pond and a Land Bank trail. The situation hardly gets better. The 3BR/2.5BA house features a deep wraparound farmer's porch, Bra...

2 Winemack St. Located at the southern end of Winemack Street, this inviting 3-bedroom, 2-bath Oak Bluffs home offers a quiet residential setting in a neighborhood of both year-round and seasonal homes, while remaining remarkably close to everything Oak Bluffs has to offer. Just approximately 1.2 miles from downtown, you'll enjoy convenient access to the ferries, Oak Bluffs Harbor, beaches, sho...

27 Island Inn Rd Unit 9C. Welcome to 27 Island Inn, Unit 9C, an inviting Martha's Vineyard retreat offering the perfect combination of personal enjoyment and rental opportunity. This comfortable studio accommodates up to four guests with two double beds, a full bath, kitchenette with a 2-burner cooktop, cable TV and free WiFi. A unique opportunity is adjoining Unit 10C, a separate 1-bedroom, 1-...

15 Meadowood Ln. Beautifully renovated Falmouth home offering spacious accommodations, modern amenities, and a private fenced backyard. The open-concept main level features a fully equipped kitchen, dining area, comfortable living room with gas fireplace and smart TV, plus two bedrooms and a full bath.The home offers four additional bedrooms across the upper and lower levels, along with three f...

96 Hammett Ln. Beautifully designed and built Post and Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher, soapstone counters and a butlers pantry with extra cupboards, shel...

36 Henry Hough Ch Ln # 206. THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnoc...

4 Sand Plain Way. This truly remarkable Chappaquiddick property offers a rare opportunity to step back in time and experience the quintessential character of Martha's Vineyard. The original historic home, built in 1892, is distinguished by its signature four-story tower with 270-degree water views and gracious wraparound porch. The main house features a spacious open living room with fireplace,...

267 Barnes Rd. Set along 163 feet of Lagoon frontage with its own sandy beach, 267 Barnes Road offers a fresh, contemporary take on waterfront living in Oak Bluffs. Set on 1.25 acres, the 4,046-square-foot home balances privacy with comfortable spaces for entertaining or relaxing. Oversized windows bring Lagoon views into nearly every room. The main level features soaring ceilings, a wood-burni...

50A Carls Wt Way # 145. THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Looking for that perfect setting with a water view? This is the one!!This cute cape is privately set with a water view and direct water access to Town Pond. You can dock your canoes and kyacks here and access Tisbury Great Pond and then right out...

Introducing the 2019 Sabre 42 SE, featuring only 430 hours on the engine and 460 hours on the genset. This stunning vessel is loaded with options and boasts high-end d cor. Meticulously maintained, this Sabre 42 was originally commissioned by Boston Yacht Sales for a boat show, ensuring that every detail was thoughtfully designed. With its striking Flag Blue hull and Sabre white decks complemen...

131 N Water St Unit 22. LUXURIOUS LIVING AWAITS at the iconic Harbor View Hotel Captain Collins Cottage. Unit 22 at 131 N. Water Street is a beautifully appointed 960+/- 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 ...

177 Bay Rd. Discover the pinnacle of coastal living with this extraordinary 2.24-acre waterfront property, perfectly positioned in the highly desirable Megansett neighborhood of North Falmouth. Offering an unparalleled canvas of sweeping, panoramic views of Buzzards Bay, this expansive parcel represents one of the last true legacy estate opportunities on the Upper Cape.Whether you choose to ren...

39 Chickawaukee St. Renovated Cape style home in the desirable East Chop neighborhood of Oak Bluffs, offering the perfect combination of coastal charm, modern updates and an exceptional location. This bright and inviting 3-bedroom, 2-bath home features a spacious open floor plan, coastal-inspired decor throughout, and comfortable spaces designed for relaxed Vineyard living and entertaining. A f...

N Road/15 Belhaven Way. Set just off North Road, this exceptional parcel offers a rare opportunity to build in a setting rich with natural beauty. Recently subdivided, this land combines privacy, character and thoughtful positioning. The lot is perfectly sited capturing serene woodland views and the natural contours of Middle Line Ridge. A 600ft stonewall lines the western property line, creati...

This Bankruptcy is located in West Tisbury, MA 02575 This is a bankruptcy listing, this property will be sold or auctioned due to the owner's bankruptcy proceedings. These listings often represent an opportunity for buyers to acquire properties at a lower price than the market value, as the primary goal is to liquidate assets to satisfy creditors.

Young; Availability Date * 10/21/2026; Location * Oak Bluffs MA, 02557, USA. Dog Breed: French Bulldog. Meet Midge! Midge is a three-year-old French Bulldog with an incredibly sweet and affectionate personality. She adores being close to her people and is happiest curled up on the couch, snuggling against your chest, or resting her head in the crook of your arm. She is house trained, walks very...

This Preforeclosure is located in Oak Bluffs, MA 02557 This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank.

This Bankruptcy is located in East Falmouth, MA 02536 3 Bed 1.0 Bath This is a bankruptcy listing, this property will be sold or auctioned due to the owner's bankruptcy proceedings. These listings often represent an opportunity for buyers to acquire properties at a lower price than the market value, as the primary goal is to liquidate assets to satisfy creditors.