Chilmark Classified Ad Listings

99 Ocean Ave. A Victorian Grand Dame overlooking Ocean Park -- in a truly spectacular setting with sweeping water views from two stories of verandas. Located in Oak Bluffs most popular and exciting neighborhood and just steps from the beaches of Nantucket Sound, fine restaurants, art galleries, shopping, harbor, ferries, the Campground and the Tabernacle. This treasured property has been home t...

188 Vineyard Meadow Farms Rd. House and Guesthouse near Long Point Beach! The Island's coveted south shore is just minutes from this charming West Tisbury compound, where the connection to nature is seamless. The main house sits high atop the trees and overlooks a park-like, fenced-in backyard, perfect for kids and dogs. The yard also encompasses a sweet vegetable garden and storage shed. Insid...

76 School House Wt Ln # 101. THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!! An elegant, whimsical house full of color, quality and artistic touches. The grounds are sumptuous, nature at its apotheosis. There is gentle movement in the landscape with flowering trees and shrubs everywhere replete with a babbling brook flowing into a pond bordering the garden behind the house. The stonework is finely cr...

123 Elain Ave. Welcome to 123 Elain Avenue in East Falmouth! Set in a wonderful neighborhood, this two bedroom, one-bath home offers an excellent opportunity to add your personal style and make it your own. Recent improvements include new interior paint and flooring, creating a fresh starting point for the next owner. The unfinished basement provides tremendous potential for additional living s...

138 Sippewissett Road. Single Family Home for sale in Falmouth, MA for $874,900 with 3 bedrooms and 2 full baths. This 1,353 square foot home was built in 1970 on a lot size of 0.47.. A House on the Hill with Deeded Beach Rights! Welcome to desirable West Falmouth, where coastal charm meets privacy and tranquility! Nestled on a peaceful hillside, this inviting 3-bedroom, 2-full-bath home offers...

7 Highland Ave. Rare opportunity in East Chop. Beautiful lot in a serene, wooded area, walking distance to town, beach, and ferries. Secluded yet accessible. This is a pre-existing nonconforming lot, with a legal opinion letter attached stating buildability. Buyer to perform all due diligence regarding town building requirements. Opportunity for buyer to design to their own specifications.

562 Waquoit Hwy. Charming 3 bedroom 2 bath farmhouse style home nestled perfectly on a.72 acre lot. The home has many great updates, including a newer roof, windows, mini splits for heat and a/c, water heater, deck, 4 bedroom septic, as well as new plumbing and electrical. Bright and inviting front living room with hardwood floors expands into a sitting area, first floor bedroom and 1/2 bath. S...

30 Hill And Plain Rd. Welcome to 30 Hill and Plain Rd, a thoughtfully designed contemporary ranch, nestled in the exclusive gated-community of Ballymeade Estates. Sited on 1.3 acres of wooded surroundings and conservation land, this 4 bed/3.5 bath home offers single-level living in a private setting. Flooded with natural sunlight, the comfortable open floor plan offers flexible spaces for tranq...

33 Fern Ln. Woods Hole furnished rental. This modern home was built in 2024 with attention to detail and high-end finishes. Enjoy the proximity to Woods Hole Village offering world class restaurants, artisan shopping, boating, fishing, and tennis. Spend time exploring Martha's Vineyard, the ferry is a short distance from this home. Also close by is the Woods Hole entrance to the Shining Sea Bik...

8 Melrose Ave. Incredible opportunity for workforce housing, live in one/rent the other, or multi generational family living. Main house has 4 levels of living space. Main floor living/kitchen/dining/full bath and laundry. 2nd floor has two bedrooms and full bath. 3rd floor is a large finished bonus room. The full walkout basement in the main house is finished with private entry, full bath, sep...

A striking statement piece showcasing exceptional mid-century coastal design and craftsmanship. Woven from dense, natural split pencil reed over a rigid frame, this large urn-shaped floor basket features a rich, dark brown stained finish. It comes complete with a beautifully contoured, fitted domed lid accented by a carved wood handle. Perfect for adding organic texture and grandmillennial char...

4 Beryl Way. A picture-perfect Vineyard gem awaits you this summer! Imagine waking up in a sunlit, Victorian cottage, walking next door to the library for a book, and spending the afternoon reading in your backyard hammock or relaxing on the beach. By evening, you can enjoy the vibrant energy and nightlife of Oak Bluffs center and Circuit Avenue, before heading back to your charming little nest...

341 Woods Hole Roost Rd Unit The. Welcome to the Roost. This charming, furnished One-Bedroom in the Heart of Woods Hole is the perfect Off-Season escape. Experience the charm of Woods Hole from this adorable, fully furnished one-bedroom, one-bath retreat. Ideally located for enjoying all that this special coastal village has to offer, this inviting rental is the perfect place to settle in for a...

71 Bartmus Luce Wt Rd # 154. THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Finest Views on the Island!! This house is set high on a hill surrounded by nature. The expansive views from the front of this house are spectacular. Enjoy the large deck or the screened porch and gaze upon one of the most amazing Vineyard V...

31 Beacon Ave. Nestled along a quiet lane, 31 Beacon Avenue is a delightful saltbox-style home offering three bedrooms and one and a half baths. The bright, open floor plan offers a warm and welcoming feel, with convenient access to the side yard. The first floor features a comfortable bedroom and half bath, while the second floor includes two additional bedrooms and a full bath. A hallway clos...

385 Barnes Ob Rd # 534. THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $18,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with water views over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet...

29 Scotchmans Ln. Discover the charm of West Tisbury with the perfect blend of country living and village convenience. Ideally located just a short stroll from the heart of town, you'll enjoy easy access to all the West Tisbury Village has to offer. Set on a lovely lot, the home features a spacious southeast-facing deck overlooking a sunny yard. Four detached outbuildings. A generous south-faci...

35 Double Ox Rd. GOING, GOING... GONE! This is the LAST 3-bedroom lot available in Cluster C. 12 lots SOLD 9 homes already built. Welcome to Lagoon Ridge Oak Bluffs' newest and most sought-after neighborhood. This exceptional 3-bedroom building lot sits on a lofty setting approximately 95 feet above Lagoon Pond, offering sweeping sky views, vibrant sunsets, and refreshing sea breezes. The lot i...

18 Fordham Rd. Welcome to Ashumet Valley! This charming 3-bedroom, 2-bath Gambrel-style home offers the opportunity to own in one of East Falmouth's desirable neighborhoods, with an association beach on beautiful Ashumet Pond and the Paul Harney Golf Club, a public course, right within the neighborhood. The home offers classic Cape Cod character and a comfortable layout with plenty of potential...

55 Samoset Ave. BOOK SUMMER 2027! Modernized 5 bed, 3 full bath Victorian in the heart of Downtown Oak Bluffs. Steps to restaurants, shopping, harbor, ferries and beaches. Accommodates 10 guests. Easy breezy outdoor living, dining, bluestone patio and BBQ grill. Relax on the covered porch surrounded by a lush flower garden or unwind in the outdoor shower. Updated stone and stainless kitchen. Fo...