Chilmark Classified Ad Listings

2 And 6 Clements Way. A compelling opportunity to acquire raw land in Edgartown with exceptional development potential. Lots 4B and 4C based on the plot plan provided, each offer the potential for a five-bedroom residence, ADU/guest house, pool, and pool cabana, providing the flexibility to create a substantial Martha's Vineyard property from the ground up. With multiple possibilities for resid...

21 Schoolhouse Rd. Located in the heart of Katama between South beach and Edgartown Village. Biking or walking distance along the the shared use path to beach or town. With 2 first floor bedrooms along with a full bath for one floor living. Second floor has 2 more bedrooms, bath along with a loft area for extra bed space. The full basement could be finished off for additional living areas. Plen...

56 N Summer St. A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest on Martha's Vineyard. Originally built in 1835 and masterfully renovated, it blends historic character with refined modern luxury just moments from Edgartown Harbor, dining, and shopping. Spanning two lots, the property features 10 bedrooms and 14 baths, designed fo...

74 Coleridge Dr. Single Family Home for sale in Falmouth, MA for $1,399,000 with 5 bedrooms and 4 full baths, 1 half bath. This 3,030 square foot home was built in 1969 on a lot size of 0.36.. Welcome to 74 Coleridge Drive in the sought after Grasmere neighborhood. Newly renovated in 2026, this light-filled five-bedroom, four-and-a-half-bath home offers approximately 3,030 square feet of versat...

4 Canonicus Ave. Overlooking Nantucket Sound and just steps from the vibrant heart of downtown Oak Bluffs, this distinctive compound blends laid-back West Coast style with classic island charm. The light-filled four-bedroom main house has been thoughtfully updated with modern, year-round comforts. Privately set at the rear, the guest house known as The Nest offers a peaceful retreat with a priv...

20 Katama Bay Ed Rd # 350. THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,100. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely Edgartown Bay Road area. This 3 bedroom newly decorated home is very close to South Beach. Easy access to town. Large grassy yard for the kids to play on.. 3 Bedrooms. 2 Bathroom. 2200 ft

238 Seaward Bnd. Enjoy easy one-floor living in the sought-after Falmouth Port community, beautifully situated along Great Pond. This spacious 2-bedroom, 2-bath condo offers a bright, open living and dining area with cathedral ceilings, abundant natural light and sliders overlooking the outdoors. The inviting country kitchen features a fireplace, breakfast bar and a comfortable sitting or dinin...

12 Avalon Drive. Single Family Home for sale in Teaticket, 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 s...

16 W Falmouth Highway APT 24. Property for Rent in Falmouth, MA for $2,000 with 1 bedroom and 1 full bath. This 537 square foot property was built in 1978.. Beautiful One Bedroom Condominium located on Shining Sea Bike Path.. Exterior Amenities Underground Sprinkler System Lighting Professional Landscaping Private Storage Fencing None Parking Features Assigned Guest Paved Water Source Public Bu...

40 Hidden Cove Rd Unit 2. Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite,...

809 Sandwich Rd. Great Land for development. Cape style Home on a Horse Farm with 30 indoor stalls. Turnouts and outbuildings included. Most of property is fenced. Almost 20 Acres of good land, great for developing.. 3 Bedrooms. 2 Bathroom. 1650 ft

14 Starbuck Neck Rd. Introducing a landmark property in Edgartown's Starbuck Neck enclave, just one tenth of a mile to Fuller Street Beach. Included in this sale is an adjoining vacant buildable lot. 14 STARBUCK NECK features a 7-bedroom house with 5 full bathrooms, garage, and plunge pool. Known as the Tower House, this home offers delightful views of the harbor from the first and second floor...

99 Old Purchase Rd. Set at the end of a cul-de-sac, this property offers a peaceful setting on.71 acres, with easy access to more than 25 acres of Land Bank conservation land. Morning Glory Farm is just a short distance away, offering a wonderful connection to the seasonal beauty and character of the Island. The bike path, Edgartown Village, and South Beach are also nearby, providing an easy ba...

74 Turkeyland Cove Ed Rd # 306. THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Less than 5 miles from the center of town, the property is a 3 bedroom uniquely-designed guest house which provides the space needed for a large family or visiting guests. Most of the living/entertaining space is on the second floor. The ...

15 Prices Ed Way # 322. THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is an inviting and affordable home with air-conditioning. As you see from the pictures the sun is welcomed through many sliders and windows. Inside the furnishings are simple but well chosen. There is a splitter in the living area that cools...

152 Central Avenue. Single Family Home for sale in East Falmouth, MA for $1,895,000 with 4 bedrooms and 3 full baths, 1 half bath. This 2,926 square foot home was built in 2026.. Experience coastal luxury in this exceptional custom-built home, just 1.5 miles from Menauhant Beach! Set on approximately one acre, its 3,600-sq-ft architectural footprint encompasses over 2,900 sq ft of finished livi...

13 West Ave. Embrace the ultimate Cape Cod lifestyle in this classic 1925 coastal home, offering spectacular water views and unbeatable rental or multi-generational family potential. Known affectionately as "Grandma's House," this charming 4BR/1.5BA property captures the essence of desirable New Silver Beach. The layout features a covered front porch and a spacious enclosed sunroom designed for...

30 Overlook Cir. Single Family Home for sale in Falmouth, MA for $450,000 with 3 bedrooms and 2 full baths. This 1,144 square foot home was built in 1984 on a lot size of 0.53.. Incredible opportunity for contractors, investors, or renovators! Tons of potential awaits in this traditional Cape Cod-style ranch offering 3 bedrooms and 2 full baths, located in the desirable South Cape Woods communi...

54 Schoolhouse Ed Rd # 330. THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Perfectly located close to South Beach and Edgartown is this absolutely wonderful 3 bedroom home with a separate guest quarters that has one twin bed and one full bed, kitchenette and bath. The main house has a formal dining room right off of...

46 Kennebec Ave. This exquisite Victorian home, lovingly preserved by the same family for over a generation, stands in outstanding condition and is perfectly situated in the vibrant heart of Oak Bluffs Center. Enjoy the convenience of being just steps away from the Public Beach, Steamship Authority, Oak Bluffs Harbor, a supermarket, and a variety of charming restaurants and shops that contribut...