Chilmark Classified Ad Listings

21 Clay Pit Rd. This home is walk in ready to enjoy while you let your imagination go to work for this ideal property. Located a short walk along the bike path to Post Office square you will find this quiet location is perfect. You feel the old Vineyard charm along this peaceful lane. This represents the best entry way into Edgartown Real Estate today so do not let this opportunity pass you by....

23 Beetle Swamp Rd. Sweetened Water Farm ~ Just off the main road, past an idyllic horse barn and conserved association land, you'll find this eight-bedroom residence that sits prominently on 2.4 acres. The sprawling main house, an expanded classic Cape featuring separate living areas, both inside and out, and six bedrooms, including two first-floor en-suites, overlooks the rolling pastures wit...

105 Whalers Walk. Renovated Edgartown Retreat With Pool, Terrace + Outdoor Entertaining Pavilions - Designed for relaxed indoor-outdoor living, this recently renovated four-bedroom, three-bath Edgartown home is set on just under an acre and centered around an exceptional new backyard retreat. From quiet mornings by the pool to leisurely dinners beneath the pergolas, the property offers a welcom...

31 Butlers Cove Rd. This charming farmhouse lies on 3-acres of land overlooking the expansive fields and horse stables, inside the gates of the exclusive Herring Creek Farm Association. The home is in lovely original form and features a large living room with fireplace, dining room, 4 bedrooms and 2 baths. Built in 1910 as one of the first houses on the storied 200-acre farm with over 2,000 ft ...

46 Lake Shore Dr. Welcome to this charming, beautifully renovated 3 bed 1 bath ranch. Ideally situated in a coveted lake community, with access to a private neighborhood beach on Jenkins Pond, known for being one of the cleanest spring fed ponds on the Cape. With pleasant sandy beaches, it is a great spot for kayaking, swimming or relaxing. The home is set on a peaceful, private and serene lot....

62 Schoolhouse Rd. Ideally situated between South Beach and Edgartown Village, this newly renovated Katama compound offers exceptional flexibility for personal use and rental income.The four-bedroom contemporary main house features a newly constructed, expansive great room with a cathedral ceiling and an abundance of windows that fill the space with natural light. The open floor plan flows from...

5 Atlantic Dr. Located in one of Katama's most coveted neighborhoods, this 2.11-acre parcel offers stunning ocean views and a direct path to South Beach. Surrounded by high-end homes and just minutes from Edgartown Village, it's an ideal setting for a custom-built retreat with room for a four bedroom residence with pool and views over the dunes. A rare opportunity to own in this prestigious coa...

30 Shore St. Welcome to this beautiful historic 4-bedroom, 3-bath home in the heart of downtown Falmouth, just steps from everything downtown has to offer and ideally situated just moments from Surf Drive Beach and the Shining Sea Bikeway. The home has been completely remodeled and thoughtfully updated, with a new addition completed in 2026 and a brand-new septic system. The custom-built kitche...

74 Coleridge Drive. Single Family Home for sale in Falmouth, MA for $1,399,000 with 5 bedrooms and 4 full baths, 1 half bath. This 3,785 square foot home was built in 1969 on a lot size of 0.36.. Welcome to 74 Coleridge Drive located in Grasmere. Newly renovated in 2026, this light-filled five-bedroom, four-and-a-half-bath home offers approximately 3,785 square feet of versatile living space in...

1 Meetinghouse Village Ed 335 Way Unit 1. THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Enjoy this well appointed and immaculately clean two bedroom condo located just steps from the association pool and a short drive to South Beach with its gorgeous white sands. An open living room, kitchen and dining room with walk-out access to the deck and back yard offer plenty of gathering spaces to enjoy y...

42 Bold Meadow Rd. A peaceful retreat close to Edgartown's amenities, thoughtfully updated and refreshed with a new kitchen and light-filled living spaces, this four bedroom three bath home offers an easy, relaxed setting for family and guests. The main body of the home features one downstairs bedroom with two additional bedrooms upstairs plus a flex space with balcony, and a fourth bedroom wit...

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...

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...

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...

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...

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...

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...

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

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...

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,...