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$1,649,900
3 Beds ⋅ 2 Baths ⋅ 73573563 MLS
Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha’s Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring comfortable living spaces ideal for year-round living or seasonal enjoyment. With 3 bedrooms and 2 full baths, the layout offers flexibility for family, guests, or a home office. Custom soapstone countertops add to this home's beauty. Expansive outdoor space invites relaxation, exploration, and the potential for future enhancements, all within a serene woodland environment. An increasingly rare opportunity to own a conservation-abutting property on Martha’s Vineyard—perfect as a primary residence, vacation home, or long-term investment in one of the island's most desireable natural settings.

43 N Slope Lane, Chilmark

Listing courtesy of Listing Agent: Barbara O Hara from Listing Office: NorthStar Real Estate, LLC.
$1,600,000
3 Beds ⋅ 3 Baths ⋅ 73546774 MLS
Nestled on a private, 1.9-acre lot along historic South Road in Chilmark, this charming New England retreat offers an exceptional sense of tranquility and classic Martha's Vineyard living. Built in 1950, Vineyard Home offers 2 bedrooms and 2 full bathrooms great light, cozy additional living spaces and fireplace. Multiple patios and gardens seamlessly connecting the living spaces to the surrounding natural landscape. In addition there is a one bedroom one bath guest cottage. The property features extensive parking and serene, tree-lined privacy back from the main road, serving as a peaceful getaway, investment property or year-round island home. Bring your personal updates and creative touch or begin anew and make this classic Chilmark estate your very own island legacy.

132 South Rd, Chilmark

Listing courtesy of Listing Agent: Lisa Da Silva from Listing Office: Compass.
$3,795,000
3 Beds ⋅ 4 Baths ⋅ 73545525 MLS
Beautifully designed and built Post & 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, shelving and a wine refrigerator. There are sliders that take you to an oversized deck and stairs to a blue stone patio and beautiful gardens. The screened-in porch off the living room steps out to the side yard, patio and outdoor shower. First floor Primary with walk-in closet, access to the deck and a private en-suite bathroom with beautiful tiled steam shower and large soaking tub. Second floor includes a loft with sitting room, 2 spacious bedrooms that share a full bath with shower and office, all with cathedral beamed ceilings. Many nice features throughout include white oak random width floors, marble and tile.

96 Hammett Ln, Chilmark

Listing courtesy of Listing Agent: Brenda Galligan from Listing Office: Karen M. Overtoom R.E..
$4,995,000
3 Beds ⋅ 2 Baths ⋅ 73531359 MLS
Rare opportunity in the Seven Gates Farm community of Chilmark. Designed by architects Jane and Christian Langmuir, this exceptional three-bedroom home is set on 5.3 acres of beautifully landscaped grounds. Thoughtfully designed to embrace natural light and its surroundings, the residence blends natural materials with contemporary architectural details.The dramatic great room features a striking fireplace with a glacial stone hearth, while the open kitchen offers custom cabinetry and premium appliances. The primary suite includes two office spaces, a media area, walk-in closet, and spa-inspired bath. A private guest suite features a full bath with soaking tub, and the third bedroom is currently configured as a wellness space with sauna. Additional amenities include an attached two-car garage, owned solar panels, EV charging station, and a six-bedroom septic system.Seven Gates Farm residents enjoy access to private beaches, docks, tennis courts, and more.1000 acres of protected land.

35 South Bowl Rd, Chilmark

Listing courtesy of Listing Agent: Tina Miller from Listing Office: Donnelly + Co..
$2,395,000
3 Beds ⋅ 2 Baths ⋅ 73520138 MLS
This Chilmark 3 bedroom, 2 bath home has been meticulously maintained inside and out. A major addition and reconstruction of the original house was completed in 1991 & included a 22 x 43 addition, The completely new second floor added over 1,500 square feet & the work included new heating, plumbing, electrical, central AC, septic & well! Many nice features include spacious living spaces, a modern kitchen with breakfast bar, open living and dining room with cathedral ceiling, oversized windows & a slider that leads out to a spacious deck. Second floor primary w/ensuite bath, walk-in closet & private deck. Large family room with skylights & built-ins. Two first floor bedrooms w/full bath, basement, wood floors, a whole house generator, Oil FHW heat & new A/C. Privately sited 1.20 acres bordered by stone walls, beautifully landscaped grounds, mature gardens & plantings. Beautiful fruit trees, a garage & shed. The property is gated and entirely enclosed with deer fencing.

26 Bijahs Way, Chilmark

Listing courtesy of Listing Agent: Brenda Galligan from Listing Office: Karen M. Overtoom R.E..
$6,800
3 Beds ⋅ 4 Baths ⋅ 73405954 MLS
September Availability weekly rental rate negotiable, cost $600-$975 per night depending on season and month 3 night min stay The "Grapevine" is located on a private road .The house has 3 generous size bedrooms all with private baths, 2 of the bedrooms are located on the second floor, 1 bedroom is located on the first floor as well as the Open concept living with a chefs Kitchen, living room ,dining area and fireplace area. Walk out the Sliding doors to your spacious deck with gas grill, wonderful views to Vineyard sound and Elizabeth Islands.Private Outdoor shower in the backThe lower level has an extra living room/ bedroom equipped with sofa,chairs and a flat screened tv. Take a stroll down the Private Trail, pass by a barn,walk out to a meadow and to Menemsha Beach.Central AC . All the amenities you could want. You will be able to get Beach Passes to the famous Lucy Vincent Beach in Chilmark. Walk to Menemsha Beach

27 Beach Plum Ln, Chilmark

Listing courtesy of Listing Agent: Bryan Hummel from Listing Office: Commonwealth Realty Group.
$36,000
3 Beds ⋅ 4 Baths ⋅ 72850912 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half bath, a master suite with private bath with jacuzzi tub and a private outside shower. The lower level offers 2 bedrooms, each with it's own bathroom and a living room with wet bar and sliders that open to a patio and rolling lawn. The house also has mini-spilt air conditioning for extra hot days. Just a short distance to a private association beach. Lucy Vincent and Squibnocket Beach access too.

29 Cemetery Rd Ch216, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$7,900
3 Beds ⋅ 3 Baths ⋅ 73007684 MLS

2 Paddock Circle Ch210, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$16,800
3 Beds ⋅ 2 Baths ⋅ 72850978 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set high on a hill in picturesque Chilmark is this absolutely wonderful 3 bedroom home with a finished walk out that has a sofa bed. Each bedroom has a window A/C unit. The grounds are beautiful. Wonderful screen porch for your morning coffee or sit in the back yard and enjoy the view. Short drive to Alleys General Store, Lucy Vincent Beach and the Chilmark Store. You have access to Lucy Vincent beach. This house accepts pets with an additional deposit of $300.

31 South Ridge Rd Ch218, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..
$22,000
3 Beds ⋅ 3 Baths ⋅ 72850887 MLS
SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Just a short distance from Chilmark Store, this newly remodeled home features 3 bedrooms and 2 1/2 baths. High end finishes with a beachy island feel. The master is located on the first floor with en-suit bath. Fully equipped kitchen with a Cuisinart 14-cup programmable drip coffee maker with glass carafe. There is a coffee grinder provided in the house, too.The other two bedrooms are located on the second floor and share a full bath. There are french doors off the living room to a patio. The finishing touch a lovely deck complete with seating and grill for your cooking needs.

2 Strikers Way Ch211, Chilmark

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

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