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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..

$15,400,000
6 Beds 9 Baths 73538291 MLS
Horizon House sits atop one of Chilmark's most private and elevated parcels, offering protected and sweeping views of the Atlantic Ocean. Framed by meadow, mature trees, stone walls, and native terrain, the estate holds an extraordinary connection to both land and sea. The 4+ bedroom main house has been thoughtfully reimagined for today's buyer, designed and built by a team of leading architects and artisans. Grounded in its natural setting, the architecture features dramatic design elements and walls of glass to connect seamlessly with the idyllic landscape. An infinity-edge pool overlooks the pastoral ocean horizon that defines Chilmark, while a screened porch and large outdoor living areas extend the home into its surroundings. A separate 2-bedroom guest house and additional 5.6 acre lot provide flexibility for expansion and subdivision, while a private path to Chilmark Pond allows for deeded access to South Beach. Horizon House is a pleasure to show, by appointment only.

8 Snail Road, Chilmark

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.

$5,200,000
5 Beds 4 Baths 73534187 MLS
Set high on the north shore with panoramic views of Vineyard Sound and deeded private beach access, this secluded 9.8-acre estate enjoys a rare setting abutting conservation land and the Menemsha Hills trail network. The meticulously maintained residence features a reverse floor plan designed to maximize natural light, soaring ceilings, and stunning water views. The upper level offers an open-concept kitchen, dining, and living area, a private primary suite, office, screened porch, and expansive decks. Thoughtfully appointed with air conditioning, a whole-house generator, integrated sound system, and outdoor lighting. The grounds include a tennis court, landscaped gardens with a water feature, and several acres of open meadow surrounded by mature woodland, ensuring exceptional privacy with no visible neighboring homes. Ample room exists for a pool, and the parcel may offer subdivision potential. Ownership includes rights to Brickyard Beach.

49 Gosnolds Way, Chilmark

Listing courtesy of Listing Agent: Bonnie Pierce from Listing Office: Wallace & Co. Sotheby's International Realty.

$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..

$45,000,000
7 Beds 13 Baths 73523462 MLS
A rare offering on the shores of Nashaquitsa Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Set on 4.9 acres with a private 115-foot deep-water dock, this one-of-a-kind compound features striking modern architecture, walls of glass, and panoramic water views throughout. The main residence offers six ensuite bedrooms, including a spectacular first-floor primary suite with dual spa-inspired baths. Dramatic living spaces with soaring cathedral ceilings open to expansive decks and a screened porch overlooking the pond. Exceptional amenities include two chef’s kitchens, a private theater, wine cellar, outdoor shower, and a hilltop writer’s cottage with sweeping views. The pool house is a private wellness retreat with a heated indoor pool, spa, sauna, steam room, cold plunge, guest suite, and retractable glass walls. Additional highlights include a tennis court, boathouse, entertainment barn with gym and recreation space, and a six-car garage.

18 Point Inner Way, Chilmark

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.

$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..

$1,200,000
2 Beds 1 Baths 73471152 MLS
Set on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and excellent potential. In a sunny clearing among mature trees, the maintained 2-bedroom house features first-floor living, an open kitchen and living area, two spacious bedrooms, a full bath with shower, an enormous three-season screened porch, a large outdoor shower, kitchen gardens, and a potting area with utility sink. Well system updated in 2011. With strong rental income, currently generating $2,500 month to month year-round, and expansion potential, this outstanding value is located close to South Road, West Tisbury's village center, and Chilmark's iconic town beaches Squibnocket and Lucy Vincent. Town records indicate a 4 bedroom septic, passed Title V Inspection in December 2025. #45 is shown as Lot 1-B on a new subdivision not yet reflected on the assessments and public records - approved plans are attached. 47 Quenames Lot 1-B is also available.

45 Quenames Rd, Chilmark

Listing courtesy of Listing Agent: Dawn Bellante from Listing Office: Sandpiper Realty, Inc..

$1,225,000
2 Beds 1 Baths 73471155 MLS
On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural woodland setting. With strong rental income, currently generating $2,500 month to month year-round, and expansion opportunities subject to town approvals, the property is conveniently located near South Road, West Tisbury's village center, and Chilmark's iconic Lucy Vincent and Squibnocket Beaches. Passed Title V in December 2025 for 3 Bedrooms. #47 is shown as Lot 1-C on a new subdivision not yet reflected on the assessments and public records - approved survey is attached. 45 Quenames Lot 1-B is also available.

47 Quenames Rd, Chilmark

Listing courtesy of Listing Agent: Dawn Bellante from Listing Office: Sandpiper Realty, Inc..

$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.

$6,000
2 Beds 2 Baths 73191193 MLS
BOOKING SUMMER 2027 AND FALL/SPRING '26 SPRING '27 Welcome to 11 Hammett Lane in Chilmark, up-island on beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. Affectionately named 'The Blueberry House' by the original owners, this 2 bedroom, 2 bath, 2 story home with outdoor shower will quickly find a place in your heart. Prime location off North Road next to North Tabor Farm, Great Rock Bight Preserve, Menemsha Beach, The Chilmark Store, Library and Community Center. The gorgeous grounds are dotted with wild blueberries and embraced by tall trees alive with local birds. Bright, light, and easy. Perfect for a long summer stay, fall leaf peeping, visiting family and friends and retreating artists alike. Furnished, Kitchenware provided, Sheets, Bath & Beach Towels provided,Washer/Dryer. Beach Access to Lucy Vincent and Squibnocket available. INQUIRE FOR AVAILABILITY. Taxes,Cleaning, Security Addtl.

11 Hammett Lane, Chilmark

Listing courtesy of Listing Agent: Allison Cameron Parry from Listing Office: Douglas Elliman Real Estate - Nantucket.

$22,000
4 Beds 2 Baths 72850761 MLS
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 Squibnocket. This spacious four bedroom, 2 bath home has an expansive rear deck that offers panoramic water views. The main level offers an open kitchen and large living room complete with fireplace. An entire wall is floor to ceiling glass with French doors opening onto a large deck. All of the rooms on this floor offer stunning views, including the Master bedroom. The first level features a large family room and three ample sized bedrooms. Black Point Beach Key included with property!!!

36 Henry Hough Lane Ch206, Chilmark

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

$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..

$40,000
6 Beds 6 Baths 72851050 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $10,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four bedrooms, and guest house, with two bedrooms, allow for comfortable space between family and guests. The gently rolling farm land and picturesque pond welcome cows and flocks of Canada geese. This excellent location is very close to Chilmark center and a quick drive, walk or hike to Lucy Vincent beach and Menemsha.

384 Middle Rd Ch222, Chilmark

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

$50,700
4 Beds 3 Baths 72852603 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,675. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set atop a hill you will find this wonderful 4 bedroom home with distant views and a wonderful lap pool. Enjoy your days on the large deck or take a swim in the pool. This great vacation home is tastefully decorated and is located on one level with plenty of space for gatherings. The living room has a fireplace with built in seating areas overlooking the yard. Each room is decorated so nicely. You will find that this is the house you will come back to year after year. By renting this home you will have access to the private town beaches that are some of the best on the island.

6 Trails End Ch241, Chilmark

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

$10,800
4 Beds 2 Baths 72843696 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Chilmark Cottage Perfection!!! You will love this quaint Vineyard Style Cottage that has been meticulously designed to include all the amenities one could imagine. This vintage charmer really boasts a lot of Style. Inside you will find really beautiful hardwood floors, a fully equipped kitchen, and a storybook bedroom complete with wonderful linens. This home is one of the most perfect spots to spend your vacation on the Vineyard. Also, renters have access to the private beaches of Lucy Vincent and Squibnocket. Great out door shower and wonderful patio complete the amenities. No pets allowed.

141 North Rd. Ch202, Chilmark

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

$13,200
2 Beds 2 Baths 72854072 MLS
THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the upmost in Luxury. Each room is exciting, charming and has a simplistic yet artistic style. The entire house is accented with beautiful light pine flooring that pairs perfectly with the expansive main room. On each side of the main living area are two one bedroom en suite areas that offers privacy between the two bedrooms. Each bedroom has a queen bed and a twin bed affording the possibility of sleeping six people. This home is set on a hill that provides privacy and tranquility PLEASE WASH AND DRY BEACH TOWELS PRIOR TO DEPARTURE.No pets allowed.

224 North Rd Ch248, Chilmark

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

$34,000
4 Beds 3 Baths 72850133 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Modern 4 bedroom home completed in 2019, in Menemsha. Located on a quiet road with waterviews from the upstairs bedrooms also offers views of the famous Menemsha sunsets from the deck. Sustainably harvested flooring features silky smooth and buttery hard wood floors from reclaimed red birch. A contemporary kitchen and clean lines throughout lead to the separate open concept dining/living room layout with sliding doors to the masterfully crafted deck. First floor main Queen bedroom and private bath with gorgeous walk in shower. Three additional bedrooms upstairs share a full bath. Powder room on the first floor and private outside shower. An extra fridge in the basement can hold anything you need for your guests.

15 Loon Lane Ch203, Chilmark

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

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