Chilmark, MA Homes

/30
$3,900,000
- 4 Beds
- 2 Baths
- 2,813 Sq Ft
179 Tisbury Ln E, West Tisbury, MA 02575

Seven Gates Farm: This warm and convivial home in one of the island’s most desirable communities is less than 1/10th of a mile to the private association beach. The house was designed to accentuate indoor-outdoor living; there is generous decking for morning or afternoon sun, and a screened porch which is the perfect place to enjoy shade and breeze after a day spent at one of the nearby beaches.

Mark Jenkins Wallace & Co. Sotheby's

179 Tisbury Ln E, West Tisbury, MA 02575
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/14
$8,400 per month
- 4 Beds
- 3 Baths
- 2,148 Sq Ft
- House for Rent
39 Old Coach Rd, West Tisbury, MA 02568

Summer weekly rental only! June weekly rate is $8,400 and July weekly rate is $10,000/week - Sunday to Saturday. Recently renovated 4 bedroom, 3 bathroom home that sits on a private 2 acre lot in West Tisbury MA! This large cape house has just been update with new stainless steel appliances, new kitchen cabinets and countertops. Other updates include, new bathroom vanities and hardware,

Joseph D'Amico Dee Development Company

39 Old Coach Rd, West Tisbury, MA 02568
/20
$1,150,000 Sold Jun 13, 2025
- 1,374 Sq Ft
- $837/SF
- 43 Days On Market
- 3 Beds
- 2 Baths
- Built 1981
46 Old Coach Rd, Vineyard Haven, MA 02568

Charming and Spacious 3-Bedroom Cape with large Loft and Deck Welcome to your dream West Tisbury home! This comfortable and spacious 3-bedroom, 2-bath Cape boasts a thoughtfully designed floor plan perfect for comfortable living. The first-floor features two bedrooms and a full bath, ideal for use as sleeping quarters or a home office. Moving to the second floor, discover privacy with a third

Lisa Gilberto C McManus Realty Group

46 Old Coach Rd, Vineyard Haven, MA 02568

/40
Not Listed For Sale
- 4 Beds
- 5 Baths
- 4,500 Sq Ft
1005 State Rd, West Tisbury, MA 02575

1005 State Rd, West Tisbury, MA 02575

/37
$3,995,000
- 5 Beds
- 3 Baths
- 2,791 Sq Ft
20 James Pond Way, Vineyard Haven, MA 02568

Nestled on a serene 4.5-acre parcel of land off Lambert's Cove Road, this exquisite property offers unparalleled privacy, views and direct access to James Pond and beyond to the Land Bank's Lambert's Cove Beach property. In addition to the custom heated Gunite pool, the expansive yard provides space for many outdoor activities while relishing the tranquility of the location. The residence

Sheila Morse Island Real Estate

20 James Pond Way, Vineyard Haven, MA 02568
/20
$4,250 per month
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
- House for Rent
11 Hammett Ln, Chilmark, MA 02535

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

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

11 Hammett Ln, Chilmark, MA 02535
/3
$1,695,000 Sold May 30, 2025
- 1,296 Sq Ft
- $1308/SF
- 2 Beds
- 2 Baths
- Built 1960
5 Vincent Rd, Vineyard Haven, MA 02568

NOT LISTED IN LINK

Alisan Lohan-Conway Alisan Lohan-Conway Properties

5 Vincent Rd, Vineyard Haven, MA 02568

/30
Est $2,453,141 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,555 Sq Ft
10 Crow Hollow Rd, Vineyard Haven, MA 02568

10 Crow Hollow Rd, Vineyard Haven, MA 02568

/25
$3,600,000
- 3 Beds
- 3 Baths
- 4,382 Sq Ft
88 & 90 Quenames Rd, Chilmark, MA 02535

Make your own Chilmark dream come true!12.6 +/- acres of prime land allows you to create your own familycompound or Island Farm. Enjoy the peacefulness of the Chilmarkwith room to expand. Two separate buildable lots provides you uniqueoptions. The Main house has three bedrooms, three bathrooms, twostudies, multiple living spaces and a large three-car garage

Julianna Flanders Flanders Real Estate

88 & 90 Quenames Rd, Chilmark, MA 02535
/10
$8,500 per month
- 3 Beds
- 2 Baths
- House for Rent
29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary

Karen Overtoom Karen M. Overtoom R.E.

29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
/15
$1,150,000 Sold May 30, 2025
- 1,338 Sq Ft
- $859/SF
- 48 Days On Market
- 4 Beds
- 2 Baths
- Built 1966
14 Galway Rd, Vineyard Haven, MA 02568

Welcome to 14 Galway Road, West Tisbury. The home and property have been lovingly maintained and used by the same family since the home was built. It offers an open eat-in kitchen/living room design with a masonry fireplace. On the first floor are two bedrooms, one full bathroom, a linen closet, and hidden washer and dryer along the hallway. The stairway brings you to a second floor which

Michele Casavant Vineyard Village Realty

14 Galway Rd, Vineyard Haven, MA 02568

/4
Est $3,141,517 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,789 Sq Ft
188 Pond Rd, Vineyard Haven, MA 02568

188 Pond Rd, Vineyard Haven, MA 02568

/41
$2,950,000
- 4 Beds
- 3 Baths
- 2,424 Sq Ft
19 Old Woods Rd, Chilmark, MA 02535

Tucked away in the heart of Chilmark, this nearly 3-acre property blends rustic Vineyard charm with unique creative potential. Chilmark was a very special place for the former owner, American artist Thomas Hart Benton, who summered on the Island for 50 years. Professor and Art Historian, Erika Doss, said “the years he spent in Chilmark honed the artistic style and subjects that led to his

Cheri Mason Landvest MV

19 Old Woods Rd, Chilmark, MA 02535
/8
$16,000 per month
- 7 Beds
- 3.5 Baths
- 4,000 Sq Ft
- House for Rent
5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as well as a second floor primary bedroom with en suite.

Karen Overtoom Karen M. Overtoom R.E.

5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
/32
$1,050,000 Sold May 29, 2025
- 1,701 Sq Ft
- $617/SF
- 28 Days On Market
- 4 Beds
- 2 Baths
- Built 1960
10 Rumpus Ridge Rd, Chilmark, MA 02535

Discover this inviting two-unit property in the heart of Chilmark! Ideally situated near Chilmark General Store, Squibnocket, Menemsha, and the pristine shores of Lucy Vincent Beach, this home offers both convenience and charm. Thoughtfully updated for year-round comfort, the property features a new metal roof, new siding, solar panels, mini-split AC, and more. The main-level residence offers

Peyton Wallace Studio Realty

10 Rumpus Ridge Rd, Chilmark, MA 02535

/34
Est $2,519,358 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 1 Sq Ft
248 Pond Rd, Vineyard Haven, MA 02568

248 Pond Rd, Vineyard Haven, MA 02568

/53
$4,800,000
- 6 Beds
- 5 Baths
- 2,960 Sq Ft
104 Pond View Farm Rd, Vineyard Haven, MA 02568

An exceptional Waterfront Compound on Tisbury Great Pond. Located across the Tisbury Great Pond from the exclusive Blue Heron Farm, this remarkable waterfront property offers a rare opportunity to own a serene compound with two homes and a private permitted dock—ideal for boating to the Atlantic barrier beach, fishing, kayaking, and enjoying the peaceful beauty of the pond.Both the main house and

Alexis Holden Tea Lane Associates

104 Pond View Farm Rd, Vineyard Haven, MA 02568
/8
$11,800 per month
- 4 Beds
- 4 Baths
- 2,612 Sq Ft
- House for Rent
46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL PROPERTY!! Beautifully updated contemporary home with impeccably landscaped lawns and gardens, a swimming pond and hot tub with two outdoor showers - one enclosed and one open to the hot tub and patio area on the side of the house. Gorgeous back deck with outdoor dining accessible through sliding glass doors from the dining room. Inside, enjoy the fully equipped and

Karen Overtoom Karen M. Overtoom R.E.

46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
/26
$1,850,000 Sold May 14, 2025
- 2,610 Sq Ft
- $709/SF
- 8 Days On Market
- 5 Beds
- 4 Baths
- Built 1986
137 Charles Neck Way, Vineyard Haven, MA 02568

Fantastic opportunity to buy a two house compound in West Tisbury close to Long Point Beach access. A perfect investment, rental income generator or to host extended family and guests.Two well built houses on 1.6 acres, that have been impeccably maintained by the original owner. Offering a total of 5 bedrooms, 4 bathrooms, 2 outdoor showers and 2 garages. There is a charming garden shed and low

Rebecca V Conroy Conroy & Company R.E., Inc.

137 Charles Neck Way, Vineyard Haven, MA 02568

/25
Est $2,060,735 Not Listed For Sale
- 5 Beds
- 3 Baths
- 3,636 Sq Ft
131 Shubael Weeks Path, Vineyard Haven, MA 02568

131 Shubael Weeks Path, Vineyard Haven, MA 02568

/26
$3,390,000
- 5 Beds
- 4 Baths
- 3,678 Sq Ft
15 Crowell Rd, West Tisbury, MA 02575

Hickory Hollow is one of the most enchanting parcels of land in Seven Gates Farm. You enter the property and feel as if you have stepped back in time. The cozy antique farmhouse is the centerpiece of the 6.8-acre property which includes rolling lawns, lichen-covered stone walls and boulders, numerous specimen trees, and no fewer than 3 ponds. In addition to the main house there are 3 additional

Mark Jenkins Wallace & Co. Sotheby's

15 Crowell Rd, West Tisbury, MA 02575
/12
$6,180 per month
- 3 Beds
- 3.5 Baths
- 1,872 Sq Ft
- House for Rent
44 Music St Wt153, West Tisbury, MA 02575

PLEASE TAKE NOTE!!!!!THIS IS A WEEKLY SUMMER RENTAL NOT A MONTHLY RENTAL. THE PRICE ON THIS LISTING IS A WEEkLY PRICE!!!!!!!

Karen Overtoom Karen M. Overtoom R.E.

44 Music St Wt153, West Tisbury, MA 02575
/13
$2,050,000 Sold May 01, 2025
- 1,007 Sq Ft
- $2036/SF
- 0 Days On Market
- 2 Beds
- 1 Bath
- Built 2016
16 Red Coat Hill Rd, Vineyard Haven, MA 02568

Exquisite West Tisbury Property: A Unique Opportunity.Discover the allure of a truly exceptional property nestled on 4.85 stunning acres in the serene locale of West Tisbury. This opportunity is not one to be missed, as it combines elegance, foresight, and sustainability in perfect harmony.The home is adorned with beautiful beams throughout, with nickelboard and shiplap covering the walls and

Joe Holland Vineyard Dream Realty LLC

16 Red Coat Hill Rd, Vineyard Haven, MA 02568

/79
Not Listed For Sale
- 6 Beds
- 3 Baths
- 2,604 Sq Ft
260 South Rd, Chilmark, MA 02535

260 South Rd, Chilmark, MA 02535

/23
$6,000,000
- 3 Beds
- 2 Baths
- 2,710 Sq Ft
35 S Bowl Rd, Chilmark, MA 02535

This exceptionally elegant and tranquil home in Seven Gates Farm combines contemporary architectural design with timeless high-end features for Vineyard casual, nature-inspired living. Extraordinary and rare, this move-in ready three-bedroom home with six-bedroom septic system sits on an oversized 5.3-acre parcel in Chilmark. This thoughtful layout has an easy flow, soothing tones with cypress

Meg Bodnar Tea Lane Associates

35 S Bowl Rd, Chilmark, MA 02535
/8
$8,250 per month
- 7 Beds
- 5 Baths
- 3,528 Sq Ft
- House for Rent
227 S Gate Rd Wt120, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY PROPERTY!! Set on 12 acres of peaceful woods, meadows, stone walls and its own pond, this charming 18th century 4 bedroom farmhouse and 3 bedroom rustic barn sleeps 12 and is perfect for larger groups wanting peace and tranquility all within a short distance to private swimming beaches. The setting, on exclusive Seven Gates Farm, offers miles of sandy trails through

Karen Overtoom Karen M. Overtoom R.E.

227 S Gate Rd Wt120, West Tisbury, MA 02575
/50
$3,000,000 Sold Apr 29, 2025
- 3,311 Sq Ft
- $906/SF
- 3 Beds
- 3 Baths
- Built 2000
34 S Pond Rd, Vineyard Haven, MA 02568

Stunning Deep Bottom Pond property with an oversized 3.77-acre lot surrounded by Mother Nature’s beauty, with exclusive association access to Tisbury Great Pond and private tennis courts. This beautiful home is lovingly maintained and ready for immediate occupancy. Through the welcoming grand foyer, a cathedral-ceiling living room with a fabulous wood-burning fireplace, and slider doors leading

Stephanie Roache Donnelly + Co

34 S Pond Rd, Vineyard Haven, MA 02568

/31
Est $2,971,133 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,300 Sq Ft
68 Meeting House Rd, Chilmark, MA 02535

68 Meeting House Rd, Chilmark, MA 02535

/13
$2,950,000
- 1 Bed
- 1 Bath
- 726 Sq Ft
18 Allen Farm Rd, Chilmark, MA 02535

Located in the agricultural heartland of Chilmark one mile from Lucy Vincent Beach this private 2.36 acre property has a charming 1 + bedroom cottage with screened porch, brick patio and outside shower. There is a large building zone located between the eighty and one hundred foot contour with exciting architectural options, especially for solar designs. The cottage is offered fully furnished,

Patty Kendall Kendall & Kendall

18 Allen Farm Rd, Chilmark, MA 02535
/2
$10,000 per month
- 6 Beds
- 3.5 Baths
- 2,100 Sq Ft
- House for Rent
15 Crowell Lane Wt119, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!Seven Gates Farm. This property has three ponds, overlooks rolling meadows and is very charming. Located in Seven Gates Farm association, the property affords access to association tennis and two miles of private beach as well as miles of walking trails. Bookings for tennis are available at the office for a slight fee.There is a $25 trash charge per

Karen Overtoom Karen M. Overtoom R.E.

15 Crowell Lane Wt119, West Tisbury, MA 02575
/35
$1,837,500 Sold Apr 18, 2025
- 1,654 Sq Ft
- $1111/SF
- 182 Days On Market
- 4 Beds
- 3 Baths
- Built 1984
55 Charles Neck Way, Vineyard Haven, MA 02568

LONG POINT BEACH RETREAT. Privately set on 1.6 acres in the highly-coveted Long Point area of West Tisbury, this reverse style beach house is an idyllic island retreat. The open-designed Great Room features vaulted ceilings and a wall of sliding glass doors that open out to an expansive deck, perfect for indoor-outdoor summer living and entertaining. There are also screened porches on both

Wendy Harman Compass | Point B

55 Charles Neck Way, Vineyard Haven, MA 02568

/36
Est $2,286,668 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,436 Sq Ft
377 State Rd, Vineyard Haven, MA 02568

377 State Rd, Vineyard Haven, MA 02568

/51
$5,295,000
- 5 Beds
- 4 Baths
- 4,044 Sq Ft
49 Gosnold's Way, Chilmark, MA 02535

Perched high on the north shore with sweeping views of the Vineyard Sound, this expansive and private property is surrounded by Menemsha Hills conservation land and trails and offers broad water views, even from ground floor of house. The house is large and well maintained with an upside down floor plan allowing for high ceilings and bright spaces in the open plan kitchen/dining/living room, as

Meg Bodnar Tea Lane Associates

49 Gosnold's Way, Chilmark, MA 02535
/8
$4,800 per month
- 3 Beds
- 3 Baths
- 3,279 Sq Ft
- House for Rent
165 Christiantown Rd, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY PROPERTY!! The home is set on six beautifully landscaped acres with original stone walls. It is located in private historic Christiantown on the North Shore, a short distance from both Lambert’s Cove Beach and Cedar Tree Neck Wildlife Reserve. Cedar Tree is a habitat with tumbling streams and freshwater ponds, sandy beaches and rocky cliffs, tall oaks and cool beech

Karen Overtoom Karen M. Overtoom R.E.

165 Christiantown Rd, West Tisbury, MA 02575
/22
$1,150,000 Sold Apr 11, 2025
- 1,264 Sq Ft
- $910/SF
- 216 Days On Market
- 3 Beds
- 2 Baths
- Built 1983
41 Old County Rd, Vineyard Haven, MA 02568

Let your imagination run wild with this peaceful, pastoral property centrally located between down and up-island. This home is perfectly sited on just over 2 acres and is ready for your vision. The cape-style main house features a spacious wrap around deck and an open floor plan on the first level. The entire home is outfitted with hardwood floors. According to the West Tisbury Board of Health,

Jared Bicknell Compass | The O'Hanlon Group

41 Old County Rd, Vineyard Haven, MA 02568

/14
Est $2,589,476 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,926 Sq Ft
30 Pond Ln, Vineyard Haven, MA 02568

30 Pond Ln, Vineyard Haven, MA 02568

/46
$3,476,000
- 4 Beds
- 3 Baths
- 3,669 Sq Ft
140 Pond Rd, Vineyard Haven, MA 02568

Welcome to this beautifully updated and privately situated home in one of West Tisbury’s most desirable associations. Residents enjoy exclusive access to tennis courts, walking trails, horse pastures and Tisbury Great Pond. Designed for both comfort and luxury, this spacious 4+ bedroom, 3 bathroom property is ideal as a year-round residence or upscale vacation retreat.The first floor features a

Jon Hartzband Martha's Vineyard Island-Wide Realty

140 Pond Rd, Vineyard Haven, MA 02568
/8
$4,500 per month
- 2 Beds
- 2 Baths
- 1,393 Sq Ft
- House for Rent
33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535

THIS IS A WEEKLY RENTAL PROPERTY!! This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.

Karen Overtoom Karen M. Overtoom R.E.

33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
/30
$1,175,000 Sold Mar 20, 2025
- 1,389 Sq Ft
- $846/SF
- 173 Days On Market
- 3 Beds
- 2 Baths
- Built 1988
12 W Farm Rd, West Tisbury, MA 02575

Welcome to 12 West Farm Road, a delightful classic cape nestled among beautiful mature evergreens in the Coffins Field neighborhood of West Tisbury. This well-kept home features 3 bedrooms and 2 bathrooms, offering 1,389 square feet of cozy and inviting living space. Skylighted ceilings and an open first-floor living/cooking/dining area combination provide a spacious feeling for everyday

Carson Crissman Compass | Point B

12 W Farm Rd, West Tisbury, MA 02575

/36
Est $1,282,862 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,780 Sq Ft
16 Rock Pond Rd, Vineyard Haven, MA 02568

16 Rock Pond Rd, Vineyard Haven, MA 02568

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