Chilmark, MA Homes

/36
$2,085,000
- 4 Beds
- 2.5 Baths
- 2,691 Sq Ft
51 Black Brook Crossing Rd, West Tisbury, MA 02568

This charming 4 bed/2.5 bath Cape style home is set in a perfect setting, carefully sited on 1 acre bordered by a beautiful stone wall with mature plantings. Newly renovated kitchen with plenty of cabinets and storage, quartz counters and dining room with sliders to a screened-in porch. There is a den and living room with access to a spacious deck. The Great Room features cathedral ceilings,

Brenda Galligan Karen M. Overtoom R.E.

51 Black Brook Crossing Rd, West Tisbury, MA 02568
/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
/50
$3,000,000 Sold Apr 29, 2025
- 3,311 Sq Ft
- $906/SF
- 14 Days On Market
- 3 Beds
- 2.5 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

/34
Est $2,431,655 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

/31
$2,450,000
- 4 Beds
- 3 Baths
- 1,918 Sq Ft
25 Fulling Mill Rd, Chilmark, MA 02535

Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to

Thomas Wallace Wallace & Co. Sotheby's International Realty

25 Fulling Mill Rd, Chilmark, MA 02535
/20
$4,250 per month
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
- House for Rent
11 Hammett Ln, Chilmark, MA 02535

**BOOKING SUMMER 2024** 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

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

11 Hammett Ln, Chilmark, MA 02535
/30
$1,837,500 Sold Apr 18, 2025
- 1,654 Sq Ft
- $1111/SF
- 0 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

55 Charles Neck Way, Vineyard Haven, MA 02568

/31
Est $2,844,232 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

/31
$2,495,000
- 5 Beds
- 3.5 Baths
- 2,685 Sq Ft
35 Woody Bottom Rd, West Tisbury, MA 02575

This Cape style 5 bed/ 3.5 bath home is located in a nice area privately sited on 3 acres. This home features a nice floor plan thatincludes a fully equipped kitchen with center island, custom cabinetry and granite counters. Just off the kitchen is a sunny breakfastroom, a separate dining room, a spacious living room with fireplace and 2 sets of sliders to a backyard deck. There is a cozy

Brenda Galligan Karen M. Overtoom R.E.

35 Woody Bottom Rd, West Tisbury, MA 02575
/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
/55
$15,000,000 Sold Apr 09, 2025
- 6,967 Sq Ft
- $2153/SF
- 25 Days On Market
- 6 Beds
- 7 Baths
- Built 2006
8 Snail Rd, Chilmark, MA 02535

LUXURY PROPERTY AUCTION: BID 11-24 APRIL. Listed for $14M. Starting Bids Expected Between $4M-$7M.Perched high on a hill, this Martha's Vineyard estate offers unparalleled privacy and commanding views of the Atlantic Ocean and Chilmark Pond. Designed by renowned architect Rick Sundberg and crafted by master builder Andrew Flake, this three-parcel residence harmoniously blends contemporary

Alyssa Halisky Wallace & Co. Sotheby's International Realty

8 Snail Rd, Chilmark, MA 02535

/48
Est $3,207,386 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 3,440 Sq Ft
8 Coffins Field Rd, Edgartown, MA 02539

8 Coffins Field Rd, Edgartown, MA 02539

/30
$3,450,000
- 5 Beds
- 3 Baths
- 2,713 Sq Ft
176 Middle Point Rd, Vineyard Haven, MA 02568

Rare private waterfront retreat on the Tisbury Great Pond. Nestled on an expansive 3.70 acres of land, this charming oasis offers a unique opportunity to enjoy serene water views and direct access to the beautiful Tisbury Great Pond and the South shore.The year-round main house spans 2,153 square feet and has three bedrooms and two bathrooms. Its seamless blend of Island charm and modern

Tina Miller Compass

176 Middle Point Rd, Vineyard Haven, MA 02568
/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
/23
$1,115,000 Sold Mar 14, 2025
- 1,286 Sq Ft
- $867/SF
- 237 Days On Market
- 2 Beds
- 1 Bath
- Built 1955
496 Lamberts Cove Rd, Vineyard Haven, MA 02568

Two peaceful acres on coveted Lamberts Cove Road with access to Lamberts Cove Beach and proximity to West Tisbury Center and Conservation Land. This property boasts mature plantings, various trees, and much Mother Nature offers, including a small pond. The home has been completely renovated and enjoys hardwood floors, skylights, a wood stove, and other special features such as antique

Stephanie Roache Donnelly + Co.

496 Lamberts Cove Rd, Vineyard Haven, MA 02568

/36
Est $2,587,653 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,791 Sq Ft
225 Great Plains Rd, Vineyard Haven, MA 02568

225 Great Plains Rd, Vineyard Haven, MA 02568

/44
$2,550,000
- 4 Beds
- 2.5 Baths
- 2,982 Sq Ft
157 Ben Chase Rd, West Tisbury, MA 02575

You will find this outstanding property at the end of a quiet country lane in West Tisbury nestled alongside hundreds of acres of conservation land and walking trails that extend all the way to Lamberts Cove Road. The setting is magical - 4 acres of rolling lawns with specimen trees and ponds. There are multiple structures to allow you to customize this compound to your personal needs. The main

Madelyn Silvia Wallace & Co. Sotheby's International Realty

157 Ben Chase Rd, West Tisbury, MA 02575
/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
/17
$1,300,000 Sold Mar 03, 2025
- 1,241 Sq Ft
- $1048/SF
- 4 Days On Market
- 2 Beds
- 2 Baths
- Built 2018
22 Briarwood Ln, Vineyard Haven, MA 02568

This Recently Constructed Carriage House in Vineyard Haven is the epitome of thoughtful planning with custom details and exceptional finishes throughout. The sunny second level has an open floor living and kitchen area with vaulted ceilings. Highlights include a farmer's sink and quartz countertops. There are two bedrooms, one is ensuite and both have been outfitted with California style

Carol Shore Donnelly + Co.

22 Briarwood Ln, Vineyard Haven, MA 02568

/34
Est $1,847,825 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,461 Sq Ft
29 Brook Hollow Rd, Vineyard Haven, MA 02568

29 Brook Hollow Rd, Vineyard Haven, MA 02568

/54
$2,999,000
- 7 Beds
- 5.5 Baths
- 4,476 Sq Ft
67 Hidden Village Rd, Vineyard Haven, MA 02568

Picturesquely sited on a spacious 4.6-acre parcel, this remarkable property is the perfect Vineyard retreat offering a luxurious home, guest house, fenced pastures, and a large barn. Just minutes from Lamberts Cove Beach, hiking trails, Up-Island Cronig's, and all the conveniences of West Tisbury Center, the location is ideal. Designed with three distinctive living levels, each area provides

Stephanie Roache Donnelly + Co.

67 Hidden Village Rd, Vineyard Haven, MA 02568
/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
/35
$2,525,000 Sold Jan 20, 2025
- 3,310 Sq Ft
- $763/SF
- 96 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1991
106 Panhandle Rd, Vineyard Haven, MA 02568

With easy access to the West Tisbury Village, this lovely 4 bedroom, 3.5 bath home is privately sited on 1.4 acres overlooking a protected pasture. Many nice features include open living spaces, a well equipped kitchen with stainless steel appliances, a center island and granite. The sun-filled great room with oversized windows offer peaceful views of the meadow, a cathedral ceiling and sliders

Brenda Galligan Karen M. Overtoom R.E.

106 Panhandle Rd, Vineyard Haven, MA 02568

/17
Est $1,081,353 Not Listed For Sale
- 3 Beds
- 2 Baths
- 934 Sq Ft
10 Briarwood Ln, Vineyard Haven, MA 02568

10 Briarwood Ln, Vineyard Haven, MA 02568

/21
$1,600,000
- 3 Beds
- 2 Baths
- 1,982 Sq Ft
19 S Vine Ln, Vineyard Haven, MA 02568

This charming Cape-style home, built in 1992, is tucked away in a quiet, subdivision on South Vine Lane. With three bedrooms and two bathrooms, it blends classic Island character with modern comforts. The inviting living room features vaulted ceilings and a double-sided fireplace, creating a bright and spacious atmosphere perfect for both relaxing and entertaining. The kitchen, filled with

Bonnie Pierce Wallace & Co. Sotheby's International Realty

19 S Vine Ln, Vineyard Haven, MA 02568
/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
/29
$2,250,000 Sold Dec 27, 2024
- 1,705 Sq Ft
- $1320/SF
- 5 Days On Market
- 4 Beds
- 3 Baths
- Built 1976
47 Stonebridge Rd, West Tisbury, MA 02568

Lamberts Cove Beach access, first and second floor water views, and a warm and inviting home in a private West Tisbury location - that is what is on offer here. The home was recently upgraded with a new kitchen and bathrooms. The primary bedroom suite has even better views than those from the first floor. The walkout lower level is a two bedroom suite with full bath, sitting area, kitchenette,

Mark Jenkins Wallace & Co. Sotheby's International Realty

47 Stonebridge Rd, West Tisbury, MA 02568

/36
Est $1,658,911 Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,144 Sq Ft
323 Lamberts Cove Rd, Vineyard Haven, MA 02568

323 Lamberts Cove Rd, Vineyard Haven, MA 02568

/15
$1,250,000
- 4 Beds
- 1.5 Baths
- 1,338 Sq Ft
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
/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
/5
$450,000 Sold Dec 12, 2024
- 708 Sq Ft
- $636/SF
- 21 Days On Market
- 2 Beds
- 1 Bath
- Built 1920
1 Carroll Ln, Chilmark, MA 02535

Discover the perfect blend of comfort and character in this delightful bungalow nestled in the heart of historic Chilmark. Surrounded by scenic landscapes and the serene beauty of Martha's Vineyard. This home will require substantial renovations and improvements or explore possibilities of a complete renovation. This property could be your idyllic escape and is less than a mile from Menemsha

1 Carroll Ln, Chilmark, MA 02535

/30
Est $3,865,949 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,748 Sq Ft
26 Pinkletink Rd, Chilmark, MA 02535

26 Pinkletink Rd, Chilmark, MA 02535

/44
$8,995,000
- 5 Beds
- 7 Baths
- 3,762 Sq Ft
85 Reservoir Rd, Vineyard Haven, MA 02568

Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone

Alyssa Halisky Wallace & Co. Sotheby's International Realty

85 Reservoir Rd, Vineyard Haven, MA 02568
/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
/4
$1,350,000 Sold Dec 03, 2024
- 2,179 Sq Ft
- $620/SF
- 0 Days On Market
- 4 Beds
- 2 Baths
- Built 1987
47 Willow Tree Hollow Rd, West Tisbury, MA 02568

SERENE & PRIVATE WEST TISBURY PROPERTY - Down a country lane off West Tisbury Road, this 1.55 acre property is a serene location for a vacation or year round home. Set on a knoll with established gardens, the outdoor spaces are cool and inviting with a large deck, level back yard, and an outdoor shower. Newly painted walls and trim throughout. There is room to spread out and relax after a day

Leslie Floyd Portfolio Real Estate Inc.

47 Willow Tree Hollow Rd, West Tisbury, MA 02568

/30
Est $1,319,628 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,464 Sq Ft
88 Hopps Farm Rd, Vineyard Haven, MA 02568

88 Hopps Farm Rd, Vineyard Haven, MA 02568

/16
$1,249,000
- 3 Beds
- 1.5 Baths
- 1,512 Sq Ft
108 Charles Neck Way, Vineyard Haven, MA 02568

This charming reverse-style home is ideally located near Long Point Beach and offers a perfect blend of comfort and functionality for year-round living or seasonal getaways. The first floor features three spacious bedrooms, a full bath, and a convenient laundry room. On the second floor, you'll find soaring cathedral ceilings and an open-concept living area, complete with a cozy living room,

Alyssa Halisky Wallace & Co. Sotheby's International Realty

108 Charles Neck Way, 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
/31
$1,180,000 Sold Nov 21, 2024
- 2,356 Sq Ft
- $501/SF
- 21 Days On Market
- 3 Beds
- 3 Baths
- Built 1974
43 Pin Oak Cir, West Tisbury, MA 02575

West Tisbury with bells and whistles! This well tended to property has seen a LONG LIST of recent IMPROVEMENTS to make ownership easy and up-island life a breeze! Nicely tucked in and off of Old County Road means easy access to up island and down. The raised ranch style provides terrific living space duality. BOTH LEVELS have living rooms with fireplaces as well as renovated bathrooms and

43 Pin Oak Cir, West Tisbury, MA 02575

/20
Est $1,304,928 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,730 Sq Ft
225 Longview Rd, Vineyard Haven, MA 02568

225 Longview Rd, Vineyard Haven, MA 02568

Showing Results 1 - 40, Page 1 of 18

Massachusetts Chilmark

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage