West Tisbury, MA Homes

/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
$8,000 per month
- 4 Beds
- 4.5 Baths
- 3,600 Sq Ft
- House for Rent
56 Chilmark Rd, Chilmark, MA 02535

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation land. The house is exquisitely crafted, well maintained and beautifully landscaped. Views of Harlock's pond are visible from the kitchen, living area and

Karen Overtoom Karen M. Overtoom R.E.

56 Chilmark Rd, Chilmark, MA 02535
/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

/43
Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,674 Sq Ft
39 Sarita Walker Rd, Vineyard Haven, MA 02568

39 Sarita Walker Rd, Vineyard Haven, MA 02568

/29
$1,695,000
- 3 Beds
- 2 Baths
- 1,986 Sq Ft
251 State Rd, Vineyard Haven, MA 02568

This private and pastoral year-round home with fine craftsmanship and loads of character is a classic up-island refuge, yet in a location that is central on the island and convenient to town. The charming home features an open living and dining room with wide plank floors and beams flowing into the kitchen, all surrounding a central brick fireplace. An expansive family room off the sunny entrance

Meg Bodnar Tea Lane Associates

251 State Rd, Vineyard Haven, MA 02568
/42
$19,000 per month
- 6 Beds
- 6.5 Baths
- 6,950 Sq Ft
- House for Rent
40 Sweet William Way, West Tisbury, MA 02575

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY! This stunning home is situated right in the heart of West Tisbury, yet set back enough for a completely private feel. On a property that encompasses 10 acres with your own private pond, you will feel the stress melt away as soon as you get to this luxury vacation home. Keys to private Quansoo Beach Association come with the house. Spend your days on the

Karen Overtoom Karen M. Overtoom R.E.

40 Sweet William Way, West Tisbury, MA 02575
/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

/41
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,598 Sq Ft
566 Scrubby Neck Rd, Vineyard Haven, MA 02568

566 Scrubby Neck Rd, Vineyard Haven, MA 02568

/37
$1,349,000
- 4 Beds
- 2 Baths
- 2,059 Sq Ft
4 Rock Pond Rd, Vineyard Haven, MA 02568

4 Bedroom ++ home, has room for your family and your in-home business. This is the home that has it all. An abundance of light, space and potential. A large Atrium off the living room invites in the light and warmth of outside, creating an oasis of possibilities-The expansive open living-kitchen-dining area has space for all to gather, the wood stove and kitchen bringing warmth and sunlight into

Kerry Quinlan-Potter Breakwater MV

4 Rock Pond Rd, Vineyard Haven, MA 02568
/39
$46,000 per month
- 6 Beds
- 4.5 Baths
- 3,800 Sq Ft
- House for Rent
99 Pond Road Wt104, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!! Beautiful bright sunny home with open concept living. Main floor features a gourmet kitchen with stainless appliances, breakfast bar and formal dining table to seat 10. Large glass sliders open up to expansive views of the deck, pool and pasture beyond. Also on the main level is a separate living area with large screen TV, powder room, and den with twin

Karen Overtoom Karen M. Overtoom R.E.

99 Pond Road Wt104, West Tisbury, MA 02575
/3
$275,000 Sold Nov 19, 2024
- Land
- 1.80 Acres
- $152,778 per Acre
- 143 Days On Market
0 Lamberts Cove Rd, Vineyard Haven, MA 02568

Wooded parcel in Vineyard Haven located off scenic Lamberts Cove Road. Conveniently located to Tisbury Center and neighboring Vineyard Open Land Foundation's Cranberry Acres. A recent survey has been completed, identifying right of way and wetlands, all other engineering and permitting is the responsibility of the buyer. A License to Sell issued by the Dukes Probate and Family Court is a

Katherine Donahue Sandpiper Realty Inc

0 Lamberts Cove Rd, Vineyard Haven, MA 02568

/15
Est $2,582,269 Not Listed For Sale
- 1 Bed
- 1 Bath
- 512 Sq Ft
119 Old Thumb Point Rd, Vineyard Haven, MA 02568

119 Old Thumb Point Rd, Vineyard Haven, MA 02568

/42
$8,750,000
- 5 Beds
- 3 Baths
- 2,269 Sq Ft
34 Edys Island Way, Chilmark, MA 02535

Waterfront house and guest house with a private dock on Menemsha Pond. This location is in the heart of Menemsha, a waterfront enclave within walking distance of this classic Harbor. Built and cared for over four generations by anIsland legacy family, this property is unique among Island estates for its combination of privacy yet convenience and seclusion yet expansive views. To the Southeast,

Jill Napior

34 Edys Island Way, Chilmark, MA 02535
/3
$13,200 per month
- 2 Beds
- 2 Baths
- 1,344 Sq Ft
- House for Rent
224 N Rd Ch248, Chilmark, MA 02535

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.

Karen Overtoom Karen M. Overtoom R.E.

224 N Rd Ch248, Chilmark, MA 02535
/35
$1,995,000 Sold Nov 15, 2024
- 1,995 Sq Ft
- $1000/SF
- 47 Days On Market
- 4 Beds
- 3 Baths
- Built 2003
159 Charles Neck Way, Vineyard Haven, MA 02568

The Whale House: Coastal-Inspired Living Near Long Point - This beautifully appointed residence is an ideal sanctuary for family and friends to indulge in relaxation and seaside splendor. The first floor welcomes you with a sun-filled open layout. A Living Area adorned with a gas fireplace sets the stage for cozy gatherings. The well-appointed Kitchen boasts a prep counter/breakfast bar and

Wendy Harman Compass

159 Charles Neck Way, Vineyard Haven, MA 02568

/7
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,092 Sq Ft
105 Charles Neck Way, Vineyard Haven, MA 02568

105 Charles Neck Way, Vineyard Haven, MA 02568

/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
/28
$32,000 per month
- 4 Beds
- 4 Baths
- 3,200 Sq Ft
- House for Rent
37 Mempremagog Ave Vh410, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous custom designed and decorated four bedroom home is located in a wooded setting that offers total privacy and is with-in walking distance to a private association beach. And yet is only 3 miles from downtown Vineyard Haven. This lovely home offers a gourmet eat-in

Karen Overtoom Karen M. Overtoom R.E.

37 Mempremagog Ave Vh410, Tisbury, MA 02568
/37
$1,115,000 Sold Nov 07, 2024
- 1,316 Sq Ft
- $847/SF
- 32 Days On Market
- 3 Beds
- 2 Baths
- Built 1991
43 Skiffs Ln, Vineyard Haven, MA 02568

Nestled on a private road, follow the long gravel driveway to this 3-bedroom, 2-bathroom home offering tranquil living on 2.48 wooded acres. The fully-applianced kitchen and vinyl flooring throughout provide ease of maintenance, while the bedrooms offer cozy carpeting. The primary bedroom features an ensuite bathroom and generous closet space. Step out from the kitchen to the back deck and enjoy

Chelsea Brennan Lamacchia Realty, Inc.

43 Skiffs Ln, Vineyard Haven, MA 02568

/31
Est $1,234,831 Not Listed For Sale
- 1 Bed
- 1.5 Baths
- 855 Sq Ft
16 Elias Ln, Vineyard Haven, MA 02568

16 Elias Ln, Vineyard Haven, MA 02568

/38
$5,475,000
- 5 Beds
- 3 Baths
- 3,440 Sq Ft
146 Quansoo Rd, Chilmark, MA 02535

Nestled along the beautiful and tranquil shoreline of Tisbury Great Pond and surrounded by a stunning natural environment of water, sand and sky, this is an unparallelled beach house experience on the south shore of Chilmark. The five-bedroom home consists of a three-bedroom main house connected by walkways to a two-bedroom guest wing with studio space above, all with spectacular water views

Meg Bodnar Tea Lane Associates

146 Quansoo Rd, Chilmark, MA 02535
/26
$50,700 per month
- 4 Beds
- 3 Baths
- 2,346 Sq Ft
- House for Rent
6 Trails End Ch241, Chilmark, MA 02535

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

Karen Overtoom Karen M. Overtoom R.E.

6 Trails End Ch241, Chilmark, MA 02535
/22
$1,500,000 Sold Nov 05, 2024
- 1,008 Sq Ft
- $1488/SF
- 361 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2010
5 Meetinghouse Rd, Chilmark, MA 02535

CHARMING CHILMARK- This sweet, sunny home comes with deeded access to Chilmark Pond and South Shore Beach. Kayak, paddleboard, sail, or motor across the pond to one of Chilmark's most pristine private beaches. The location is also convenient, being centrally located and close to West Tisbury Center, Grey Barn, the Yoga Barn, Chilmark Center, Beetlebung Farm, Chilmark Store, and Chilmark Tavern.

Tina Miller Compass

5 Meetinghouse Rd, Chilmark, MA 02535

/24
Est $1,778,847 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 2,856 Sq Ft
280 Oak Ln, Vineyard Haven, MA 02568

280 Oak 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
/19
$24,000 per month
- 4 Beds
- 4 Baths
- 2,000 Sq Ft
- House for Rent
44 Flanders Ln, Chilmark, MA 02535

THIS IS A WEEKLY SUMMER RENTAL ONLY.!! SEE WEB SITE FOR WEEKLY PRICING. This house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Visit town to watch sunsets in Menemsha, dine in one of the places to eat there or take in a day at the beach.Access to and parking for beautiful private association beach.

Karen Overtoom Karen M. Overtoom R.E.

44 Flanders Ln, Chilmark, MA 02535
/26
$950,000 Sold Oct 25, 2024
- 1,182 Sq Ft
- $804/SF
- 8 Days On Market
- 1 Bed
- 1 Bath
- Built 1977
4 Elias Ln, Vineyard Haven, MA 02568

This iconic West Tisbury property features a rustic post and beam farmhouse with endless charm. The inviting home highlights original wide-planked wood floors, cathedral ceiling, wood-burning stove and fireplace, and exposed brick. Enjoy the cozy kitchen, dining, and living area on the first floor, including a full bath and mudroom. The bedroom occupies the second floor with room for an

Stephanie Roache Donnelly + Co.

4 Elias Ln, Vineyard Haven, MA 02568

/16
Est $1,278,011 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,408 Sq Ft
35 Skiffs Ln, Vineyard Haven, MA 02568

35 Skiffs Ln, 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
/31
$40,000 per month
- 6 Beds
- 6 Baths
- 3,960 Sq Ft
- House for Rent
384 Middle Rd Ch222, Chilmark, MA 02535

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

Karen Overtoom Karen M. Overtoom R.E.

384 Middle Rd Ch222, Chilmark, MA 02535
/19
$2,200,000 Sold Oct 25, 2024
- 2,450 Sq Ft
- $898/SF
- 182 Days On Market
- 4 Beds
- 3 Baths
- Built 1964
27 Ocean View Farm Rd, Chilmark, MA 02535

27 Ocean View Farm Road is a unique house with the main living spaces designed by architect Elizabeth Carlhian in 1964 along with a connected, yet private bed and bath suite designed by architects Modigliani/Noyes in 1987. A covered breezeway between the two spaces frames the ocean views while providing cover from the weather. Taken together the house consists of 4 bedrooms and 3 baths sited high

27 Ocean View Farm Rd, Chilmark, MA 02535

/26
Est $4,732,468 Not Listed For Sale
- 8 Beds
- 4 Baths
- 4,800 Sq Ft
48 Forest Rd, Vineyard Haven, MA 02568

48 Forest Rd, Vineyard Haven, MA 02568

/47
$1,625,000
- 5 Beds
- 3 Baths
- 1,822 Sq Ft
21 Coffins Field Rd, Edgartown, MA 02539

EDGARTOWN SOUTH SHORE BEACH HOUSE. Imagine a countryside abode with nearby access to a pristine south shore stretch of beach and less than 6 miles to Edgartown Village and Harbor. Architect-designed as a low-key getaway, this delightful five bedroom year-round home has three full bathrooms plus a freestanding outdoor shower, decks, screened-in porch and is comfortably sited in an established well

Helena Kirschenbaum

21 Coffins Field Rd, Edgartown, MA 02539
/20
$16,800 per month
- 3 Beds
- 2 Baths
- 1,638 Sq Ft
- House for Rent
31 S Ridge Rd Ch218, Chilmark, MA 02535

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

Karen Overtoom Karen M. Overtoom R.E.

31 S Ridge Rd Ch218, Chilmark, MA 02535
/19
$1,800,000 Sold Oct 17, 2024
- 1,822 Sq Ft
- $988/SF
- 224 Days On Market
- 3 Beds
- 2 Baths
- Built 1989
7 Parsonage Woods Rd, West Tisbury, MA 02568

This rare and cherished setting is truly in the heart of West Tisbury. With old growth cedar, oaks and evergreen trees this level 4.8 acre parcel includes a main house and timber barn, perfectly sited to enjoy serene views and southern exposure. Currently set up as a horse farm with a two stall barn, paddocks, full size arena, interconnecting grazing areas and multiple watering stations, it could

7 Parsonage Woods Rd, West Tisbury, MA 02568

/33
Est $1,596,642 Not Listed For Sale
- 2 Beds
- 1 Bath
- 770 Sq Ft
2 Creek Hill, Chilmark, MA 02535

2 Creek Hill, 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
/32
$36,000 per month
- 3 Beds
- 3.5 Baths
- 2,600 Sq Ft
- House for Rent
29 Cemetery Rd Ch216, Chilmark, MA 02535

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

Karen Overtoom Karen M. Overtoom R.E.

29 Cemetery Rd Ch216, Chilmark, MA 02535
/8
$660,000 Sold Oct 04, 2024
- Land
- 1.60 Acres
- $412,500 per Acre
- 175 Days On Market
87 Longview Rd, West Tisbury, MA 02575

This lovely 1.60 acre wooded parcel is located in an outstanding neighborhood off Lambert's Cove Road with paved roads and easy access to beautiful Lambert's Cove Beach, less than a mile away. This lot is ready to build on. It has been staked, there is an approved septic design for 4 bedrooms, well has been installed and electric and cable are to the lot. This is the chance to build the house of

Brenda Galligan Karen M. Overtoom R.E.

87 Longview Rd, West Tisbury, MA 02575

/18
Est $4,089,275 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,316 Sq Ft
1 Pond Mark, Chilmark, MA 02535

1 Pond Mark, Chilmark, MA 02535

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