Chilmark, MA Homes

/46
$3,500,000
- 4 Beds
- 3 Baths
- 2,383 Sq Ft
100 Gosnolds Way, Chilmark, MA 02535

Well designed and maintained home, situated on 5 acres in a private, desirable neighborhood. Open floor plan with high ceilings that allows a lot of great light into house. The screened in porch is perfect for family dinners or relaxing. Nice water views of Vineyard Sound & the Elizabeth Islands. Short walk to the Brickyard Beach on the North Shore, rights are included with property, where

Julianna Flanders Flanders Real Estate

100 Gosnolds 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
/22
$1,115,000 Sold Mar 14, 2025
- 1,286 Sq Ft
- $867/SF
- 212 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

/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

/54
$2,999,000 Pending
- 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
/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
/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, quartz countertops, pull out kitchen cabinets and self-closing drawers. There are two bedrooms, one is ensuite and the

Carol Shore Donnelly + Co

22 Briarwood Ln, Vineyard Haven, MA 02568

/75
Est $4,314,985 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,362 Sq Ft
4 Tilton Rd, Chilmark, MA 02535

4 Tilton Rd, Chilmark, MA 02535

/38
$1,895,000
- 3 Beds
- 2.5 Baths
- 1,918 Sq Ft
234 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

LONG POINT BEACH RETREAT. Privately set on a spacious 1.4-acre parcel in the highly coveted Long Point area of West Tisbury, this beautifully renovated beach house offers the ultimate Vineyard escape. Move-in ready and being sold turnkey, it combines style, comfort, and convenience in an unbeatable location. The sun-filled living room with a cathedral ceiling and gas fireplace, and dining area

Stephanie Roache Donnelly + Co.

234 Vineyard Meadow Farms Rd, West Tisbury, 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
/45
$990,000 Sold Feb 19, 2025
- 1,618 Sq Ft
- $612/SF
- 145 Days On Market
- 3 Beds
- 2 Baths
- Built 1999
5 Rock Pond Rd, Vineyard Haven, MA 02568

Fantastic opportunity to own a South Mountain designed and built home in the coveted Island Co-Housing community. House #5 sits back from the community road with a great side yard, patio and outdoor shower.3 Large Bedrooms include a downstairs master w/ensuite bath off the living room area with a mid-way access leading to a private patio. The entryway opens on the kitchen, with thick shaker style

Kerry Quinlan-Potter Breakwater MV

5 Rock Pond Rd, Vineyard Haven, MA 02568

/31
Est $2,090,243 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,386 Sq Ft
7 the Aerie, Chilmark, MA 02535

7 the Aerie, Chilmark, MA 02535

/36
$1,495,000
- 4 Beds
- 2 Baths
- 1,332 Sq Ft
40 Scotchmans Ln, Vineyard Haven, MA 02568

A Home with history, built in the early 1800's this dwelling was originally built on a local farm and moved to its present location in the 1920's. The structure sits nestled amongst mature plantings and out buildings facing the Mill Brook. The studio and covered patio offer opportunities to entertain, relax and reflect. This 3.76 parcel was created from a larger parcel by the owner (see attached

Jim Osmundsen Donnelly + Co.

40 Scotchmans Ln, Vineyard Haven, MA 02568
/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
/2
$1,600,000 Sold Feb 04, 2025
- Land
- 3.60 Acres
- $444,444 per Acre
- 0 Days On Market
493 South Rd, Chilmark, MA 02535

Lovely pastoral lot within walking distance of beach and center of town.Perc test completed, septic being designed and well to be drilled shortly.Includes conservation restricted lot which consists of 10.6 acres.Build the home of your dreams in this amazing location.

Julianna Flanders Flanders Real Estate

493 South Rd, Chilmark, MA 02535

/36
Est $2,520,028 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

/45
$1,795,000
- 7 Beds
- 5 Baths
- 3,213 Sq Ft
51 Skiffs Ln, Vineyard Haven, MA 02568

Roomy, 5 bedroom, 3.5 bath home warmed by walls of knotty pine and sited on a 3-acre parcel with nicely cleared areas around the house bringing in the sunlight and enticing you outside for games, gardening and relaxation on the expansive deck. There is a wood-burning brick fireplace in the living room to gather around on chilly nights - and a full, dry basement great for kids games on rainy days

Candy DaRosa Feiner Real Estate

51 Skiffs Ln, Vineyard Haven, 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
/49
$1,750,000 Sold Jan 31, 2025
- 2,548 Sq Ft
- $687/SF
- 186 Days On Market
- 4 Beds
- 3 Baths
- Built 1984
75 Skiffs Ln, Vineyard Haven, MA 02568

Located on a beautiful, private 2.6 acre lot, this well-maintained home is move-in ready and awaiting your personal touch! Pool, manicured yard, plentiful parking, attached garage, large basement, outdoor shower and many more features make this spacious family home versatile and accommodating to your needs. You're able to enjoy the patio and pool with a built in fire pit during the summer months

Kelly Mercier Match Point Properties

75 Skiffs Ln, Vineyard Haven, MA 02568

/34
Est $1,580,132 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,452 Sq Ft
84 Christiantown Rd, Vineyard Haven, MA 02568

84 Christiantown Rd, Vineyard Haven, MA 02568

/37
$1,985,000
- Land
- 3.58 Acres
- $554,469 per Acre
4 Cedar Ln Unit 2.2, Chilmark, MA 02535

Premier Build-Ready Lot with Private Beach AccessGet to know Stonewall Association, one of Chilmark’s most sought-after enclaves on the South Shore. This sunny, build-ready parcel offers a rare opportunity to own land with deeded private access to Stonewall Beach—a beloved destination for swimming, surfing, and summer memories.Set on beautifully contoured land with southern exposure, the property

Jill Napior Tea Lane Associates

4 Cedar Ln Unit 2.2, 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
/31
$2,525,000 Sold Jan 17, 2025
- 3,310 Sq Ft
- $763/SF
- 80 Days On Market
- 4 Beds
- 4 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

/36
Est $2,208,000 Not Listed For Sale
- 6 Beds
- 4 Baths
- 2,705 Sq Ft
9 Heather Trail, Vineyard Haven, MA 02568

9 Heather Trail, Vineyard Haven, MA 02568

/12
$1,325,000
- Land
- 4.12 Acres
- $321,602 per Acre
25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568

This beautiful wooded 4.12 acre parcel of land is peaceful, serene and ready to build. The well is installed, boundaries staked, perc test approved for a five-bedroom home and a septic plan designed. This is an opportunity to realize your vision and build a home that reflects your lifestyle. The large, flat building envelope offers many siting possibilities and, should you choose, the property

Abby Rabinovitz Tea Lane Associates

25 Plum Bush Point Rd Unit 6, West Tisbury, 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
/39
$2,895,000 Sold Jan 10, 2025
- 4,239 Sq Ft
- $683/SF
- 341 Days On Market
- 5 Beds
- 5 Baths
- Built 1999
18 S Pond Rd, Vineyard Haven, MA 02568

DEEP BOTTOM POND: 5-bedroom custom home with heated Pebbletec pool and exclusive association access to Tisbury Great Pond. This spacious layout features two primary suites, two guest rooms, and a third private guest suite. Perfect for entertaining, the open floor plan centers around the kitchen, dining, and living areas. The dramatic living room has cathedral ceilings, floor-to-ceiling windows, a

Rose Ryley Sandpiper Realty

18 S Pond Rd, Vineyard Haven, MA 02568

/18
Est $1,860,348 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,461 Sq Ft
29 Brook Hollow Rd, Vineyard Haven, MA 02568

29 Brook Hollow Rd, Vineyard Haven, MA 02568

/38
$1,775,000
- 4 Beds
- 3 Baths
- 2,856 Sq Ft
175 Great Plains Rd, West Tisbury, MA 02568

Located in a peaceful corner of West Tisbury, this well-built, single-story home offers both privacy and convenience, with easy access to thousands of acres of conservation land. Designed with practical living in mind, this home is perfect for single-floor living, multi-generational households, or those needing space for a live-in nanny or helper.Built in 2012 with an additional wing added in

Jon Hartzband Martha's Vineyard Island-Wide Realty

175 Great Plains Rd, West Tisbury, 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
/32
$3,000,000 Sold Jan 09, 2025
- 3,500 Sq Ft
- $857/SF
- 194 Days On Market
- 4 Beds
- 4 Baths
- Built 2023
4 Bartlett Woods, Chilmark, MA 02535

NEW BRIGHT & AIRY CONTEMPORARY OFF SOUTH ROAD! The house newly completed in 2023 & the one car garage in 2024 are nicely situated on a 4.56 acre lot. The 4 bedroom residence offers 3500 sf of finished living on two levels. On the first level are 2 primary bedrooms, each with en suite bathrooms, and a spacious open floor plan for living, dining and kitchen. An office off the kitchen allows you to

Kathryn Tate Kathryn Tate Gothard

4 Bartlett Woods, Chilmark, MA 02535

/16
Est $1,351,510 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,150 Sq Ft
31 Music St, Vineyard Haven, MA 02568

31 Music St, Vineyard Haven, MA 02568

/35
$14,000,000
- 5 Beds
- 5 Baths
- 3,758 Sq Ft
6 Wakeman Rd, Chilmark, MA 02535

A 1930s-built home that has been remarkably updated to retain its historic charm while incorporating sophisticated and modern amenities. The house overlooks the Chilmark Great Pond and the Atlantic Ocean beyond. The Main House includes 3 bedrooms, 3 beautifully renovated bathrooms, a walk-in closet, a Pantry, a Library/Media room, a full basement, Outdoor showers, and a screened-in porch. The

Julianna Flanders Flanders Real Estate

6 Wakeman Rd, Chilmark, MA 02535
/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
/39
$1,650,000 Sold Jan 07, 2025
- 2,146 Sq Ft
- $769/SF
- 202 Days On Market
- 3 Beds
- 2 Baths
- Built 1982
3 Danls Way, Vineyard Haven, MA 02568

Discover a unique opportunity to own 4.5 acres in the picturesque heart of West Tisbury, complete with the potential for a guest house of up to 1,000 square feet. This property, cherished and maintained by the same family for over two centuries, offers a serene pastoral setting that invites you to embrace the beauty of nature. Enjoy sweeping views of lush meadows adorned with a diverse array of

Marilyn Moses Ocean Park Realty Inc

3 Danls Way, Vineyard Haven, MA 02568

/17
Est $1,081,259 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

/6
$2,950,000
- Land
- 2.36 Acres
- $1,250,000 per Acre
18 Allen Farm Rd Unit 20-2, Chilmark, MA 02535

This private and serene 2.36 acre property is located one mile from Lucy Vincent Beach. There is a large building envelope located between the eighty and one hundred foot contour with exciting architectural options. The land has open woodlands, a small pasture and a fenced garden area. A charming cottage on the property is offered fully furnished and has everything you need to enjoy your stays

Patty Kendall Kendall & Kendall

18 Allen Farm Rd Unit 20-2, Chilmark, MA 02535
/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
/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 $1,651,769 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

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