Oak Bluffs, MA Homes

/16
$3,200,000
- 4 Beds
- 3 Baths
- 2,346 Sq Ft
6 Trails End, Chilmark, MA 02535

Step into timeless mid-century modern style and comfort in this single-level, 4-bedroom, 3-bathroom home located in the heart of Chilmark. This home features an open layout with large glass panel doors that lead to a sun-drenched deck, heated in-ground pool, and grassy lawn. This home is offered completely furnished with a well-equipped kitchen, large living room with wood burning fireplace,

Russell Maloney Russell Maloney Real Estate

6 Trails End, Chilmark, MA 02535
/21
$7,000 total monthly price
- 4 Beds
- 3.5 Baths
- 3,000 Sq Ft
- House for Rent
27 Beach Plum Ln, Chilmark, MA 02535

weekly rental rate negotiable, cost $400-$975 per night depending on season and month 3 night min stay The "Grapevine" is located on a private road next door to the Beach Plum Inn, It was completely rebuilt . it 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

Bryan Hummel Commonwealth Realty Group

27 Beach Plum Ln, Chilmark, MA 02535
/28
$1,400,000 Sold Nov 26, 2025
- 1,592 Sq Ft
- $879/SF
- 126 Days On Market
- 4 Beds
- 1.5 Baths
- Built 1968
5 Scottys Ln, Vineyard Haven, MA 02568

BUYER PAID FOR NEW SEPTIC AND BUYER BROKER FEE. Attention Developers and Island Lovers! Take note of this rare opportunity in a prime West Tisbury Location. This mid-century home with excellent bones fronts on Seth's Pond, a beloved locale perfect for swimming, paddle-boarding, and kayaking. 5 Scotty's Lane has an existing 4-bedroom main house with the first floor and lower walk-out level

Idalyn Macchia Gilstad Wallace & Co. Sotheby's

5 Scottys Ln, Vineyard Haven, MA 02568

/30
Est $2,449,577 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,555 Sq Ft
10 Crow Hollow Rd, Vineyard Haven, MA 02568

10 Crow Hollow Rd, Vineyard Haven, MA 02568

/39
$2,600,000
- 3 Beds
- 4 Baths
- 2,300 Sq Ft
229 Oak Ln, West Tisbury, MA 02575

A hidden gem in West Tisbury! Beautifully manicured, fenced in 2.2 - acre parcel with 100% privacy, and 84 evergreen trees. This modern, contemporary well maintained home is 3-bedroom, 3 bath with two levels of living and a partially finished basement. The first floor is a sunlight filled, open kitchen and dinning room, with hardwood floors throughout. There are multiple decks leading out to a

Doug Burke Cronigs Real Estate

229 Oak Ln, West Tisbury, MA 02575
/20
$4,250 total monthly price
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
- House for Rent
11 Hammett Ln, Chilmark, MA 02535

** WEEKLY SUMMER RATE** 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.

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

11 Hammett Ln, Chilmark, MA 02535
/43
$2,100,000 Sold Nov 25, 2025
- 1,968 Sq Ft
- $1,067/SF
- 50 Days On Market
- 4 Beds
- 3 Baths
- Built 1993
6 Tabor Hills, Chilmark, MA 02535

Set on 3 acres of natural beauty, this 1968 s/f post-and-beam home offers a tranquil and inviting setting surrounded by stone walls, serene gardens, and the glacial erratic stones that distinguish the Chilmark landscape.The main residence features three levels of living. A chef's kitchen with a Viking gas range and pantry overlooks the open floor plan, awash in natural light with wide-plank

Dawn Bellante Sandpiper Realty Inc

6 Tabor Hills, Chilmark, MA 02535

/2
Est $2,469,488 Not Listed For Sale
- 4 Beds
- 4 Baths
- 3,527 Sq Ft
230 Pond Rd, Vineyard Haven, MA 02568

230 Pond Rd, Vineyard Haven, MA 02568

/42
$4,250,000
- 3 Beds
- 6 Baths
- 3,171 Sq Ft
15 Old Farm Rd, Chilmark, MA 02535

CHILMARK BLISS – Refined Retreat | 15 Old Farm Road. Set on 3+ acres of manicured grounds, this 2020 Peter Breese–redesigned home blends elegance and tranquility. A serene pond, stream, and custom hardscape set the tone. Inside, a dramatic open kitchen/living area boasts high-end appliances, stone countertops, and a striking fireplace, with a pantry leading to a screened porch. The main-level

Tina Miller Donnelly + Co.

15 Old Farm Rd, Chilmark, MA 02535
/10
$8,500 total monthly price
- 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
/30
$1,416,500 Sold Nov 25, 2025
- 780 Sq Ft
- $1,816/SF
- 34 Days On Market
- 1 Bed
- 1 Bath
- Built 1989
11 Ephriam Allen Rd, West Tisbury, MA 02568

TOTAL SALE with FURNISHINGS $1,440,000. Charming cottage with spectacular water views across stone walls and rolling meadows to Vineyard Sound and the Elizabeth Islands. Set on 1.2 acres, this custom-built home was thoughtfully designed to embrace its serene surroundings, with wood and tile floors, a recent roof (2023), a water filtration system, 3 bedroom septic system, annual maintenance

Dawn Bellante-Holand Sandpiper Realty

11 Ephriam Allen Rd, West Tisbury, MA 02568

/4
Est $2,880,204 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

/42
$3,995,000
- 3 Beds
- 4 Baths
- 3,426 Sq Ft
96 Hammett Ln, Chilmark, MA 02535

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

Brenda Galligan Karen M. Overtoom R.E.

96 Hammett Ln, Chilmark, MA 02535
/8
$11,800 total monthly price
- 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
/28
$1,416,500 Sold Nov 25, 2025
- 780 Sq Ft
- $1,816/SF
- 54 Days On Market
- 1 Bed
- 1 Bath
- Built 1989
11 Ephraim Allen Rd, Vineyard Haven, MA 02568

Charming cottage with spectacular water views across stone walls and rolling meadows to Vineyard Sound and the Elizabeth Islands. Set on 1.2 acres, this custom-built home was thoughtfully designed to embrace its serene surroundings, with wood and tile floors, a recent roof (2023), and an open-plan kitchen, dining, and living area framing commanding views of the water. Perched at the edge of the

Dawn Bellante Sandpiper Realty Inc

11 Ephraim Allen Rd, Vineyard Haven, MA 02568

/34
Est $2,309,824 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

/39
$3,500,000
- 3 Beds
- 4 Baths
- 2,500 Sq Ft
27 Clambelly Rd, Chilmark, MA 02535

A place of serenity tucked in the woods of Chilmark. Complete renovation 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media

Julianna Flanders Flanders Real Estate

27 Clambelly Rd, Chilmark, MA 02535
/8
$16,000 total monthly price
- 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
$1,250,000 Sold Nov 12, 2025
- 1,845 Sq Ft
- $678/SF
- 60 Days On Market
- 6 Beds
- 2 Baths
- Built 1881
1054 State Rd, Vineyard Haven, MA 02568

This historic Sea Captain’s home offers a rare opportunity to own a piece of West Tisbury’s rich heritage. Owned by the same family since 1947, the home exudes warmth, character, and timeless Vineyard charm. The property sits in an ideal in-town location, near beloved local landmarks like Alley's General Store, 7a Foods, the West Tisbury Library, the Field Gallery, and the Grange Hall. The

Stephanie Roache Donnelly + Co.

1054 State Rd, Vineyard Haven, MA 02568

/25
Est $1,984,778 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

/19
$2,675,000
- 3 Beds
- 1.5 Baths
- 1,540 Sq Ft
5 Ocean View Farm Rd, Chilmark, MA 02535

Designed by the famous mid century architect Andrew Geller, this contemporary home is situated at the top of the parcel with ocean views and a glimpse of Chilmark pond. There is ample open space to accommodate family and friends and overlooks the large meadow which follows the stone wall to South Road. Access to walking trails, and Lucy Vincent Beach is a short distance away.

Natalie Conroy Conroy & Company R.E., Inc.

5 Ocean View Farm Rd, Chilmark, MA 02535
/12
$6,180 total monthly price
- 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
/48
$1,775,000 Sold Nov 07, 2025
- 1,728 Sq Ft
- $1,027/SF
- 170 Days On Market
- 3 Beds
- 2 Baths
- Built 1976
3 Fulling Mill Rd, Chilmark, MA 02535

Tucked away in a prime location just off Middle Road is this bright modern home offering the perfect blend of comfort and style. The main level features a large bedroom or first-floor office and a full bath, while the upper floor boasts two additional bedrooms and a beautifully appointed bathroom with a steam shower and double vanity. The open concept living and dining areas flow effortlessly

Jill Napior Tea Lane Associates

3 Fulling Mill Rd, Chilmark, MA 02535

/2
Est $1,698,838 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,102 Sq Ft
26 Old Coach Rd, Vineyard Haven, MA 02568

26 Old Coach Rd, Vineyard Haven, MA 02568

/77
$2,995,000
- 4 Beds
- 3.5 Baths
- 2,515 Sq Ft
300 North Rd, Chilmark, MA 02535

Winding tree lined driveway off North Rd brings you to this commanding, custom designed residence built by a top tier island builder. This home is set on over 4 private acres of rolling meadows and big sky views. Main living space is all on one level which includes primary bedroom with en-suite bath, large living area with fireplace, bright sunroom or second living room, custom kitchen and two

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

300 North Rd, Chilmark, MA 02535
/8
$8,250 total monthly price
- 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
/25
$1,125,000 Sold Oct 28, 2025
- 1,432 Sq Ft
- $786/SF
- 97 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1964
140 Longview Rd, Vineyard Haven, MA 02568

Nestled in the hills of Longview, less than 1 mile from beautiful Lambert's Cove Beach, this 3-bedroom retreat is a cozy year-round home or an airy summer getaway - whatever your needs might be. The vaulted ceilings throughout the home allow it to live much larger than its square footage - and the expansive front deck stretches the living space all through the spring, summer and even fall

Candy DaRosa Feiner Real Estate

140 Longview Rd, Vineyard Haven, MA 02568

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

260 South Rd, Chilmark, MA 02535

/39
$3,299,000
- 3 Beds
- 3.5 Baths
- 3,082 Sq Ft
53 Stoney Hill Rd, Vineyard Haven, MA 02568

This custom-built residence is nestled in one of Martha’s Vineyard’s most coveted up-island towns. At the heart of the home lies a professionally designed chef’s kitchen, featuring bespoke cabinetry, honed Carrara marble countertops, Wolf stove and wall oven, Sub-Zero refrigerator, Miele dishwasher, Kohler farmhouse sink, and Rohl satin nickel gooseneck faucet. A custom bar is appointed with

Jennifer B. DaSilva Compass

53 Stoney Hill Rd, Vineyard Haven, MA 02568
/8
$4,500 total monthly price
- 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
/44
$8,178,500 Sold Oct 27, 2025
- 4,104 Sq Ft
- $1,993/SF
- 38 Days On Market
- 6 Beds
- 4.5 Baths
- Built 2001
94 Menemsha Inn Rd, Chilmark, MA 02535

Walk to a private beach and enjoy the beautifully manicured gardens and landscape of this well-loved and privately situated home! Custom designed with a charming Vineyard feel and tasteful interior design. Water view from a gourmet kitchen and formal dining area. Large open living room and spacious bedrooms. Large deck with exceptional views of the North shore and Elizabeth Island's A large

Julianna Flanders Flanders Real Estate

94 Menemsha Inn Rd, Chilmark, MA 02535

/36
Est $2,328,792 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,436 Sq Ft
377 State Rd, Vineyard Haven, MA 02568

377 State Rd, Vineyard Haven, MA 02568

/36
$4,950,000
- 5 Beds
- 4 Baths
- 3,413 Sq Ft
122 Old Farm Rd, Chilmark, MA 02535

An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The historic house has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to

Mark Jenkins Wallace & Co. Sotheby's

122 Old Farm Rd, Chilmark, MA 02535
/8
$4,800 total monthly price
- 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
/39
$2,225,000 Sold Oct 24, 2025
- 2,968 Sq Ft
- $750/SF
- 98 Days On Market
- 4 Beds
- 3 Baths
- Built 1994
9 Beetlebung Grove Way, Chilmark, MA 02535

Beautifully sited on 3.4 acres, this distinctive Chilmark home offers a rare blend of privacy, comfort, and expansive living space, ideal for entertaining, both inside and outside. From the welcoming foyer, step into the dramatic vaulted living room, where wood-paneled ceilings, a gas fireplace, and abundant natural light from skylights and picture windows create a warm and inviting atmosphere.

Stephanie Roache Donnelly + Co.

9 Beetlebung Grove Way, Chilmark, MA 02535

/14
Est $2,461,695 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,926 Sq Ft
30 Pond Ln, Vineyard Haven, MA 02568

30 Pond Ln, Vineyard Haven, MA 02568

/34
$4,950,000
- 5 Beds
- 4.5 Baths
- 3,413 Sq Ft
124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535

An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The historic house has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to

Mark Jenkins Wallace & Co. Sotheby's International Realty

124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
/8
$8,000 total monthly price
- 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
/12
$1,250,000 Sold Oct 23, 2025
- Land
- 4.12 Acres
- $303,398 per Acre
- 127 Days On Market
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 is

Abby Rabinovitz Tea Lane Associates

25 Plum Bush Point Rd Unit 6, West Tisbury, MA 02568

/36
Est $1,179,160 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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