Oak Bluffs, MA Homes

/80
$1,892,500
- 5 Beds
- 3 Baths
- 2,552 Sq Ft
10 Danls Way, West Tisbury, MA 02575

West Tisbury Farmhouse with all of the Historic Charm! 1743/1850, once owned by the renowned sailor & author Joshua Slocum. Located on a lush 1.27 acres, this property has all the makings of a perfect family compound with a 4 bedroom, 2 Bathroom Main House and a 1 Bedroom, 1 Bathroom Guest Cottage. From the patio entry you will arrive into the bright, custom kitchen with new appliances, vaulted

Emma Bryant Landmarks at TODAY Real Estate

10 Danls Way, West Tisbury, MA 02575
/29
$34,000 total monthly price
- 4 Beds
- 2.5 Baths
- 2,300 Sq Ft
- House for Rent
15 Loon Lane Ch203, Chilmark, MA 02535

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Modern 4 bedroom home completed in 2019, in Menemsha. Located on a quiet road with waterviews from the upstairs bedrooms also offers views of the famous Menemsha sunsets from the deck. Sustainably harvested flooring features silky smooth and buttery hard wood floors from

Karen Overtoom Karen M. Overtoom R.E.

15 Loon Lane Ch203, Chilmark, MA 02535
/28
$2,550,000 Sold Oct 02, 2025
- 1,524 Sq Ft
- $1,673/SF
- 130 Days On Market
- 3 Beds
- 2 Baths
- Built 1926
10 Mollys Way, Chilmark, MA 02535

The Salt Shack merges historic preservation with modern updates in Menemsha. Designed by husband-and-wife luxury boutique design firm, Morgan Studio, the renovation of this 100-year-old ocean view cottage preserves its charm and historical integrity while incorporating contemporary design elements to enhance both comfort and aesthetics. Nestled behind Menemsha Pond, the cottage boasts a prime

Peyton Wallace Studio Realty

10 Mollys Way, Chilmark, MA 02535

/23
Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 2,229 Sq Ft
51 Blueberry Ridge Ln, Chilmark, MA 02535

51 Blueberry Ridge Ln, Chilmark, MA 02535

/23
$6,500,000
- 6 Beds
- 5.5 Baths
- 4,753 Sq Ft
16 Red Coat Hill Rd, Vineyard Haven, MA 02568

Private West Tisbury Oasis – Modern Luxury on 4.85 AcresBuilt by the highly regarded Novo Builds and designed by acclaimed architect Zander Auerbach, this newly constructed estate in the heart of West Tisbury offers the perfect blend of architectural sophistication, privacy, and resort-style amenities. Set on 4.85 acres, the main residence spans 3,806 square feet with an additional

Joe & Nicole Holland Vineyard Dream Realty LLC

16 Red Coat Hill Rd, Vineyard Haven, MA 02568
/8
$18,000 total monthly price
- 3 Beds
- 2.5 Baths
- House for Rent
71 Bartmus Luce Road Wt154, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Finest Views on the Island!! This house is set high on a hill surrounded by nature. The expansive views from the front of this house are spectacular. Enjoy the large deck or the screened porch and gaze upon one of the most amazing Vineyard Views available. It is a short

Karen Overtoom Karen M. Overtoom R.E.

71 Bartmus Luce Road Wt154, West Tisbury, MA 02575
/30
$3,375,000 Sold Sep 26, 2025
- 2,813 Sq Ft
- $1,200/SF
- 73 Days On Market
- 4 Beds
- 2 Baths
- Built 1982
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

/36
Est $1,668,978 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

/29
$1,200,000
- 3 Beds
- 2 Baths
- 1,120 Sq Ft
34 Pine Ln, Vineyard Haven, MA 02568

One level living! This ranch-style home has a great layout and some sweet, unexpected features. The living spaces are opened up to each other allowing the wall of sliders in the living room to flood the rooms with light - and these sliders give access out to the deck with serene views of the woodlands beyond; where Stoney Hill Path bounds the entire south side of the property. The primary suite

Candy DaRosa Feiner Real Estate

34 Pine Ln, Vineyard Haven, MA 02568
/28
$38,000 total monthly price
- 4 Beds
- 3.5 Baths
- 3,000 Sq Ft
- House for Rent
17 Otis Bassett Rd, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL NOT MONTHLY. AUGUST WEEKLY IS $9,500. SEE OUR WEB SITE FOR WEEKLY PRICING!!!!!Are you looking for the perfect back yard Oasis? Well here it is!! Surrounding a large pool you will be able to relax on the expansive deck areas that include plenty of space for gathering. Inside is an amazing kitchen with every amenity you could want. Coffee lovers will appreciate a regular

Karen Overtoom Karen M. Overtoom R.E.

17 Otis Bassett Rd, West Tisbury, MA 02575
/23
$1,500,000 Sold Sep 25, 2025
- 1,400 Sq Ft
- $1,071/SF
- 43 Days On Market
- 3 Beds
- 2 Baths
- Built 1995
190 Longview Rd, Vineyard Haven, MA 02568

Welcome to 190 Longview Road in the lovely Longview Association. **This FULLY FURNISHED home is just minutes away from the iconic and sought-after Lambert's Cove Beach to which access is granted by right of ownership here. This home is located on a hilltop with dappled sunlight and cooling breezes on a warm summer day. A minisplit in the main living area combined with ceiling fan keeps the living

Kathleen Kendrick Kendrick Real Estate

190 Longview Rd, Vineyard Haven, MA 02568

/35
Est $2,034,014 Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,995 Sq Ft
159 Charles Neck Way, Vineyard Haven, MA 02568

159 Charles Neck Way, Vineyard Haven, MA 02568

/63
$5,000,000
- 6 Beds
- 3.5 Baths
- 3,312 Sq Ft
31 Josiah Sachem Way, Vineyard Haven, MA 02568

An inspirational Oasis - come unwind and behold what this secluded multi-home compound has to offer. With two driveways and an open wildflower field bordered with plantings, the main house, studio barn, guesthouse and in-ground pool area at this private retreat are beautifully positioned and landscaped. Each structure is available for year-round use with abundant parking and unique charms.

Helena Kirschenbaum Studio Realty

31 Josiah Sachem Way, Vineyard Haven, MA 02568
/19
$17,600 total monthly price
- 4 Beds
- 2 Baths
- 1,584 Sq Ft
- House for Rent
50 Carls Way, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Looking for that perfect setting with a water view? This is the one!!This cute cape is privately set with a water view and direct water access to Town Pond. You can dock your canoes and kyacks here and access Tisbury Great Pond and then right out to the beach. There are

Karen Overtoom Karen M. Overtoom R.E.

50 Carls Way, West Tisbury, MA 02575
/17
$1,790,000 Sold Sep 23, 2025
- Land
- 3.3 Acres
- $542,424 per Acre
- 77 Days On Market
32 Stonewall Rd Unit 2.1, Chilmark, MA 02535

South shore beachy living in Stonewall Association with private parking and access to a lovely swim and surf beach in a beloved area of Chilmark. There are second floor water views over Squibnocket Point and the Atlantic Ocean. This lot is fully engineered and ready to be built on! Single-family dwelling, plus a detached bedroom and accessory buildings, permitted according to the Chilmark

Jill Napior Tea Lane Associates

32 Stonewall Rd Unit 2.1, Chilmark, MA 02535

/30
Est $1,410,218 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

/7
$400,000
- Land
- 0.2 Acre
- $2,000,000 per Acre
99 Cygnet Way Unit 103, Chilmark, MA 02535

Escape the crowds at Lucy Vincent and Squibnocket and take advantage of this very rare opportunity to own a private, 17 member, Atlantic Ocean beach lot at Thumb Cove (abuts Hancock Beach). Included in the sale of this property is a deeded .2 acres of sandy beach, a deeded parking spot at Chilmark Pond and the right to launch boats from a dock in the pond. Sail, kayak, row, swim(!) or motor

Russell Maloney Russell Maloney Real Estate

99 Cygnet Way Unit 103, Chilmark, MA 02535
/17
$17,600 total monthly price
- 4 Beds
- 4 Baths
- 2,676 Sq Ft
- House for Rent
40 Summer Cir, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This beautiful tasteful modern home has many charming elements. The bright open airy floor plan offers a generous kitchen, welcoming dining room and living room surrounded by windows and decks with an outdoor table and extra seating. An "upside down" house with the living

Karen Overtoom Karen M. Overtoom R.E.

40 Summer Cir, West Tisbury, MA 02575
/46
$3,120,000 Sold Sep 16, 2025
- 3,669 Sq Ft
- $850/SF
- 84 Days On Market
- 4 Beds
- 3 Baths
- Built 1993
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

Jon Hartzband Martha's Vineyard Island-Wide Realty

140 Pond Rd, Vineyard Haven, MA 02568

/33
Est $1,848,157 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 2,508 Sq Ft
163 Charles Neck Way, Vineyard Haven, MA 02568

163 Charles Neck Way, Vineyard Haven, MA 02568

/27
$1,800,000
- 3 Beds
- 3 Baths
- 2,293 Sq Ft
10 Trotters Ln, West Tisbury, MA 02575

Centrally located and surrounded by lush landscaping, this inviting cape offers three bedrooms and three full baths. Warm, mellow wood floors, tiled bathrooms and a spacious living area anchored by a cozy fireplace. The full basement provides ample storage or expansion potential, while a versatile bonus room on the second level is perfect as an art studio, home office or guest overflow.

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

10 Trotters Ln, West Tisbury, MA 02575
/21
$8,000 total monthly price
- 1 Bed
- 1 Bath
- 936 Sq Ft
- House for Rent
10 James Pond Way, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This spacious and well appointed one bedroom guest house has a cozy living area and kitchen which opens up to a large second story deck with outdoor furniture, table and chairs where you can enjoy dining amidst the trees. One A/C unit is in the bedroom along with a

Karen Overtoom Karen M. Overtoom R.E.

10 James Pond Way, West Tisbury, MA 02575
/18
$4,250,000 Sold Sep 09, 2025
- 4,125 Sq Ft
- $1,030/SF
- 21 Days On Market
- 5 Beds
- 3 Baths
- Built 1900
420 Lamberts Cove Rd, Vineyard Haven, MA 02568

Charming West Tisbury Estate with Waterfront on Seth's Pond. This stunning property offers the perfect blend of vintage charm and modern convenience, set against the tranquil backdrop of Seth's Pond. Featuring a main house, guest house, boathouse, and barn/workshop, this property provides a rare opportunity for both relaxation and recreation. The main house, a well maintained farmhouse dating

Alyssa Halisky Wallace & Co. Sotheby's International Realty

420 Lamberts Cove Rd, Vineyard Haven, MA 02568

/30
Est $2,753,820 Not Listed For Sale
- 3 Beds
- 5 Baths
- 2,926 Sq Ft
23 Alex Way, Vineyard Haven, MA 02568

23 Alex Way, Vineyard Haven, MA 02568

/48
$1,595,000
- 5 Beds
- 4 Baths
- 2,516 Sq Ft
651 State Rd, Vineyard Haven, MA 02568

Fabulous multi-building compound offered in West Tisbury. Well maintained main house dating to 1880 has many features common to classic older homes but has been updated to provide comfort and year-round livability. Bright and cozy there are lots of rooms and spaces to provide for a larger group of individuals with a total of 4 bedrooms in the main house and a partially finished walk-out

Jim Feiner Feiner Real Estate

651 State Rd, Vineyard Haven, MA 02568
/20
$12,000 total monthly price
- 3 Beds
- 1 Bath
- 1,068 Sq Ft
- House for Rent
76 Ben Chase Rd Wt136, West Tisbury, MA 02575

Experience a wonderful glimpse of country living in the peaceful, quiet setting of Serene Pond Cottage! This charming Martha's Vineyard retreat features a cozy interior with ample natural light, a private deck where you can take your breakfast and coffee, and a tree-lined backyard to enjoy on lazy summer days. Comfortable three bedroom single story home with one brand new renovated full bath with

Karen Overtoom Karen M. Overtoom R.E.

76 Ben Chase Rd Wt136, West Tisbury, MA 02575
/38
$1,850,000 Sold Sep 09, 2025
- 1,918 Sq Ft
- $965/SF
- 60 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1988
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

/20
Est $1,224,880 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

/25
$3,200,000
- Land
- 19.3 Acres
- $165,803 per Acre
32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575

A Rare Offering in West Tisbury — Over 19 Acres of OpportunityAn exceptional opportunity to own just over 19 acres in the heart of rural West Tisbury. This expansive parcel offers tremendous flexibility, with potential for multiple dwellings or subdivision into a thoughtfully designed niche development. Ideally situated near all island towns, the property is also just minutes from the

Jill Napior Tea Lane Associates

32 Edgartown - West Tisbury Rd Unit 81, West Tisbury, MA 02575
/19
$30,000 total monthly price
- 5 Beds
- 4 Baths
- 3,600 Sq Ft
- House for Rent
37 Sachem Cir, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely pastoral setting with an elegant farm house and guest house. Abutting Land Bank property on two sides. Quiet privacy, yet just minutes to Lambert’s Cove Beach. The four bedroom house and separate guest house are impeccably decorated and the floor plan lends itself

Karen Overtoom Karen M. Overtoom R.E.

37 Sachem Cir, West Tisbury, MA 02575
/34
$2,475,000 Sold Sep 05, 2025
- 2,300 Sq Ft
- $1,076/SF
- 117 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1983
31 N Slope Ln, Chilmark, MA 02535

Located on a private lane along North Road in the heart of Chilmark, this hilltop four bedroom home was perfectly sited to enjoy fantastic water views of Vineyard Sound toward the Elizabeth Islands. Built in 1983 and lived in seasonally, this home has been meticulously cared for. There is a new forced air HVAC system, and recently upgraded electrical. In addition, there are three working

Bill Rossi Studio Realty

31 N Slope Ln, Chilmark, MA 02535

/2
Est $2,217,673 Not Listed For Sale
- 4 Beds
- 4 Baths
- 3,269 Sq Ft
59 Field View Ln, Vineyard Haven, MA 02568

59 Field View Ln, Vineyard Haven, MA 02568

/43
$1,599,000
- 3 Beds
- 2 Baths
- 1,562 Sq Ft
111 Charles Neck Way, Vineyard Haven, MA 02568

Tucked away on 1.6 wooded acres in West Tisbury, this classic Cape-style home offers both privacy and convenience, with easy access to the charm of Up-Island and the amenities of Down-Island. Located on a paved road near Long Point Beach, it also includes coveted access to Lambert’s Cove Beach.The bright, open interior features a living and dining area with a wood-burning fireplace, a kitchen

Emma Kennedy Sandpiper Realty

111 Charles Neck Way, Vineyard Haven, MA 02568
/29
$10,900 total monthly price
- 3 Beds
- 1 Bath
- 936 Sq Ft
- House for Rent
58 Forest Rd Wt140, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,725.. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming rustic home is set within Seven Gates Farm in West Tisbury. Walk down your own path to a beautiful private association beach. There are shared tennis courts and miles of walking trails.

Karen Overtoom Karen M. Overtoom R.E.

58 Forest Rd Wt140, West Tisbury, MA 02575
/21
$1,325,000 Sold Aug 29, 2025
- 1,982 Sq Ft
- $669/SF
- 89 Days On Market
- 3 Beds
- 2 Baths
- Built 1992
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

/34
Not Listed For Sale
- 6 Beds
- 4.5 Baths
- 3,859 Sq Ft
391 Middle Rd, Chilmark, MA 02535

391 Middle Rd, Chilmark, MA 02535

/40
$1,895,000
- 4 Beds
- 3.5 Baths
- 2,061 Sq Ft
174 Middle Rd, Chilmark, MA 02535

Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming

Sheila Morse Island Real Estate

174 Middle Rd, Chilmark, MA 02535
/22
$20,000 total monthly price
- 4 Beds
- 2.5 Baths
- 2,400 Sq Ft
- House for Rent
709 Old County Rd Wt134, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY. The weekly price in August is $5,000. per week. See website for additional weekly pricing. Mill Pond House is a completely restored 1890s farmhouse on the old Mill Pond in historic West Tisbury. Remodeled by the present owner, an interior designer, it is beautifully appointed with antiques and charming accessories. An old pine floor and columns add to the

Karen Overtoom Karen M. Overtoom R.E.

709 Old County Rd Wt134, West Tisbury, MA 02575
/37
$1,925,000 Sold Aug 28, 2025
- 1,736 Sq Ft
- $1,109/SF
- 0 Days On Market
- 3 Beds
- 2 Baths
- Built 1965
50 Bradley Martin Rd, Vineyard Haven, MA 02568

Two level contemporary residence located in West Tisbury off Tiah's Cove Road, close to the 174 Acre Land Bank Sepiessa Point Reserve on Tisbury Great Pond. Light filled rooms with high ceilings, solarium, large screened in porch & fireplace in this completely renovated home. Private 3 acre site is laden with specimen trees, walking trails and meditation gardens. Close proximity to West Tisbury

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

50 Bradley Martin Rd, Vineyard Haven, 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

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