Tisbury, MA Homes

/2
$1,250,000
- 1 Bed
- 1 Bath
- 855 Sq Ft
0 Pennsylvania Ave Unit 43914, Oak Bluffs, MA 02568

Unique new construction opportunity on Pennsylvania Ave in Oak Bluffs! Offered preconstruction so there is the ability to customize, this modern carriage house includes a spacious 1-bedroom apartment (855 sq ft with full kitchen, living room and bathroom) above a 2-car garage. Ideal for year round or seasonal residents, or businesses seeking to solve workforce housing needs along with secure

Peyton Wallace Studio Realty

0 Pennsylvania Ave Unit 43914, Oak Bluffs, MA 02568
/22
$3,000 total monthly price
- 4 Beds
- 2.5 Baths
- 2,703 Sq Ft
- House for Rent
41 Oak Lane Wt147, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Inside the front entrance is a large open living room with a comfortable L-shaped couch facing the floor to ceiling windows which look out onto the spacious tree lined back yard and a wall mounted flat screen television. Off the open concept living/dining room is a large

Karen Overtoom Karen M. Overtoom R.E.

41 Oak Lane Wt147, West Tisbury, MA 02575
/32
$941,000 Sold Oct 03, 2025
- 1,323 Sq Ft
- $711/SF
- 64 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1972
4 Quail Run Rd, Oak Bluffs, MA 02568

Amazing Turnkey End Unit with Kayak & EV Charger! Not to be missed!Island living made easy in this private 3-story Year Round end-unit townhouse with carport parking for 3, saltwater access, dock, and mooring potential. Features 2 bedrooms plus a versatile loft, open-concept living area with gas fireplace, modern kitchen with granite countertops, and a large private deck overlooking park-like

Janna O'Loughlin Portfolio Properties

4 Quail Run Rd, Oak Bluffs, MA 02568

/47
Est $2,347,232 Not Listed For Sale
- 6 Beds
- 4 Baths
- 3,627 Sq Ft
24 Peacegate Way, Vineyard Haven, MA 02568

24 Peacegate Way, Vineyard Haven, MA 02568

/18
$1,100,000
- 2 Beds
- 2 Baths
- 1,583 Sq Ft
25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

Prime Martha’s Vineyard location! Nestled on 1.4 acres in the sought-after Vineyard Meadow Farms neighborhood, this property offers an exceptional combination of privacy, convenience, and potential. Ideally situated in West Tisbury, close to Edgartown and Vineyard Haven, residents enjoy easy access to local shops, restaurants, and amenities, as well as the island’s most beautiful

Maranda Post Compass | The O'Hanlon Group

25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
/22
$10,000 total monthly price
- 3 Beds
- 1.5 Baths
- 1,500 Sq Ft
- House for Rent
21 Leona Lane Wt115, West Tisbury, MA 02575

THIS IS A SUMMER RENTAL ONLY. This very charming post & beam home is the perfect getaway for those who appreciate West Tisbury's rural character. The home is very nicely furnished and equipped, has a lovely, big yard, and the location, adjacent to the bike path, is central to up-Island shopping and the fantastic sandy beaches of Lambert's Cove and Long Point Reservation. There is no land line

Karen Overtoom Karen M. Overtoom R.E.

21 Leona Lane Wt115, West Tisbury, MA 02575
/6
$1,800,000 Sold Oct 02, 2025
- Land
- 2.06 Acres
- $874,211 per Acre
- 83 Days On Market
34 Paddock Rd Unit 27.11, Oak Bluffs, MA 02568

The Preserve - A terrific opportunity to build in this beautiful and prestigious neighborhood in Oak Bluffs. The Preserve has matured into an enclave of significant residences and offers excellent privacy, with convenience to downtown, harbor and beaches. The orientation of this parcel is prime with southern exposure for backyard pool and patio, and it is abutting dedicated open space on two

Lesley Heidt Sandpiper Realty

34 Paddock Rd Unit 27.11, Oak Bluffs, MA 02568

/17
Est $1,268,728 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,503 Sq Ft
165 Weaver Ln, Vineyard Haven, MA 02568

165 Weaver Ln, Vineyard Haven, MA 02568

/20
$1,200,000
- 3 Beds
- 1.5 Baths
- 1,304 Sq Ft
14 21st St N, Edgartown, MA 02539

Move-in ready 3-bedroom, 1.5-bathroom house with a warm and welcoming interior. The main level includes an efficient kitchen, living room, dining room with sliders to the mahogany deck and outdoor shower, 1 bedroom, laundry, and convenient half-bath. A one car garage is attached to the main level. The 2 large bedrooms and a full bath are located upstairs. Enjoy the private backyard with its well

Fran Agnoli The Agency

14 21st St N, Edgartown, MA 02539
/21
$11,000 total monthly price
- 2 Beds
- 1.5 Baths
- 800 Sq Ft
- House for Rent
55 Dr Fisher Rd Unit 1, West Tisbury, MA 02575

THIS IS A SUMMER RENTAL ONLY. Nestled on a quiet country lane, this charming two BR guest house will enchant you with its inviting character and custom features throughout. From the cathedral living area and newly furnished interior to the covered front porch and expansive deck, this lovely cottage has it all. Privately situated , yet convenient to the village, bike path and local

Karen Overtoom Karen M. Overtoom R.E.

55 Dr Fisher Rd Unit 1, West Tisbury, MA 02575
/7
$1,800,000 Sold Oct 02, 2025
- Land
- 2.06 Acres
- $873,786 per Acre
- 97 Days On Market
34 Paddock Rd, Oak Bluffs, MA 02568

The Preserve - A terrific opportunity to build in this beautiful and prestigious neighborhood in Oak Bluffs. The Preserve has matured into an enclave of significant residences and offers excellent privacy, with convenience to downtown, harbor and beaches. The orientation of this parcel is prime with southern exposure for backyard pool and patio, and it is abutting dedicated open space on two

Lesley Heidt Sandpiper Realty Inc

34 Paddock Rd, Oak Bluffs, MA 02568

/21
Est $1,438,643 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,066 Sq Ft
23 Anthiers Way, Edgartown, MA 02539

23 Anthiers Way, Edgartown, MA 02539

/26
$1,650,000
- 5 Beds
- 3 Baths
- 1,810 Sq Ft
22 Old Lighthouse Rd, Vineyard Haven, MA 02568

This spacious 5-bedroom, 3-bathroom home is located in a quiet enclave off Main Street, Vineyard Haven. Just half a mile to the vibrant restaurant and shopping scene in the village, and even closer to the library, Owen Little Beach, and Yacht Club. Thoughtfully designed across three finished levels featuring hardwood floors, a cozy fireplace, and a seamless layout, the home is ideal for

Jessie Holtham Wallace & Co. Sotheby's

22 Old Lighthouse Rd, Vineyard Haven, MA 02568
/15
$21,000 total monthly price
- 6 Beds
- 2 Baths
- 1,700 Sq Ft
- House for Rent
12 John Wesley Ave Ob519, Oak Bluffs, MA 02557

THIS IS A SUMMER RENTAL ONLY. EAST CHOP LOCATION!! Located across from the historic Baptist Temple Town Park. This charming 1885 Victorian cottage is original to days gone by and a significant part of the Vineyard Highlands. Six bedrooms and two full bathrooms allow for friends and family to visit along with a cozy, bright vintage kitchen. This is a house of distinctive "Carpenter Gothic"

Karen Overtoom Karen M. Overtoom R.E.

12 John Wesley Ave Ob519, Oak Bluffs, MA 02557
/7
$1,000,000 Sold Oct 02, 2025
- 1,176 Sq Ft
- $850/SF
- 9 Days On Market
- 2 Beds
- 1 Bath
- Built 1948
13 County Rd, Oak Bluffs, MA 02557

Welcome to an inviting single-story ranch nestled in the heart of Oak Bluffs. This cozy and charming home offers a comfortable living space and is set on a generous, water view landscaped lot with mature trees and natural privacy. Inside, the home features a functional layout with a mix of wood and carpet flooring, a cozy wood-burning fireplace, and abundant natural light throughout.The classic

Jennifer B. DaSilva Compass

13 County Rd, Oak Bluffs, MA 02557

/17
Est $1,085,887 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

/42
$2,289,000
- 4 Beds
- 3.5 Baths
- 1,900 Sq Ft
113 Dukes County Ave Unit Multi-Family, Oak Bluffs, MA 02557

UNIQUE IN-TOWN INVESTMENT opportunity in the heart of Oak Bluffs. This COMMERCIALLY ZONED B1 property offers flexibility and a strong existing rental history. Built in 2017, the MULTI-FAMILY building combines modern efficiency with an unbeatable location — just a short stroll to Oak Bluffs harbor, the Inkwell Beach, art galleries, shopping on Circuit Avenue, restaurants, the Historic Flying

Grace Hagerty Grace Hagerty Real Estate Inc

113 Dukes County Ave Unit Multi-Family, Oak Bluffs, MA 02557
/21
$13,000 total monthly price
- 4 Beds
- 3 Baths
- 2,500 Sq Ft
- House for Rent
14 Pulpit Rock Rd, Oak Bluffs, MA 02557

PRICES ARE WEEKLY NOT MONTHLY. Located in Waterview Farms, this four bedroom home features a private beach on Sengekontacket Pond, private dock access to Land Bank boat launch and several walking trails. Just minutes to Farm Neck Golf Course, beaches and town.

Karen Overtoom Karen M. Overtoom R.E.

14 Pulpit Rock Rd, Oak Bluffs, MA 02557
/22
$2,899,000 Sold Oct 01, 2025
- 1,889 Sq Ft
- $1,535/SF
- 0 Days On Market
- 4 Beds
- 2 Baths
- Built 1956
78 Winemack St, Oak Bluffs, MA 02557

STUNNNING EAST CHOP WATERVIEW RETREAT w/a flair of HOLLYWOOD HILLS GLAMOUR! WATCH THE SAILBOATS SAIL BY on the outer harbor from this delightful 3 bedroom + den, well maintained Contemporary home in the exclusive East Chop community. A blend of timeless Martha's Vineyard serenity with a flair of vintage Hollywood Hills design delights all! Clean architectural lines, vaulted ceilings, and

Susan Austin Austin R.E. Properties of MV

78 Winemack St, Oak Bluffs, MA 02557

/32
Est $2,265,538 Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,276 Sq Ft
232 Lagoon Pond Rd, Vineyard Haven, MA 02568

232 Lagoon Pond Rd, Vineyard Haven, MA 02568

/44
$1,650,000
- 4 Beds
- 2.5 Baths
- 1,815 Sq Ft
105 Stoney Hill Rd, Vineyard Haven, MA 02568

Welcome to 105 Stoney Hill Road, a serene retreat tucked in the heart of West Tisbury. This inviting Vineyard property combines comfort, thoughtful design, and practical amenities across 1,815 square feet of living space. The main level welcomes you with soaring ceilings and a natural flow. The living room features engineered hickory plank hardwood, while pine flooring carries warmth throughout

Lisa Da Silva Compass | Point B

105 Stoney Hill Rd, Vineyard Haven, MA 02568
/35
$112,000 total monthly price
- 6 Beds
- 9 Baths
- 5,732 Sq Ft
- House for Rent
31 Lamberts Cove Road Vh434, Tisbury, MA 02568

Karen Overtoom Karen M. Overtoom R.E.

31 Lamberts Cove Road Vh434, Tisbury, MA 02568
/53
$2,036,000 Sold Oct 01, 2025
- 3,273 Sq Ft
- $622/SF
- 55 Days On Market
- 5 Beds
- 3.5 Baths
- Built 2004
23 Crowell Ln, Vineyard Haven, MA 02568

WEST CHOP! Farmhouse charm and comfortable elegance define this very spacious 5 Bedroom, 3,200 s/f home that is set on just over an acre on a private wooded lot. Hear the ferry, spot the osprey, and unwind on the back deck. This is your invitation to island living! The home welcomes you with an expansive front porch that overlooks a mature landscape that is framed with a stone wall and beautiful

Rene Jackson Island Real Estate

23 Crowell Ln, Vineyard Haven, MA 02568

/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

/20
$1,450,000
- 3 Beds
- 2 Baths
- 1,428 Sq Ft
5 Seth's Path, Oak Bluffs, MA 02557

Desirable picturesque Deer Run location. Just steps from the bike path, this centrally located home is a perfect island retreat. You can enjoy the multi level deck and patio overlooking a wonderful in ground pool. The large lot provides for plenty of room for gardening or games and backs up to an idyllic open field. This house is perfectly set back off of the small cul de sac. Wonderful

Robin Perschel Feiner Real Estate

5 Seth's Path, Oak Bluffs, MA 02557
/35
$2,025,000 Sold Sep 30, 2025
- 3,009 Sq Ft
- $673/SF
- 5 Days On Market
- 6 Beds
- 3 Baths
- Built 1853
1 Rowland Ave, Oak Bluffs, MA 02557

This ideally located property is the tasteful blend of old world Victorian charm and 21st century convenience. From your expansive front porch, you look directly onto Lakeside Park, which extends from Rowland Avenue all the way to Sunset Lake. From the serenity of your elevated perch you overlook all the fascinating attractions of Oak Bluffs, without being in the middle of the activity. In 2015,

Lynn Buder Sandpiper Realty Inc

1 Rowland Ave, Oak Bluffs, MA 02557

/44
Est $1,609,195 Not Listed For Sale
- 3 Beds
- 4 Baths
- 3,114 Sq Ft
30 Hillside Path, Vineyard Haven, MA 02568

30 Hillside Path, Vineyard Haven, MA 02568

/20
$640,000
- 1 Bed
- 1 Bath
- 354 Sq Ft
2 Lincoln Ave, Oak Bluffs, MA 02568

Nestled in the heart of the historic Martha’s Vineyard Camp Meeting Association, this beautifully updated suite cottage offers the rare opportunity for year-round living in Oak Bluffs’ campground community. Fully renovated in 2023, including kitchen, bath, floors and winterization, the home seamlessly blends classic Vineyard charm with modern comfort — featuring upgraded systems and finishes that

Stacy Ickes Donnelly + Co

2 Lincoln Ave, Oak Bluffs, MA 02568
/20
$975,000 Sold Sep 30, 2025
- 836 Sq Ft
- $1,166/SF
- 29 Days On Market
- 3 Beds
- 2 Baths
- Built 1920
32 Beach Rd, Oak Bluffs, MA 02557

Tucked along a main road in Oak Bluffs, this small yet cozy year-round cottage offers a charming Vineyard lifestyle with surprising touches of serenity. While compact in size, the home lives larger than expected with its inviting layout, warm interiors, and thoughtful use of space. A standout feature: peeks of the Lagoon and Vineyard Haven harbor, offering glimmers of coastal beauty to brighten

Bonnie Pierce Wallace & Co. Sotheby's International Realty

32 Beach Rd, Oak Bluffs, MA 02557

/34
Est $2,279,850 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,783 Sq Ft
338 Bigelow Rd, Vineyard Haven, MA 02568

338 Bigelow Rd, Vineyard Haven, MA 02568

/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
/27
$1,735,000 Sold Sep 29, 2025
- 2,526 Sq Ft
- $687/SF
- 2 Days On Market
- 3 Beds
- 4 Baths
- Built 1996
56 Bridle Path Rd, Vineyard Haven, MA 02568

POOL & LUSH GARDENS — Nestled on 3 acres beside 25 acres of conservation land, this 2,500+ sq. ft. home offers tranquility and convenience. The sun-filled living room with fireplace flows to the kitchen, dining area, screened porch, and sunny deck—perfect for enjoying serene views. The main floor hosts a spacious primary suite with en-suite bath; upstairs offers two large bedrooms, a full bath,

Tina Miller Donnelly + Co.

56 Bridle Path Rd, Vineyard Haven, MA 02568

/18
Est $994,992 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1 Sq Ft
10 Canterbury Ln, Vineyard Haven, MA 02568

10 Canterbury Ln, Vineyard Haven, MA 02568

/28
$1,650,000
- 3 Beds
- 1.5 Baths
- 2,448 Sq Ft
38 Rogers Way, Oak Bluffs, MA 02557

Tucked away in a private desirable Oak Bluffs neighborhood yet only minutes from the charm of downtown and the incredible OB beaches, this home is a wonderful island retreat. With four levels of finished living space, it offers room to gather, relax, entertain, and create memories in every season. Hardwood floors, open concept kitchen and living areas, crackling fireplace set the tone indoors.

Jon Hartzband Martha's Vineyard Island-Wide Realty

38 Rogers Way, Oak Bluffs, MA 02557
/39
$2,500,000 Sold Sep 29, 2025
- 1,350 Sq Ft
- $1,852/SF
- 124 Days On Market
- 3 Beds
- 2 Baths
- Built 1988
31 The Blvd, Edgartown, MA 02539

Waterfront Charmer on Sengekontacket Pond - Perched on the shoreline, this contemporary cottage is enveloped by stone walls, lush gardens, and stunning water views. Inside, a bright, airy living space features an open dining area and a well-appointed kitchen. The all-white interior is complemented by hardwood floors, vaulted ceilings, skylights, air conditioning, and ceiling fans. Three sliding

Wendy Harman Compass

31 The Blvd, Edgartown, MA 02539

/32
Est $1,276,286 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,118 Sq Ft
58 Hagerty Dr, Vineyard Haven, MA 02568

58 Hagerty Dr, Vineyard Haven, MA 02568

/15
$625,000
- 2 Beds
- 1 Bath
- 704 Sq Ft
124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568

MOVE RIGHT IN! This sunny end unit is being offered furnished! Spacious living area opens to an eat-in kitchen with a new Bosch dishwasher. Bedroom number one has a queen bed. Bedroom two has two single beds. Conveniently located within close proximity to Main Street shops, the ferry and bus terminal, and the scenic bike path that extends across the island. At the bottom of the hill you will find

Rene Jackson Island Real Estate

124 Skiff Ave Unit C-12, Vineyard Haven, MA 02568
/2
$505,000 Sold Sep 26, 2025
- Land
- 1.3 Acres
- $388,462 per Acre
- 120 Days On Market
02 John Hoft Rd Unit 2, Tisbury, MA 02568

A nicely treed lot that gradually rises to an uplifting elevation, and is near to the wonderful 90+ acres of Ripley's Field Preserve. The town's zoning allows for a sizable house, a detached garage, and probably an in-house apartment or Accessory Dwelling Unit ("ADU"), and a pool--though a special permit would probably be required for that. Of course, confirm the aforesaid with the Town of

Tony Tobia Tobia Real Estate, LTD

02 John Hoft Rd Unit 2, Tisbury, MA 02568

/18
Est $1,184,786 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,038 Sq Ft
5 Windsor Dr, Edgartown, MA 02539

5 Windsor Dr, Edgartown, MA 02539

/30
$999,000
- 2 Beds
- 1 Bath
- 1,232 Sq Ft
28 Barling Ave, Vineyard Haven, MA 02568

Oak Bluffs: Home Sweet HomeSituated on over a quarter acre of beautifully landscaped, level grounds with colorful perennial plantings and mature trees, this sun-filled ranch offers a perfect blend of comfort and charm. The open kitchen, dining, and living areas feature cathedral ceilings, classic vertical knotty pine walls, and a cozy brick fireplace. Enjoy a convenient first-floor bedroom

Alan Schweikert Ocean Park Realty Inc

28 Barling Ave, Vineyard Haven, MA 02568

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