Vineyard Haven, 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
/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
/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

/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
$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
$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
/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

/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

/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
/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
/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

/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

/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
/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

/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

/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
/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

/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

/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
/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

/22
Est $1,053,648 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,025 Sq Ft
10 Saddle Club Rd, Edgartown, MA 02539

10 Saddle Club Rd, Edgartown, MA 02539

/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
/43
$1,775,000 Sold Sep 26, 2025
- 2,512 Sq Ft
- $707/SF
- 157 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1991
10 Bridge Ln, Vineyard Haven, MA 02568

This thoughtfully designed post and beam home blends craftsmanship with character, featuring artistic touches throughout that make it truly one-of-a-kind. The kitchen flows beautifully between the main living areas and an inviting dining space surrounded by windows offering access to one of several outdoor decks for effortless indoor-outdoor living. On the first floor, the primary suite includes

Jill Napior Tea Lane Associates

10 Bridge Ln, Vineyard Haven, MA 02568

/32
Est $1,104,871 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,429 Sq Ft
10 Elm St, Vineyard Haven, MA 02568

10 Elm St, 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
/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

/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

/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
/42
$1,250,000 Sold Sep 25, 2025
- 2,210 Sq Ft
- $566/SF
- 137 Days On Market
- 4 Beds
- 3 Baths
- Built 1969
58 Weaver Ct, Vineyard Haven, MA 02568

Located near the Lagoon, hiking trails, downtown Vineyard Haven, and Steamship Authority. A private wooded sanctuary sited on 1.5 acres of land with backyard covered patio, covered front porch and new mahogany deck railings at each entry. Many recent updates include hardwood floors on the first floor, remodeled bathrooms, kitchen cabinets and countertops, baseboard trim, baseboard heat and

Skip Dostal, Jr Martha's Vineyard Real Estate

58 Weaver Ct, Vineyard Haven, MA 02568

/22
Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,250 Sq Ft
33 Summer St, Vineyard Haven, MA 02568

33 Summer St, 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
/25
$3,925,000 Sold Sep 24, 2025
- 3,954 Sq Ft
- $993/SF
- 4 Days On Market
- 8 Beds
- 4.5 Baths
- Built 1730
966 Main St, Vineyard Haven, MA 02568

Nestled along the iconic Main Street of West Chop, this classic gem offers a rare opportunity to own a piece of Martha's Vineyard's rich heritage. Built with timeless elegance and enhanced with modern comforts, this distinguished residence boasts 8 bedrooms, 4 1/2 bathrooms, and captivating views of the Vineyard Sound, ensuring an unparalleled island living experience.Immerse yourself in the

Grant Rudolph Viewpoints

966 Main St, Vineyard Haven, MA 02568

/44
Est $4,630,193 Not Listed For Sale
- 6 Beds
- 7 Baths
- 5,034 Sq Ft
59 Hagerty Dr, Vineyard Haven, MA 02568

59 Hagerty Dr, Vineyard Haven, MA 02568

/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
/35
$1,500,000 Sold Sep 22, 2025
- 2,336 Sq Ft
- $642/SF
- 277 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1980
8 Schoolhouse Village, Oak Bluffs, MA 02557

Located in a desirable Oak Bluffs neighborhood, surrounded by mature plantings and attractive, colorful landscaping, this property offers a pleasantly appointed 3-bedroom, 2.5-bath home and a recently renovated 1-bedroom, 1-bath apartment above the 2-car garage. The first floor features a spacious living room with a pellet stove and a fabulous great room with a wood-burning stove. French doors

Stephanie Roache Donnelly + Co.

8 Schoolhouse Village, Oak Bluffs, MA 02557

/15
Est $1,062,670 Not Listed For Sale
- 3 Beds
- 2 Baths
- 966 Sq Ft
73 Leonard Cir, Vineyard Haven, MA 02568

73 Leonard Cir, 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
/21
$500,000 Sold Sep 12, 2025
- 604 Sq Ft
- $828/SF
- 58 Days On Market
- 1 Bed
- 1 Bath
- Built 1870
21 Rock Ave, Oak Bluffs, MA 02557

Experience the charm of 21 Rock Avenue, nestled in the Historic Martha's Vineyard Camp Meeting Association. This year-round cottage features 1 bedroom and 1 bath, and is just moments away from Oak Bluffs Harbor, ferry ports, sandy beaches, art galleries, and delightful restaurants. Recent exterior enhancements include cedar fencing, refreshed house trim, new paint, and an upgraded roof. Please

Marilyn Moses Ocean Park Realty Inc

21 Rock Ave, Oak Bluffs, MA 02557

/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

/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

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