Vineyard Haven, MA Homes

/32
$560,000
- 1 Bed
- 1.5 Baths
- 590 Sq Ft
21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568

Own a piece of the Vineyard dream with a fully furnished, beautifully updated condo perfectly designed for comfort and vacation living at the Island Inn Country Club in Oak Bluffs. The location is just off Beach Road, a short distance to beaches, downtown Circuit Ave, and a lovely drive along Beach Road to Edgartown Village. The bike path, public transportation, and a popular restaurant with live

Diana Gilmore Island Real Estate

21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
/26
$50,000 total monthly price
- 4 Beds
- 3 Baths
- 3,237 Sq Ft
- House for Rent
29 Naushon Rd Wt142, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Waterfront home in spectacular location overlooking the Vineyard Sound and the Elizabeth Islands. This casual and comfortable single level 4 BR 3 bath home has central air and heat. Enjoy summer star-studded skies from your patio or through skylights in each bedroom.

Karen Overtoom Karen M. Overtoom R.E.

29 Naushon Rd Wt142, West Tisbury, MA 02575
/2
$3,500,000 Sold Oct 07, 2025
- 2,448 Sq Ft
- $1,430/SF
- 0 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2001
339 Lake St, Vineyard Haven, MA 02568

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339 Lake St, Vineyard Haven, MA 02568

/31
Est $1,369,730 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,999 Sq Ft
48 Puritan Dr, Vineyard Haven, MA 02568

48 Puritan Dr, Vineyard Haven, MA 02568

/20
$1,300,000
- 4 Beds
- 2 Baths
- 1,566 Sq Ft
344 Greenwood Ave, Vineyard Haven, MA 02568

This move-in ready four-bedroom, being offered fully furnished, delivers effortless living, simply bring your swimsuit and settle in. Featuring an open and inviting layout, the living space seamlessly extends to the large deck and heated pool, perfect for relaxing or entertaining. Conveniently located just one mile from the shops and restaurants of downtown Vineyard Haven and less than two miles

Katie Donahue Sandpiper Realty

344 Greenwood Ave, Vineyard Haven, MA 02568
/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
/30
$1,050,000 Sold Oct 06, 2025
- 1,323 Sq Ft
- $794/SF
- 62 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1972
4 Quail Run Unit 2, Oak Bluffs, MA 02557

FULLY FURNISHED ready to live in or rent year round~ COASTAL CHIC CONDO with OCEAN ACCESS and dock ~LOW HOA Fees- ~Meticulously crafted and exceptionally appointed, this end unit condo/townhouse has been architecturally designed with style. Featuring 2 bedrooms, a flexible third-floor loft flex room, and 1.5 bathrooms, this stylish 1,323 sq. ft. residence blends designer touches with top-tier

Marilyn Moses Ocean Park Realty Inc

4 Quail Run Unit 2, Oak Bluffs, MA 02557

/14
Est $1,585,012 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,717 Sq Ft
13 Saddle Club Rd, Edgartown, MA 02539

13 Saddle Club Rd, Edgartown, MA 02539

/30
$985,000
- 3 Beds
- 1 Bath
- 1,008 Sq Ft
22 Clark Ave, Vineyard Haven, MA 02568

A Sweet Spot to call Home. West Chop charms are many in this delightful setting. Acres upon acres of nearby conservation trails make walks, hikes and bike rides an easy daily appeal. Equal distance to Owen Little Way town beach and Vineyard Haven Main Street shops and amenities as well as harbor and ferry port. This move-in ready Clark Avenue abode offers the magic formula of single level living

Helena Kirschenbaum Studio Realty

22 Clark Ave, 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
/31
$941,000 Sold Oct 03, 2025
- 1,323 Sq Ft
- $711/SF
- 52 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1972
4 Quail Run Unit 7, Oak Bluffs, MA 02557

Turnkey End Unit with Kayak & EV Charger! Private End Unit being Sold Turnkey including a kayak, paddles and lifejacket!Island living made easy in this private 3-story end-unit townhouse with 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

Janna O'Loughlin Portfolio Real Estate, Inc.

4 Quail Run Unit 7, Oak Bluffs, MA 02557

/20
Est $1,783,233 Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,240 Sq Ft
11 Pine Tree Ln, Vineyard Haven, MA 02568

11 Pine Tree Ln, Vineyard Haven, MA 02568

/26
$875,000
- 2 Beds
- 1 Bath
- 861 Sq Ft
24 School St, Oak Bluffs, MA 02557

An unbeatable location ~ just a short distance to the harbor, beaches, ferry ports, the public library, and all the vibrant attractions of Oak Bluffs. This 2-bedroom, 1-bathroom ranch-style home is sited on a 10,454 sf level lot with a detached garage/shed. The property offers one-floor living, a convenient location, and great potential. The main living area includes an open living and dining

Stephanie Roache Donnelly + Co.

24 School St, Oak Bluffs, MA 02557
/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
/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

/27
Est $903,569 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,116 Sq Ft
84 Pine Tree Rd, Vineyard Haven, MA 02568

84 Pine Tree Rd, Vineyard Haven, MA 02568

/12
$1,495,000
- 3 Beds
- 4 Baths
- 2,304 Sq Ft
33 Alyssa Ln, Vineyard Haven, MA 02568

Country Living so close to Town! Lovely 3 Bedroom 2,304 sq ft Colonial Cape with Garage and lower level living space. with half bath. Open kitchen, dining & entertainment area. Large side deck. Living Room with additional nook. Half bath. Interior stairs to lower level with private exterior entrance and garage. 2nd floor has large primary bedroom with cathedral ceilings, walk through double

Stephanie Burke Portfolio Properties

33 Alyssa Ln, Vineyard Haven, MA 02568
/9
$19,000 total monthly price
- 6 Beds
- 2.5 Baths
- 2,155 Sq Ft
- House for Rent
17 Umbagog Ave Wt109, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,750. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three story home is located in a very desirable area off of Lambert's Cove Road, Makonikey, with access to a private association beach and walking trails. There are four plus bedrooms and bright and open living spaces that lead out to a deck and a screened-in porch.

Karen Overtoom Karen M. Overtoom R.E.

17 Umbagog Ave Wt109, 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

/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

/12
$1,495,000
- 3 Beds
- 4 Baths
- 2,304 Sq Ft
33 Alyssa Ln, Vineyard Haven, MA 02568

Country Living so close to Town! Lovely 3/4 Bedroom 2,304sq ft. Colonial Cape perched on a rise on Alyssa Lane off West Spring Street. Open Kitchen with handcrafted side cabinets and Island with stool seating. Dining, sitting, entertainment area with sliders open to a generous front to back side deck. Living room with propane fired wood stove and half bath also on the first floor. Interior stairs

Stephanie Burke Portfolio Real Estate, Inc.

33 Alyssa Ln, Vineyard Haven, MA 02568
/25
$13,600 total monthly price
- 2 Beds
- 2 Baths
- 792 Sq Ft
- House for Rent
64 Bartimus Luce Road Wt125, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!!!!Idyllic location right above a sandy private beach on the North Shore. This beach cottage affords views of the Sound and the Elizabeth Islands with a front row seat on unrivaled sunsets. It is rustic and cozy with a large screened porch overlooking the view. Have a getaway like in days of yore when life was simple and the beach at your doorstep.Take

Karen Overtoom Karen M. Overtoom R.E.

64 Bartimus Luce Road Wt125, 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

/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

/3
$700,000
- Land
- 0.26 Acre
- $2,738,654 per Acre
2 Hope's Way Unit 31, Oak Bluffs, MA 02557

ESTEEMED BUILDER READY to BREAK GROUND! Purchase this exceptional lot in Lagoon Ridge and start designing and building your dream 3BR + home today! Execute a BUILDING CONTRACT or choose your own builder... Call for details and schedule a tour! Welcome to Oak Bluffs’ newest and most sought-after neighborhood, where you can construct your 3-bedroom home on a lofty setting, 95 feet above Lagoon

Marilyn Moses Ocean Park Realty Inc

2 Hope's Way Unit 31, Oak Bluffs, MA 02557
/34
$12,000 total monthly price
- 3 Beds
- 2.5 Baths
- 2,240 Sq Ft
- House for Rent
267 Great Plains Road Wt117, West Tisbury, MA 02575

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Large spacious home with open concept living and dining area. This house has gorgeous hardwood floors throughout, separate media room, and loads of natural sunlight. It also features an exceptionally large master bedroom with en-suite bath, and private deck. There is

Karen Overtoom Karen M. Overtoom R.E.

267 Great Plains Road Wt117, West Tisbury, MA 02575
/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

/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

/20
$1,095,000
- 3 Beds
- 1.5 Baths
- 1,487 Sq Ft
12 Wheelhouse Way, Oak Bluffs, MA 02557

Custom-built 3-bedroom, 1.5-bath Oak Bluffs home on a quiet circle, offering a peaceful setting with convenient access to down-island attractions, charming town centers and year-round ferries. Features include a large primary bedroom, a convenient first floor bedroom, and an open kitchen dining area flowing to a spacious wooden deck and outdoor shower--perfect for indoor-outdoor living.

Dawn Bellante Sandpiper Realty Inc

12 Wheelhouse Way, Oak Bluffs, MA 02557
/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
/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

/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

/14
$835,000
- 2 Beds
- 1 Bath
- 768 Sq Ft
51 Lantern Ln, Vineyard Haven, MA 02568

Find your sweet spot in this charming starter home, ideally located on a quiet street yet within an effortless walk of everything. Forget the car and get your steps in! You're a short jaunt to essentials like Cronig's Market and Shirley's Hardware, AND local favorites including The Maker, Black Dog Cafe, Island Fresh Pizza, Pie Chicks, and Island Adventures Mini Golf. Also within walking distance

Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

51 Lantern Ln, Vineyard Haven, MA 02568
/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
/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

/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

/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
/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
/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

/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

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Massachusetts Dukes County Vineyard Haven

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