Vineyard Haven, MA Homes

/23
$1,790,000
- 2 Beds
- 1 Bath
- 600 Sq Ft
11 Beach Rd, Oak Bluffs, MA 02557

Oak Bluffs: Waterfront Property at Vineyard Haven Outer Harbor**This is an exceptional opportunity to acquire a stunning white sandy beach property on Vineyard Haven Harbor. This charming Island cottage boasts breathtaking panoramic views of the harbor and sound, showcasing magnificent sunsets each evening over the West Chop Peninsula. You can enjoy the lively boating scene, with yachts from

Alan Schweikert Ocean Park Realty Inc

11 Beach Rd, Oak Bluffs, MA 02557
/34
$25,000 total monthly price
- 4 Beds
- 3.5 Baths
- 2,334 Sq Ft
- House for Rent
100 Connie's Way Vh401, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,250. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

Karen Overtoom Karen M. Overtoom R.E.

100 Connie's Way Vh401, Tisbury, MA 02568
/17
$1,200,000 Sold Oct 28, 2025
- 1,680 Sq Ft
- $714/SF
- 209 Days On Market
- 4 Beds
- 2 Baths
- Built 1987
211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568

MULTIFAMILY OPPORTUNITYA wonderful compound on the outskirts of town. Set nicely back off the Edgartown Road, the existing home has 4/5 comfortable bedrooms and 2 baths on a nice 1-acre parcel with a good sense of privacy. Behind the home is a fire pit, a shed and another septic system already installed that will serve an additional 5 bedrooms! This property is on a trail to the Bare Hill

Jim Feiner Feiner Real Estate

211 Edgartown Vineyard Haven Rd, Tisbury, MA 02568

/20
Est $1,723,617 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,971 Sq Ft
21 Bold Meadow Ln, Edgartown, MA 02539

21 Bold Meadow Ln, Edgartown, MA 02539

/37
$1,995,000
- 4 Beds
- 3 Baths
- 3,058 Sq Ft
2 Farm Path, Oak Bluffs, MA 02557

"Turn-key" offering! This custom cape design with a delightful farmer's porch provides ample opportunities to entertain. Set upon nearly an acre of level and landscaped land with irrigation, it abuts the State Forrest, has an open floor plan with cathedral ceilings and skylights. The three bedroom main, has A/C, a finished basement rec room, a large rear deck that spills forth onto a large yard

Sean Federowicz Landmarks at TODAY Real Estate

2 Farm Path, Oak Bluffs, MA 02557
/17
$12,000 total monthly price
- 3 Beds
- 2 Baths
- 1,750 Sq Ft
- House for Rent
223 Sandpiper Lane Vh405, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This three bedroom two bath condo is just a short walk to association tennis, pool and the beach. Comfortable easy summer living with outdoor shower, spacious deck, and central AC for those really hot August days!Amenities include Direct TV DVD set up. There is an open

Karen Overtoom Karen M. Overtoom R.E.

223 Sandpiper Lane Vh405, Tisbury, MA 02568
/39
$1,470,000 Sold Oct 27, 2025
- 1,620 Sq Ft
- $907/SF
- 23 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2007
26 Winne Ave, Vineyard Haven, MA 02568

Welcome to your dream home just a short walk to the lagoon. This home offers easy access for dropping a kayak or taking a refreshing afternoon dip from a public access point. Discover this charming home nestled on a corner lot within a serene neighborhood. This beach home has an updated kitchen and bathrooms. The kitchen is equipped with new appliances and gorgeous quartz countertops, making it a

Joe & Nicole Holland Vineyard Dream Realty LLC

26 Winne Ave, Vineyard Haven, MA 02568

/19
Est $1,286,014 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,520 Sq Ft
46 Windsor Dr, Edgartown, MA 02539

46 Windsor Dr, Edgartown, MA 02539

/20
$1,995,000 Pending
- 4 Beds
- 5 Baths
- 2,820 Sq Ft
71 Netock Ave, Oak Bluffs, MA 02557

On the doorstep of vibrant Oak Bluffs, discover this exquisitely renovated four bedroom home with separate office or studio space, all ensconced in professionally landscaped grounds. Blending modern comfort with timeless island charm, the house features wide plank white oak floors, beautiful ceiling height and natural light, an open-concept living-dining space with a new kitchen, a first-floor

Ellen Valentgas Sotheby's International Realty

71 Netock Ave, Oak Bluffs, MA 02557
/40
$32,500 total monthly price
- 6 Beds
- 4.5 Baths
- 3,222 Sq Ft
- House for Rent
100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living

Karen Overtoom Karen M. Overtoom R.E.

100 Connie's Way &83 Ashtonw Vh408, Tisbury, MA 02568
/3
$3,067,050 Sold Oct 22, 2025
- 1,872 Sq Ft
- $1,638/SF
- 0 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1985
114 Park, Oak Bluffs, MA 02557

Not Listed in LINK

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114 Park, Oak Bluffs, MA 02557

/36
Est $2,466,989 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,791 Sq Ft
225 Great Plains Rd, Vineyard Haven, MA 02568

225 Great Plains Rd, Vineyard Haven, MA 02568

/19
$1,995,000 Pending
- 4 Beds
- 5 Baths
- 2,820 Sq Ft
71 Netock Ave, Oak Bluffs, MA 02557

On the doorstep of vibrant Oak Bluffs, discover this exquisitely renovated four bedroom home with separate office or studio space, all ensconced in professionally landscaped grounds. Blending modern comfort with timeless island charm, the house features wide plank white oak floors, beautiful ceiling height and natural light, an open-concept living-dining space with a new kitchen, a first-floor

Ellen Valentgas Sotheby's International Realty

71 Netock Ave, Oak Bluffs, MA 02557
/29
$64,000 total monthly price
- 4 Beds
- 7 Baths
- 3,600 Sq Ft
- House for Rent
385 Barnes Rd Ob534, Oak Bluffs, MA 02557

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $18,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with water views over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in

Karen Overtoom Karen M. Overtoom R.E.

385 Barnes Rd Ob534, Oak Bluffs, MA 02557
/19
$1,330,000 Sold Oct 17, 2025
- 1,404 Sq Ft
- $947/SF
- 112 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1983
32 MacHipscat Trail, Vineyard Haven, MA 02568

This Cape Style home privately sited on 1.89 acres at the end of a cul-de-sac abutting conservation land with many walking trails. Nice features include spacious living spaces that include a well equipped kitchen with custom cherry cabinets, dining room, living room with fireplace, wood stove and french doors that lead you out to a private patio and backyard. Second floor offers two guest

Brenda Galligan Karen M. Overtoom R.E.

32 MacHipscat Trail, Vineyard Haven, MA 02568

/39
Est $7,234,025 Not Listed For Sale
- 5 Beds
- 6 Baths
- 6,546 Sq Ft
103 Main St, Vineyard Haven, MA 02568

103 Main St, Vineyard Haven, MA 02568

/26
$1,950,000 Pending
- 5 Beds
- 3 Baths
- 1,916 Sq Ft
14 Rebekahs Way, Vineyard Haven, MA 02568

Affectionately referred to as ‘The Treehouse', this property encompasses all the elements of a modern, sophisticated residence while providing the warmth and comfort of a private retreat. Professionally designed by Hutker Architects, this four-bedroom home, with a den/potential fifth bedroom, is sited in a private area, conveniently located with easy access to grocery store, pharmacy, and post

Sheila Morse Island Real Estate

14 Rebekahs Way, Vineyard Haven, MA 02568
/20
$20,000 total monthly price
- 3 Beds
- 3 Baths
- House for Rent
40 Hidden Cove Rd, Oak Bluffs, MA 02557

THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Welcome to "Shangri-la" A beautiful townhouse condominium end unit with magnificent views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great living room with views and bedrooms

Karen Overtoom Karen M. Overtoom R.E.

40 Hidden Cove Rd, Oak Bluffs, MA 02557
/30
$1,550,000 Sold Oct 16, 2025
- 1,986 Sq Ft
- $780/SF
- 114 Days On Market
- 3 Beds
- 2 Baths
- Built 1986
251 State Rd, Vineyard Haven, MA 02568

This private and pastoral year-round home with fine craftsmanship and loads of character is a classic up-island refuge, yet in a location that is central on the island and convenient to town. Abutting Land Bank property, the charming home features an open living and dining room with wide plank floors and beams flowing into the kitchen, all surrounding a central brick fireplace. An expansive

Meg Bodnar Tea Lane Associates

251 State Rd, Vineyard Haven, MA 02568

/34
Est $1,535,030 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,452 Sq Ft
84 Christiantown Rd, Vineyard Haven, MA 02568

84 Christiantown Rd, Vineyard Haven, MA 02568

/81
$1,785,000 Pending
- 4 Beds
- 3.5 Baths
- 2,194 Sq Ft
209 Cove Rd, Vineyard Haven, MA 02568

Wonderful Tashmoo Wood Association - West Chop. Welcome to this spacious and inviting home in the wonderful Tashmoo Wood Community. Rarely does a Single Family Home come on the market in this Private Association. This four (4) bedroom home, nestled on a private 1 acre lot with a tree lined driveway, abuts common land, is adjacent to Mink Meadows Golf Course and offers the ultimate in the

Alisan Lohan-Conway Alisan Lohan-Conway Properties

209 Cove Rd, Vineyard Haven, MA 02568
/25
$24,000 total monthly price
- 3 Beds
- 2 Baths
- 1,257 Sq Ft
- House for Rent
5 Laurel Ave, Oak Bluffs, MA 02557

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Wonderful, fully redecorated Gingerbread house on East Chop, just minutes from the excitement of Oak Bluffs. There are three bedrooms and two full baths. The interior is clean and crisp, with beach cottage decor and beautiful bamboo floors. Entertainment options include

Karen Overtoom Karen M. Overtoom R.E.

5 Laurel Ave, Oak Bluffs, MA 02557
/30
$1,226,500 Sold Oct 16, 2025
- 1,637 Sq Ft
- $749/SF
- 6 Days On Market
- 3 Beds
- 2 Baths
- Built 1988
9 Grovedale Rd, Oak Bluffs, MA 02557

Welcome to a home full of character and charm in the heart of Oak Bluffs. This 3-bedroom, 2-bathroom property offers comfortable living with a sun-filled open kitchen and dining area featuring a picturesque bay window that flows seamlessly into a warm living room centered around a welcoming fireplace. Just a short distance from the Lagoon, the setting is enhanced by mature plantings that surround

Bonnie Pierce Wallace & Co. Sotheby's International Realty

9 Grovedale Rd, Oak Bluffs, MA 02557

/19
Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 1,714 Sq Ft
43 Look St, Vineyard Haven, MA 02568

43 Look St, Vineyard Haven, MA 02568

/23
$1,795,000 Pending
- 4 Beds
- 3 Baths
- 2,038 Sq Ft
25 Hampson Ave, Oak Bluffs, MA 02568

Location is everything. Fantastic Cape in a quiet neighborhood, just a 10-minute walk to harbor and downtown. The first-floor plan includes a spacious living-room that opens to an eat-in kitchen, large Master with full bath, and a second bedroom with a full bath. The second floor has a beautiful large open space area for a media room, study or playroom and 2 more large bedrooms with another full

Lenny Altieri Premier Properties

25 Hampson Ave, Oak Bluffs, MA 02568
/30
$20,000 total monthly price
- 4 Beds
- 2 Baths
- 1,920 Sq Ft
- House for Rent
291 Barnes Rd Ob516, Oak Bluffs, MA 02557

THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Feel the ocean breezes from this classic waterfront home. There are four bedrooms, an open living room and dining room that open up to large deck overlooking beautiful views across the Lagoon. Walking path to private sandy beach. BOAT MOORING INCLUDED.

Karen Overtoom Karen M. Overtoom R.E.

291 Barnes Rd Ob516, Oak Bluffs, MA 02557
/26
$1,800,000 Sold Oct 15, 2025
- 1,913 Sq Ft
- $941/SF
- 128 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2020
82 Skiff Ave, Tisbury, MA 02568

This pristine hidden gem, recently developed home is located downtown, a short walk from shops, the lagoon, the beach, the harbor,and the MV Museum.S et back from the road, the home offers a quiet and peaceful luxury living experience. The property boasts solid hw floors, ducted heating and AC, a gas fireplace, quartz countertops, tiled baths, an open floor plan, a 1st-floor primary bedroom, 2

Lenny Altieri Premier Properties

82 Skiff Ave, Tisbury, MA 02568

/18
Est $1,717,310 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,461 Sq Ft
29 Brook Hollow Rd, Vineyard Haven, MA 02568

29 Brook Hollow Rd, Vineyard Haven, MA 02568

/46
$1,675,000 Under Contract
- 4 Beds
- 2.5 Baths
- 2,127 Sq Ft
5 Bayes Hill Cir, Vineyard Haven, MA 02568

Beautiful Bayes Hill Association! This nicely maintained 4 bedroom colonial-style home, located on a quiet cul-de-sac, is the perfect blend of comfort and charm. A new Red Cedar Shingle Roof, a newer high-efficiency furnace, newer state-of-the-art 75-gallon hot water heater, central air conditioning, 2 car garage and a freshly painted exterior this residence combines modern conveniences with

Rene Jackson Island Real Estate

5 Bayes Hill Cir, Vineyard Haven, MA 02568
/14
$14,200 total monthly price
- 3 Beds
- 2 Baths
- 1,500 Sq Ft
- House for Rent
59 Prospect Ave Ob502, Oak Bluffs, MA 02557

THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. This immaculate home is located in a quiet neighborhood that is just a bike ride's distance from several lovely beaches as well as the center of Oak Bluffs. The home offers open living spaces, generously proportioned sunny bedrooms and is well equipped.

Karen Overtoom Karen M. Overtoom R.E.

59 Prospect Ave Ob502, Oak Bluffs, MA 02557
/27
$1,475,000 Sold Oct 10, 2025
- 1,304 Sq Ft
- $1,131/SF
- 103 Days On Market
- 4 Beds
- 1.5 Baths
- Built 1905
11 John Wesley Ave, Oak Bluffs, MA 02568

East Chop Living in this 4 Bedroom Victorian home perched near the shoreline in Oak Bluffs-just a short stroll to the harbor, the shores of East Chop beaches, and the shops and restaurants of downtown Oak Bluffs. Built in 1905, and updated throughout the years, with its Victorian architecture softened by time and salt air, giving it an inviting, warm charm. The exterior features a wide wraparound

Lisa Lucier Anchor Realty of MV

11 John Wesley Ave, Oak Bluffs, MA 02568

/25
Est $1,415,526 Not Listed For Sale
- 5 Beds
- 3 Baths
- 2,287 Sq Ft
101 Dunham Ave, Vineyard Haven, MA 02568

101 Dunham Ave, Vineyard Haven, MA 02568

/35
$1,870,000 Under Contract
- 5 Beds
- 3 Baths
- 2,432 Sq Ft
32 Flamingo Dr, Edgartown, MA 02539

This well-maintained country farmhouse is centrally located and is situated on just over one acre of land. A circular driveway welcomes you to the home with plenty of parking. There is a garden storage shed, irrigation system, playground, fire pit with outdoor seating, and wraparound covered porch. The rear entry door from the kitchen leads to the outdoor shower and spacious sunny deck. The first

Skip Dostal Martha's Vineyard R.E.

32 Flamingo Dr, Edgartown, MA 02539
/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
/31
$1,685,000 Sold Oct 09, 2025
- 2,251 Sq Ft
- $749/SF
- 337 Days On Market
- 3 Beds
- 3 Baths
- Built 1979
126 Border Rd, Vineyard Haven, MA 02568

Designed and built by the owner's architect father, Nembhard N. Culin in 1975. The unique mid-century style house is perfectly sited on a knoll overlooking the head of Lagoon Pond. Follow the private path to the sandy beach for walking, swimming, kayaking or boating. The property includes a permitted boat mooring and the beach is perfect for launching small boats. The house was built as a solar

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

126 Border Rd, Vineyard Haven, MA 02568

/35
Est $2,576,066 Not Listed For Sale
- 4 Beds
- 5 Baths
- 2,728 Sq Ft
89 Main St, Vineyard Haven, MA 02568

89 Main St, Vineyard Haven, MA 02568

/42
$1,350,000
- 3 Beds
- 2 Baths
- 1,809 Sq Ft
169 Clover Hill Dr, Vineyard Haven, MA 02568

Located on a cul-de-sac in a serene neighborhood, this classic Cape-style home sits on a generous 0.86-acre lot less than 1.5 miles from Main Street, Vineyard Haven. The location is ideal—close to restaurants, shopping, and the ferry, yet with enough land to accommodate the existing detached two-car garage and the potential for an Accessory Dwelling Unit. The three-bedroom home offers a

Stephanie Roache Donnelly + Co

169 Clover Hill Dr, 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
/45
$1,700,000 Sold Oct 08, 2025
- 3,213 Sq Ft
- $529/SF
- 52 Days On Market
- 7 Beds
- 4.5 Baths
- Built 1979
51 Skiffs Ln, Vineyard Haven, MA 02568

Roomy, 5 bedroom, 3.5 bath home warmed by walls of knotty pine and sited on a 3-acre parcel with nicely cleared areas around the house bringing in the sunlight and enticing you outside for games, gardening and relaxation on the expansive deck. There is a wood-burning brick fireplace in the living room to gather around on chilly nights - and a full, dry basement great for kids games on rainy days

Candy DaRosa Feiner Real Estate

51 Skiffs Ln, Vineyard Haven, MA 02568

/48
Est $1,502,250 Not Listed For Sale
- 6 Beds
- 5.5 Baths
- 2,417 Sq Ft
152 Main St, Vineyard Haven, MA 02568

152 Main St, Vineyard Haven, MA 02568

Showing Results 81 - 120, Page 3 of 18

Massachusetts Dukes County Vineyard Haven

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