10,865

Vineyard Haven, MA Homes

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  • /22

    $260,000

    • 1 Bed
    • 1 Bath
    • 319 Sq Ft

    33 Island Inn Rd Unit 25 F, Oak Bluffs, MA 02568

    Welcome to 27 Island Inn, Unit 25F, a comfortable studio offering the perfect combination of a Martha's Vineyard getaway and rental opportunity. Accommodating up to four guests, this inviting unit features two double beds, one full bath, a convenient kitchenette, cable TV and free WiFi. Island Inn is a seasonal resort, open April through October, offering a relaxed, pet-friendly setting with a

    Agent Photo

    Rene Ben David

    Ocean Park Realty, Inc.

    33 Island Inn Rd Unit 25 F, Oak Bluffs, MA 02568
  • /36

    $7,389

    Total Monthly Price

    • 4 Beds
    • 3 Baths
    • 2,281 Sq Ft
    • Condo for Rent

    13 N Meadow Ln Unit SI ID1514673P, Oak Bluffs, MA 02568

    The advertised rate of $7,390/month is the lowest available price, based on a 30 day(s) stay with a move-in date of January 3, 2027. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    13 N Meadow Ln Unit SI ID1514673P, Oak Bluffs, MA 02568
  • /42

    $1,300,000

    Sold Feb 13, 2026

    169 Clover Hill Dr, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,809 Sq Ft
    • Built 1977

    Last Sold Summary

    • 4% Below List Price
    • $719/SF
    • 9 Days On Market

    Current Estimated Value $1,418,628

    Last Listing Agent Stephanie Roache Donnelly + Co

    169 Clover Hill Dr, Vineyard Haven, MA 02568
    • /35

      Not Listed For Sale

      8 Schoolhouse Village, Oak Bluffs, MA 02557

      • 4 Beds
      • 3.5 Baths
      • 2,336 Sq Ft
      • Built 1980
      8 Schoolhouse Village, Oak Bluffs, MA 02557

      Last Sold Summary

      • 277 Days On Market

      Last Listing Agent Stephanie Roache Donnelly + Co.

  • /53

    $2,295,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 3,015 Sq Ft

    3 Hidden Cove Rd, Oak Bluffs, MA 02557

    HIDDEN COVE GEM WITH SERENE POND VIEWS AND COVETED WATER ACCESS. Located in the desirable Hidden Cove enclave, a 65+ acre water-access community with direct access to Sengekontacket Pond and Nantucket Sound, this inviting contemporary home offers privacy, comfort, and high-end finishes throughout. Community amenities include a private boat dock, walking trails, pickleball and tennis, all

    Agent Photo

    Wendy Harman

    Compass | Point B

    3 Hidden Cove Rd, Oak Bluffs, MA 02557
  • /20

    $7,323

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,022 Sq Ft
    • Condo for Rent

    25 Simpson Ave Unit SI ID1514679P, Oak Bluffs, MA 02568

    The advertised rate of $7,323/month is the lowest available price, based on a 30 day(s) stay with a move-in date of December 4, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    25 Simpson Ave Unit SI ID1514679P, Oak Bluffs, MA 02568
  • /32

    $487,500

    Sold Jun 30, 2026

    21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568

    • 1 Bed
    • 1.5 Baths
    • 590 Sq Ft
    • Built 1983

    Last Sold Summary

    • 13% Below List Price
    • $826/SF
    • 205 Days On Market

    Last Listing Agent Diana Gilmore Island Real Estate

    21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
    • /3

      Est $1,660,470

      Not Listed For Sale

      18 Towanticut Ave, Oak Bluffs, MA 02557

      • 4 Beds
      • 2.5 Baths
      • 2,329 Sq Ft
      • Built 1989
      18 Towanticut Ave, Oak Bluffs, MA 02557

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Brenda Galligan Karen M. Overtoom R.E.

  • /8

    $1,049,000

    $151K PRICE DROP
    • Land
    • 10,890 Sq Ft
    • $4,196,000 per Acre

    0 Temahigan Ave & Dover St Unit 22602202, Oak Bluffs, MA 02557

    Welcome to # 0 Temahigan Ave & Dover Street, Oak Bluffs. Build Your Martha's Vineyard Dream Home. Rare opportunity to own a level, cleared corner lot in desirable Oak Bluffs, with paved roads bordering two sides, ready for construction of your Martha's Vineyard dream home. Approved for up to 6 bedrooms, this exceptional property includes an approved 6-bedroom septic design, with room for a

    Agent Photo

    Rene Ben David

    Ocean Park Realty, Inc.

    0 Temahigan Ave & Dover St Unit 22602202, Oak Bluffs, MA 02557
  • /29

    $64,000 Per Month

    • 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
  • /30

    $1,550,000

    Sold Oct 16, 2025

    251 State Rd, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,986 Sq Ft
    • Built 1986

    Last Sold Summary

    • 9% Below List Price
    • $780/SF
    • 114 Days On Market

    Current Estimated Value $1,751,931

    Last Listing Agent Meg Bodnar Tea Lane Associates

    251 State Rd, Vineyard Haven, MA 02568
    • /2

      Est $2,878,297

      Not Listed For Sale

      28 Woodhaven Dr, Edgartown, MA 02539

      • 3 Beds
      • Built 2013
      28 Woodhaven Dr, Edgartown, MA 02539

      Last Sold Summary

      • 6,292 Days On Market

      Last Listing Agent LINK Email Cache LINK

  • /35

    $2,325,000

    $270K PRICE DROP Pending
    • 4 Beds
    • 4 Baths
    • 2,288 Sq Ft

    54 Amelias Crossing, Vineyard Haven, MA 02568

    COASTAL CHIC RETREAT IN VINEYARD HAVEN. Located less than five blocks from Main Street in Vineyard Haven, this classically styled home is perfectly positioned for easy access to restaurants, shops, the harbor, and the ferry, offering the ideal blend of in-town convenience, relaxed island living, and timeless Vineyard appeal.The open-designed living area flows seamlessly to the outdoor

    Agent Photo

    Wendy Harman

    Compass | Point B

    54 Amelias Crossing, Vineyard Haven, MA 02568
  • /12

    $15,000 Per Month

    • 5 Beds
    • 6.5 Baths
    • 4,137 Sq Ft
    • House for Rent

    41 Naushon Rd Wt116, Aquinnah, MA 02575

    Stunning water views from this expansive beachfront estate in Makonikey off Lambert's Cove Rd. Enjoy the large living area with comfortable couches, floor to ceiling windows and french doors for seamless indoor to outdoor living and dining. There is a fully equipped kitchen. Some folks will enjoy the treadmill and elliptical while watching boats pass by or even play squash in the indoor squash

    Karen Overtoom Karen M. Overtoom R.E.

    41 Naushon Rd Wt116, Aquinnah, MA 02575
  • /28

    $1,350,000

    Sold Nov 20, 2025

    16 Majors Cove Ln, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 1,965 Sq Ft
    • Built 1986

    Last Sold Summary

    • 26% Below List Price
    • $687/SF
    • 156 Days On Market

    Current Estimated Value $1,526,197

    Last Listing Agent Stephanie Roache Donnelly + Co

    16 Majors Cove Ln, Edgartown, MA 02539
    • /10

      Not Listed For Sale

      0 Bridle Path Rd, Vineyard Haven, MA 02568

      0 Bridle Path Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Julianna Flanders Flanders Real Estate

  • /13

    $1,325,000

    $170K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,304 Sq Ft

    33 Alyssa Ln, Vineyard Haven, MA 02568

    Country Living so close to Town! Lovely 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

    Agent Photo

    Stephanie Burke

    Portfolio Properties

    33 Alyssa Ln, Vineyard Haven, MA 02568
  • /20

    $20,000 Per Month

    • 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
  • /39

    $1,390,000

    Sold Sep 21, 2026

    26 Sea Glen Rd, Vineyard Haven, MA 02568

    • 4 Beds
    • 3 Baths
    • 1,514 Sq Ft
    • Built 1985

    Last Sold Summary

    • 14% Below List Price
    • $918/SF
    • 106 Days On Market

    Last Listing Agent Jennifer B. DaSilva Compass

    26 Sea Glen Rd, Vineyard Haven, MA 02568
    • /15

      Est $1,160,319

      Not Listed For Sale

      15 14th St N, Edgartown, MA 02539

      • 2 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 2018
      15 14th St N, Edgartown, MA 02539

      Last Sold Summary

      • 55 Days On Market

      Last Listing Agent Mike Sawyer Sawyer Realty Group

  • /25

    $389,000

    $139K PRICE DROP
    • 1 Bed
    • 1.5 Baths
    • 590 Sq Ft

    21 Island Inn Rd Unit 38G, Oak Bluffs, MA 02568

    Welcome to Unit 38G at the Island Inn, offering resort-style living in an exceptional Oak Bluffs location just steps from the beach. This desirable ground-floor end unit features a large glass slider opening to the patio, with stairs leading to the heated outdoor pool just a few feet away. Accommodating up to six guests, the unit features one bedroom with a queen bed, a separate sleeping area

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    21 Island Inn Rd Unit 38G, Oak Bluffs, MA 02568
  • /26

    $50,000 Per Month

    • 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
  • /26

    $1,500,000

    Sold Mar 30, 2026

    68 20th St S, Edgartown, MA 02539

    • 4 Beds
    • 3 Baths
    • 1,975 Sq Ft
    • Built 1997

    Last Sold Summary

    • 6% Below List Price
    • $759/SF
    • 28 Days On Market

    Current Estimated Value $1,567,254

    Last Listing Agent Carol Shore Donnelly + Co

    68 20th St S, Edgartown, MA 02539
    • /16

      Est $841,205

      Not Listed For Sale

      21 Norris Ave, Vineyard Haven, MA 02568

      • 2 Beds
      • 1 Bath
      • 1,086 Sq Ft
      • Built 1948
      21 Norris Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Rene Ben David Ocean Park Realty Inc

  • /9

    $1,325,000

    $170K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,304 Sq Ft

    33 Alyssa Ln, Vineyard Haven, MA 02568

    Country Living so close to Town! Lovely 4 Bedroom 2,304 sq ft Colonial Cape with Garage and lower level living space . Open kitchen, dining & entertainment area. Sliders open to Large side deck. High Ceilings Wood floors Living Room with additional nook. Half bath. Interior stairs to lower level with office/bedroom, half bath, private exterior entrance and garage. 2nd floor has large primary

    Agent Photo

    Stephanie Burke

    Portfolio Properties

    33 Alyssa Ln, Vineyard Haven, MA 02568
  • /22

    $15,000 Per Month

    • 5 Beds
    • 3 Baths
    • 3,000 Sq Ft
    • House for Rent

    55 Samoset Ave, Oak Bluffs, MA 02557

    BOOK SUMMER 2027! Modernized 5 bed, 3 full bath Victorian in the heart of Downtown Oak Bluffs. Steps to restaurants, shopping, harbor, ferries and beaches. Accommodates 10 guests. Easy breezy outdoor living, dining, bluestone patio and BBQ grill. Relax on the covered porch surrounded by a lush flower garden or unwind in the outdoor shower. Updated stone and stainless kitchen. Formal dining for

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    55 Samoset Ave, Oak Bluffs, MA 02557
  • /16

    $1,865,000

    Sold Dec 04, 2025

    71 Netock Ave, Oak Bluffs, MA 02557

    • 4 Beds
    • 5 Baths
    • 2,820 Sq Ft
    • Built 1982

    Last Sold Summary

    • 7% Below List Price
    • $661/SF
    • 11 Days On Market

    Current Estimated Value $1,978,938

    Last Listing Agent Ellen Valentgas Sotheby's International Realty

    71 Netock Ave, Oak Bluffs, MA 02557
    • /38

      Est $1,056,884

      Not Listed For Sale

      287 County Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 1 Bath
      • 1,120 Sq Ft
      • Built 1998
      287 County Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Jill Napior Tea Lane Associates

  • /12

    $1,049,000

    $151K PRICE DROP
    • Land
    • 10,890 Sq Ft
    • $4,196,000 per Acre

    0 Temahigan Ave Unit 160, Oak Bluffs, MA 02568

    Welcome to # 0 Temahigan Ave & Dover Street, Oak Bluffs.Build Your Martha’s Vineyard Dream Home.Rare opportunity to own a level, cleared corner lot in desirable Oak Bluffs, with paved roads bordering two sides, ready for construction of your Martha’s Vineyard dream home. Approved for up to 6 bedrooms, this exceptional property includes an approved 6-bedroom septic design, with room for a

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    0 Temahigan Ave Unit 160, Oak Bluffs, MA 02568
  • /25

    $24,000 Per Month

    • 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 décor and beautiful bamboo floors. Entertainment options include

    Karen Overtoom Karen M. Overtoom R.E.

    5 Laurel Ave, Oak Bluffs, MA 02557
  • /2

    $525,000

    Sold May 29, 2026

    0 Lyle Ln Unit 2A, Vineyard Haven, MA 02568

    • Land
    • 31,180 Sq Ft
    • $733,445 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent LINK Email Cache LINK

    0 Lyle Ln Unit 2A, Vineyard Haven, MA 02568
    • /2

      Est $1,121,236

      Not Listed For Sale

      11 Onondaga Ave, Vineyard Haven, MA 02568

      • 3 Beds
      • 3 Baths
      • 1,996 Sq Ft
      • Built 1996
      11 Onondaga Ave, Vineyard Haven, MA 02568

  • /8

    $310,000

    • 1 Bed
    • 1 Bath
    • 783 Sq Ft

    27 Island Inn Rd Unit 10C, Oak Bluffs, MA 02568

    Welcome to 27 Island Inn, Unit 10C, a comfortable one-bedroom, one-bath Martha's Vineyard retreat offering an ideal combination of personal enjoyment and rental opportunity. Accommodating up to four guests, 10C features a queen bedroom, sofa bed, cozy living area, well-equipped kitchenette. A unique feature is the adjoining door to Unit 9C, a studio with two double beds, full bath and

    Agent Photo

    Rene Ben David

    Ocean Park Realty, Inc.

    27 Island Inn Rd Unit 10C, Oak Bluffs, MA 02568
  • /8

    $6,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,000 Sq Ft
    • House for Rent

    33 Kennebago Ave Vh414, Tisbury, MA 02568

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This beautiful home has lots of open space for cooking, yard activities or just plain relaxing. Private association beach overlooking the Elizabethan Islands. Plan a sunset picnic on the beach or plan in the morning to see the rays of sun break on the water.

    Karen Overtoom Karen M. Overtoom R.E.

    33 Kennebago Ave Vh414, Tisbury, MA 02568
  • /26

    $1,935,000

    Sold May 06, 2026

    34 Davis St, Tisbury, MA 02568

    • 3 Beds
    • 3.5 Baths
    • 2,453 Sq Ft
    • Built 2025

    Last Sold Summary

    • 19% Below List Price
    • $789/SF
    • 160 Days On Market

    Last Listing Agent Andrew McElhinney Compass LLC

    34 Davis St, Tisbury, MA 02568
    • /26

      Est $1,558,733

      Not Listed For Sale

      19 Quantapog Rd, Vineyard Haven, MA 02568

      • 3 Beds
      • 3 Baths
      • 1,822 Sq Ft
      • Built 1988
      19 Quantapog Rd, Vineyard Haven, MA 02568

      Last Sold Summary

      • 177 Days On Market

      Last Listing Agent Frank Markwica Sandpiper Realty

  • /27

    $389,000

    $139K PRICE DROP
    • 1 Bed
    • 1.5 Baths
    • 590 Sq Ft

    21 Island Inn Rd Unit 38 G, Oak Bluffs, MA 02568

    Welcome to Unit 38G at the Island Inn, offering resort-style living in an exceptional Oak Bluffs location just steps from the beach. This desirable ground-floor end unit features a large glass slider opening to the patio, with stairs leading to the heated outdoor pool just a few feet away. Accommodating up to six guests, the unit features one bedroom with a queen bed, a separate sleeping area

    Agent Photo

    Rene Ben David

    Ocean Park Realty, Inc.

    21 Island Inn Rd Unit 38 G, Oak Bluffs, MA 02568
  • /27

    $21,700 Per Month

    • 5 Beds
    • 3 Baths
    • 2,168 Sq Ft
    • House for Rent

    97 3rd St N, Edgartown, MA 02539

    YOUR VINEYARD ESCAPE AWAITS! This sizable vintage rental with water views of Sengekontacket Pond and beyond is ideal for your island getaway. Boasting multiple levels of living and porches that take advantage of views, the main floor is awash in seaside tones. Display a raw bar on the center island and top off beverages in the kitchen before relaxing in the sunroom as you enjoy the painterly sky

    Fine Homes Group Keller Williams Realty Boston-Metro | Back Bay

    97 3rd St N, Edgartown, MA 02539
  • /2

    $1,850,000

    Sold Mar 31, 2026

    7 S Meadow Ln, Oak Bluffs, MA 02557

    • 4 Beds
    • 3 Baths
    • 3,142 Sq Ft
    • Built 1987

    Last Sold Summary

    • 1% Above List Price
    • $589/SF
    • 74 Days On Market

    Current Estimated Value $2,047,658

    Last Listing Agent Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

    7 S Meadow Ln, Oak Bluffs, MA 02557
    • /12

      Est $1,204,550

      Not Listed For Sale

      3 Carole Ave, Vineyard Haven, MA 02568

      • 4 Beds
      • 2 Baths
      • 1,997 Sq Ft
      • Built 1985
      3 Carole Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 209 Days On Market

      Last Listing Agent Bob Sparks American Real Estate LLC

Showing Results 1 - 40, Page 1 of 18

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