5,177

Oak Bluffs Homes

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  • /8

    $1,200,000

    • Land
    • 10,890 Sq Ft
    • $4,800,000 per Acre

    0 Temahigan Ave Unit 22602202, 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 22602202, Oak Bluffs, MA 02568
  • /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 $1,618,728

      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

  • /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

    $7,389

    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 December 2, 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

    13 N Meadow Ln Unit SI ID1514673P, Oak Bluffs, MA 02568
  • /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 $2,585,414

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

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

  • /12

    $1,200,000

    • Land
    • 10,890 Sq Ft
    • $4,800,000 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
  • /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
  • /19

    $750,000

    Sold Nov 07, 2025

    41 Trinity Park, Oak Bluffs, MA 02557

    • 4 Beds
    • 1 Bath
    • 1,154 Sq Ft
    • Built 1867

    Last Sold Summary

    • 6% Below List Price
    • $650/SF
    • 14 Days On Market

    Current Estimated Value $985,799

    Last Listing Agent Stacy Ickes Donnelly + Co.

    41 Trinity Park, Oak Bluffs, MA 02557
    • /38

      Est $1,068,930

      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

  • /5

    $975,000

    • Land
    • 1.07 Acres
    • $911,215 per Acre

    68 Pond View Dr, Oak Bluffs, MA 02557

    Create your ideal island retreat on this exceptional 1.068-acre parcel in Oak Bluffs. This desirable homesite comes with approved plans for a six-bedroom septic system, saving valuable time and expense as you begin the building process. The property also includes a topographic/boundary survey and soil test, providing a strong foundation for planning and development. Subject to the Town of Oak

    Casandra Hyland Sandpiper Realty, Inc.

    68 Pond View Dr, Oak Bluffs, MA 02557
  • /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
  • /26

    $1,600,000

    Sold Nov 07, 2025

    96 Pondview Dr, Oak Bluffs, MA 02536

    • 4 Beds
    • 2.5 Baths
    • 2,115 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Below List Price
    • $757/SF
    • 35 Days On Market

    Last Listing Agent Doug Burke Signal House Group at Compass

    96 Pondview Dr, Oak Bluffs, MA 02536
    • /26

      Est $1,543,428

      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

  • /23

    $1,800,000

    • 4 Beds
    • 3 Baths
    • 2,864 Sq Ft

    18 Wood Duck Way, Edgartown, MA 02539

    Welcome to your coastal retreat in sought-after Sengekontacket, offered fully turnkey and ready to enjoy from day one. This light-filled contemporary home blends comfort, style, and exceptional community amenities in one of Martha's Vineyard's most desirable central Island locations. Designed with soaring vaulted ceilings and oversized windows, the home is flooded with natural sunlight

    Janna O'Loughlin Portfolio Properties

    18 Wood Duck Way, Edgartown, MA 02539
  • /22

    $15,000 Per Month

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

    55 Samoset Ave, Oak Bluffs, MA 02557

    AVAILABLE SUMMER 2026: JULY 12-AUGUST 9. 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

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    55 Samoset Ave, Oak Bluffs, MA 02557
  • /27

    $1,625,000

    Sold May 12, 2026

    7 Upper Meadow Ln, Oak Bluffs, MA 02557

    • 4 Beds
    • 2.5 Baths
    • 3,268 Sq Ft
    • Built 1994

    Last Sold Summary

    • 10% Below List Price
    • $497/SF
    • 74 Days On Market

    Current Estimated Value $1,764,524

    Last Listing Agent Lesley Heidt Sandpiper Realty, Inc.

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

      Est $1,197,532

      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

  • /28

    $1,850,000

    • 3 Beds
    • 6 Baths
    • 2,641 Sq Ft

    33 Tia Anna Ln, Oak Bluffs, MA 02557

    33 Tia Anna Lane has so much to offer; a charming, bright, renovated main and guest house on a half-acre in Oak Bluffs with proximity to town and walking distance to Lagoon Pond for swimming, fishing, boating and sunset enjoyment. The property is ready to enjoy, offering a turn-key home on a quiet side street as well as a detached guest house with it's own yard and deck. The inviting main house

    Elissa Lash Tea Lane Associates

    33 Tia Anna Ln, Oak Bluffs, MA 02557
  • /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
  • /21

    $982,000

    Sold Dec 19, 2025

    25 Windy Hill Rd, Oak Bluffs, MA 02557

    • 3 Beds
    • 1 Bath
    • 980 Sq Ft
    • Built 1971

    Last Sold Summary

    • 1% Below List Price
    • $1,002/SF
    • 10 Days On Market

    Current Estimated Value $1,306,084

    Last Listing Agent Rene Jackson Island Real Estate

    25 Windy Hill Rd, Oak Bluffs, MA 02557
    • /29

      Est $1,252,605

      Not Listed For Sale

      33 Menahan St, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,428 Sq Ft
      • Built 1993
      33 Menahan St, Vineyard Haven, MA 02568

      Last Sold Summary

      • 30 Days On Market

  • /39

    $1,495,000

    $130K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,514 Sq Ft

    26 Sea Glen Rd, Oak Bluffs, MA 02557

    Nestled in a desirable neighborhood, this beautifully maintained cape style home offers a rare blend of charm, flexibility and convenience in a serene island setting. Thoughtfully appointed throughout, the home welcomes you with an open living room that flows effortlessly into a bright dining area, where French doors open to a private stone patio—creating an inviting connection between indoor

    Jennifer B. DaSilva Compass

    26 Sea Glen Rd, Oak Bluffs, MA 02557
  • /30

    $20,000 Per Month

    • 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
  • /31

    $1,350,000

    Sold Aug 15, 2025

    35 Vineyard Avenue Extension, Oak Bluffs, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,864 Sq Ft
    • Built 1970

    Last Sold Summary

    • 7% Below List Price
    • $724/SF
    • 9 Days On Market

    Last Listing Agent Lesley Heidt Sandpiper Realty

    35 Vineyard Avenue Extension, Oak Bluffs, MA 02568
    • /14

      Est $977,443

      Not Listed For Sale

      51 Manchester Ave, Vineyard Haven, MA 02568

      • 2 Beds
      • 1 Bath
      • 1,024 Sq Ft
      • Built 1978
      51 Manchester Ave, Vineyard Haven, MA 02568

      Last Sold Summary

      • 22 Days On Market

  • /4

    $625,000

    • Land
    • 14,997 Sq Ft
    • $1,815,277 per Acre

    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568

    Oak Bluffs Buildable Lot – Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the

    Andrew McElhinney Compass LLC

    0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
  • /30

    $28,500 Per Month

    • 9 Beds
    • 6.5 Baths
    • 3,500 Sq Ft
    • House for Rent

    9 Tuckernuck Ave, Oak Bluffs, MA 02557

    **SHORT TERM ONLY - WEEKLY RATE ADVERTISED ** Water view Victorian fronting Waban Park, steps to Inkwell Beach. Newly restored 9-bed, 6+ bath Main and Guest House houses 18 guests. Internet, A/C and cable TV. Coastal chic interior with all new furnishings. Large open floor plan, ample gathering and relaxation spaces. Dining for 10, Wet Bar, gourmet kitchen, gas range, stainless appliances and

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    9 Tuckernuck Ave, Oak Bluffs, MA 02557
  • /19

    $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 $2,433,494

    Last Listing Agent Ellen Valentgas Sotheby's International Realty

    71 Netock Ave, Oak Bluffs, MA 02557
    • /31

      Est $1,419,170

      Not Listed For Sale

      48 Puritan Dr, Vineyard Haven, MA 02568

      • 3 Beds
      • 2 Baths
      • 1,999 Sq Ft
      • Built 1985
      48 Puritan Dr, Vineyard Haven, MA 02568

      Last Sold Summary

      • 25 Days On Market

  • /5

    $975,000

    • Land
    • 1.07 Acres
    • $912,921 per Acre

    68 Pond View Dr Unit 2, Oak Bluffs, MA 02557

    Create your ideal island retreat on this exceptional 1.068-acre parcel in Oak Bluffs. This desirable homesite comes with approved plans for a six-bedroom septic system, saving valuable time and expense as you begin the building process.The property also includes a topographic/boundary survey and soil test, providing a strong foundation for planning and development.Subject to the Town of

    Casandra Hyland Sandpiper Realty

    68 Pond View Dr Unit 2, Oak Bluffs, MA 02557
  • /10

    $20,000 Per Month

    • 5 Beds
    • 3 Baths
    • 2,352 Sq Ft
    • House for Rent

    55 Samoset Ave Unit 1, Oak Bluffs, MA 02557

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated, Great for Family Gatherings, Corporate Retreats, Central Air & Heat, very close to Circuit Ave and Beach, 5 Bedrooms, 3 full baths, galley kitchen, new appliances, dining room, family room, Flat Screen TV, FREE Wifi, washer & dryer, bay window breakfast nook, Oak and Pine wood flooring, outdoor shower, wrap around porch, blue stone

    Karen Overtoom Karen M. Overtoom R.E.

    55 Samoset Ave Unit 1, Oak Bluffs, MA 02557
  • /37

    $2,775,000

    Sold Jun 29, 2026

    33 Ocean Ave, Oak Bluffs, MA 02557

    • 3 Beds
    • 2.5 Baths
    • 1,845 Sq Ft
    • Built 1875

    Last Sold Summary

    • 6% Below List Price
    • $1,504/SF
    • 140 Days On Market

    Current Estimated Value $2,967,052

    Last Listing Agent Katrina Lima Donnelly + Co

    33 Ocean Ave, Oak Bluffs, MA 02557
    • /27

      Not Listed For Sale

      2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557

      • 3 Beds
      • 2 Baths
      • 1,594 Sq Ft
      • Built 1933
      2 E Side Road & 60 Bay View Ave, Oak Bluffs, MA 02557

      Last Sold Summary

      • 532 Days On Market

  • /18

    $1,199,000

    • 3 Beds
    • 2 Baths
    • 1,302 Sq Ft

    47 Winemack St, Oak Bluffs, MA 02557

    Oak Bluffs -East Chop-Close to the beach. Two Year-round cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one

    Lisa Lucier Anchor Realty of MV

    47 Winemack St, Oak Bluffs, MA 02557
  • /14

    $14,200 Per Month

    • 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
  • /30

    $1,995,000

    Sold Aug 29, 2025

    26 Box Turtle Ln, Oak Bluffs, MA 02557

    • 4 Beds
    • 3.5 Baths
    • 2,891 Sq Ft
    • Built 1980

    Last Sold Summary

    • $690/SF
    • 5 Days On Market

    Current Estimated Value $2,708,272

    Last Listing Agent Jayne Isford Ocean Park Realty Inc

    26 Box Turtle Ln, Oak Bluffs, MA 02557
    • /31

      Not Listed For Sale

      107 & 105 Barnes Rd, Oak Bluffs, MA 02557

      • 5 Beds
      • 2 Baths
      • 1,520 Sq Ft
      • Built 1945
      107 & 105 Barnes Rd, Oak Bluffs, MA 02557

      Last Sold Summary

      • 51 Days On Market

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$1,424,500
Median Single Family Sale Price
$1,600,000
Median 2 Bedroom Sale Price
$940,000
Median 1 Bedroom Sale Price
$869,000
Average Price Per Sq Ft
$1,017
Number of Homes for Sale
51
Last 12 months Home Sales
118
Months of Supply
5.20
Median List Price
$1,595,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
30%
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