5,155

Oak Bluffs Homes

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  • /41

    $2,295,000

    • 4 Beds
    • 3.5 Baths
    • 3,016 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—this inviting contemporary home offers privacy and high-end finishes with direct access to Sengekontacket Pond and Nantucket Sound. Community amenities include a private boat dock, walking trails, pickleball and tennis, all near Oak Bluffs. The

    Agent Photo

    Wendy Harman

    Compass

    (508) 456-9911

    3 Hidden Cove Rd, 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
  • /27

    $1,070,000

    Sold Apr 17, 2026

    70 Carol Ln, Oak Bluffs, MA 02557

    • 2 Beds
    • 2.5 Baths
    • 1,500 Sq Ft
    • Built 1971

    Last Sold Summary

    • 14% Below List Price
    • $713/SF
    • 463 Days On Market

    Current Estimated Value $1,131,267

    Last Listing Agent Lisa Lucier Anchor Realty of Martha's Vineyard

    70 Carol Ln, Oak Bluffs, MA 02557
    • /3

      Est $1,558,471

      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

      • 4% Above List Price
      • $644/SF
      • 13 Days On Market
      • Last Sold Price $1,500,000
      • Apr 29, 2024

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

  • /21

    $869,000

    • 1 Bed
    • 1 Bath
    • 797 Sq Ft

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

    In the heart of Downtown Oak Bluffs Restless Winds Unit #5 comes with an amazing roof top deck shared with only one other condo (unit #4). You're in the middle of it all with this great location, yet you have easy access to a private and peaceful deck overlooking the town of Oak Bluffs and the surrounding waters. This incredible space takes you to another level of relaxation and a birds eye view

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 544-0253

    37 Circuit Ave Unit 5, 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
  • /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 $2,021,820

    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
      • Last Sold Price $885,000
      • Jun 29, 2023

      Last Listing Agent Diana Gilmore Island Real Estate

  • /37

    $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

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 905-5649

    47 Winemack St, Oak Bluffs, MA 02557
  • /22

    $20,000 Per Month

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

    55 Samoset Ave, Oak Bluffs, MA 02557

    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 eight. A/C, WIFI and

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    55 Samoset Ave, 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 $766,740

    Last Listing Agent Stacy Ickes Donnelly + Co.

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

      Est $1,020,600

      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

      • 20% Above List Price
      • $759/SF
      • 10 Days On Market
      • Last Sold Price $850,000
      • Dec 14, 2023

      Last Listing Agent Jill Napior Tea Lane Associates

  • /24

    $899,000

    • 2 Beds
    • 1 Bath
    • 990 Sq Ft

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

    In the heart of Downtown Oak Bluffs- Restless Winds Condominium Unit #4 comes with an amazing roof top deck that is only shared with one other condo (#5). This spacious unit just under 1,000 sq. ft. has a ships feel with custom wood features and a ships ladder leading to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area, a guest bedroom, a tiled bathroom

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 546-9282

    37 Circuit Ave Unit 4, 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
  • /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 $1,529,549

      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

      • 11% Above List Price
      • $757/SF
      • 177 Days On Market
      • Last Sold Price $1,380,000
      • Jan 23, 2014

      Last Listing Agent Leslie C. Floyd Portfolio Properties

  • /36

    $1,595,000

    $30K 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
  • /15

    $5,200 Per Month

    • 3 Beds
    • 2 Baths
    • 1,430 Sq Ft
    • House for Rent

    85 Winemack St, Oak Bluffs, MA 02557

    This charming property located in East Chop is the perfect retreat for up to 6 guests, offering 3 cozy bedrooms and 2 full bathrooms. Walk into the spacious living area complete with comfortable seating and a Smart TV for your entertainment needs. The fully equipped kitchen features modern appliances and a kitchen island with seating for the kids. Enjoy your meals at the dining table with seating

    Benjamin Snow Coldwell Banker Realty - Boston

    85 Winemack St, 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 $1,822,307

    Last Listing Agent Lesley Heidt Sandpiper Realty, Inc.

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

      Est $1,192,024

      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

      • 4% Above List Price
      • $576/SF
      • 209 Days On Market
      • Last Sold Price $1,150,000
      • Jan 30, 2024

      Last Listing Agent Bob Sparks American Real Estate LLC

  • /46

    $2,400,000

    Under Contract
    • 5 Beds
    • 3.5 Baths
    • 3,873 Sq Ft

    50 Hidden Cove Rd, Edgartown, MA 02539

    Sengekontacket–Walk into a “turn-key” opportunity located within the desirable Hidden Cove community, centrally located to the down-Island villages, ferries, shopping and dininig, and just steps (.3 miles) from Sengekontacket Pond with access to State Beach and Nantucket Sound beyond. The lovingly-maintained 4 bedroom, 2.5 bath, 2 car garage main home sits high on the 1.5 acre property offering

    Sean Federowicz Landmarks at TODAY Real Estate

    50 Hidden Cove Rd, Edgartown, MA 02539
  • /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
  • /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 $977,036

    Last Listing Agent Rene Jackson Island Real Estate

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

      Est $1,248,599

      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

      • 5% Above List Price
      • $830/SF
      • 30 Days On Market
      • Last Sold Price $1,185,000
      • Feb 18, 2021

      Last Listing Agent Katherine Donahue Sandpiper Realty

  • /27

    $2,260,000

    Open Sat 9AM - 12PM $335K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,810 Sq Ft

    4 High Meadow Ln, Oak Bluffs, MA 02557

    Set within the coveted Meadow View Farms community, this exceptional post-and-beam residence offers timeless craftsmanship, generous living spaces, and nearly an acre of private beautifully landscaped grounds with significant potential for expansion. A full-length farmer’s porch creates a gracious arrival and provides the perfect setting to relax. Inside, the sun-drenched main level is defined by

    Kate Burnside Portfolio Properties

    4 High Meadow Ln, Oak Bluffs, MA 02557
  • /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
  • /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 $981,636

      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

      • 3% Above List Price
      • $933/SF
      • 22 Days On Market
      • Last Sold Price $955,000
      • Aug 23, 2024

      Last Listing Agent Roy Cutrer LAER Realty Partners

  • /26

    $2,600,000

    Pending
    • 3 Beds
    • 1 Bath

    23 Circuit Avenue Extension, Oak Bluffs, MA 02557

    Rare Opportunity with Endless Possibilities - Unmatched Harbor & Vineyard Sound Views. Location, Location, Location! A truly rare offering in the heart of Oak Bluffs, where properties like this seldom become available. Positioned directly across from the iconic Oak Bluffs Harbor, this property boasts unobstructed harbor views and sweeping vistas of Vineyard Sound--a setting that captures the very

    Rene Ben David

    23 Circuit Avenue Extension, 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
  • /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 $1,858,736

    Last Listing Agent Ellen Valentgas Sotheby's International Realty

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

      Est $1,404,719

      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

      • 24% Above List Price
      • $565/SF
      • 25 Days On Market
      • Last Sold Price $1,130,000
      • Feb 27, 2024

      Last Listing Agent Jennifer B. DaSilva Compass

  • /27

    $1,850,000

    • 4 Beds
    • 2 Baths
    • 1,833 Sq Ft

    22 Old Harbor Ln, Oak Bluffs, MA 02557

    Quintessential Waterview Farm! Built as a year-round home with the charm of the original cottages, this well-loved retreat awaits its next chapter. The sunny, open floor plan offers two bedrooms and a full bath on each level, with generous gathering spaces throughout. A skylit kitchen is tucked into a corner of the main living area, where a curved wall of glass opens to a deck and private yard.

    Lisa Stewart Sandpiper Realty, Inc.

    22 Old Harbor Ln, Oak Bluffs, MA 02557
  • /41

    $8,750 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,811 Sq Ft
    • House for Rent

    11 High Meadow Ln, Vineyard Haven, MA 02568

    **SUMMER WEEKLY RATE ** INQUIRE FOR LONG TERM OFFSEASON RATE**Discover the perfect summer retreat in this beautifully updated Meadow View Farms home. Nestled on a private hilltop and minutes from beaches, bike paths, Farm Neck Gand Downtown Oak Bluffs, this home offers a serene escape close to the island’s best attractions. 4 spacious bedrooms, first floor primary ensuite, shared secondary floor

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    11 High Meadow Ln, Vineyard Haven, MA 02568
  • /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 $2,091,936

    Last Listing Agent Jayne Isford Ocean Park Realty Inc

    26 Box Turtle Ln, Oak Bluffs, MA 02557
    • /18

      Est $1,319,857

      Not Listed For Sale

      46 Lake Ave, Edgartown, MA 02539

      • 3 Beds
      • 1.5 Baths
      • 1,764 Sq Ft
      • Built 1870
      46 Lake Ave, Edgartown, MA 02539

      Last Sold Summary

      • 10% Above List Price
      • $680/SF
      • 2 Days On Market
      • Last Sold Price $1,200,000
      • Jun 30, 2023

      Last Listing Agent Ed Charter Arrowhead Homes

  • /26

    $1,750,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,862 Sq Ft

    103 Meadow View Rd, Oak Bluffs, MA 02557

    Nestled on a rare, oversized 1.5-acre lot, this spacious 3-bed/2 1/2 bath contemporary home offers a perfect blend of privacy and coastal convenience. Perched elegantly upon a gentle rise, the residence is bathed in natural light and framed by a beautifully landscaped lawn with mature plantings. The interior is designed for both comfort and scale. An expansive front living room has soaring

    Alyson Parker Karen M. Overtoom R.E.

    103 Meadow View Rd, 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
  • /32

    $899,000

    Sold Jul 11, 2025

    8 Rock Ave, Oak Bluffs, MA 02557

    • 3 Beds
    • 1.5 Baths
    • 955 Sq Ft
    • Built 1871

    Last Sold Summary

    • $941/SF
    • 6 Days On Market

    Current Estimated Value $943,726

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    8 Rock Ave, 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

      • $1,645/SF
      • 51 Days On Market
      • Last Sold Price $2,500,000
      • Aug 07, 2024

      Last Listing Agent Christine Rose Martha's Vineyard Island-Wide Realty

Showing Results 1 - 40, Page 1 of 18

Home Trends in Oak Bluffs, MA

Housing Trends

Median Sale Price
$1,449,000
Median Single Family Sale Price
$1,595,000
Median 2 Bedroom Sale Price
$933,000
Median 1 Bedroom Sale Price
$869,000
Average Price Per Sq Ft
$976
Number of Homes for Sale
44
Last 12 months Home Sales
104
Months of Supply
5.10
Median List Price
$1,605,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
27%
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