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Recently Sold Oak Bluffs Homes

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  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /26

    $2,450,000

    Sold Jun 02, 2026

    23 Circuit Avenue Extension, Oak Bluffs, MA 02557

    • 3 Beds
    • 1 Bath
    • 1,336 Sq Ft
    • Built 1953

    Last Sold Summary

    • 6% Below List Price
    • $1,834/SF
    • 66 Days On Market

    Last Listing Agent Rene Ben David

    23 Circuit Avenue Extension, Oak Bluffs, MA 02557
  • /3

    $665,000

    Sold Mar 06, 2026

    2 Hope's Way Unit 31, Oak Bluffs, MA 02557

    • Land
    • 11,133 Sq Ft
    • $2,601,721 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 37 Days On Market

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    2 Hope's Way Unit 31, Oak Bluffs, MA 02557
  • /2

    $880,000

    Sold Oct 17, 2025

    5 Johns Way, Oak Bluffs, MA 02557

    • 3 Beds
    • 2 Baths
    • 1,365 Sq Ft
    • Built 1987

    Last Sold Summary

    • $645/SF
    • 0 Days On Market

    Current Estimated Value $1,273,903

    Last Listing Agent LINK Email Cache LINK

    5 Johns Way, Oak Bluffs, MA 02557
  • /30

    $1,050,000

    Sold Oct 06, 2025

    4 Quail Run Unit 2, Oak Bluffs, MA 02557

    • 2 Beds
    • 1.5 Baths
    • 1,323 Sq Ft
    • Built 1972

    Last Sold Summary

    • 11% Below List Price
    • $794/SF
    • 62 Days On Market

    Current Estimated Value $1,348,422

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    4 Quail Run Unit 2, Oak Bluffs, MA 02557
  • /36

    $2,900,000

    Sold Mar 30, 2026

    63 Bayes Hill Rd, Oak Bluffs, MA 02557

    • 4 Beds
    • 5 Baths
    • 5,165 Sq Ft
    • Built 1988

    Last Sold Summary

    • $561/SF
    • 35 Days On Market

    Current Estimated Value $3,833,462

    Last Listing Agent Casandra Hyland Sandpiper Realty, Inc.

    63 Bayes Hill Rd, Oak Bluffs, MA 02557
  • /23

    $1,800,000

    Sold Aug 26, 2025

    12 Martha's Park Rd, Oak Bluffs, MA 02557

    • 4 Beds
    • 1.5 Baths
    • 1,351 Sq Ft
    • Built 1910

    Last Sold Summary

    • 1% Below List Price
    • $1,332/SF
    • 0 Days On Market

    Current Estimated Value $2,281,072

    Last Listing Agent Michele Moore Island Real Estate

    12 Martha's Park Rd, Oak Bluffs, MA 02557
  • /12

    $860,000

    Sold Feb 09, 2026

    8 Hitchings Cir, Oak Bluffs, MA 02557

    • 2 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1985

    Last Sold Summary

    • 6% Below List Price
    • $698/SF
    • 22 Days On Market

    Last Listing Agent Peyton Wallace Studio Realty

    8 Hitchings Cir, Oak Bluffs, MA 02557
  • /19

    $980,000

    Sold Aug 11, 2025

    249 County Rd, Oak Bluffs, MA 02557

    • 1 Bed
    • 2 Baths
    • 1,401 Sq Ft
    • Built 2005

    Last Sold Summary

    • 7% Below List Price
    • $700/SF
    • 83 Days On Market

    Current Estimated Value $1,310,646

    Last Listing Agent Katherine Donahue Sandpiper Realty

    249 County Rd, Oak Bluffs, MA 02557
  • /2

    $825,000

    Sold Dec 03, 2025

    69 Summit Ave, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Built 1998

    Last Sold Summary

    • $661/SF
    • 1 Day On Market

    Current Estimated Value $1,093,126

    Last Listing Agent Susie Wallo Compass

    69 Summit Ave, Vineyard Haven, MA 02568
  • /40

    $650,000

    Sold Sep 10, 2025

    25 Oak Ave, Oak Bluffs, MA 02557

    • 2 Beds
    • 0.5 Baths
    • 759 Sq Ft
    • Built 1900

    Last Sold Summary

    • 4% Below List Price
    • $856/SF
    • 251 Days On Market

    Current Estimated Value $771,387

    Last Listing Agent Alisan Lohan-Conway Alisan Lohan-Conway Properties

    25 Oak Ave, Oak Bluffs, MA 02557
  • /40

    $1,600,000

    Sold Jan 06, 2026

    44 Tiffany Dr, Oak Bluffs, MA 02557

    • 4 Beds
    • 4 Baths
    • 3,927 Sq Ft
    • Built 1987

    Last Sold Summary

    • 24% Below List Price
    • $407/SF
    • 115 Days On Market

    Current Estimated Value $2,100,859

    Last Listing Agent Sheila Morse Island Real Estate

    44 Tiffany Dr, Oak Bluffs, MA 02557
  • /41

    $1,850,000

    Sold Aug 04, 2025

    26 Tia Anna Ln, Oak Bluffs, MA 02557

    • 3 Beds
    • 3 Baths
    • 2,210 Sq Ft
    • Built 1980

    Last Sold Summary

    • 7% Below List Price
    • $837/SF
    • 22 Days On Market

    Current Estimated Value $2,352,826

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    26 Tia Anna Ln, Oak Bluffs, MA 02557
  • /30

    $968,750

    Sold Jun 05, 2026

    28 Barling Ave, Vineyard Haven, MA 02568

    • 2 Beds
    • 1 Bath
    • 1,232 Sq Ft
    • Built 1981

    Last Sold Summary

    • 8% Below List Price
    • $786/SF
    • 206 Days On Market

    Current Estimated Value $983,733

    Last Listing Agent Michael Schweikert Ocean Park Realty Inc

    28 Barling Ave, Vineyard Haven, MA 02568
  • /20

    $1,000,000

    Sold Dec 12, 2025

    1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557

    • 2 Beds
    • 2.5 Baths
    • 2,128 Sq Ft
    • Built 2001

    Last Sold Summary

    • 9% Below List Price
    • $470/SF
    • 13 Days On Market

    Current Estimated Value $1,171,431

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

    1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557
  • /26

    $1,687,500

    Sold Jul 10, 2026

    103 Meadow View Rd, Oak Bluffs, MA 02557

    • 3 Beds
    • 2.5 Baths
    • 2,862 Sq Ft
    • Built 1988

    Last Sold Summary

    • 4% Below List Price
    • $590/SF
    • 31 Days On Market

    Current Estimated Value $1,750,048

    Last Listing Agent Alyson Parker Karen M. Overtoom R.E.

    103 Meadow View Rd, Oak Bluffs, MA 02557
  • /21

    $895,000

    Sold May 13, 2026

    22 Montgomery Square, Oak Bluffs, MA 02557

    • 3 Beds
    • 1 Bath
    • 931 Sq Ft
    • Built 1870

    Last Sold Summary

    • $961/SF
    • 7 Days On Market

    Current Estimated Value $910,304

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    22 Montgomery Square, Oak Bluffs, MA 02557
  • /34

    $3,746,925

    Sold Nov 14, 2025

    39 Sengekontacket Rd, Edgartown, MA 02539

    • 4 Beds
    • 3.5 Baths
    • 2,861 Sq Ft
    • Built 1974

    Last Sold Summary

    • 8% Below List Price
    • $1,310/SF
    • 114 Days On Market

    Current Estimated Value $3,668,475

    Last Listing Agent Jayne Isford Ocean Park Realty Inc

    39 Sengekontacket Rd, Edgartown, MA 02539
  • /37

    $1,705,000

    Sold Mar 24, 2026

    2 Farm Path, Oak Bluffs, MA 02557

    • 4 Beds
    • 3 Baths
    • 3,058 Sq Ft
    • Built 1992

    Last Sold Summary

    • 15% Below List Price
    • $558/SF
    • 347 Days On Market

    Current Estimated Value $2,268,423

    Last Listing Agent Sean Federowicz Landmarks at TODAY Real Estate

    2 Farm Path, Oak Bluffs, MA 02557
  • /20

    $1,050,000

    Sold Jun 29, 2026

    12 Wheelhouse Way, Oak Bluffs, MA 02557

    • 3 Beds
    • 1.5 Baths
    • 1,487 Sq Ft
    • Built 1999

    Last Sold Summary

    • 4% Below List Price
    • $706/SF
    • 125 Days On Market

    Current Estimated Value $1,086,936

    Last Listing Agent Dawn Bellante Sandpiper Realty, Inc.

    12 Wheelhouse Way, Oak Bluffs, MA 02557
  • /2

    $1,125,000

    Sold Jan 23, 2026

    96 Manchester Ave, Oak Bluffs, MA 02557

    • 3 Beds
    • 2 Baths
    • 3,192 Sq Ft
    • Built 1999

    Last Sold Summary

    • 2% Below List Price
    • $352/SF
    • 7 Days On Market

    Current Estimated Value $1,398,636

    Last Listing Agent Michele Moore Island Real Estate

    96 Manchester Ave, Oak Bluffs, MA 02557
  • /13

    $1,187,500

    Sold Jun 12, 2026

    54 Columbian Ave, Oak Bluffs, MA 02557

    • 4 Beds
    • 2 Baths
    • 1,764 Sq Ft
    • Built 1989

    Last Sold Summary

    • 8% Below List Price
    • $673/SF
    • 93 Days On Market

    Current Estimated Value $1,270,421

    Last Listing Agent Katrina Lima Donnelly + Co

    54 Columbian Ave, Oak Bluffs, MA 02557
  • /24

    $3,050,000

    Sold Apr 15, 2026

    35 New York Ave, Oak Bluffs, MA 02568

    • 7 Beds
    • 5 Baths
    • 3,880 Sq Ft
    • Built 1884

    Last Sold Summary

    • 13% Below List Price
    • $786/SF
    • 23 Days On Market

    Last Listing Agent Emma Kennedy Sandpiper Realty, Inc.

    35 New York Ave, Oak Bluffs, MA 02568
  • /16

    $970,000

    Sold Dec 08, 2025

    6 Sachem Way, Oak Bluffs, MA 02557

    • 3 Beds
    • 1 Bath
    • 1,546 Sq Ft
    • Built 1973

    Last Sold Summary

    • 8% Above List Price
    • $627/SF
    • 4 Days On Market

    Current Estimated Value $1,300,287

    Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's

    6 Sachem Way, Oak Bluffs, MA 02557
  • /22

    $2,899,000

    Sold Oct 01, 2025

    78 Winemack St, Oak Bluffs, MA 02557

    • 4 Beds
    • 2 Baths
    • 1,889 Sq Ft
    • Built 1956

    Last Sold Summary

    • $1,535/SF
    • 0 Days On Market

    Current Estimated Value $2,993,612

    Last Listing Agent Susan Austin Austin R.E. Properties of MV

    78 Winemack St, Oak Bluffs, MA 02557
  • /20

    $1,295,000

    Sold Sep 05, 2025

    2 Upper Douglas Ln, Oak Bluffs, MA 02557

    • 4 Beds
    • 2 Baths
    • 1,584 Sq Ft
    • Built 1988

    Last Sold Summary

    • 3% Below List Price
    • $818/SF
    • 5 Days On Market

    Current Estimated Value $1,746,019

    Last Listing Agent Lynn Buder Sandpiper Realty

    2 Upper Douglas Ln, Oak Bluffs, MA 02557
  • /42

    $1,700,000

    Sold Nov 03, 2025

    35 Tower Ridge Rd, Oak Bluffs, MA 02557

    • 3 Beds
    • 4 Baths
    • 2,558 Sq Ft
    • Built 1986

    Last Sold Summary

    • 20% Below List Price
    • $665/SF
    • 106 Days On Market

    Current Estimated Value $2,206,611

    Last Listing Agent Katherine Donahue Sandpiper Realty

    35 Tower Ridge Rd, Oak Bluffs, MA 02557
  • /30

    $815,000

    Sold Nov 14, 2025

    17 Siloam Ave, Oak Bluffs, MA 02557

    • 3 Beds
    • 1 Bath
    • 907 Sq Ft
    • Built 1870

    Last Sold Summary

    • 2% Below List Price
    • $899/SF
    • 100 Days On Market

    Current Estimated Value $805,256

    Last Listing Agent Marilyn Moses Ocean Park Realty Inc

    17 Siloam Ave, Oak Bluffs, MA 02557
  • /25

    $1,300,000

    Sold Dec 18, 2025

    23 Laurel Ave, Oak Bluffs, MA 02557

    • 4 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Built 1900

    Last Sold Summary

    • 13% Below List Price
    • $1,042/SF
    • 64 Days On Market

    Current Estimated Value $1,662,702

    Last Listing Agent Sandra Grymes Martha's Vineyard Island-Wide Realty

    23 Laurel Ave, Oak Bluffs, MA 02557
  • /24

    $2,125,000

    Sold Oct 30, 2025

    30 Sengekontacket Rd, Oak Bluffs, MA 02557

    • 4 Beds
    • 3 Baths
    • 2,262 Sq Ft
    • Built 1978

    Last Sold Summary

    • 11% Below List Price
    • $939/SF
    • 265 Days On Market

    Current Estimated Value $2,847,712

    Last Listing Agent Cassie Courtney Wallace & Co. Sotheby's

    30 Sengekontacket Rd, 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

    • 30% Below List Price
    • $661/SF
    • 176 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

Showing Results 1 - 40, Page 1 of 3

Frequently Asked Questions

What is the average time to sell a house in Oak Bluffs, MA?
The houses for sale in Oak Bluffs, MA spend an average of 85 days on the market.
What is the number of active homes for sale in Oak Bluffs, MA?
There are 52 active homes for sale in Oak Bluffs, MA.

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
$1,021
Number of Homes for Sale
52
Last 12 months Home Sales
118
Months of Supply
5.30
Median List Price
$1,595,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
30%
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