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Single-Family Homes in Oak Bluffs, MA
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3 bedsNew constructionWith a pool

Single-Family Homes in Oak Bluffs, MA

Single-Family Homes in Oak Bluffs, MA

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23 of 27 Listings
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Single-Family Homes in Oak Bluffs, MA

23 of 27 Listings

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Thomas O'Leary

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  1. 234 County Road — photo12Active

    $1,375,000

    5 bd · 2 ba · 1,952 sqft

    234 County Road, Oak Bluffs, MA

    Emma Kennedy · Sandpiper Realty, Inc.

  2. 20 Hidden Cove — photoPrice Reduced39Active

    $1,595,000

    4 bd · 3 ba · 1,898 sqft

    20 Hidden Cove, Oak Bluffs, MA

    Jennifer DaSilva · Compass

  3. 61 Canonicus Ave — photo41Active

    $2,200,000

    3 bd · 3 ba · 2,420 sqft

    61 Canonicus Ave, Oak Bluffs, MA

  4. 68 Front Street — photo36Active

    $1,755,000

    3 bd · 3 ba · 2,815 sqft

    68 Front Street, Oak Bluffs, MA

  5. 267 Barnes Road — photo42Active

    $4,395,000

    3 bd · 6 ba · 4,046 sqft

    267 Barnes Road, Oak Bluffs, MA

  6. 31 Temahigan Avenue — photo9Active

    $2,678,000

    4 bd · 4 ba · 2,363 sqft

    31 Temahigan Avenue, Oak Bluffs, MA

    J.R. C Ross (J.R.) · Portfolio Properties

  7. 27 Beach Road — photo31Active

    $2,995,000

    5 bd · 2 ba · 1,731 sqft

    27 Beach Road, Oak Bluffs, MA

    Bonnie J Pierce · Wallace & Co. Sotheby's International Realty

  8. 11 Stanley Street — photo17Active

    $1,255,000

    3 bd · 2 ba · 912 sqft

    11 Stanley Street, Oak Bluffs, MA

    Lisa Lucier · Anchor Realty of MV

  9. 2 Winemack Street — photoPrice Reduced28Active

    $1,095,000

    3 bd · 2 ba · 2,173 sqft

    2 Winemack Street, Oak Bluffs, MA

    Rene A Ben David · Ocean Park Realty, Inc.

  10. 323 County Road — photoPrice Reduced30Active

    $1,095,000

    1 bd · 2 ba · 1,428 sqft

    323 County Road, Oak Bluffs, MA

    Nancy J Beckwith · Anchor Realty of MV

  11. 43 Sengekontacket Road — photoPrice Reduced25Active

    $5,495,000

    3 bd · 3 ba · 2,234 sqft

    43 Sengekontacket Road, Oak Bluffs, MA

    Peyton Wallace · Studio Realty LLC

  12. 59 Tuckernuck Ave — photoPrice Reduced41Active

    $2,595,000

    4 bd · 3 ba · 1,858 sqft

    59 Tuckernuck Ave, Oak Bluffs, MA

    Jennifer DaSilva · Compass

  13. 14 High Meadow Ln — photo39Active

    $1,750,000

    3 bd · 3 ba · 1,932 sqft

    14 High Meadow Ln, Oak Bluffs, MA

  14. 40 Hidden Cove Road Unit 2 #2 — photoPrice Reduced28Active

    $1,495,000

    3 bd · 4 ba · 2,739 sqft

    40 Hidden Cove Road Unit 2 #2, Oak Bluffs, MA

    Rose Ryley · Wallace & Co. Sotheby's International Realty

  15. 11 Beach Road — photo22Active

    $1,745,000

    2 bd · 1 ba · 561 sqft

    11 Beach Road, Oak Bluffs, MA

    Lisa Lucier · Anchor Realty of MV

  16. 60R Carol Lane — photoPrice Reduced1Active

    $785,000

    2 bd · 1 ba · 624 sqft

    60R Carol Lane, Oak Bluffs, MA

    Michele A Moore · Island Real Estate

  17. 27 Double Ox Rd — photo12Active

    $3,400,000

    3 bd · 5 ba · 3,260 sqft

    27 Double Ox Rd, Oak Bluffs, MA

  18. 47 Winemack Street — photoPrice Reduced18Active

    $1,100,000

    3 bd · 2 ba · 1,302 sqft

    47 Winemack Street, Oak Bluffs, MA

    Lisa Lucier · Anchor Realty of MV

  19. 7 Ploughshare Lane — photoPrice Reduced33Active

    $1,499,000

    3 bd · 3 ba · 1,645 sqft

    7 Ploughshare Lane, Oak Bluffs, MA

  20. 44 Tiffany Dr — photoPrice Reduced15Active

    $2,595,000

    4 bd · 5 ba · 3,927 sqft

    44 Tiffany Dr, Oak Bluffs, MA

  21. 15 Tamarack Lane — photoPrice Reduced42Active

    $4,600,000

    6 bd · 6 ba · 3,998 sqft

    15 Tamarack Lane, Oak Bluffs, MA

  22. 19 Perkins Avenue — photo14Active

    $825,000

    2 bd · 1 ba · 985 sqft

    19 Perkins Avenue, Oak Bluffs, MA

  23. 33 Vineyard Ave — photoPrice Reduced32Active

    $1,875,000

    3 bd · 3 ba · 1,431 sqft

    33 Vineyard Ave, Oak Bluffs, MA

12

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Listing data & MLS disclosures

Cape Cod & Islands Association of REALTORS
The data relating to real estate for sale on this site comes from the Broker Reciprocity of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than the brokerage firm owning this website are marked with the IDX Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor the brokerage firm owning this website shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. All properties are subject to prior sale, changes, or withdrawal. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright © 2026 Cape Cod & Islands Multiple Listing Service, Inc. All Rights Reserved.
MLS Property Information Network (MLS PIN)
The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
Listing information ©2026 MLS Property Information Network, Inc®. All Rights Reserved. Last Updated: 2026-09-28 14:48:00 UTC
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    Your local brokerage

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    Thomas O'Leary

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    Call Thomas

    Oak Bluffs, MA community profile

    Area
    0.6 sq. mi.

    Source: HJN community data

    Oak Bluffs housing market

    August 2026 · This period is still settling

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 5, 2026

    Median home size
    1,454 sq. ft.