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

Single-Family Homes in Osterville, MA

Single-Family Homes in Osterville, MA

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24 of 35 Listings
Map

Single-Family Homes in Osterville, MA

24 of 35 Listings

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TO

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas
  1. 82 Falling Leaf Lane — photoNew43Active

    $990,000

    3 bd · 3 ba · 2,116 sqft

    82 Falling Leaf Lane, Osterville, MA

    John R Peacock · Sotheby's International Realty

  2. 23 & 27 Swift Avenue — photo46Active

    $1,485,000

    3 bd · 3 ba · 1,844 sqft

    23 & 27 Swift Avenue, Osterville, MA

    Livia A Freitas Monteforte · Compass Massachusetts, LLC

  3. 175 Hickory Hill Circle — photo40Active

    $1,250,000

    3 bd · 3 ba · 3,355 sqft

    175 Hickory Hill Circle, Osterville, MA

    Michelle Curran · Coastal Real Estate Advisors LLC

  4. 329 Swift Avenue — photo37Active

    $799,000

    3 bd · 2 ba · 1,856 sqft

    329 Swift Avenue, Osterville, MA

    Lauren T Scioletti · Sotheby's International Realty

  5. 112 Osterville West Barnstable Road — photoPrice Reduced32Active

    $629,000

    3 bd · 1 ba · 1,156 sqft

    112 Osterville West Barnstable Road, Osterville, MA

    Karen B Rozell · Kinlin Grover Compass

  6. 51 Falling Leaf Lane — photoPrice Reduced38Active

    $1,075,000

    2 bd · 2 ba · 2,010 sqft

    51 Falling Leaf Lane, Osterville, MA

    Sam Amara · William Raveis Real Estate & Home Services

  7. 111 Westwind Circle — photo37Active

    $795,000

    3 bd · 2 ba · 1,248 sqft

    111 Westwind Circle, Osterville, MA

    W&W Boston/Cape Cod Connection · Compass Massachusetts, LLC

  8. 72 Hathaway Rd Road — photo24Active

    $2,700,000

    4 bd · 3 ba · 2,050 sqft

    72 Hathaway Rd Road, Osterville, MA

    Tom P Foley · The Foley Company

  9. 47 Sunset Point — photo22Active

    $18,500,000

    7 bd · 11 ba · 10,104 sqft

    47 Sunset Point, Osterville, MA

    Paul E Grover · Berkshire Hathaway HomeServices Robert Paul Properties

  10. 35 Blue Heron Drive — photo40Active

    $4,250,000

    3 bd · 4 ba · 2,721 sqft

    35 Blue Heron Drive, Osterville, MA

    Tom P Foley · The Foley Company

  11. 313 Bridge Street — photo47Active

    $4,950,000

    5 bd · 8 ba · 5,970 sqft

    313 Bridge Street, Osterville, MA

    Paul E Grover · Berkshire Hathaway HomeServices Robert Paul Properties

  12. 177 Bayview Circle — photoPrice Reduced38Active

    $829,900

    3 bd · 3 ba · 2,100 sqft

    177 Bayview Circle, Osterville, MA

    Derek J Greene · The Greene Realty Group

  13. 25 Oyster Way — photoPrice Reduced56Active

    $8,800,000

    5 bd · 6 ba · 7,157 sqft

    25 Oyster Way, Osterville, MA

    Robert B Kinlin · Berkshire Hathaway HomeServices Robert Paul Properties

  14. 22 Scudder Road — photoPrice Reduced59Active

    $4,795,000

    5 bd · 7 ba · 4,100 sqft

    22 Scudder Road, Osterville, MA

    Sean Dacey · Coldwell Banker Realty

  15. 63 Main Street — photo48Active

    $8,625,000

    7 bd · 8 ba · 9,011 sqft

    63 Main Street, Osterville, MA

    Christa Zevitas · Berkshire Hathaway HomeServices Robert Paul Properties

  16. 114 King Arthur Drive — photoPrice Reduced30Active

    $744,000

    3 bd · 2 ba · 1,426 sqft

    114 King Arthur Drive, Osterville, MA

    Christine L Case · C. Case Realty, LLC

  17. 420 Starboard Lane — photo46Active

    $1,995,000

    4 bd · 3 ba · 2,636 sqft

    420 Starboard Lane, Osterville, MA

    Jack B Cotton, Jr · Sotheby's International Realty

  18. 48 Starboard Lane — photoPrice Reduced49Active

    $11,500,000

    6 bd · 8 ba · 8,387 sqft

    48 Starboard Lane, Osterville, MA

    Paul E Grover · Berkshire Hathaway HomeServices Robert Paul Properties

  19. 140 Seapuit Road — photo89Active

    $3,500,000

    4 bd · 5 ba · 5,049 sqft

    140 Seapuit Road, Osterville, MA

    Rick Shechtman · Kinlin Grover Compass

  20. 156 E Bay Road — photo60Active

    $3,450,000

    4 bd · 5 ba · 3,924 sqft

    156 E Bay Road, Osterville, MA

    Barbara Corcoran · William Raveis Real Estate & Home Services

  21. 179 Pineleigh Path — photo28Active

    $5,950,000

    5 bd · 8 ba · 8,740 sqft

    179 Pineleigh Path, Osterville, MA

    Paul E Grover · Berkshire Hathaway HomeServices Robert Paul Properties

  22. 46 Great Bay Road — photoPrice Reduced52Active

    $7,500,000

    3 bd · 6 ba · 4,831 sqft

    46 Great Bay Road, Osterville, MA

    Chuck Tuttle · William Raveis Real Estate & Home Services

  23. 55 Seth Goodspeed Way — photoPrice Reduced49Active

    $649,000

    2 bd · 2 ba · 1,040 sqft

    55 Seth Goodspeed Way, Osterville, MA

    Donna Christopher · Sotheby's International Realty

  24. 12 Cockachoiset Lane — photo41Active

    $2,950,000

    3 bd · 3 ba · 3,178 sqft

    12 Cockachoiset Lane, Osterville, MA

    Robert B Kinlin · Berkshire Hathaway HomeServices Robert Paul Properties

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.
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #1000018

    Call Thomas

    Osterville, MA community profile

    Area
    8.2 sq. mi.

    Source: HJN community data

    Osterville housing market

    August 2026 · This period is still settling

    Homes on the market · MLS, as of Aug 31, 2026

    Median list price
    $1,750,000
    Homes for sale
    41

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 12, 2026

    Median home size
    1,980 sq. ft.