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3 bedsNew constructionWith a pool
Luxury Homes in Osterville, MA
26 listings

Luxury Homes in Osterville, MA

Luxury Homes in Osterville, MA

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24 of 26 Listings
Map

Luxury Homes in Osterville, MA

24 of 26 Listings

  1. 23 & 27 Swift Avenue — photo46

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas
Active

$1,485,000

3 bd · 3 ba · 1,844 sqft

23 & 27 Swift Avenue, Osterville, MA

Livia A Freitas Monteforte · Compass Massachusetts, LLC

  • 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

  • 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

  • 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

  • 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

  • 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

  • 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

  • 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

  • 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

  • 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

  • 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

  • 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

  • 140 Seapuit Road — photo89Active

    $3,500,000

    4 bd · 5 ba · 5,049 sqft

    140 Seapuit Road, Osterville, MA

    Rick Shechtman · Kinlin Grover Compass

  • 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

  • 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

  • 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

  • 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

  • 81 Osterville West Barnstable Road — photoPrice Reduced38Active

    $1,750,000

    3 bd · 3 ba · 3,084 sqft

    81 Osterville West Barnstable Road, Osterville, MA

    Paul E Grover · Berkshire Hathaway HomeServices Robert Paul Properties

  • 162 Main Street — photoPrice Reduced50Active

    $1,675,000

    3 bd · 3 ba · 2,048 sqft

    162 Main Street, Osterville, MA

    Kim A Gazal Santos · Property Cape Cod

  • 955 Main Street — photoPrice Reduced57Active

    $1,475,000

    3 bd · 2 ba · 1,765 sqft

    955 Main Street, Osterville, MA

    Karen D Lilly · Property Cape Cod

  • 93 Oyster Way — photoPrice Reduced27Active

    $4,045,500

    4 bd · 4 ba · 4,964 sqft

    93 Oyster Way, Osterville, MA

    Kelly Crosby · LandVest, Inc.

  • 168 Garrison Lane — photoPrice Reduced52Active

    $7,995,000

    5 bd · 6 ba · 7,565 sqft

    168 Garrison Lane, Osterville, MA

    Robert B Kinlin · Berkshire Hathaway HomeServices Robert Paul Properties

  • 14 Indian Trail — photoPrice Reduced43Active

    $9,850,000

    5 bd · 5 ba · 3,087 sqft

    14 Indian Trail, Osterville, MA

    Robert B Kinlin · Berkshire Hathaway HomeServices Robert Paul Properties

  • 440 Grand Island Drive — photoPrice Reduced68Active

    $7,250,000

    7 bd · 11 ba · 11,546 sqft

    440 Grand Island Drive, Osterville, MA

    Robert B Kinlin · Berkshire Hathaway HomeServices Robert Paul Properties

  • 12

    Explore Osterville homes

    By price

    • Under $300K
    • Under $500K
    • Under $700K
    • Luxury

    By bedrooms

    • 2 beds
    • 3 beds
    • 4 beds
    • 5 beds

    By type

    • Single family
    • Townhomes
    • Condos
    • Manufactured homes
    • Multi-family homes
    • Co-ops

    By feature

    • New construction
    • With a pool
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #1000018

    Call Thomas

    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.

    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.

    Osterville, MA community profile

    Area
    8.2 sq. mi.

    Source: HJN community data