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3 beds
Luxury Homes in Chatham, MA
74 listings

Luxury Homes in Chatham, MA

Luxury Homes in Chatham, MA

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15 of 74 Listings
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Luxury Homes in Chatham, MA

15 of 74 Listings

  1. 153 Shore Rd — photoNew38

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas
Active

$9,495,000

3 bd · 3 ba · 3,079 sqft

153 Shore Rd, Chatham, MA

Sarah Keith · eXp Realty LLC

  • 789 Riverview Drive — photoNew42Active

    $1,175,000

    2 bd · 3 ba · 1,764 sqft

    789 Riverview Drive, Chatham, MA

    Timothy Bailey · John C. Ricotta & Associates, Inc.

  • 160 Woodland Way — photo4Active

    $5,800,000

    3 bd · 6 ba · 4,902 sqft

    160 Woodland Way, Chatham, MA

    Chris Rhinesmith · Compass

  • 200 Crows Pond Road — photo5Active

    $6,495,000

    5 bd · 6 ba · 4,588 sqft

    200 Crows Pond Road, Chatham, MA

    Chris Rhinesmith · Compass

  • 312 Round Cove Road — photoOpen house Sun, Oct 25 · 12:00 PM72Active

    $2,199,000

    3 bd · 3 ba · 2,848 sqft

    312 Round Cove Road, Chatham, MA

    Guthrie Schofield Group · Berkshire Hathaway HomeServices Robert Paul Properties

  • 112 Soundview Ave — photo27Active

    $1,415,000

    3 bd · 3 ba · 1,920 sqft

    112 Soundview Ave, Chatham, MA

    Dawn Marie Boynton · Berkshire Hathaway HomeServices Robert Paul Properties

  • 764 Riverview Drive — photo42Active

    $1,650,000

    3 bd · 3 ba · 1,902 sqft

    764 Riverview Drive, Chatham, MA

    Dawn Boynton · Berkshire Hathaway HomeServices Robert Paul Properties

  • 35 Crows Pond Road — photo27Active

    $3,995,000

    3 bd · 5 ba · 4,400 sqft

    35 Crows Pond Road, Chatham, MA

    Betsy Hargreaves · Gibson Sotheby's International Realty

  • 2118 Main St — photoPrice Reduced26Active

    $1,275,000

    4 bd · 3 ba · 2,670 sqft

    2118 Main St, Chatham, MA

    Marcie Smith · Gibson Sotheby's International Realty

  • Active

    $3,299,900

    3 bd · 4 ba · 3,157 sqft

    9 Bassing Harbor Road, Chatham, MA

    The Grattan Group · Christie's International Real Estate Atlantic Brokerage

  • 20 Stoughton Lane — photo32Active

    $2,285,000

    5 bd · 4 ba · 2,478 sqft

    20 Stoughton Lane, Chatham, MA

    Elaine Babineau Lomenzo · William Raveis Real Estate & Home Services

  • 12 Pond Street — photo91Active

    $6,875,000

    4 bd · 5 ba · 4,512 sqft

    12 Pond Street, Chatham, MA

    Guthrie Schofield Group · Berkshire Hathaway HomeServices Robert Paul Properties

  • 169 Tisquantum Road — photoOpen house Sun, Oct 25 · 2:30 PM80Active

    $4,495,000

    5 bd · 5 ba · 5,887 sqft

    169 Tisquantum Road, Chatham, MA

    Guthrie Schofield Group · Berkshire Hathaway HomeServices Robert Paul Properties

  • 288 Training Field Road — photo31Active

    $1,200,000

    2 bd · 3 ba · 2,380 sqft

    288 Training Field Road, Chatham, MA

    Karen Quinn · William Raveis Real Estate & Home Services

  • 20 Lords Pond Road — photoOpen house Sun, Oct 25 · 10:00 AM48Active

    $2,199,900

    3 bd · 3 ba · 2,576 sqft

    20 Lords Pond Road, Chatham, MA

    The Grattan Group · Christie's International Real Estate Atlantic Brokerage

  • 12…4

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    • 3 Bedroom Homes
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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.
    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: 2026-10-24 17:13:00 UTC

    Chatham, MA community profile

    Area
    16.7 sq. mi.

    Source: HJN community data

    Chatham housing market

    September 2026

    Chatham 12-month median sale price trend

    Selling at 97.2% of asking price

    Buyers here are paying below asking. MLS · 22 sales · as of Sep 28, 2026

    Homes that sold · County records, as of Sep 25, 2026

    Median sale price
    $2,075,000$1,060,000–$2,875,000 typical range
    Price per sq. ft.
    $1,012
    Sales
    17
    Paid in cash
    35.3%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 28, 2026

    Median list price
    $3,100,000
    Homes for sale
    38
    Median days on market
    20 days

    Price trend · Assessor repeat sales, as of Sep 30, 2026

    Year-over-year
    -17.4%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 9, 2026

    Median home size
    1,902 sq. ft.