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Luxury Homes in Chatham, MA
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3 beds

Luxury Homes in Chatham, MA

Luxury Homes in Chatham, MA

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16 of 72 Listings
Map

Luxury Homes in Chatham, MA

16 of 72 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas
  1. Open house Sat, Oct 10 · 2:00 PMActive

    $1,415,000

    3 bd · 3 ba · 1,920 sqft

    112 Soundview Avenue, Chatham, MA

    Dawn Boynton · Berkshire Hathaway HomeServices Robert Paul Properties

  2. 764 Riverview Dr — photoOpen house Sat, Oct 10 · 10:30 AM24Active

    $1,650,000

    3 bd · 3 ba · 1,902 sqft

    764 Riverview Dr, Chatham, MA

    Sharon Mabile · Berkshire Hathaway HomeServices Robert Paul Properties

  3. 35 Crows Pond Rd — photoOpen house Sat, Oct 10 · 12:30 PM29Active

    $3,995,000

    3 bd · 5 ba · 4,400 sqft

    35 Crows Pond Rd, Chatham, MA

    Betsy Hargreaves · Gibson Sotheby's International Realty

  4. 2118 Main Street — photoOpen house Sun, Oct 11 · 10:30 AM33Active

    $1,399,000

    4 bd · 3 ba · 2,670 sqft

    2118 Main Street, Chatham, MA

    Marcie Smith · Gibson Sotheby's International Realty

  5. 20 Stoughton Lane — photoOpen house Sat, Oct 10 · 11:00 AM32Active

    $2,285,000

    5 bd · 4 ba · 2,478 sqft

    20 Stoughton Lane, Chatham, MA

    Elaine Babineau Lomenzo · William Raveis Real Estate & Home Services

  6. 26 Chatham Heights Road — photo62Active

    $3,100,000

    3 bd · 4 ba · 4,053 sqft

    26 Chatham Heights Road, Chatham, MA

    Chris Rhinesmith · Compass Massachusetts, LLC

  7. 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

  8. 169 Tisquantum Road — photoOpen house Sat, Oct 10 · 1:00 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

  9. 288 Training Field Road — photoOpen house Sat, Oct 10 · 10:00 AM31Active

    $1,200,000

    2 bd · 3 ba · 2,380 sqft

    288 Training Field Road, Chatham, MA

    Karen Quinn · William Raveis Real Estate & Home Services

  10. 20 Lords Pond Road — photo48Active

    $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

  11. 20 Lords Pond Lane — photo42Active

    $2,199,900

    3 bd · 4 ba · 2,576 sqft

    20 Lords Pond Lane, Chatham, MA

    Andrew Grattan · Christie's International Real Estate Atlantic Brokerage

  12. 39 Jedidiah Way — photo43Active

    $1,495,000

    2 bd · 2 ba · 1,810 sqft

    39 Jedidiah Way, Chatham, MA

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

  13. Open house Sat, Oct 10 · 1:00 PMActive

    $5,950,000

    4 bd · 4 ba · 2,688 sqft

    5 Hillcrest Lane, Chatham, MA

    Emily A Boynton · BMTF Partnership

  14. 22 Moonpenny Lane — photoOpen house Sat, Oct 10 · 11:00 AM54Active

    $4,250,000

    4 bd · 5 ba · 4,298 sqft

    22 Moonpenny Lane, Chatham, MA

    Lori Jurkowski · Christie's International Real Estate Atlantic Brokerage

  15. Active

    $4,995,000

    5 bd · 6 ba · 4,763 sqft

    65 Harbor View Road, Chatham, MA

    Chris Rhinesmith · Compass Massachusetts, LLC

  16. 72 Ridgevale Rd So — photoOpen house Sat, Oct 10 · 10:30 AM42Active

    $2,499,000

    2 bd · 2 ba · 1,547 sqft

    72 Ridgevale Rd So, Chatham, MA

    Shane Masaschi · Compass

123

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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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Listing information ©2026 MLS Property Information Network, Inc®. All Rights Reserved. Last Updated: 2026-10-09 14:34:00 UTC
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #1000018

    Call Thomas

    Chatham, MA community profile

    Area
    16.7 sq. mi.

    Source: HJN community data

    Chatham housing market

    September 2026 · This period is still settling

    Selling at 97.2% of asking price

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

    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
    22 days

    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.