Luxury Homes in Chatham, MA

74 listings

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3 beds New construction With a pool

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18 of 74 Listings

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Luxury Homes in Chatham, MA

18 of 74 Listings

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Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

16Active
$4,000,000
5 bd · 3 ba · 2,303 sqft
64 Harbor View Road, Chatham, MA
The Bohman Hartung Group · Gibson Sotheby's International Realty
42Active
$2,600,000
3 bd · 3 ba · 2,160 sqft
10 Mill Hill Lane, Chatham, MA
42Active
$2,995,000
3 bd · 4 ba · 2,405 sqft
5 Kingsbury Way, Chatham, MA
42Active
$4,950,000
3 bd · 4 ba · 3,441 sqft
103 Aunt Nabby's Lane, Chatham, MA
Price Reduced76Active
$6,990,000
5 bd · 6 ba · 4,248 sqft
108 Queen Anne Road, Chatham, MA
Dawn Boynton · Berkshire Hathaway HomeServices Robert Paul Properties
48Active
$1,340,000
3 bd · 3 ba · 2,155 sqft
116 Vineyard Avenue, Chatham, MA
Allison Beavan · William Raveis Real Estate & Home Services
49Active
$1,495,000
3 bd · 2 ba · 1,415 sqft
87 Cranberry Lane, Chatham, MA
David C Carter · Compass Massachusetts, LLC
42Active
$1,375,000
2 bd · 3 ba · 2,306 sqft
1114 Orleans Rd #8, Chatham, MA
Price Reduced22Active
$1,795,000
2 bd · 2 ba · 1,398 sqft
71 Rowland Drive, Chatham, MA
Price Reduced42Active
$1,695,000
2 bd · 4 ba · 2,331 sqft
43 Tobey Turtle, Chatham, MA
Price Reduced47Active
$1,695,000
2 bd · 4 ba · 2,331 sqft
43 Tobey Turtle Road, Chatham, MA
Timothy P Bailey · John C Ricotta & Assoc.
Price Reduced55Active
$1,175,000
3 bd · 3 ba · 1,884 sqft
190 Heritage Lane, Chatham, MA
Shane K Masaschi · Compass
Price Reduced100Active
$8,950,000
4 bd · 3 ba · 1,738 sqft
166 Shore Road, Chatham, MA
Guthrie Schofield Group · Berkshire Hathaway HomeServices Robert Paul Properties
2Active
$4,500,000
4 bd · 5 ba · 4,689 sqft
66 Ethelma Drive, Chatham, MA
Guthrie Schofield Group · Berkshire Hathaway HomeServices Robert Paul Properties
24Active
$4,250,000
3 bd · 4 ba · 3,071 sqft
600 Fox Hill Rd, Chatham, MA

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: 2026-09-07 07:05:00 UTC

Chatham housing market

July 2026

Selling at 98.2% of asking price

Buyers here are paying below asking. MLS · 17 sales · as of Jul 31, 2026

Homes that sold · County records, as of Jul 31, 2026

Median sale price: $1,495,000$1,050,000–$2,722,500 typical range
Price per sq. ft.: $662
Sales: 19
Paid in cash: 57.9%

Homes on the market · MLS, as of Jul 21, 2026–Jul 31, 2026

Median list price: $2,995,000
Homes for sale: 54
Median days on market: 12 days

Price trend · Assessor repeat sales, as of Jul 31, 2026

Year-over-year: 3.1%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 14, 2026

Median home size: 1,890 sq. ft.

Chatham, MA community profile

Area: 16.7 sq. mi.

Source: HJN community data

Explore Chatham homes

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: 2026-09-07 07:05:00 UTC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

Co-ops

Your local brokerage

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

July 2026

Selling at 98.2% of asking price

Buyers here are paying below asking. MLS · 17 sales · as of Jul 31, 2026

Homes that sold · County records, as of Jul 31, 2026

Median sale price: $1,495,000$1,050,000–$2,722,500 typical range
Price per sq. ft.: $662
Sales: 19
Paid in cash: 57.9%

Homes on the market · MLS, as of Jul 21, 2026–Jul 31, 2026

Median list price: $2,995,000
Homes for sale: 54
Median days on market: 12 days

Price trend · Assessor repeat sales, as of Jul 31, 2026

Year-over-year: 3.1%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 14, 2026

Median home size: 1,890 sq. ft.

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Your local brokerage

Listing data & MLS disclosures

Chatham housing market

Homes that sold · County records, as of Jul 31, 2026

Homes on the market · MLS, as of Jul 21, 2026–Jul 31, 2026

Price trend · Assessor repeat sales, as of Jul 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 14, 2026

Chatham, MA community profile

Explore Chatham homes

Listing data & MLS disclosures

Your local brokerage

Your local brokerage

Chatham, MA community profile

Chatham housing market

Homes that sold · County records, as of Jul 31, 2026

Homes on the market · MLS, as of Jul 21, 2026–Jul 31, 2026

Price trend · Assessor repeat sales, as of Jul 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 14, 2026