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Chatham, MA Homes for Sale — Page 2 | Realty.com

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Homes for Sale in Chatham, MA

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16 of 86 Listings

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16 of 86 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

Price Reduced39Active
$8,950,000
4 bd · 3 ba · 1,738 sqft
166 Shore Road, Chatham, MA
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
28Active
$4,250,000
3 bd · 4 ba · 3,071 sqft
600 Fox Hill Road, Chatham, MA
Chris Rhinesmith · Compass Massachusetts, LLC

59Active
$9,995,000
3 bd · 3 ba · 3,079 sqft
153 Shore Road, Chatham, MA
Sarah Keith · eXp Realty, LLC
44Active
$2,390,000
4 bd · 4 ba · 4,066 sqft
55 Winterset Drive, Chatham, MA
Janet Stuart · Coldwell Banker Realty
39Active
$1,469,000
5 bd · 10 ba · 11,000 sqft
558 Fox Hill Road, Chatham, MA
Guthrie Schofield Group · Berkshire Hathaway HomeServices Robert Paul Properties
41Active
$5,900,000
4 bd · 5 ba · 4,394 sqft
95 Cotchpinicut, Chatham, MA
73Active
$5,900,000
4 bd · 5 ba · 4,394 sqft
95 Cotchpinicut Road, Chatham, MA
John B Burke · William Raveis Real Estate & Home Services
Price Reduced48Active
$995,000
3 bd · 3 ba · 3,384 sqft
65 Captain Kendrick Drive, Chatham, MA
Barbara P Garside · eXp Realty, LLC
49Active
$2,100,000
1 bd · 2 ba · 1,479 sqft
409 Main Street, Chatham, MA
Rick Smith · Gibson Sotheby's International Realty
29Active
$6,500,000
10 bd · 10 ba · 7,658 sqft
150-154 Cross Street, Chatham, MA
Chris Rhinesmith · Compass Massachusetts, LLC
1Active
$5,900,000
6 bd · 8 ba · 6,183 sqft
50 Sylvan Way, Chatham, MA
Price Reduced40Active
$1,250,000
3 bd · 2 ba · 2,176 sqft
35 Duncan Lane, Chatham, MA
Price Reduced41Active
$4,995,000
4 bd · 4 ba · 2,932 sqft
56 Stage Island Road, Chatham, MA
Price Reduced42Active
$1,899,000
3 bd · 3 ba · 3,514 sqft
70 Uncle Deane's Rd, Chatham, MA
47Active
$4,950,000
4 bd · 5 ba · 5,371 sqft
15 Bay Lane, Chatham, MA
Chris Rhinesmith · Compass Massachusetts, LLC

1 2 3 4

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: 2026-09-03 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

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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: 2026-09-03 07:05:00 UTC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

New construction
With a pool

Nearby areas

ZIP codes

02633 (77)
02601 (65)
02631 (65)
02664 (55)
02642 (53)
02675 (53)
02653 (50)
02673 (48)

Cities

Barnstable (81)
Dennis (74)
Yarmouth (72)
Brewster (65)
Eastham (52)
Orleans (52)
Wellfleet (47)
Harwich (45)

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.

Nearby areas

ZIP codes

02633 (77)
02601 (65)
02631 (65)
02664 (55)
02642 (53)
02675 (53)
02653 (50)
02673 (48)

Cities

Barnstable (81)
Dennis (74)
Yarmouth (72)
Brewster (65)
Eastham (52)
Orleans (52)
Wellfleet (47)
Harwich (45)