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Chatham, MA Homes for Sale — Page 3 | Realty.com

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Homes for Sale in Chatham, MA

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17 of 83 Listings

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17 of 83 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

24Active
$4,250,000
3 bd · 4 ba · 3,071 sqft
600 Fox Hill Road, Chatham, MA
Chris Rhinesmith · Compass Massachusetts, LLC
Price ReducedOpen house Sat, Oct 24 · 10:30 AM35Active
$2,295,000
4 bd · 4 ba · 4,072 sqft
55 Winterset Drive, Chatham, MA
Janet Stuart · Coldwell Banker Realty - Concord
36Active
$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

69Active
$5,900,000
4 bd · 5 ba · 4,394 sqft
95 Cotchpinicut Road, Chatham, MA
John B Burke · William Raveis Real Estate & Home Services
41Active
$5,900,000
4 bd · 5 ba · 4,394 sqft
95 Cotchpinicut, Chatham, MA
John Burke · William Raveis Chatham
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
Guthrie Schofield Group · Berkshire Hathaway HomeServices Robert Paul Properties
Price Reduced38Active
$1,195,000
3 bd · 2 ba · 2,176 sqft
35 Duncan Lane, Chatham, MA
John Habeeb · Alliance Realty Advisors, Inc.
Price Reduced42Active
$4,995,000
4 bd · 4 ba · 2,932 sqft
56 Stage Island Road, Chatham, MA
James Lowenstern · eXp Realty LLC
Price ReducedOpen house Sat, Oct 24 · 11:00 AM42Active
$1,599,000
3 bd · 3 ba · 3,514 sqft
70 Uncle Deane's Rd, Chatham, MA
Patrick Davison · Shining Sea Realty
Price ReducedOpen house Sat, Oct 24 · 1:00 PM78Active
$2,699,000
3 bd · 3 ba · 2,205 sqft
336 Stage Island Road, Chatham, MA
Guthrie Schofield Group · Berkshire Hathaway HomeServices Robert Paul Properties
Price Reduced51Active
$5,450,000
5 bd · 5 ba · 4,060 sqft
70 Judges Way, Chatham, MA
Lori Jurkowski · Christie's International Real Estate Atlantic Brokerage
20Active
$12,999,900
4 bd · 7 ba · 6,234 sqft
157 Bridge Street, Chatham, MA
The Grattan Group · Christie's International Real Estate Atlantic Brokerage
Price Reduced90Active
$5,850,000
5 bd · 6 ba · 5,620 sqft
15 Windy Hill Way, Chatham, MA
Timothy P Bailey · John C Ricotta & Assoc.
34Active
$4,500,000
4 bd · 4 ba · 2,850 sqft
346 Morris Island Road, Chatham, MA
Chris Rhinesmith · Compass Massachusetts, LLC
Price Reduced60Active
$1,175,000
3 bd · 2 ba · 2,278 sqft
243 Crowell Road, Chatham, MA
Michael Hall · William Raveis Real Estate & Home Services

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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: 2026-10-21 21:37:00 UTC

Chatham housing market

September 2026

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.

Chatham, MA community profile

Area: 16.7 sq. mi.

Source: HJN community data

Explore Chatham homes

By price

Homes Under $1.5M
Homes Under $1.75M
Homes Under $2M
Homes Under $2.25M
Homes Under $2.5M
Homes Under $2.75M
Homes Under $3M
Homes Over $3M
Luxury Homes

By bedrooms

3 Bedroom Homes

Nearby areas

ZIP codes

02601 (80)
02653 (78)
02633 (70)
02675 (70)
02631 (69)
02664 (61)
02642 (59)
02645 (49)

Cities

Barnstable (117)
Orleans (78)
Brewster (69)
Dennis (68)
Harwich (62)
Eastham (59)
Wellfleet (48)
Yarmouth Port (41)

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: 2026-10-21 21:37:00 UTC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

Nearby areas

ZIP codes

02601 (80)
02653 (78)
02633 (70)
02675 (70)
02631 (69)
02664 (61)
02642 (59)
02645 (49)

Cities

Barnstable (117)
Orleans (78)
Brewster (69)
Dennis (68)
Harwich (62)
Eastham (59)
Wellfleet (48)
Yarmouth Port (41)

Chatham, MA community profile

Area: 16.7 sq. mi.

Source: HJN community data

Chatham housing market

September 2026

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.