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5 Bedroom Homes in Chatham, MA

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5 Bedroom Homes in Chatham, MA

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7 Listings

5 Bedroom Homes in Chatham, MA

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7 Listings

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5 Bedroom Homes in Chatham, MA

7 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

5Active
$6,495,000
5 bd · 6 ba · 4,588 sqft
200 Crows Pond Road, Chatham, MA
Chris Rhinesmith · Compass
Open house Sat, Oct 24 · 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
Open house Sat, Oct 24 · 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

Active
$4,995,000
5 bd · 6 ba · 4,763 sqft
65 Harbor View Road, Chatham, MA
Chris Rhinesmith · Compass Massachusetts, LLC
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
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
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.

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: 2026-10-20 07:05:00 UTC

About 5 Bedroom Homes in Chatham, MA

5 Bedroom Homes in Chatham, MA: 7 active listings as of October 23, 2026, 07:44 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

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

By bedrooms

3 Bedroom Homes

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: 2026-10-20 07:05:00 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

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