5 Bedroom Homes in Chatham, MA

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3 beds New construction With a pool

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5 Bedroom Homes in Chatham, MA

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5 Bedroom Homes in Chatham, MA

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5 Bedroom Homes in Chatham, MA

1 Listing

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Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

Price Reduced42Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

$5,850,000

5 bd · 6 ba · 5,620 sqft

15 Windy Hill Way, Chatham, MA

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

Listing data & MLS disclosures

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: 2026-06-28 08:05:00 UTC

Chatham housing market

July 2026 · This period is still settling

Selling at 98.2% of asking price

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

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

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas

Listing data & MLS disclosures

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: 2026-06-28 08:05:00 UTC

Chatham, MA community profile

Area: 16.7 sq. mi.

Source: HJN community data

Chatham housing market

July 2026 · This period is still settling

Selling at 98.2% of asking price

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

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

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Chatham housing market

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

Your local brokerage

Listing data & MLS disclosures

Chatham, MA community profile

Chatham housing market

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