5 Bedroom Homes in Chestertown, MD

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3 beds New construction With a pool

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6 Listings

5 Bedroom Homes in Chestertown, MD

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6 Listings

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5 Bedroom Homes in Chestertown, MD

6 Listings

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Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Price Reduced45Active
$424,900
5 bd · 3 ba · 1,936 sqft
8630 Elm Rd, Chestertown, MD
Lawrence M. Lessin · Save 6, Incorporated
74Active
$824,900
5 bd · 4 ba · 4,353 sqft
8999 Orchard Dr, Chestertown, MD
Terri L Kulp · Coldwell Banker Chesapeake Real Estate Company
43Active
$885,000
5 bd · 4 ba · 2,639 sqft
7680 Country Club Ln, Chestertown, MD
John J Burke · Gunther-McClary Real Estate

Listing data & MLS disclosures

Bright MLS: The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Realty.com participates, and is provided by BRIGHT through a licensing agreement. 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. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.
Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-09-18 16:37:53 UTC

Chestertown housing market

August 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 15 sales · as of Aug 27, 2026

Homes that sold · County records, as of Aug 28, 2026

Median sale price: $324,000$195,000–$645,000 typical range
Price per sq. ft.: $184
Sales: 17
Paid in cash: 29.4%

Homes on the market · MLS, as of Aug 27, 2026–Aug 31, 2026

Median list price: $478,000
Homes for sale: 59
Median days on market: 17 days

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

Year-over-year: 3.6%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 1,735 sq. ft.

Chestertown, MD community profile

Population: 5,632
Median income: $48,766
Housing units: 2,458
People per sq. mi.: 42.6
Area: 132.2 sq. mi.

Source: HJN community data

Explore Chestertown homes

Listing data & MLS disclosures

Bright MLS: The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Realty.com participates, and is provided by BRIGHT through a licensing agreement. 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. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.
Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-09-18 16:37:53 UTC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Chestertown, MD community profile

Population: 5,632
Median income: $48,766
Housing units: 2,458
People per sq. mi.: 42.6
Area: 132.2 sq. mi.

Source: HJN community data

Chestertown housing market

August 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 15 sales · as of Aug 27, 2026

Homes that sold · County records, as of Aug 28, 2026

Median sale price: $324,000$195,000–$645,000 typical range
Price per sq. ft.: $184
Sales: 17
Paid in cash: 29.4%

Homes on the market · MLS, as of Aug 27, 2026–Aug 31, 2026

Median list price: $478,000
Homes for sale: 59
Median days on market: 17 days

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

Year-over-year: 3.6%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 1,735 sq. ft.

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Your local brokerage

Listing data & MLS disclosures

Chestertown housing market

Homes that sold · County records, as of Aug 28, 2026

Homes on the market · MLS, as of Aug 27, 2026–Aug 31, 2026

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

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Chestertown, MD community profile

Explore Chestertown homes

Listing data & MLS disclosures

Your local brokerage

Your local brokerage

Chestertown, MD community profile

Chestertown housing market

Homes that sold · County records, as of Aug 28, 2026

Homes on the market · MLS, as of Aug 27, 2026–Aug 31, 2026

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

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026