Homes Under $500K in Chestertown, MD

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4 Listings

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Thomas O'Leary

Realty.com

Lic. #01-6355

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51Active
$489,000
2 bd · 2 ba · 1,098 sqft
105 N Water St #3, Chestertown, MD
Lisa P Raffetto · Coldwell Banker Chesapeake Real Estate Company
20Active
$200,000
1 bd · 1 ba · 700 sqft
117 Water St N #1B, Chestertown, MD
Liddy Campbell · TTR Sotheby's International Realty
24Active
$375,000
2 bd · 1 ba · 787 sqft
117 Water St N #2a, Chestertown, MD
Liddy Campbell · TTR Sotheby's International Realty

23Active
$350,000
1 bd · 1 ba · 850 sqft
117 Water St N #2B, Chestertown, MD
Liddy Campbell · TTR Sotheby's International Realty

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: 2026-10-01 13:31:33 UTC

Chestertown housing market

September 2026

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 18 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 24, 2026

Median sale price: $365,000$267,500–$645,000 typical range
Price per sq. ft.: $219
Sales: 23
Paid in cash: 43.5%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $404,950
Homes for sale: 58
Median days on market: 19 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: 35.2%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 2026

Median home size: 1,728 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

Homes Under $500K in Chestertown, MD

Homes Under $500K in Chestertown, MD

Your local brokerage

Listing data & MLS disclosures

Chestertown housing market

Homes that sold · County records, as of Sep 24, 2026

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Price trend · Assessor repeat sales, as of Sep 30, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 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 Sep 24, 2026

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Price trend · Assessor repeat sales, as of Sep 30, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 2026