Chestertown, MD Homes for Sale

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3 beds New construction With a pool

60 listings

Homes for Sale in Chestertown, MD

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24 of 60 Listings

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Homes for Sale in Chestertown, MD

24 of 60 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

32Active

$304,000

3 bd · 2 ba · 1,232 sqft

7464 Shortall St, Chestertown, MD

Samantha A Grimes · Chesapeake Real Estate Associates, LLC

61Active

$649,000

4 bd · 3 ba · 2,864 sqft

22400 Great Oak Landing Rd., Chestertown, MD

Terri L Kulp · Coldwell Banker Chesapeake Real Estate Company

35Active

$349,900

3 bd · 3 ba · 1,650 sqft

23208 Buck Neck Rd, Chestertown, MD

David J. Moore · Real Broker, LLC - Chester

45Active

$375,000

4 bd · 3 ba · 2,504 sqft

123 Trafford Dr, Chestertown, MD

Maryn J. LeClair · Chesapeake Real Estate Associates, LLC

43Active

$524,900

3 bd · 3 ba · 2,076 sqft

1003 Twin Ct, Chestertown, MD

Jody Baker · Cross Street Realtors LLC

18Active

$295,000

1 bd · 1 ba · 0 sqft

117 N Water St #3B, Chestertown, MD

Michael ONeill · Coldwell Banker Chesapeake Real Estate Company

Price Reduced37Active

$455,000

2 bd · 2 ba · 1,904 sqft

7982 Radcliffe Rd, Chestertown, MD

Abigail H Usilton · Doug Ashley Realtors, LLC

26Active

$299,900

3 bd · 1 ba · 1,056 sqft

124 Wilton Rd, Chestertown, MD

Elizabeth Middleton Green · Doug Ashley Realtors, LLC

35Active

$369,000

2 bd · 2 ba · 1,036 sqft

101 S College Ave, Chestertown, MD

Michele A Palmer · Doug Ashley Realtors, LLC

Price Reduced45Active

$424,900

5 bd · 3 ba · 1,936 sqft

8630 Elm Rd, Chestertown, MD

Lawrence M. Lessin · Save 6, Incorporated

21Active

$279,000

3 bd · 2 ba · 1,404 sqft

10540 Tonopah Rd, Chestertown, MD

Michele A Palmer · Doug Ashley Realtors, LLC

55Active

$315,000

3 bd · 2 ba · 1,288 sqft

109 Parma Rd, Chestertown, MD

Joseph S. Ciganek · Coldwell Banker Chesapeake Real Estate Company

15Active

$480,000

3 bd · 3 ba · 3,176 sqft

129 Trafford Dr, Chestertown, MD

Teresa A Queen · Elevated Real Estate Solutions

16Active

$375,000

4 bd · 2 ba · 1,476 sqft

1010 Twin Ct, Chestertown, MD

Jason Dey · Kevin Dey Realty

17Active

$1,195,000

2 bd · 1 ba · 806 sqft

302 S Mill St, Chestertown, MD

Joseph S. Ciganek · Coldwell Banker Chesapeake Real Estate Company

74Active

$824,900

5 bd · 4 ba · 4,353 sqft

8999 Orchard Dr, Chestertown, MD

Terri L Kulp · Coldwell Banker Chesapeake Real Estate Company

17Active

$225,000

4 bd · 2 ba · 1,800 sqft

533 Round Top Rd, Chestertown, MD

Christopher Craddock · EXP Realty, LLC

10Active

$259,900

3 bd · 2 ba · 1,280 sqft

115 Metcalf Rd, Chestertown, MD

David J. Moore · Real Broker, LLC - Chester

34Active

$325,000

4 bd · 2 ba · 2,198 sqft

200 Manor Ave, Chestertown, MD

Liddy Campbell · TTR Sotheby's International Realty

52Active

$750,000

3 bd · 3 ba · 2,176 sqft

216 Birch Run Rd, Chestertown, MD

Liddy Campbell · TTR Sotheby's International Realty

Price Reduced9Active

$145,000

3 bd · 2 ba · 1,192 sqft

409 Calvert St, Chestertown, MD

Mikeshia D Lindsey · Chesapeake Real Estate Associates, LLC

43Active

$885,000

5 bd · 4 ba · 2,639 sqft

7680 Country Club Ln, Chestertown, MD

John J Burke · Gunther-McClary Real Estate

Price Reduced20Active

$324,000

3 bd · 2 ba · 1,216 sqft

9126 Fairlee Rd, Chestertown, MD

Mikeshia D Lindsey · Chesapeake Real Estate Associates, LLC

Price Reduced21Active

$179,900

2 bd · 1 ba · 1,232 sqft

21324 Persimmon Dr, Chestertown, MD

Taylor Leaverton · Benson & Mangold, LLC

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: 2026-09-02 19:36:41 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 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

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

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Co-ops

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

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: 2026-09-02 19:36:41 UTC

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 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

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.

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Listing data & MLS disclosures

Chestertown housing market

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

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Chestertown, MD community profile

Chestertown housing market

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

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