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Start here

Homes for sale by state
Home buying tips
Before you start looking
The buying timeline

Afford it

Today's mortgage rates
Mortgage calculator
How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
Inspections & appraisals
Closing costs, itemized
Find a buyer's agent

Save search Advertise Sign In

Saved homes Saved searches Your tours Your inquiries Recently viewed Account settings

Safety & registry resources

Review official public-safety information for any area from these government sources:

U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
FBI: state sex-offender registry directory

Selling Options

What's my home worth?
Compare selling options
Get an instant cash offer
Buy before you sell

Resources

How selling works
When should I sell?
Home selling tips
Pricing your home
What's worth fixing first
Find a seller's agent

59 listings

Homes for Sale in 21620, MD

Homes for Sale in 21620, MD

24 of 59 Listings

Homes for Sale in 21620, MD

24 of 59 Listings

32Active

$304,000

3 bd · 2 ba · 1,232 sqft

7464 Shortall St, Chestertown, MD

Samantha A Grimes · Chesapeake Real Estate Associates, LLC

$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

$349,900

3 bd · 3 ba · 1,650 sqft

23208 Buck Neck Rd, Chestertown, MD

David J. Moore · Real Broker, LLC - Chester

$375,000

4 bd · 3 ba · 2,504 sqft

123 Trafford Dr, Chestertown, MD

Maryn J. LeClair · Chesapeake Real Estate Associates, LLC

$524,900

3 bd · 3 ba · 2,076 sqft

1003 Twin Ct, Chestertown, MD

Jody Baker · Cross Street Realtors LLC

$295,000

1 bd · 1 ba · 0 sqft

117 N Water St #3B, Chestertown, MD

Michael ONeill · Coldwell Banker Chesapeake Real Estate Company

$478,000

2 bd · 2 ba · 1,904 sqft

7982 Radcliffe Rd, Chestertown, MD

Abigail H Usilton · Doug Ashley Realtors, LLC

$299,900

3 bd · 1 ba · 1,056 sqft

124 Wilton Rd, Chestertown, MD

Elizabeth Middleton Green · Doug Ashley Realtors, LLC

$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

$279,000

3 bd · 2 ba · 1,404 sqft

10540 Tonopah Rd, Chestertown, MD

Michele A Palmer · Doug Ashley Realtors, LLC

$480,000

3 bd · 3 ba · 3,176 sqft

129 Trafford Dr, Chestertown, MD

Teresa A Queen · Elevated Real Estate Solutions

$375,000

4 bd · 2 ba · 1,476 sqft

1010 Twin Ct, Chestertown, MD

Jason Dey · Kevin Dey Realty

$1,195,000

2 bd · 1 ba · 806 sqft

302 S Mill St, Chestertown, MD

Joseph S. Ciganek · Coldwell Banker Chesapeake Real Estate Company

$824,900

5 bd · 4 ba · 4,353 sqft

8999 Orchard Dr, Chestertown, MD

Terri L Kulp · Coldwell Banker Chesapeake Real Estate Company

$259,900

3 bd · 2 ba · 1,280 sqft

115 Metcalf Rd, Chestertown, MD

David J. Moore · Real Broker, LLC - Chester

$325,000

4 bd · 2 ba · 2,198 sqft

200 Manor Ave, Chestertown, MD

Liddy Campbell · TTR Sotheby's International Realty

$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

$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

$325,000

3 bd · 1 ba · 1,000 sqft

896 Washington Ave, Chestertown, MD

Peter D Heller · Coldwell Banker Chesapeake Real Estate Company

$799,000

3 bd · 3 ba · 2,857 sqft

7828 Country Club Ln, Chestertown, MD

Sarah E. King · Cross Street Realtors LLC

1 2 3

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.

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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: 2026-09-01 00:02:37 UTC

21620, MD Homes for Sale | Realty.com

Nearby areas

ZIP codes

21220 (138)
21221 (91)
21078 (87)
21001 (82)
21666 (82)
21014 (78)
21403 (72)
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