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Homes for sale by state
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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

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63 listings

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63 listings

Homes for Sale in Chestertown, MD

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24 of 63 Listings

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24 of 63 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

New29

Active

$450,000

2 bd · 3 ba · 1,632 sqft

111 Kent St S, Chestertown, MD

Retha J Arrabal · Doug Ashley Realtors, LLC

New22Active

$135,000

3 bd · 2 ba · 1,136 sqft

403 Calvert St, Chestertown, MD

Mikeshia D Lindsey · Chesapeake Real Estate Associates, LLC

8Active

$229,900

3 bd · 2 ba · 2,344 sqft

317 Rolling Rd, Chestertown, MD

William H Norris III · Select Land & Homes, LLC

18Active

$175,000

3 bd · 1 ba · 1,360 sqft

7545 Quaker Neck Rd, Chestertown, MD

Byron K. Brooks · Thurston Wyatt Real Estate, LLC

28Active

$365,000

3 bd · 3 ba · 2,294 sqft

24607 Chestertown Rd, Chestertown, MD

William Sutton · Coldwell Banker Chesapeake Real Estate Company

50Active

$519,900

3 bd · 3 ba · 2,475 sqft

7655 James Ln, Chestertown, MD

Ryan Michael Fitzwater · RE/MAX Advantage Realty

51Active

$525,000

3 bd · 3 ba · 1,833 sqft

8901 S Bayview Dr, Chestertown, MD

Grace M Crockett · Doug Ashley Realtors, LLC

47Active

$400,000

2 bd · 2 ba · 1,000 sqft

21338 Virginia Ave, Chestertown, MD

Retha J Arrabal · Doug Ashley Realtors, LLC

68Active

$425,000

4 bd · 3 ba · 3,165 sqft

106 Harlan Loop, Chestertown, MD

Barbara A McPhail · Douglas Realty LLC

Price Reduced24Active

$281,500

3 bd · 2 ba · 1,080 sqft

8820 Cumberland St, Chestertown, MD

Frederick A Golding · RE/MAX Advantage Realty

Price Reduced41Active

$300,000

5 bd · 2 ba · 1,802 sqft

234 N Kent St, Chestertown, MD

Liddy Campbell · TTR Sotheby's International Realty

39Active

$495,000

3 bd · 3 ba · 1,656 sqft

10 Cedar Chase Ct, Chestertown, MD

Sarah E. King · Cross Street Realtors LLC

53Active

$679,900

3 bd · 4 ba · 3,228 sqft

8986 Orchard Dr, Chestertown, MD

Taylor Leaverton · Benson & Mangold, LLC

Price Reduced22Active

$315,000

2 bd · 2 ba · 1,440 sqft

22974 Bay Shore Rd, Chestertown, MD

Mae Nordhoff · Benson & Mangold, LLC

Price Reduced51Active

$459,000

2 bd · 2 ba · 1,098 sqft

105 N Water St #3, Chestertown, MD

Lisa P Raffetto · Coldwell Banker Chesapeake Real Estate Company

55Active

$2,895,000

5 bd · 4 ba · 5,938 sqft

6324 Quaker Neck Rd, Chestertown, MD

John Boniface · Cross Street Realtors LLC

23Active

$200,000

4 bd · 1 ba · 1,816 sqft

223 Mount Vernon Ave, Chestertown, MD

Maryn J. LeClair · Chesapeake Real Estate Associates, LLC

24Active

$289,000

3 bd · 2 ba · 1,056 sqft

8732 Elm Rd, Chestertown, MD

Tracy A Stone · Coldwell Banker Chesapeake Real Estate Company

16Active

$259,900

3 bd · 3 ba · 1,280 sqft

103 Metcalf Rd, Chestertown, MD

David J. Moore · Real Broker, LLC - Chester

Price Reduced23Active

$222,000

3 bd · 1 ba · 936 sqft

7415 Wilkins Ln, Chestertown, MD

Retha J Arrabal · Doug Ashley Realtors, LLC

Price Reduced142Active

$549,900

4 bd · 3 ba · 2,464 sqft

329 Union Church Rd, Chestertown, MD

Heather Dolan · Chesapeake Real Estate Associates, LLC

Price Reduced25Active

$305,000

3 bd · 1 ba · 1,008 sqft

24775 Langford Rd, Chestertown, MD

Joseph A Zang III · RE/MAX Chesapeake

Price Reduced30Active

$275,000

3 bd · 1 ba · 960 sqft

104 Lincoln Dr, Chestertown, MD

Crystal M Smith · RE/MAX Executive

39Active

$675,000

5 bd · 3 ba · 2,838 sqft

212 Washington Ave, Chestertown, MD

Mary C Carlisle · Coldwell Banker Chesapeake Real Estate Company

1 2 3

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: 2026-11-04 00:08:19 UTC

Chestertown housing market

October 2026 · This period is still settling

Homes on the market · MLS, as of Oct 25, 2026

Median list price: $444,250
Homes for sale: 60

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 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

Explore Chestertown homes

By price

Homes Under $400K
Homes Under $500K
Homes Under $600K
Homes Under $700K
Homes Under $800K
Homes Under $900K
Homes Under $1M

By bedrooms

3 Bedroom Homes

By type

Single-Family Homes

Nearby areas

ZIP codes

21220 (130)
21001 (102)
21078 (96)
21221 (93)
21666 (88)
21015 (82)
21403 (80)
21014 (77)

Cities

Bel Air (159)
Annapolis (155)
Baltimore (140)
Aberdeen (103)
Havre de Grace (96)

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.

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

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Nearby areas

ZIP codes

21220 (130)
21001 (102)
21078 (96)
21221 (93)
21666 (88)
21015 (82)
21403 (80)
21014 (77)

Cities

Bel Air (159)
Annapolis (155)
Baltimore (140)
Aberdeen (103)
Havre de Grace (96)

Middle River (93)

Stevensville (88)

Chester (72)

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: 2026-11-04 00:08:19 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

October 2026 · This period is still settling

Homes on the market · MLS, as of Oct 25, 2026

Median list price: $444,250
Homes for sale: 60

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

Median home size: 1,728 sq. ft.

Chestertown, MD Homes for Sale | Realty.com