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Before you start looking
The buying timeline

Afford it

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How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
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Closing costs, itemized
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Rentals
Commercial

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

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

28Active

$296,000

3 bd · 2 ba · 1,248 sqft

203 Manor Ave, Chestertown, MD

Jennifer L Mobley · Coldwell Banker Chesapeake Real Estate Company

23Active

$312,500

3 bd · 2 ba · 1,080 sqft

8820 Cumberland St, Chestertown, MD

Frederick A Golding · RE/MAX Advantage Realty

41Active

$325,000

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

22Active

$329,900

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

56Active

$2,895,000

5 bd · 4 ba · 5,938 sqft

6324 Quaker Neck Rd, Chestertown, MD

John Boniface · Cross Street Realtors 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

142Active

$568,900

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

Price Reduced36Active

$325,000

3 bd · 2 ba · 1,398 sqft

217 Edmore Rd, Chestertown, MD

Michele A Palmer · Doug Ashley Realtors, LLC

35Active

$349,900

3 bd · 3 ba · 1,650 sqft

23208 Buck Neck Rd, Chestertown, MD

David J. Moore · Real Broker, LLC - Chester

Price Reduced45Active

$370,000

4 bd · 3 ba · 2,504 sqft

123 Trafford Dr, Chestertown, MD

Maryn J. LeClair · Chesapeake Real Estate Associates, LLC

Price Reduced34Active

$259,000

3 bd · 2 ba · 1,140 sqft

115 Chester Arms Dr, Chestertown, MD

Jarnell Preston Foster · Samson Properties

Price Reduced23Active

$294,900

3 bd · 1 ba · 1,056 sqft

124 Wilton Rd, Chestertown, MD

Elizabeth Middleton Green · Doug Ashley Realtors, LLC

Price Reduced35Active

$359,000

2 bd · 2 ba · 1,036 sqft

101 S College Ave, Chestertown, MD

Michele A Palmer · Doug Ashley Realtors, LLC

Price Reduced53Active

$424,900

5 bd · 3 ba · 1,936 sqft

8630 Elm Rd, Chestertown, MD

Lawrence M. Lessin · Save 6, Incorporated

Price Reduced21Active

$269,000

3 bd · 2 ba · 1,404 sqft

10540 Tonopah Rd, Chestertown, MD

Michele A Palmer · Doug Ashley Realtors, LLC

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: 2026-10-15 20:48:54 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

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 (139)
21403 (124)
21001 (97)
21078 (90)
21666 (88)
21014 (86)
21221 (85)
21222 (81)

Cities

Annapolis (236)
Baltimore (200)
Bel Air (164)
Aberdeen (98)
Middle River (95)

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 (139)
21403 (124)
21001 (97)
21078 (90)
21666 (88)
21014 (86)
21221 (85)
21222 (81)

Cities

Annapolis (236)
Baltimore (200)
Bel Air (164)
Aberdeen (98)
Middle River (95)

Havre de Grace (90)

Stevensville (88)

Abingdon (67)

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: 2026-10-15 20:48:54 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

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

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 Homes for Sale | Realty.com