Homes Under $500K in Chestertown, MD

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3 beds New construction With a pool

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24 of 38 Listings

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Homes Under $500K in Chestertown, MD

24 of 38 Listings

22Active

38 listings

Homes Under $500K in Chestertown, MD

Hide Map

24 of 38 Listings

Map

Homes Under $500K in Chestertown, MD

24 of 38 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

22Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

$329,900

2 bd · 2 ba · 1,440 sqft

22974 Bay Shore Rd, Chestertown, MD

Mae Nordhoff · Benson & Mangold, LLC

22Active

$200,000

4 bd · 1 ba · 1,816 sqft

223 Mount Vernon Ave, Chestertown, MD

Maryn J. LeClair · Chesapeake Real Estate Associates, LLC

18Active

$289,000

3 bd · 2 ba · 1,056 sqft

8732 Elm Rd, Chestertown, MD

Tracy A Stone · Coldwell Banker Chesapeake Real Estate Company

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

23Active

$229,000

3 bd · 1 ba · 936 sqft

7415 Wilkins Ln, Chestertown, MD

Retha J Arrabal · Doug Ashley Realtors, LLC

Price Reduced30Active

$295,000

3 bd · 1 ba · 960 sqft

104 Lincoln Dr, Chestertown, MD

Crystal M Smith · RE/MAX Executive

32Active

$345,000

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

45Active

$375,000

4 bd · 3 ba · 2,504 sqft

123 Trafford Dr, Chestertown, MD

Maryn J. LeClair · Chesapeake Real Estate Associates, LLC

Price Reduced43Active

$499,900

3 bd · 3 ba · 2,076 sqft

1003 Twin Ct, Chestertown, MD

Jody Baker · Cross Street Realtors LLC

40Active

$275,000

3 bd · 1 ba · 975 sqft

7482 Poplar Ave, Chestertown, MD

Lona Sue Todd · Taylor Properties

34Active

$263,000

3 bd · 2 ba · 1,140 sqft

115 Chester Arms Dr, Chestertown, MD

Jarnell Preston Foster · Samson Properties

Price Reduced37Active

$455,000

2 bd · 2 ba · 1,904 sqft

7982 Radcliffe Rd, Chestertown, MD

Abigail H Usilton · Doug Ashley Realtors, LLC

23Active

$299,900

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 Reduced45Active

$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

15Active

$480,000

3 bd · 3 ba · 3,176 sqft

129 Trafford Dr, Chestertown, MD

Teresa A Queen · Elevated Real Estate Solutions

Price Reduced25Active

$369,900

4 bd · 2 ba · 1,476 sqft

1010 Twin Ct, Chestertown, MD

Jason Dey · Kevin Dey Realty

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

Price Reduced20Active

$314,000

3 bd · 2 ba · 1,216 sqft

9126 Fairlee Rd, Chestertown, MD

Mikeshia D Lindsey · Chesapeake Real Estate Associates, LLC

34Active

$325,000

3 bd · 1 ba · 1,000 sqft

896 Washington Ave, Chestertown, MD

Peter D Heller · Coldwell Banker Chesapeake Real Estate Company

10Active

$264,900

3 bd · 2 ba · 0 sqft

121 Metcalf Rd, Chestertown, MD

David J. Moore · Real Broker, LLC - Chester

Price Reduced3Active

$85,000

2 bd · 1 ba · 1,296 sqft

234 N College Ave, Chestertown, MD

Anastasia Marie Zivkovic Palmer · Cummings & Co Realtors

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: 2026-09-22 13:12:17 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 that sold · County records, as of Aug 28, 2026

Median sale price: $324,000$195,000–$645,000 typical range
Price per sq. ft.: $184
Sales: 17
Paid in cash: 29.4%

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

Median list price: $478,000

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

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: 2026-09-22 13:12:17 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 that sold · County records, as of Aug 28, 2026

Median sale price: $324,000$195,000–$645,000 typical range
Price per sq. ft.: $184
Sales: 17
Paid in cash: 29.4%

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

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: 4.5%

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

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Chestertown housing market

Homes that sold · County records, as of Aug 28, 2026

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

Chestertown, MD community profile

Explore Chestertown homes

Your local brokerage

Listing data & MLS disclosures

Chestertown, MD community profile

Chestertown housing market

Homes that sold · County records, as of Aug 28, 2026

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

Price trend · Assessor repeat sales, as of Aug 31, 2026

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