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Homes for sale in Chestertown, Maryland

Maryland

Homes for Sale in Chestertown

“Discover your next home in Chestertown”

43 listings

Avg $563,358

128 days avg

Search All 43 Homes

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Market Overview

Chestertown Real Estate at a Glance

Current market statistics for Chestertown, MD

43

Active Listings

$563K

Avg Price

$420K

Median Price

2,430

Avg Sqft

128

Avg Days

Price Range

From

$6,000

To

$2,200,000

Handpicked

Editor's Picks

Our curated selection of the finest chestertown homes homes

116 HARLAN Loop, Chestertown, MD - $509K

$509K

116 HARLAN Loop

Chestertown, MD

218 CAMELOT Drive - Single Family for sale in Chestertown, MD

$500K

218 CAMELOT Drive

Chestertown, MD

6746 QUAKER NECK Road - Single Family for sale in Chestertown, MD

$384K

6746 QUAKER NECK Road

Chestertown, MD

21172 WYOMING Avenue - Single Family for sale in Chestertown, MD

$200K

21172 WYOMING Avenue

8276 BROAD NECK Road - Single Family for sale in Chestertown, MD

$1.5M

8276 BROAD NECK Road

Featured

More Chestertown Homes

Discover more properties that match this lifestyle

116 HARLAN Loop, Chestertown, MD

$509K

116 HARLAN Loop

Chestertown, MD

218 CAMELOT Drive, Chestertown, MD

$500K

218 CAMELOT Drive

Chestertown, MD

6746 QUAKER NECK Road, Chestertown, MD

$384K

6746 QUAKER NECK Road

Chestertown, MD

21172 WYOMING Avenue, Chestertown, MD

$200K

21172 WYOMING Avenue

Chestertown, MD

8276 BROAD NECK Road, Chestertown, MD

$1.5M

8276 BROAD NECK Road

Chestertown, MD

311 DEVON Drive, Chestertown, MD

$499K

311 DEVON Drive

Chestertown, MD

23043 BAY SHORE Spur, Chestertown, MD

$385K

23043 BAY SHORE Spur

Chestertown, MD

304 HADAWAY Drive, Chestertown, MD

$323K

304 HADAWAY Drive

Chestertown, MD

Browse

Homes for Sale in Chestertown

Every active listing in Chestertown, browsable page by page.

25416 COMMERCE Lane - Other for sale in Chestertown, MD

$1.1M

25416 COMMERCE Lane

Chestertown, MD

8796 MARYLAND Parkway - Single Family for sale in Chestertown, MD

$1.6M

8796 MARYLAND Parkway

Chestertown, MD

8796 MARYLAND Parkway - Other for sale in Chestertown, MD

$1.6M

8796 MARYLAND Parkway

Chestertown, MD

205 RIVER Road - Single Family for sale in Chestertown, MD

$870K

205 RIVER Road

Chestertown, MD

21172 WYOMING Avenue - Single Family for sale in Chestertown, MD

$200K

21172 WYOMING Avenue

Chestertown, MD

213 BYFORD Drive - Single Family for sale in Chestertown, MD

$380K

213 BYFORD Drive

Chestertown, MD

956 WASHINGTON Avenue - Single Family for sale in Chestertown, MD

$285K

956 WASHINGTON Avenue

Chestertown, MD

24295 LANGFORD Road - Single Family for sale in Chestertown, MD

$445K

24295 LANGFORD Road

Chestertown, MD

102 FLYING CLOUD DR - Single Family for sale in Chestertown, MD

$340K

102 FLYING CLOUD DR

Chestertown, MD

240 MERGANSER Drive - Single Family for sale in Chestertown, MD

$399K

240 MERGANSER Drive

Chestertown, MD

23683 L Road - Land for sale in Chestertown, MD

$6K

23683 L Road

Chestertown, MD

107 FLYING CLOUD Drive - Single Family for sale in Chestertown, MD

$395K

107 FLYING CLOUD Drive

Chestertown, MD

304 HADAWAY Drive - Single Family for sale in Chestertown, MD

$323K

304 HADAWAY Drive

Chestertown, MD

109 2ND Street - Land for sale in Chestertown, MD

$150K

109 2ND Street

Chestertown, MD

214 SILVER HEEL Road - Single Family for sale in Chestertown, MD

$350K

214 SILVER HEEL Road

Chestertown, MD

215 FAIRVIEW DR - Single Family for sale in Chestertown, MD

$425K

215 FAIRVIEW DR

Chestertown, MD

103 TRAFFORD Drive - Single Family for sale in Chestertown, MD

$420K

103 TRAFFORD Drive

Chestertown, MD

8706 ELM Road - Single Family for sale in Chestertown, MD

$320K

8706 ELM Road

Chestertown, MD

208 CENTRAL Drive - Single Family for sale in Chestertown, MD

$299K

208 CENTRAL Drive

Chestertown, MD

21217 TEXAS Avenue - Single Family for sale in Chestertown, MD

$245K

21217 TEXAS Avenue

Chestertown, MD

139 PROSPECT Street - Single Family for sale in Chestertown, MD

$225K

139 PROSPECT Street

Chestertown, MD

101 COLEMAN Drive - Single Family for sale in Chestertown, MD

$525K

101 COLEMAN Drive

Chestertown, MD

8276 BROAD NECK Road - Single Family for sale in Chestertown, MD

$1.5M

8276 BROAD NECK Road

Chestertown, MD

206 BURCHARD SAWMILL Road - Land for sale in Chestertown, MD

$29K

206 BURCHARD SAWMILL Road

Chestertown, MD

109 WILTON Road - Single Family for sale in Chestertown, MD

$345K

109 WILTON Road

Chestertown, MD

201 N LYNCHBURG Street - Land for sale in Chestertown, MD

$750K

201 N LYNCHBURG Street

Chestertown, MD

201 N LYNCHBURG Street - Single Family for sale in Chestertown, MD

$750K

201 N LYNCHBURG Street

Chestertown, MD

204 DOUBLE CREEK Road - Single Family for sale in Chestertown, MD

$565K

204 DOUBLE CREEK Road

Chestertown, MD

201 N LYNCHBURG Street - Other for sale in Chestertown, MD

$750K

201 N LYNCHBURG Street

Chestertown, MD

22681 WOOD YARD Lane - Land for sale in Chestertown, MD

$15K

22681 WOOD YARD Lane

Chestertown, MD

6746 QUAKER Road - Other for sale in Chestertown, MD

$384K

6746 QUAKER Road

Chestertown, MD

6746 QUAKER NECK Road - Single Family for sale in Chestertown, MD

$384K

6746 QUAKER NECK Road

Chestertown, MD

110 TRAFFORD Drive - Single Family for sale in Chestertown, MD

$450K

110 TRAFFORD Drive

Chestertown, MD

218 CAMELOT Drive - Single Family for sale in Chestertown, MD

$500K

218 CAMELOT Drive

Chestertown, MD

311 DEVON Drive - Single Family for sale in Chestertown, MD

$499K

311 DEVON Drive

Chestertown, MD

105 HIGH Street - Single Family for sale in Chestertown, MD

$1.3M

105 HIGH Street

Chestertown, MD

8620 PARK Drive - Single Family for sale in Chestertown, MD

$500K

8620 PARK Drive

Chestertown, MD

404 SPRING Road - Land for sale in Chestertown, MD

$20K

404 SPRING Road

Chestertown, MD

7989 QUAKER NECK Road - Single Family for sale in Chestertown, MD

$2.2M

7989 QUAKER NECK Road

Chestertown, MD

103 LANDING Lane - Condo for sale in Chestertown, MD

$500K

103 LANDING Lane

Chestertown, MD

23043 BAY SHORE Spur - Single Family for sale in Chestertown, MD

$385K

23043 BAY SHORE Spur

Chestertown, MD

116 HARLAN Loop - Single Family for sale in Chestertown, MD

$509K

116 HARLAN Loop

Chestertown, MD

515 WASHINGTON Avenue - Other for sale in Chestertown, MD

$899K

515 WASHINGTON Avenue

Chestertown, MD

Showing 1–43 of 43 · Page 1 of 1

About Chestertown Real Estate

Chestertown, Maryland offers a diverse real estate market with 43 homes currently for sale. Whether you're looking for a starter home, family property, or luxury estate, Chestertown has options for every budget and lifestyle.

Average listing price: $563,358 · 43 homes available

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