Chestertown Maryland Homes for Sale

43 total properties

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21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 1

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 2

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 3

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 4

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 5

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 6

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 7

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 8

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 9

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 10

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 11

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 12

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 13

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 14

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 15

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 16

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 17

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 18

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 19

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 20

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 21

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 22

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 23

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 24

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 25

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 26

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 27

21363 Lynn Lane Chestertown, MD MLS# MDKE2006556 - Image 28

Virtual Tour

1 of 28

$205,000

Beds

1.0

Baths

1,314

Sq.Ft.

21363 Lynn Lane

Chestertown, MD

Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 1

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 2

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 3

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 4

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 5

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 6

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 7

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 8

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 9

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 10

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 11

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 12

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 13

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 14

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 15

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 16

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 17

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 18

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 19

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 20

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 21

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 22

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 23

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 24

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 25

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 26

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 27

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 28

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 29

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 30

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 31

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 32

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 33

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 34

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 35

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 36

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 37

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 38

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 39

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 40

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 41

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 42

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 43

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 44

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 45

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 46

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 47

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 48

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 49

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 50

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 51

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 52

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 53

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 54

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 55

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 56

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 57

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 58

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 59

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 60

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 61

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 62

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 63

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 64

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 65

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 66

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 67

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 68

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 69

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 70

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 71

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 72

117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164 - Image 73

Virtual Tour

1 of 73

$200,000

Beds

1.0

Baths

700

Sq.Ft.

117 Water Street N # 1B

Chestertown, MD

Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY

21172 Wyoming Avenue Chestertown, MD MLS# MDKE2006642 - Image 1

Recently Listed

1 of 1

$200,000

Beds

1.0

Baths

2,920

Sq.Ft.

21172 Wyoming Avenue

Chestertown, MD

Courtesy of BLUE STAR REAL ESTATE, LLC

THE TIME TO SELL IS NOW!

Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918 - Image 1

Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918 - Image 2

Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918 - Image 3

Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918 - Image 4

Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918 - Image 5

Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918 - Image 6

Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918 - Image 7

Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918 - Image 8

Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918 - Image 9

Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918 - Image 10

Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918 - Image 11

Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918 - Image 12

Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918 - Image 13

Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918 - Image 14

Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918 - Image 15

Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918 - Image 16

Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918 - Image 17

Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918 - Image 18

Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918 - Image 19

Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918 - Image 20

1 of 20

$185,000

Studio

Beds

0.0

Baths

Lot 9 Prestwick Drive

Chestertown, MD

Courtesy of GUNTHER-MCCLARY REAL ESTATE

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 1

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 2

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 3

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 4

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 5

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 6

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 7

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 8

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 9

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 10

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 11

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 12

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 13

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 14

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 15

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 16

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 17

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 18

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 19

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 20

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 21

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 22

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 23

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 24

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 25

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 26

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 27

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 28

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 29

423 Calvert Street Chestertown, MD MLS# MDKE2006578 - Image 30

1 of 30

$185,000

Beds

1.1

Baths

1,136

Sq.Ft.

423 Calvert Street

Chestertown, MD

Courtesy of COMPASS

144 Prospect Street Chestertown, MD MLS# MDKE2006494 - Image 1

144 Prospect Street Chestertown, MD MLS# MDKE2006494 - Image 2

144 Prospect Street Chestertown, MD MLS# MDKE2006494 - Image 3

144 Prospect Street Chestertown, MD MLS# MDKE2006494 - Image 4

144 Prospect Street Chestertown, MD MLS# MDKE2006494 - Image 5

144 Prospect Street Chestertown, MD MLS# MDKE2006494 - Image 6

144 Prospect Street Chestertown, MD MLS# MDKE2006494 - Image 7

144 Prospect Street Chestertown, MD MLS# MDKE2006494 - Image 8

144 Prospect Street Chestertown, MD MLS# MDKE2006494 - Image 9

144 Prospect Street Chestertown, MD MLS# MDKE2006494 - Image 10

144 Prospect Street Chestertown, MD MLS# MDKE2006494 - Image 11

144 Prospect Street Chestertown, MD MLS# MDKE2006494 - Image 12

144 Prospect Street Chestertown, MD MLS# MDKE2006494 - Image 13

144 Prospect Street Chestertown, MD MLS# MDKE2006494 - Image 14

144 Prospect Street Chestertown, MD MLS# MDKE2006494 - Image 15

144 Prospect Street Chestertown, MD MLS# MDKE2006494 - Image 16

144 Prospect Street Chestertown, MD MLS# MDKE2006494 - Image 17

144 Prospect Street Chestertown, MD MLS# MDKE2006494 - Image 18

1 of 18

$159,000

Beds

1.1

Baths

1,082

Sq.Ft.

144 Prospect Street

Chestertown, MD

Courtesy of DOUG ASHLEY REALTORS, LLC

Georgetown Road SE Chestertown, MD MLS# MDKE2005076 - Image 1

Georgetown Road SE Chestertown, MD MLS# MDKE2005076 - Image 2

Georgetown Road SE Chestertown, MD MLS# MDKE2005076 - Image 3

1 of 3

$150,000

Studio

Beds

0.0

Baths

Georgetown Road SE

Chestertown, MD

Courtesy of RE/MAX ALLEGIANCE

Caulks Field Road Chestertown, MD MLS# MDKE2005120 - Image 1

Caulks Field Road Chestertown, MD MLS# MDKE2005120 - Image 2

Caulks Field Road Chestertown, MD MLS# MDKE2005120 - Image 3

Caulks Field Road Chestertown, MD MLS# MDKE2005120 - Image 4

Caulks Field Road Chestertown, MD MLS# MDKE2005120 - Image 5

Caulks Field Road Chestertown, MD MLS# MDKE2005120 - Image 6

Caulks Field Road Chestertown, MD MLS# MDKE2005120 - Image 7

Caulks Field Road Chestertown, MD MLS# MDKE2005120 - Image 8

1 of 8

$150,000

Studio

Beds

0.0

Baths

Caulks Field Road

Chestertown, MD

Courtesy of RE/MAX ALLEGIANCE

234 N College Avenue Chestertown, MD MLS# MDKE2006670 - Image 1

234 N College Avenue Chestertown, MD MLS# MDKE2006670 - Image 2

234 N College Avenue Chestertown, MD MLS# MDKE2006670 - Image 3

Recently Listed

1 of 3

$120,000

Beds

1.0

Baths

1,296

Sq.Ft.

234 N College Avenue

Chestertown, MD

Courtesy of CUMMINGS & CO REALTORS

110 Prospect Street Chestertown, MD MLS# MDKE2006626 - Image 1

110 Prospect Street Chestertown, MD MLS# MDKE2006626 - Image 2

110 Prospect Street Chestertown, MD MLS# MDKE2006626 - Image 3

110 Prospect Street Chestertown, MD MLS# MDKE2006626 - Image 4

110 Prospect Street Chestertown, MD MLS# MDKE2006626 - Image 5

110 Prospect Street Chestertown, MD MLS# MDKE2006626 - Image 6

Recently Listed

1 of 6

$119,900

Beds

1.1

Baths

2,210

Sq.Ft.

110 Prospect Street

Chestertown, MD

Courtesy of ANR REALTY, LLC

108 Pine Street Chestertown, MD MLS# MDKE2006322 - Image 1

1 of 1

$115,000

Beds

1.0

Baths

910

Sq.Ft.

108 Pine Street

Chestertown, MD

Courtesy of REAL BROKER, LLC - CHESTER

116 Cross Street Chestertown, MD MLS# MDKE2006420 - Image 1

116 Cross Street Chestertown, MD MLS# MDKE2006420 - Image 2

116 Cross Street Chestertown, MD MLS# MDKE2006420 - Image 3

116 Cross Street Chestertown, MD MLS# MDKE2006420 - Image 4

116 Cross Street Chestertown, MD MLS# MDKE2006420 - Image 5

116 Cross Street Chestertown, MD MLS# MDKE2006420 - Image 6

116 Cross Street Chestertown, MD MLS# MDKE2006420 - Image 7

116 Cross Street Chestertown, MD MLS# MDKE2006420 - Image 8

116 Cross Street Chestertown, MD MLS# MDKE2006420 - Image 9

1 of 9

$109,999

Studio

Beds

0.0

Baths

116 Cross Street

Chestertown, MD

Courtesy of SELECT LAND & HOMES, LLC

Georgetown Road Chestertown, MD MLS# MDKE2005844 - Image 1

Georgetown Road Chestertown, MD MLS# MDKE2005844 - Image 2

Georgetown Road Chestertown, MD MLS# MDKE2005844 - Image 3

Georgetown Road Chestertown, MD MLS# MDKE2005844 - Image 4

Georgetown Road Chestertown, MD MLS# MDKE2005844 - Image 5

Georgetown Road Chestertown, MD MLS# MDKE2005844 - Image 6

Georgetown Road Chestertown, MD MLS# MDKE2005844 - Image 7

Georgetown Road Chestertown, MD MLS# MDKE2005844 - Image 8

1 of 8

$90,000

Studio

Beds

0.0

Baths

Georgetown Road

Chestertown, MD

Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC

8886 Georgetown Road Chestertown, MD MLS# MDKE2006634 - Image 1

8886 Georgetown Road Chestertown, MD MLS# MDKE2006634 - Image 2

Recently Listed

1 of 2

$85,000

Studio

Beds

0.0

Baths

8886 Georgetown Road

Chestertown, MD

Courtesy of SAMSON PROPERTIES

Sandy Bottom Road Chestertown, MD MLS# MDKE2006554 - Image 1

Sandy Bottom Road Chestertown, MD MLS# MDKE2006554 - Image 2

Sandy Bottom Road Chestertown, MD MLS# MDKE2006554 - Image 3

Sandy Bottom Road Chestertown, MD MLS# MDKE2006554 - Image 4

Sandy Bottom Road Chestertown, MD MLS# MDKE2006554 - Image 5

Sandy Bottom Road Chestertown, MD MLS# MDKE2006554 - Image 6

1 of 6

$79,000

Studio

Beds

0.0

Baths

Sandy Bottom Road

Chestertown, MD

Courtesy of VILLAGE REAL ESTATE COMPANY LLC

Fairlee Road Chestertown, MD MLS# MDKE2006672 - Image 1

Fairlee Road Chestertown, MD MLS# MDKE2006672 - Image 2

Fairlee Road Chestertown, MD MLS# MDKE2006672 - Image 3

Fairlee Road Chestertown, MD MLS# MDKE2006672 - Image 4

Fairlee Road Chestertown, MD MLS# MDKE2006672 - Image 5

Fairlee Road Chestertown, MD MLS# MDKE2006672 - Image 6

Fairlee Road Chestertown, MD MLS# MDKE2006672 - Image 7

Recently Listed

1 of 7

$75,000

Studio

Beds

0.0

Baths

Fairlee Road

Chestertown, MD

Courtesy of RE/MAX CHESAPEAKE

Georgetown Rd Chestertown, MD MLS# MDKE2005218 - Image 1

Georgetown Rd Chestertown, MD MLS# MDKE2005218 - Image 2

Georgetown Rd Chestertown, MD MLS# MDKE2005218 - Image 3

Georgetown Rd Chestertown, MD MLS# MDKE2005218 - Image 4

Georgetown Rd Chestertown, MD MLS# MDKE2005218 - Image 5

Georgetown Rd Chestertown, MD MLS# MDKE2005218 - Image 6

Georgetown Rd Chestertown, MD MLS# MDKE2005218 - Image 7

Georgetown Rd Chestertown, MD MLS# MDKE2005218 - Image 8

Georgetown Rd Chestertown, MD MLS# MDKE2005218 - Image 9

1 of 9

$60,000

Studio

Beds

0.0

Baths

Georgetown Rd

Chestertown, MD

Courtesy of DOUG ASHLEY REALTORS, LLC

Old Morgnec Road Chestertown, MD MLS# MDKE2004974 - Image 1

1 of 1

$59,000

Studio

Beds

0.0

Baths

Old Morgnec Road

Chestertown, MD

Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY

Map 36 Parcel 80 Watertower Road Chestertown, MD MLS# MDKE2006592 - Image 1

Map 36 Parcel 80 Watertower Road Chestertown, MD MLS# MDKE2006592 - Image 2

Map 36 Parcel 80 Watertower Road Chestertown, MD MLS# MDKE2006592 - Image 3

1 of 3

$55,000

Studio

Beds

0.0

Baths

Map 36 Parcel 80 Watertower Road

Chestertown, MD

Courtesy of DOUG ASHLEY REALTORS, LLC

Montgomery Avenue Chestertown, MD MLS# MDKE2003418 - Image 1

Montgomery Avenue Chestertown, MD MLS# MDKE2003418 - Image 2

1 of 2

$40,000

Studio

Beds

0.0

Baths

Montgomery Avenue

Chestertown, MD

Courtesy of THE HOGANS AGENCY

About Chestertown

Home of George Washington College, Chestertown is the center of amenities and the hub of life in Kent County. Located on the banks of the Chester River, Chestertown began as a prosperous shipbuilding, trade and government center during the colonial movement and still maintains the state’s oldest records. The popular autumn Candlelight Walking Tour offers a glimpse into many of the spectacular homes built by wealthy merchants of the 18th and 19th centuries. Quaint red-brick sidewalks and broad, shaded streets form an idyllic backdrop for specialty shops, galleries and eateries. On cool summer evenings, residents can relax to the strains of concerts held around the antique fountain in the town square. Lovely homes, a stimulating college-town atmosphere and community pride make Chestertown the ideal place to call home.

Listings in Chestertown, MD: 129
Estimated median home price: $340,000

Chestertown MD Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Chestertown, Maryland real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Chestertown, MD.

Homes for Sale by Price in Chestertown, MD

Price	Count
$0 - 100K	31
$100K - 200K	11
$200K - 300K	14
$300K - 400K	20
$400K - 500K	13
$500K - 600K	6
$600K - 700K	3
$700K - 800K	8
$800K - 900K	6
$900K - 1M	0
$1M - Max	17

Homes for Sale by Type in Chestertown, MD

Property Type	Count
Single Family	57
Townhouse	6
Condo	16
Commercial	10
Rental	13
Lots and Land	40
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 6/13/2026)

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Information deemed reliable but not guaranteed.

Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker Reciprocity^SM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

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 sold or are no longer being offered for sale.

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Chestertown Maryland Homes for Sale

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