Chestertown Maryland Homes for Sale

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#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 1

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 2

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 3

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 4

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 5

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 6

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 7

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 8

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 9

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 10

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 11

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 12

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 13

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 14

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 15

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 16

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 17

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 18

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 19

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 20

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 21

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 22

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 23

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 24

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 25

#36 Landing Lane Chestertown, MD MLS# MDKE2005958 - Image 26

New Construction

1 of 26

$753,500

Beds

2.1

Baths

1,964

Sq.Ft.

#36 Landing Lane

Chestertown, MD

Courtesy of GUNTHER-MCCLARY REAL ESTATE

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006082 - Image 1

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006082 - Image 2

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006082 - Image 3

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006082 - Image 4

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006082 - Image 5

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006082 - Image 6

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006082 - Image 7

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006082 - Image 8

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006082 - Image 9

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006082 - Image 10

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006082 - Image 11

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006082 - Image 12

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006082 - Image 13

1 of 13

$750,000

2,045

Sq.Ft.

201 N Lynchburg Street

Chestertown, MD

Courtesy of RE/MAX ASSOCIATES-HOCKESSIN

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006142 - Image 1

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006142 - Image 2

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006142 - Image 3

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006142 - Image 4

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006142 - Image 5

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006142 - Image 6

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006142 - Image 7

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006142 - Image 8

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006142 - Image 9

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006142 - Image 10

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006142 - Image 11

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006142 - Image 12

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006142 - Image 13

1 of 13

$750,000

Studio

Beds

0.2

Baths

2,045

Sq.Ft.

201 N Lynchburg Street

Chestertown, MD

Courtesy of RE/MAX ASSOCIATES-HOCKESSIN

THE TIME TO SELL IS NOW!

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006144 - Image 1

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006144 - Image 2

201 N Lynchburg Street Chestertown, MD MLS# MDKE2006144 - Image 3

1 of 3

$750,000

Studio

Beds

0.0

Baths

201 N Lynchburg Street

Chestertown, MD

Courtesy of RE/MAX ASSOCIATES-HOCKESSIN

210 N Queen Street Chestertown, MD MLS# MDKE2006744 - Image 1

210 N Queen Street Chestertown, MD MLS# MDKE2006744 - Image 2

210 N Queen Street Chestertown, MD MLS# MDKE2006744 - Image 3

210 N Queen Street Chestertown, MD MLS# MDKE2006744 - Image 4

210 N Queen Street Chestertown, MD MLS# MDKE2006744 - Image 5

210 N Queen Street Chestertown, MD MLS# MDKE2006744 - Image 6

210 N Queen Street Chestertown, MD MLS# MDKE2006744 - Image 7

210 N Queen Street Chestertown, MD MLS# MDKE2006744 - Image 8

210 N Queen Street Chestertown, MD MLS# MDKE2006744 - Image 9

210 N Queen Street Chestertown, MD MLS# MDKE2006744 - Image 10

210 N Queen Street Chestertown, MD MLS# MDKE2006744 - Image 11

210 N Queen Street Chestertown, MD MLS# MDKE2006744 - Image 12

1 of 12

$735,000

Beds

2.1

Baths

2,730

Sq.Ft.

210 N Queen Street

Chestertown, MD

Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 1

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 2

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 3

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 4

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 5

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 6

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 7

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 8

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 9

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 10

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 11

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 12

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 13

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 14

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 15

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 16

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 17

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 18

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 19

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 20

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 21

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117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 23

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117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 25

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 26

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 27

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 28

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 29

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 30

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 31

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 32

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 33

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 34

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 35

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 36

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 37

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 38

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 39

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 40

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 41

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 42

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 43

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 44

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 45

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 46

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 47

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 48

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 49

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 50

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 51

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 52

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 53

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 54

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 55

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 56

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 57

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 58

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 59

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 60

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 61

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 62

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 63

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 64

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 65

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 66

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 67

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 68

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 69

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 70

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 71

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 72

117 Water Street N # 1A Chestertown, MD MLS# MDKE2006162 - Image 73

Virtual Tour

1 of 73

$685,000

Beds

3.0

Baths

3,000

Sq.Ft.

117 Water Street N # 1A

Chestertown, MD

Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 1

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 2

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 3

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 4

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 5

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 6

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 7

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 8

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 9

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 10

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 11

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 12

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 13

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 14

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 15

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 16

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 17

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 18

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 19

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 20

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 21

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 22

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 23

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 24

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 25

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 26

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 27

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 28

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 29

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 30

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 31

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 32

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 33

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 34

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 35

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 36

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 37

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 38

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 39

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 40

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 41

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 42

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 43

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 44

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 45

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 46

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 47

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 48

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 49

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 50

7844 Chester Court Chestertown, MD MLS# MDKE2005796 - Image 51

1 of 51

$670,000

Beds

2.1

Baths

3,248

Sq.Ft.

7844 Chester Court

Chestertown, MD

Courtesy of DOUG ASHLEY REALTORS, LLC

108 Little Harbor Way Chestertown, MD MLS# MDKE2005902 - Image 1

108 Little Harbor Way Chestertown, MD MLS# MDKE2005902 - Image 2

108 Little Harbor Way Chestertown, MD MLS# MDKE2005902 - Image 3

108 Little Harbor Way Chestertown, MD MLS# MDKE2005902 - Image 4

108 Little Harbor Way Chestertown, MD MLS# MDKE2005902 - Image 5

1 of 5

$635,000

Studio

Beds

0.0

Baths

108 Little Harbor Way

Chestertown, MD

Courtesy of GUNTHER-MCCLARY REAL ESTATE

103 Maple Avenue Chestertown, MD MLS# MDKE2006676 - Image 1

103 Maple Avenue Chestertown, MD MLS# MDKE2006676 - Image 2

103 Maple Avenue Chestertown, MD MLS# MDKE2006676 - Image 3

103 Maple Avenue Chestertown, MD MLS# MDKE2006676 - Image 4

103 Maple Avenue Chestertown, MD MLS# MDKE2006676 - Image 5

103 Maple Avenue Chestertown, MD MLS# MDKE2006676 - Image 6

103 Maple Avenue Chestertown, MD MLS# MDKE2006676 - Image 7

103 Maple Avenue Chestertown, MD MLS# MDKE2006676 - Image 8

103 Maple Avenue Chestertown, MD MLS# MDKE2006676 - Image 9

103 Maple Avenue Chestertown, MD MLS# MDKE2006676 - Image 10

103 Maple Avenue Chestertown, MD MLS# MDKE2006676 - Image 11

103 Maple Avenue Chestertown, MD MLS# MDKE2006676 - Image 12

103 Maple Avenue Chestertown, MD MLS# MDKE2006676 - Image 13

1 of 13

$615,000

Beds

2.1

Baths

4,536

Sq.Ft.

103 Maple Avenue

Chestertown, MD

Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 1

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 2

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 3

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 4

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 5

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 6

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 7

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 8

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 9

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 10

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 11

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 12

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 13

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 14

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 15

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 16

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 17

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 18

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103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 20

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 21

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103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 35

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103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 37

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 38

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 39

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 40

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 41

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 42

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 43

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 44

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 45

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 46

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 47

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 48

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 49

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 50

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 51

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 52

103 Sutton Way Chestertown, MD MLS# MDKE2006344 - Image 53

Virtual Tour

1 of 53

$550,000

Beds

3.1

Baths

3,816

Sq.Ft.

103 Sutton Way

Chestertown, MD

Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 1

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 2

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 3

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 4

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 5

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 6

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 7

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 8

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 9

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 10

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 11

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 12

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 13

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 14

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 15

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 16

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 17

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 18

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 19

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9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 21

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9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 39

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9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 41

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9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 43

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9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 46

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 47

9816 Fairlee Road Chestertown, MD MLS# MDKE2006488 - Image 48

Virtual Tour

1 of 48

$535,000

Beds

3.0

Baths

1,624

Sq.Ft.

9816 Fairlee Road

Chestertown, MD

Courtesy of LONG & FOSTER REAL ESTATE, INC.

110 S Queen Street Chestertown, MD MLS# MDKE2006520 - Image 1

110 S Queen Street Chestertown, MD MLS# MDKE2006520 - Image 2

110 S Queen Street Chestertown, MD MLS# MDKE2006520 - Image 3

110 S Queen Street Chestertown, MD MLS# MDKE2006520 - Image 4

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110 S Queen Street Chestertown, MD MLS# MDKE2006520 - Image 30

1 of 30

$525,000

Beds

1.1

Baths

1,785

Sq.Ft.

110 S Queen Street

Chestertown, MD

Courtesy of CROSS STREET REALTORS LLC

110 S Queen Street Chestertown, MD MLS# MDKE2006536 - Image 1

110 S Queen Street Chestertown, MD MLS# MDKE2006536 - Image 2

110 S Queen Street Chestertown, MD MLS# MDKE2006536 - Image 3

110 S Queen Street Chestertown, MD MLS# MDKE2006536 - Image 4

110 S Queen Street Chestertown, MD MLS# MDKE2006536 - Image 5

110 S Queen Street Chestertown, MD MLS# MDKE2006536 - Image 6

110 S Queen Street Chestertown, MD MLS# MDKE2006536 - Image 7

110 S Queen Street Chestertown, MD MLS# MDKE2006536 - Image 8

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1 of 29

$525,000

1,785

Sq.Ft.

110 S Queen Street

Chestertown, MD

Courtesy of CROSS STREET REALTORS LLC

101 S Mill Street Chestertown, MD MLS# MDKE2006674 - Image 1

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101 S Mill Street Chestertown, MD MLS# MDKE2006674 - Image 39

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101 S Mill Street

Chestertown, MD

Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY

103 Landing Lane Chestertown, MD MLS# MDKE2005670 - Image 1

103 Landing Lane Chestertown, MD MLS# MDKE2005670 - Image 2

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103 Landing Lane Chestertown, MD MLS# MDKE2005670 - Image 70

1 of 70

$499,999

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2.1

Baths

2,100

Sq.Ft.

103 Landing Lane

Chestertown, MD

Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY

218 Camelot Drive Chestertown, MD MLS# MDKE2005982 - Image 1

218 Camelot Drive Chestertown, MD MLS# MDKE2005982 - Image 2

218 Camelot Drive Chestertown, MD MLS# MDKE2005982 - Image 3

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218 Camelot Drive Chestertown, MD MLS# MDKE2005982 - Image 45

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218 Camelot Drive Chestertown, MD MLS# MDKE2005982 - Image 47

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218 Camelot Drive Chestertown, MD MLS# MDKE2005982 - Image 55

218 Camelot Drive Chestertown, MD MLS# MDKE2005982 - Image 56

218 Camelot Drive Chestertown, MD MLS# MDKE2005982 - Image 57

Virtual Tour

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218 Camelot Drive

Chestertown, MD

Courtesy of COLDWELL BANKER REALTY

8620 Park Drive Chestertown, MD MLS# MDKE2005850 - Image 1

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8620 Park Drive Chestertown, MD MLS# MDKE2005850 - Image 64

8620 Park Drive Chestertown, MD MLS# MDKE2005850 - Image 65

8620 Park Drive Chestertown, MD MLS# MDKE2005850 - Image 66

Virtual Tour

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$499,900

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2.1

Baths

2,524

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8620 Park Drive

Chestertown, MD

Courtesy of DOUG ASHLEY REALTORS, LLC

311 Devon Drive Chestertown, MD MLS# MDKE2005930 - Image 1

311 Devon Drive Chestertown, MD MLS# MDKE2005930 - Image 2

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311 Devon Drive Chestertown, MD MLS# MDKE2005930 - Image 39

311 Devon Drive Chestertown, MD MLS# MDKE2005930 - Image 40

311 Devon Drive Chestertown, MD MLS# MDKE2005930 - Image 41

Virtual Tour

1 of 41

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Baths

3,504

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311 Devon Drive

Chestertown, MD

Courtesy of DOUG ASHLEY REALTORS, LLC

105 N Water Street # 2 Chestertown, MD MLS# MDKE2006680 - Image 1

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105 N Water Street # 2 Chestertown, MD MLS# MDKE2006680 - Image 48

105 N Water Street # 2 Chestertown, MD MLS# MDKE2006680 - Image 49

Recently Listed with Virtual Tour

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OPEN HOUSE: Friday 7/3 4:00 PM - 6:00 PM

$475,000

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Baths

1,011

Sq.Ft.

105 N Water Street # 2

Chestertown, MD

Courtesy of NORTHROP REALTY

25750 Collins Avenue Chestertown, MD MLS# MDKE2006546 - Image 1

25750 Collins Avenue Chestertown, MD MLS# MDKE2006546 - Image 2

25750 Collins Avenue Chestertown, MD MLS# MDKE2006546 - Image 3

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Recently Listed with Virtual Tour

1 of 50

$468,000

Beds

2.0

Baths

3,262

Sq.Ft.

25750 Collins Avenue

Chestertown, MD

Courtesy of DOUG ASHLEY REALTORS, LLC

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: 121
Estimated median home price: $325,000

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	33
$100K - 200K	9
$200K - 300K	14
$300K - 400K	16
$400K - 500K	10
$500K - 600K	5
$600K - 700K	4
$700K - 800K	10
$800K - 900K	5
$900K - 1M	0
$1M - Max	15

Homes for Sale by Type in Chestertown, MD

Property Type	Count
Single Family	48
Townhouse	6
Condo	17
Commercial	10
Rental	15
Lots and Land	40
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 6/30/2026)

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21620

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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.

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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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