Chestertown Maryland Homes for Sale

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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

$770,000

Beds

2.1

Baths

3,248

Sq.Ft.

7844 Chester Court

Chestertown, MD

Courtesy of DOUG ASHLEY REALTORS, LLC

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 1

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 2

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 3

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 4

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 5

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 6

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 7

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 8

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 9

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 10

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 11

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 12

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 13

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 14

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 15

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 16

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 17

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 18

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 19

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 20

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 21

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 22

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 23

#37 Landing Lane Chestertown, MD MLS# MDKE2005960 - Image 24

Recently Listed

1 of 24

$765,900

Beds

2.1

Baths

1,964

Sq.Ft.

#37 Landing Lane

Chestertown, MD

Courtesy of GUNTHER-MCCLARY REAL ESTATE

#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

Recently Listed

1 of 26

$753,500

Beds

2.1

Baths

1,964

Sq.Ft.

#36 Landing Lane

Chestertown, MD

Courtesy of GUNTHER-MCCLARY REAL ESTATE

THE TIME TO SELL IS NOW!

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 1

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 2

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 3

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 4

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 5

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 6

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 7

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 8

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 9

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 10

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 11

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 12

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 13

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 14

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 15

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 16

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 17

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 18

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 19

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 20

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 21

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 22

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 23

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 24

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 25

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 26

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 27

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 28

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 29

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 30

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 31

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 32

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 33

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 34

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 35

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 36

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 37

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 38

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 39

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 40

10230 John Carvill Road Chestertown, MD MLS# MDKE2005716 - Image 41

1 of 41

$750,000

Beds

3.0

Baths

2,350

Sq.Ft.

10230 John Carvill Road

Chestertown, MD

Courtesy of SHORELINE REALTY

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 1

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 2

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 3

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 4

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 5

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 6

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 7

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 8

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 9

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 10

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 11

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 12

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 13

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 14

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 15

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 16

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 17

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 18

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 19

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 20

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 21

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 22

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 23

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 24

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 25

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 26

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 27

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 28

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 29

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 30

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 31

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 32

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 33

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 34

200 Washington Avenue Chestertown, MD MLS# MDKE2005538 - Image 35

1 of 35

$695,000

Beds

3.1

Baths

2,917

Sq.Ft.

200 Washington Avenue

Chestertown, MD

Courtesy of CROSS STREET REALTORS LLC

118 Little Harbor Way # 202 Chestertown, MD MLS# MDKE2005800 - Image 1

118 Little Harbor Way # 202 Chestertown, MD MLS# MDKE2005800 - Image 2

118 Little Harbor Way # 202 Chestertown, MD MLS# MDKE2005800 - Image 3

118 Little Harbor Way # 202 Chestertown, MD MLS# MDKE2005800 - Image 4

118 Little Harbor Way # 202 Chestertown, MD MLS# MDKE2005800 - Image 5

118 Little Harbor Way # 202 Chestertown, MD MLS# MDKE2005800 - Image 6

118 Little Harbor Way # 202 Chestertown, MD MLS# MDKE2005800 - Image 7

118 Little Harbor Way # 202 Chestertown, MD MLS# MDKE2005800 - Image 8

118 Little Harbor Way # 202 Chestertown, MD MLS# MDKE2005800 - Image 9

118 Little Harbor Way # 202 Chestertown, MD MLS# MDKE2005800 - Image 10

118 Little Harbor Way # 202 Chestertown, MD MLS# MDKE2005800 - Image 11

118 Little Harbor Way # 202 Chestertown, MD MLS# MDKE2005800 - Image 12

118 Little Harbor Way # 202 Chestertown, MD MLS# MDKE2005800 - Image 13

118 Little Harbor Way # 202 Chestertown, MD MLS# MDKE2005800 - Image 14

118 Little Harbor Way # 202 Chestertown, MD MLS# MDKE2005800 - Image 15

118 Little Harbor Way # 202 Chestertown, MD MLS# MDKE2005800 - Image 16

118 Little Harbor Way # 202 Chestertown, MD MLS# MDKE2005800 - Image 17

118 Little Harbor Way # 202 Chestertown, MD MLS# MDKE2005800 - Image 18

118 Little Harbor Way # 202 Chestertown, MD MLS# MDKE2005800 - Image 19

1 of 19

$695,000

Beds

2.0

Baths

1,600

Sq.Ft.

118 Little Harbor Way # 202

Chestertown, MD

Courtesy of BENSON & MANGOLD, LLC

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 1

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 2

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 3

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 4

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 5

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 6

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 7

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 8

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 9

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 10

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 11

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 12

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 13

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 14

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 15

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 16

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 17

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 18

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 19

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 20

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 21

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 22

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 23

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 24

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 25

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 26

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 27

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 28

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 29

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 30

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 31

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 32

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 33

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 34

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 35

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 36

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 37

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 38

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 39

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 40

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 41

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 42

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 43

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 44

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 45

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 46

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 47

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 48

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 49

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 50

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 51

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 52

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 53

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 54

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 55

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 56

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 57

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 58

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 59

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 60

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 61

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 62

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 63

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 64

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 65

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 66

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 67

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 68

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 69

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 70

11040 Kylie Lane Chestertown, MD MLS# MDKE2004586 - Image 71

Virtual Tour

1 of 71

$649,000

Beds

3.1

Baths

3,684

Sq.Ft.

11040 Kylie Lane

Chestertown, MD

Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY

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

26933 Mallard Road Chestertown, MD MLS# MDKE2005422 - Image 1

26933 Mallard Road Chestertown, MD MLS# MDKE2005422 - Image 2

26933 Mallard Road Chestertown, MD MLS# MDKE2005422 - Image 3

26933 Mallard Road Chestertown, MD MLS# MDKE2005422 - Image 4

26933 Mallard Road Chestertown, MD MLS# MDKE2005422 - Image 5

26933 Mallard Road Chestertown, MD MLS# MDKE2005422 - Image 6

26933 Mallard Road Chestertown, MD MLS# MDKE2005422 - Image 7

26933 Mallard Road Chestertown, MD MLS# MDKE2005422 - Image 8

26933 Mallard Road Chestertown, MD MLS# MDKE2005422 - Image 9

26933 Mallard Road Chestertown, MD MLS# MDKE2005422 - Image 10

26933 Mallard Road Chestertown, MD MLS# MDKE2005422 - Image 11

26933 Mallard Road Chestertown, MD MLS# MDKE2005422 - Image 12

26933 Mallard Road Chestertown, MD MLS# MDKE2005422 - Image 13

26933 Mallard Road Chestertown, MD MLS# MDKE2005422 - Image 14

26933 Mallard Road Chestertown, MD MLS# MDKE2005422 - Image 15

1 of 15

$625,000

Beds

2.1

Baths

1,600

Sq.Ft.

26933 Mallard Road

Chestertown, MD

Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 1

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 2

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 3

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 4

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 5

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 6

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 7

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 8

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 9

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 10

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 11

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 12

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 13

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 14

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 15

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 16

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 17

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 18

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 19

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 20

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 21

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 22

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 23

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 24

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 25

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 26

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 27

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 28

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 29

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 30

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 31

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 32

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 33

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 34

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 35

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 36

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 37

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 38

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 39

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 40

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 41

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 42

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 43

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 44

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 45

206 S Water Street Chestertown, MD MLS# MDKE2005840 - Image 46

1 of 46

$619,000

Beds

3.1

Baths

2,008

Sq.Ft.

206 S Water Street

Chestertown, MD

Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY

206 Valley Chestertown, MD MLS# MDKE2005762 - Image 1

206 Valley Chestertown, MD MLS# MDKE2005762 - Image 2

206 Valley Chestertown, MD MLS# MDKE2005762 - Image 3

206 Valley Chestertown, MD MLS# MDKE2005762 - Image 4

206 Valley Chestertown, MD MLS# MDKE2005762 - Image 5

206 Valley Chestertown, MD MLS# MDKE2005762 - Image 6

206 Valley Chestertown, MD MLS# MDKE2005762 - Image 7

206 Valley Chestertown, MD MLS# MDKE2005762 - Image 8

206 Valley Chestertown, MD MLS# MDKE2005762 - Image 9

206 Valley Chestertown, MD MLS# MDKE2005762 - Image 10

206 Valley Chestertown, MD MLS# MDKE2005762 - Image 11

206 Valley Chestertown, MD MLS# MDKE2005762 - Image 12

206 Valley Chestertown, MD MLS# MDKE2005762 - Image 13

206 Valley Chestertown, MD MLS# MDKE2005762 - Image 14

206 Valley Chestertown, MD MLS# MDKE2005762 - Image 15

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206 Valley Chestertown, MD MLS# MDKE2005762 - Image 35

1 of 35

$615,000

Beds

2.0

Baths

2,869

Sq.Ft.

206 Valley

Chestertown, MD

Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY

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 40

Recently Listed with Virtual Tour

1 of 40

$598,000

Beds

3.1

Baths

3,504

Sq.Ft.

311 Devon Drive

Chestertown, MD

Courtesy of DOUG ASHLEY REALTORS, LLC

251 Devon Drive Chestertown, MD MLS# MDKE2005536 - Image 1

251 Devon Drive Chestertown, MD MLS# MDKE2005536 - Image 2

251 Devon Drive Chestertown, MD MLS# MDKE2005536 - Image 3

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251 Devon Drive Chestertown, MD MLS# MDKE2005536 - Image 54

1 of 54

$595,000

Beds

2.1

Baths

3,935

Sq.Ft.

251 Devon Drive

Chestertown, MD

Courtesy of DOUG ASHLEY REALTORS, LLC

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

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

103 Landing Lane Chestertown, MD MLS# MDKE2005670 - Image 3

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103 Landing Lane Chestertown, MD MLS# MDKE2005670 - Image 69

1 of 69

$539,999

Beds

2.1

Baths

2,100

Sq.Ft.

103 Landing Lane

Chestertown, MD

Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 1

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 2

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 3

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 4

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 5

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 6

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 7

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 8

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 9

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 10

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 11

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 12

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 13

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 14

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 15

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 16

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 17

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 18

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 19

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 20

116 Harlan Loop Chestertown, MD MLS# MDKE2005610 - Image 21

1 of 21

$519,000

Beds

3.1

Baths

4,067

Sq.Ft.

116 Harlan Loop

Chestertown, MD

Courtesy of SAMSON PROPERTIES

100 Adela Way Chestertown, MD MLS# MDKE2005636 - Image 1

100 Adela Way Chestertown, MD MLS# MDKE2005636 - Image 2

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100 Adela Way Chestertown, MD MLS# MDKE2005636 - Image 70

100 Adela Way Chestertown, MD MLS# MDKE2005636 - Image 71

Virtual Tour

1 of 71

$515,000

Beds

3.1

Baths

3,799

Sq.Ft.

100 Adela Way

Chestertown, MD

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 1

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 2

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 3

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101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 36

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 37

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 38

Virtual Tour

1 of 38

$499,999

Beds

2.0

Baths

1,961

Sq.Ft.

101 Birch Run Road

Chestertown, MD

Courtesy of REMAX VISION

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

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8620 Park Drive Chestertown, MD MLS# MDKE2005850 - Image 52

8620 Park Drive Chestertown, MD MLS# MDKE2005850 - Image 53

Virtual Tour

1 of 53

$499,900

Beds

2.1

Baths

2,524

Sq.Ft.

8620 Park Drive

Chestertown, MD

Courtesy of DOUG ASHLEY REALTORS, LLC

110 Trafford Drive Chestertown, MD MLS# MDKE2005964 - Image 1

1 of 1

$475,000

Beds

2.1

Baths

2,880

Sq.Ft.

110 Trafford Drive

Chestertown, MD

Courtesy of RE/MAX ADVANTAGE REALTY

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 1

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 2

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 3

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 4

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 5

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 6

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 7

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 8

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 9

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 10

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 11

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 12

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 13

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 14

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 15

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 16

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 17

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 18

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 19

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 20

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 21

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 22

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 23

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 24

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 25

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 26

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 27

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 28

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 29

222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876 - Image 30

1 of 30

$470,000

Beds

2.0

Baths

1,656

Sq.Ft.

222 Mount Vernon Avenue

Chestertown, MD

Courtesy of LONG & FOSTER REAL ESTATE, INC.

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: 113
Estimated median home price: $350,000

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	10
$200K - 300K	10
$300K - 400K	16
$400K - 500K	7
$500K - 600K	5
$600K - 700K	7
$700K - 800K	6
$800K - 900K	6
$900K - 1M	0
$1M - Max	13

Homes for Sale by Type in Chestertown, MD

Property Type	Count
Single Family	41
Townhouse	8
Condo	13
Commercial	6
Rental	5
Lots and Land	42
Condo/Town/CoOp	0
CoOp	0
Multi Family	2
Mobile Home	0
Farms	1

(Data as of 12/10/2025)

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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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