Chestertown Maryland Homes for Sale

97 total properties

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515 Washington Avenue Chestertown, MD MLS# MDKE2000776 - Image 1

515 Washington Avenue Chestertown, MD MLS# MDKE2000776 - Image 2

515 Washington Avenue Chestertown, MD MLS# MDKE2000776 - Image 3

515 Washington Avenue Chestertown, MD MLS# MDKE2000776 - Image 4

1 of 4

$899,000

42,000

Sq.Ft.

515 Washington Avenue

Chestertown, MD

Courtesy of ESHORE

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 1

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 2

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 3

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 4

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 5

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 6

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 7

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 8

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 9

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 10

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 11

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 12

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 13

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 14

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 15

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 16

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 17

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 18

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 19

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 20

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 21

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 22

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 23

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 24

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 25

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 26

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 27

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 28

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 29

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 30

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 31

228 S Water St Chestertown, MD MLS# MDKE2005812 - Image 32

New Construction

1 of 32

$878,000

Beds

3.1

Baths

2,310

Sq.Ft.

228 S Water St

Chestertown, MD

Courtesy of GUNTHER-MCCLARY REAL ESTATE

201 N Lynchburg Street Chestertown, MD MLS# MDKE2005278 - Image 1

201 N Lynchburg Street Chestertown, MD MLS# MDKE2005278 - Image 2

201 N Lynchburg Street Chestertown, MD MLS# MDKE2005278 - Image 3

201 N Lynchburg Street Chestertown, MD MLS# MDKE2005278 - Image 4

201 N Lynchburg Street Chestertown, MD MLS# MDKE2005278 - Image 5

201 N Lynchburg Street Chestertown, MD MLS# MDKE2005278 - Image 6

201 N Lynchburg Street Chestertown, MD MLS# MDKE2005278 - Image 7

201 N Lynchburg Street Chestertown, MD MLS# MDKE2005278 - Image 8

201 N Lynchburg Street Chestertown, MD MLS# MDKE2005278 - Image 9

201 N Lynchburg Street Chestertown, MD MLS# MDKE2005278 - Image 10

201 N Lynchburg Street Chestertown, MD MLS# MDKE2005278 - Image 11

201 N Lynchburg Street Chestertown, MD MLS# MDKE2005278 - Image 12

201 N Lynchburg Street Chestertown, MD MLS# MDKE2005278 - Image 13

1 of 13

$850,000

2,045

Sq.Ft.

201 N Lynchburg Street

Chestertown, MD

Courtesy of RE/MAX ASSOCIATES-HOCKESSIN

THE TIME TO SELL IS NOW!

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 1

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 2

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 3

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 4

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 5

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 6

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 7

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 8

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 9

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 10

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 11

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 12

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 13

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 14

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 15

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 16

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 17

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 18

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 19

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 20

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 21

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 22

104 Little Harbor Way Chestertown, MD MLS# MDKE2005894 - Image 23

New Construction

1 of 23

$849,900

Beds

2.1

Baths

1,980

Sq.Ft.

104 Little Harbor Way

Chestertown, MD

Courtesy of GUNTHER-MCCLARY REAL ESTATE

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 1

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 2

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 3

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 4

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 5

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 6

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 7

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 8

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 9

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 10

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 11

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 12

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 13

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 14

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 15

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 16

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 17

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 18

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 19

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 20

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 21

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 22

102 Little Harbor Way Chestertown, MD MLS# MDKE2005950 - Image 23

New Construction

1 of 23

$839,500

Beds

2.1

Baths

1,964

Sq.Ft.

102 Little Harbor Way

Chestertown, MD

Courtesy of GUNTHER-MCCLARY REAL ESTATE

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 1

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 2

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 3

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 4

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 5

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 6

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 7

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 8

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 9

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 10

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 11

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 12

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 13

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 14

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 15

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 16

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 17

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 18

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 19

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 20

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 21

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 22

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 23

104 Landing Lane Chestertown, MD MLS# MDKE2005952 - Image 24

New Construction

1 of 24

$813,900

Beds

3.1

Baths

2,192

Sq.Ft.

104 Landing Lane

Chestertown, MD

Courtesy of GUNTHER-MCCLARY REAL ESTATE

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 1

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 2

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 3

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 4

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 5

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 6

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 7

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 8

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 9

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 10

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 11

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 12

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 13

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 14

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 15

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 16

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 17

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 18

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 19

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 20

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 21

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 22

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 23

106 Landing Lane Chestertown, MD MLS# MDKE2005892 - Image 24

New Construction

1 of 24

$799,900

Beds

3.1

Baths

2,092

Sq.Ft.

106 Landing Lane

Chestertown, MD

Courtesy of GUNTHER-MCCLARY REAL ESTATE

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 1

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 2

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 3

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 4

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 5

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 6

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 7

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 8

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 9

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 10

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 11

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 12

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 13

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 14

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 15

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 16

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 17

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 18

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 19

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 20

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 21

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 22

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 23

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 24

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 25

#35 Landing Lane Chestertown, MD MLS# MDKE2005956 - Image 26

New Construction

1 of 26

$786,900

Beds

2.1

Baths

1,964

Sq.Ft.

#35 Landing Lane

Chestertown, MD

Courtesy of GUNTHER-MCCLARY REAL ESTATE

#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

New Construction

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

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

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

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

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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

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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

$745,000

Beds

2.1

Baths

3,248

Sq.Ft.

7844 Chester Court

Chestertown, MD

Courtesy of DOUG ASHLEY REALTORS, LLC

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

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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

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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

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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 Valley Chestertown, MD MLS# MDKE2005762 - Image 1

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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 39

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

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

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1 of 54

$595,000

Beds

2.1

Baths

3,935

Sq.Ft.

251 Devon Drive

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: 108
Estimated median home price: $329,450

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	34
$100K - 200K	9
$200K - 300K	10
$300K - 400K	15
$400K - 500K	6
$500K - 600K	5
$600K - 700K	6
$700K - 800K	6
$800K - 900K	6
$900K - 1M	0
$1M - Max	11

Homes for Sale by Type in Chestertown, MD

Property Type	Count
Single Family	38
Townhouse	8
Condo	12
Commercial	5
Rental	4
Lots and Land	43
Condo/Town/CoOp	0
CoOp	0
Multi Family	1
Mobile Home	0
Farms	1

(Data as of 12/25/2025)

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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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