Chestertown Maryland Homes for Sale

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109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 1

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 2

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 3

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 4

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 5

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 6

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 7

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 8

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 9

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 10

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 11

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 12

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 13

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 14

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 15

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 16

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 17

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 18

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 19

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 20

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 21

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 22

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 23

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 24

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 25

109 S College Avenue Chestertown, MD MLS# MDKE2005818 - Image 26

1 of 26

$449,900

Beds

2.1

Baths

1,216

Sq.Ft.

109 S College Avenue

Chestertown, MD

Courtesy of CROSS STREET REALTORS LLC

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 1

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 2

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 3

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 4

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 5

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 6

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 7

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 8

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 9

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 10

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 11

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 12

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 13

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 14

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 15

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 16

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 17

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 18

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 19

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 20

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 21

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 22

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 23

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 24

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 25

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 26

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 27

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 28

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 29

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 30

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 31

303 E Campus Avenue Chestertown, MD MLS# MDKE2005756 - Image 32

Virtual Tour

1 of 32

$363,000

Beds

2.0

Baths

1,532

Sq.Ft.

303 E Campus Avenue

Chestertown, MD

Courtesy of DOUG ASHLEY REALTORS, LLC

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

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

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

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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

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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

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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

THE TIME TO SELL IS NOW!

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

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 1

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 2

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 3

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 4

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 5

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 6

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 7

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 8

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 9

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 10

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 11

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 12

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 13

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 14

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 15

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 16

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 17

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 18

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 19

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 20

318 Lincoln Chestertown, MD MLS# MDKE2005842 - Image 21

1 of 21

OPEN HOUSE: Saturday 12/13 12:00 PM - 3:00 PM

$269,000

Beds

2.0

Baths

960

Sq.Ft.

318 Lincoln

Chestertown, MD

Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 1

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 2

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 3

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 4

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 5

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 6

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 7

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 8

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 9

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 10

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 11

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 12

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 13

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 14

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 15

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 16

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 17

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 18

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 19

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 20

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 21

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 22

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 23

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 24

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 25

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 26

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 27

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 28

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 29

8750 Georgetown Road Chestertown, MD MLS# MDKE2005834 - Image 30

1 of 30

$339,000

Beds

2.0

Baths

1,900

Sq.Ft.

8750 Georgetown Road

Chestertown, MD

Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 1

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 2

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 3

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 4

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 5

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 6

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 7

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 8

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 9

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 10

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 11

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 12

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 13

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 14

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 15

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 16

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 17

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 18

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 19

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 20

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 21

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 22

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 23

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 24

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 25

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 26

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 27

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 28

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 29

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 30

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 31

411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824 - Image 32

Virtual Tour

1 of 32

$419,000

Beds

2.1

Baths

1,676

Sq.Ft.

411 Greenwood Avenue

Chestertown, MD

Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY

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

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 4

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 5

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 6

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 7

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 8

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 9

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 10

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 11

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 12

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 13

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 14

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 15

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 16

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 17

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 18

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 19

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 20

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 21

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 22

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 23

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 24

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 25

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 26

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 27

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 28

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 29

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 30

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 31

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 32

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 33

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 34

101 Birch Run Road Chestertown, MD MLS# MDKE2005810 - Image 35

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

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

Clarissa Road Chestertown, MD MLS# MDKE2005786 - Image 1

1 of 1

$10,000

Studio

Beds

0.0

Baths

Clarissa Road

Chestertown, MD

Courtesy of SAMSON PROPERTIES

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 1

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 2

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 3

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 4

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 5

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107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 7

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 8

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 9

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107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 13

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 14

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 15

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 16

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 17

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 18

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 19

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 20

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 21

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 22

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 23

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 24

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 25

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 26

107 Malone Avenue Chestertown, MD MLS# MDKE2005764 - Image 27

Virtual Tour

1 of 27

$290,000

Beds

1.0

Baths

1,200

Sq.Ft.

107 Malone Avenue

Chestertown, MD

Courtesy of DOUGLAS REALTY LLC

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

206 Valley Chestertown, MD MLS# MDKE2005762 - Image 16

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206 Valley Chestertown, MD MLS# MDKE2005762 - Image 20

206 Valley Chestertown, MD MLS# MDKE2005762 - Image 21

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206 Valley Chestertown, MD MLS# MDKE2005762 - Image 23

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206 Valley Chestertown, MD MLS# MDKE2005762 - Image 31

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206 Valley Chestertown, MD MLS# MDKE2005762 - Image 33

206 Valley Chestertown, MD MLS# MDKE2005762 - Image 34

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

8833 Georgetown Road Chestertown, MD MLS# MDKE2005766 - Image 1

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8833 Georgetown Road Chestertown, MD MLS# MDKE2005766 - Image 45

8833 Georgetown Road Chestertown, MD MLS# MDKE2005766 - Image 46

8833 Georgetown Road Chestertown, MD MLS# MDKE2005766 - Image 47

1 of 47

$364,000

Beds

2.0

Baths

1,625

Sq.Ft.

8833 Georgetown Road

Chestertown, MD

Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY

423 Calvert Street Chestertown, MD MLS# MDKE2005718 - Image 1

423 Calvert Street Chestertown, MD MLS# MDKE2005718 - Image 2

423 Calvert Street Chestertown, MD MLS# MDKE2005718 - Image 3

423 Calvert Street Chestertown, MD MLS# MDKE2005718 - Image 4

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423 Calvert Street Chestertown, MD MLS# MDKE2005718 - Image 6

423 Calvert Street Chestertown, MD MLS# MDKE2005718 - Image 7

423 Calvert Street Chestertown, MD MLS# MDKE2005718 - Image 8

423 Calvert Street Chestertown, MD MLS# MDKE2005718 - Image 9

423 Calvert Street Chestertown, MD MLS# MDKE2005718 - Image 10

423 Calvert Street Chestertown, MD MLS# MDKE2005718 - Image 11

423 Calvert Street Chestertown, MD MLS# MDKE2005718 - Image 12

423 Calvert Street Chestertown, MD MLS# MDKE2005718 - Image 13

423 Calvert Street Chestertown, MD MLS# MDKE2005718 - Image 14

423 Calvert Street Chestertown, MD MLS# MDKE2005718 - Image 15

423 Calvert Street Chestertown, MD MLS# MDKE2005718 - Image 16

423 Calvert Street Chestertown, MD MLS# MDKE2005718 - Image 17

423 Calvert Street Chestertown, MD MLS# MDKE2005718 - Image 18

423 Calvert Street Chestertown, MD MLS# MDKE2005718 - Image 19

423 Calvert Street Chestertown, MD MLS# MDKE2005718 - Image 20

Virtual Tour

1 of 20

$135,000

Beds

1.1

Baths

1,136

Sq.Ft.

423 Calvert Street

Chestertown, MD

Courtesy of REDFIN CORP

7653 Broad Neck Road Chestertown, MD MLS# MDKE2005742 - Image 1

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7653 Broad Neck Road Chestertown, MD MLS# MDKE2005742 - Image 3

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7653 Broad Neck Road Chestertown, MD MLS# MDKE2005742 - Image 37

7653 Broad Neck Road Chestertown, MD MLS# MDKE2005742 - Image 38

7653 Broad Neck Road Chestertown, MD MLS# MDKE2005742 - Image 39

Virtual Tour

1 of 39

$375,000

Beds

3.0

Baths

1,790

Sq.Ft.

7653 Broad Neck Road

Chestertown, MD

Courtesy of BENSON & MANGOLD, LLC

517 High Street Chestertown, MD MLS# MDKE2005736 - Image 1

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517 High Street Chestertown, MD MLS# MDKE2005736 - Image 51

1 of 51

$389,900

Beds

0.0

Baths

517 High Street

Chestertown, MD

Courtesy of L. C. PARKER REAL ESTATE

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 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

103 Metcalf Rd Chestertown, MD MLS# MDKE2005688 - Image 1

103 Metcalf Rd Chestertown, MD MLS# MDKE2005688 - Image 2

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103 Metcalf Rd Chestertown, MD MLS# MDKE2005688 - Image 25

New Construction

1 of 25

$259,900

Beds

1.1

Baths

1,280

Sq.Ft.

103 Metcalf Rd

Chestertown, MD

Courtesy of REAL BROKER, LLC

23110 Old Fairlee Road Chestertown, MD MLS# MDKE2005676 - Image 1

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23110 Old Fairlee Road Chestertown, MD MLS# MDKE2005676 - Image 30

1 of 30

$349,900

Beds

1.0

Baths

1,805

Sq.Ft.

23110 Old Fairlee Road

Chestertown, MD

Courtesy of REAL BROKER LLC

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

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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

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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21620

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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