Chestertown Maryland Homes for Sale

53 total properties

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23741 L Road Chestertown, MD MLS# MDKE2006622 - Image 1

23741 L Road Chestertown, MD MLS# MDKE2006622 - Image 2

Recently Listed

1 of 2

$15,000

Studio

Beds

0.0

Baths

23741 L Road

Chestertown, MD

Courtesy of BENSON & MANGOLD, LLC

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 1

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 2

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 3

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 4

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 5

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 6

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 7

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 8

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 9

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 10

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 11

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 12

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 13

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 14

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 15

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 16

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 17

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 18

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 19

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 20

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 21

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 22

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 23

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 24

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 25

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 26

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 27

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 28

956 Washington Avenue Chestertown, MD MLS# MDKE2006394 - Image 29

Recently Listed with Virtual Tour

1 of 29

$285,000

Beds

1.0

Baths

1,248

Sq.Ft.

956 Washington Avenue

Chestertown, MD

Courtesy of DOUG ASHLEY REALTORS, LLC

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

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

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

Recently Listed

1 of 3

$55,000

Studio

Beds

0.0

Baths

Map 36 Parcel 80 Watertower Road

Chestertown, MD

Courtesy of DOUG ASHLEY REALTORS, LLC

THE TIME TO SELL IS NOW!

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

1 of 30

$185,000

Beds

1.1

Baths

1,136

Sq.Ft.

423 Calvert Street

Chestertown, MD

Courtesy of COMPASS

23683 L Road Chestertown, MD MLS# MDKE2006580 - Image 1

23683 L Road Chestertown, MD MLS# MDKE2006580 - Image 2

23683 L Road Chestertown, MD MLS# MDKE2006580 - Image 3

Recently Listed

1 of 3

$6,000

Studio

Beds

0.0

Baths

23683 L Road

Chestertown, MD

Courtesy of ALEX COOPER AUCTIONEERS, INC.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Virtual Tour

1 of 28

$205,000

Beds

1.0

Baths

1,314

Sq.Ft.

21363 Lynn Lane

Chestertown, MD

Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY

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

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

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

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

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

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

Recently Listed

1 of 6

$79,000

Studio

Beds

0.0

Baths

Sandy Bottom Road

Chestertown, MD

Courtesy of VILLAGE REAL ESTATE COMPANY LLC

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 1

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 2

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 3

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 4

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 5

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 6

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 7

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 8

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 9

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 10

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 11

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 12

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 13

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 14

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 15

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 16

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 17

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 18

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 19

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 20

100 Prospect Street Chestertown, MD MLS# MDKE2006544 - Image 21

1 of 21

$215,000

Beds

1.0

Baths

1,373

Sq.Ft.

100 Prospect Street

Chestertown, MD

Courtesy of REAL BROKER, LLC - CHESTER

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

1 of 18

$159,000

Beds

1.1

Baths

1,082

Sq.Ft.

144 Prospect Street

Chestertown, MD

Courtesy of DOUG ASHLEY REALTORS, LLC

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 1

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 2

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 3

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 4

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 5

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 6

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 7

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 8

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 9

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 10

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 11

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 12

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 13

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 14

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 15

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 16

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 17

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 18

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 19

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 20

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 21

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 22

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 23

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 24

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 25

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 26

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 27

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 28

24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342 - Image 29

1 of 29

$229,990

Beds

2.0

Baths

1,352

Sq.Ft.

24581 Willow Oak Lane

Chestertown, MD

Courtesy of DOUG ASHLEY REALTORS, LLC

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

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

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

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

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

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

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

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

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

1 of 9

$109,999

Studio

Beds

0.0

Baths

116 Cross Street

Chestertown, MD

Courtesy of SELECT LAND & HOMES, LLC

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 1

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 2

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 3

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 4

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 5

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 6

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 7

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 8

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 9

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 10

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 11

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 12

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 13

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 14

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 15

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 16

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 17

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 18

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 19

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 20

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 21

103 Metcalf Rd Chestertown, MD MLS# MDKE2006446 - Image 22

New Construction

1 of 22

$259,900

Beds

1.1

Baths

1,280

Sq.Ft.

103 Metcalf Rd

Chestertown, MD

Courtesy of REAL BROKER, LLC - CHESTER

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 1

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 2

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 3

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 4

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 5

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 6

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 7

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 8

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 9

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 10

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 11

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 12

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 13

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 14

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 15

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 16

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 17

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 18

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 19

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 20

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 21

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 22

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 23

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 24

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 25

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 26

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 27

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 28

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 29

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 30

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 31

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 32

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 33

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 34

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 35

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 36

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 37

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 38

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 39

115 Acorn Drive Chestertown, MD MLS# MDKE2006360 - Image 40

Virtual Tour

1 of 40

$296,000

Beds

2.1

Baths

1,864

Sq.Ft.

115 Acorn Drive

Chestertown, MD

Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC

21217 Texas Avenue Chestertown, MD MLS# MDKE2006364 - Image 1

21217 Texas Avenue Chestertown, MD MLS# MDKE2006364 - Image 2

21217 Texas Avenue Chestertown, MD MLS# MDKE2006364 - Image 3

21217 Texas Avenue Chestertown, MD MLS# MDKE2006364 - Image 4

21217 Texas Avenue Chestertown, MD MLS# MDKE2006364 - Image 5

21217 Texas Avenue Chestertown, MD MLS# MDKE2006364 - Image 6

21217 Texas Avenue Chestertown, MD MLS# MDKE2006364 - Image 7

21217 Texas Avenue Chestertown, MD MLS# MDKE2006364 - Image 8

21217 Texas Avenue Chestertown, MD MLS# MDKE2006364 - Image 9

21217 Texas Avenue Chestertown, MD MLS# MDKE2006364 - Image 10

21217 Texas Avenue Chestertown, MD MLS# MDKE2006364 - Image 11

21217 Texas Avenue Chestertown, MD MLS# MDKE2006364 - Image 12

21217 Texas Avenue Chestertown, MD MLS# MDKE2006364 - Image 13

21217 Texas Avenue Chestertown, MD MLS# MDKE2006364 - Image 14

21217 Texas Avenue Chestertown, MD MLS# MDKE2006364 - Image 15

21217 Texas Avenue Chestertown, MD MLS# MDKE2006364 - Image 16

21217 Texas Avenue Chestertown, MD MLS# MDKE2006364 - Image 17

21217 Texas Avenue Chestertown, MD MLS# MDKE2006364 - Image 18

21217 Texas Avenue Chestertown, MD MLS# MDKE2006364 - Image 19

21217 Texas Avenue Chestertown, MD MLS# MDKE2006364 - Image 20

1 of 20

$244,500

Beds

1.0

Baths

912

Sq.Ft.

21217 Texas Avenue

Chestertown, MD

Courtesy of RE/MAX LEADING EDGE

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

1 of 1

$115,000

Beds

1.0

Baths

910

Sq.Ft.

108 Pine Street

Chestertown, MD

Courtesy of REAL BROKER, LLC - CHESTER

Cogar Road Chestertown, MD MLS# MDKE2006304 - Image 1

Cogar Road Chestertown, MD MLS# MDKE2006304 - Image 2

Cogar Road Chestertown, MD MLS# MDKE2006304 - Image 3

1 of 3

$3,000

Studio

Beds

0.0

Baths

Cogar Road

Chestertown, MD

Courtesy of ASHLAND AUCTION GROUP LLC

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 1

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 2

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 3

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 4

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 5

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 6

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 7

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 8

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 9

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 10

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 11

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 12

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 13

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 14

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 15

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 16

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 17

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 18

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 19

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 20

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 21

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 22

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 23

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 24

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 25

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 26

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 27

139 Prospect Street Chestertown, MD MLS# MDKE2006250 - Image 28

1 of 28

$225,000

Beds

1.0

Baths

1,200

Sq.Ft.

139 Prospect Street

Chestertown, MD

Courtesy of REDFIN CORP

Haacke Drive Lot 3 Chestertown, MD MLS# MDKE2006274 - Image 1

Haacke Drive Lot 3 Chestertown, MD MLS# MDKE2006274 - Image 2

Haacke Drive Lot 3 Chestertown, MD MLS# MDKE2006274 - Image 3

Haacke Drive Lot 3 Chestertown, MD MLS# MDKE2006274 - Image 4

Haacke Drive Lot 3 Chestertown, MD MLS# MDKE2006274 - Image 5

Haacke Drive Lot 3 Chestertown, MD MLS# MDKE2006274 - Image 6

Haacke Drive Lot 3 Chestertown, MD MLS# MDKE2006274 - Image 7

1 of 7

$225,000

Studio

Beds

0.0

Baths

Haacke Drive Lot 3

Chestertown, MD

Courtesy of SELECT LAND & HOMES, LLC

Scheeler Road Lot 2 Chestertown, MD MLS# MDKE2006290 - Image 1

Scheeler Road Lot 2 Chestertown, MD MLS# MDKE2006290 - Image 2

Scheeler Road Lot 2 Chestertown, MD MLS# MDKE2006290 - Image 3

Scheeler Road Lot 2 Chestertown, MD MLS# MDKE2006290 - Image 4

1 of 4

$250,000

Studio

Beds

0.0

Baths

Scheeler Road Lot 2

Chestertown, MD

Courtesy of SELECT LAND & HOMES, LLC

Scheeler Road Lot 2 Chestertown, MD MLS# MDKE2006298 - Image 1

Scheeler Road Lot 2 Chestertown, MD MLS# MDKE2006298 - Image 2

Scheeler Road Lot 2 Chestertown, MD MLS# MDKE2006298 - Image 3

Scheeler Road Lot 2 Chestertown, MD MLS# MDKE2006298 - Image 4

New Construction

1 of 4

$250,000

37,026

Sq.Ft.

Scheeler Road Lot 2

Chestertown, MD

Courtesy of SELECT LAND & HOMES, 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: 120
Estimated median home price: $345,000

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	29
$100K - 200K	8
$200K - 300K	15
$300K - 400K	17
$400K - 500K	12
$500K - 600K	6
$600K - 700K	4
$700K - 800K	7
$800K - 900K	7
$900K - 1M	0
$1M - Max	15

Homes for Sale by Type in Chestertown, MD

Property Type	Count
Single Family	52
Townhouse	5
Condo	17
Commercial	8
Rental	13
Lots and Land	38
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 6/1/2026)

Find Properties in Chestertown, MD

Chestertown, MD Information

Find Properties by Zip

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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Chestertown Maryland Homes for Sale

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