Chester Maryland Homes for Sale

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307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 1

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 2

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 3

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 4

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 5

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 6

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 7

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 8

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 9

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 10

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 11

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 12

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 13

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 14

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 15

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 16

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 17

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 18

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 19

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 20

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 21

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 22

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 23

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 24

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 25

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 26

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 27

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 28

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 29

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 30

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 31

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 32

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 33

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 34

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 35

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 36

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 37

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 38

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 39

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 40

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 41

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 42

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 43

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 44

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 45

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 46

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 47

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 48

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 49

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 50

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 51

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 52

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 53

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 54

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 55

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 56

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 57

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 58

307 Kingfisher Lane Chester, MD MLS# MDQA2016408 - Image 59

Adult Community

1 of 59

$979,990

Beds

3.0

Baths

2,789

Sq.Ft.

307 Kingfisher Lane

Chester, MD

Courtesy of KOVO REALTY

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 1

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 2

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 3

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 4

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 5

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 6

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 7

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 8

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 9

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 10

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 11

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 12

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 13

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 14

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 15

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 16

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1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 19

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 20

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 21

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 22

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 23

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 24

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 25

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 26

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 27

1905 Bayside Drive Chester, MD MLS# MDQA2016340 - Image 28

1 of 28

$299,900

Beds

1.1

Baths

1,220

Sq.Ft.

1905 Bayside Drive

Chester, MD

Courtesy of CUMMINGS & CO. REALTORS

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 1

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 2

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 3

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110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 28

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 29

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 30

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110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 34

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 35

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 36

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 37

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 38

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 39

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110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 41

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 42

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 43

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 44

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 45

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 46

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 47

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 48

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 49

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 50

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 51

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 52

Adult Community

1 of 52

$799,990

Beds

2.1

Baths

1,900

Sq.Ft.

110 Boatswain Way # 3042

Chester, MD

Courtesy of KOVO REALTY

THE TIME TO SELL IS NOW!

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 1

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 2

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 3

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 4

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110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 11

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110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 13

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110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 19

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 20

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 21

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110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 28

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110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 36

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 37

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 38

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 39

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 40

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 41

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 42

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 43

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 44

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 45

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 46

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 47

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 48

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 49

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 50

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 51

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 52

Adult Community

1 of 52

$799,990

Beds

2.1

Baths

1,900

Sq.Ft.

110 Boatswain Way # 3043

Chester, MD

Courtesy of KOVO REALTY

110 Boatswain Way # 3041 Chester, MD MLS# MDQA2016362 - Image 1

110 Boatswain Way # 3041 Chester, MD MLS# MDQA2016362 - Image 2

110 Boatswain Way # 3041 Chester, MD MLS# MDQA2016362 - Image 3

110 Boatswain Way # 3041 Chester, MD MLS# MDQA2016362 - Image 4

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110 Boatswain Way # 3041 Chester, MD MLS# MDQA2016362 - Image 6

110 Boatswain Way # 3041 Chester, MD MLS# MDQA2016362 - Image 7

110 Boatswain Way # 3041 Chester, MD MLS# MDQA2016362 - Image 8

110 Boatswain Way # 3041 Chester, MD MLS# MDQA2016362 - Image 9

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110 Boatswain Way # 3041 Chester, MD MLS# MDQA2016362 - Image 12

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110 Boatswain Way # 3041 Chester, MD MLS# MDQA2016362 - Image 14

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110 Boatswain Way # 3041 Chester, MD MLS# MDQA2016362 - Image 18

110 Boatswain Way # 3041 Chester, MD MLS# MDQA2016362 - Image 19

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110 Boatswain Way # 3041 Chester, MD MLS# MDQA2016362 - Image 31

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110 Boatswain Way # 3041 Chester, MD MLS# MDQA2016362 - Image 39

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110 Boatswain Way # 3041 Chester, MD MLS# MDQA2016362 - Image 41

110 Boatswain Way # 3041 Chester, MD MLS# MDQA2016362 - Image 42

110 Boatswain Way # 3041 Chester, MD MLS# MDQA2016362 - Image 43

110 Boatswain Way # 3041 Chester, MD MLS# MDQA2016362 - Image 44

Adult Community

1 of 44

$949,990

Beds

2.1

Baths

2,602

Sq.Ft.

110 Boatswain Way # 3041

Chester, MD

Courtesy of KOVO REALTY

110 Boatswain Way # 3044 Chester, MD MLS# MDQA2016364 - Image 1

110 Boatswain Way # 3044 Chester, MD MLS# MDQA2016364 - Image 2

110 Boatswain Way # 3044 Chester, MD MLS# MDQA2016364 - Image 3

110 Boatswain Way # 3044 Chester, MD MLS# MDQA2016364 - Image 4

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110 Boatswain Way # 3044 Chester, MD MLS# MDQA2016364 - Image 6

110 Boatswain Way # 3044 Chester, MD MLS# MDQA2016364 - Image 7

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110 Boatswain Way # 3044 Chester, MD MLS# MDQA2016364 - Image 9

110 Boatswain Way # 3044 Chester, MD MLS# MDQA2016364 - Image 10

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110 Boatswain Way # 3044 Chester, MD MLS# MDQA2016364 - Image 14

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110 Boatswain Way # 3044 Chester, MD MLS# MDQA2016364 - Image 42

110 Boatswain Way # 3044 Chester, MD MLS# MDQA2016364 - Image 43

110 Boatswain Way # 3044 Chester, MD MLS# MDQA2016364 - Image 44

Adult Community

1 of 44

$989,990

Beds

2.1

Baths

2,602

Sq.Ft.

110 Boatswain Way # 3044

Chester, MD

Courtesy of KOVO REALTY

2613 Cecil Drive Chester, MD MLS# MDQA2016320 - Image 1

2613 Cecil Drive Chester, MD MLS# MDQA2016320 - Image 2

2613 Cecil Drive Chester, MD MLS# MDQA2016320 - Image 3

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1 of 52

$949,900

Beds

2.1

Baths

2,496

Sq.Ft.

2613 Cecil Drive

Chester, MD

Courtesy of BENSON & MANGOLD, LLC

1000 Herons Nest Way # 23 Chester, MD MLS# MDQA2016230 - Image 1

1000 Herons Nest Way # 23 Chester, MD MLS# MDQA2016230 - Image 2

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1000 Herons Nest Way # 23 Chester, MD MLS# MDQA2016230 - Image 20

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1000 Herons Nest Way # 23 Chester, MD MLS# MDQA2016230 - Image 32

Adult Community

1 of 32

$494,900

Beds

2.1

Baths

2,003

Sq.Ft.

1000 Herons Nest Way # 23

Chester, MD

Courtesy of EXP REALTY, LLC

1150 Little Creek Road Chester, MD MLS# MDQA2016206 - Image 1

1150 Little Creek Road Chester, MD MLS# MDQA2016206 - Image 2

1150 Little Creek Road Chester, MD MLS# MDQA2016206 - Image 3

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1150 Little Creek Road Chester, MD MLS# MDQA2016206 - Image 27

1150 Little Creek Road Chester, MD MLS# MDQA2016206 - Image 28

Virtual Tour

1 of 28

$375,000

Beds

1.1

Baths

2,200

Sq.Ft.

1150 Little Creek Road

Chester, MD

Courtesy of COLDWELL BANKER REALTY

27 Queen Mary Court # F Chester, MD MLS# MDQA2016200 - Image 1

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27 Queen Mary Court # F Chester, MD MLS# MDQA2016200 - Image 3

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27 Queen Mary Court # F Chester, MD MLS# MDQA2016200 - Image 39

27 Queen Mary Court # F Chester, MD MLS# MDQA2016200 - Image 40

1 of 40

$419,000

Beds

2.0

Baths

1,380

Sq.Ft.

27 Queen Mary Court # F

Chester, MD

Courtesy of LONG & FOSTER REAL ESTATE, INC.

1868 Roberta Drive Chester, MD MLS# MDQA2016194 - Image 1

1868 Roberta Drive Chester, MD MLS# MDQA2016194 - Image 2

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1 of 42

$749,500

Beds

3.1

Baths

3,250

Sq.Ft.

1868 Roberta Drive

Chester, MD

Courtesy of COLDWELL BANKER REALTY

230 Switchgrass Way # 21 Chester, MD MLS# MDQA2016166 - Image 1

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Adult Community with Virtual Tour

1 of 106

$675,000

Beds

2.1

Baths

2,602

Sq.Ft.

230 Switchgrass Way # 21

Chester, MD

Courtesy of LONG & FOSTER REAL ESTATE, INC.

129 Sailcloth Way Chester, MD MLS# MDQA2016176 - Image 1

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129 Sailcloth Way Chester, MD MLS# MDQA2016176 - Image 53

129 Sailcloth Way Chester, MD MLS# MDQA2016176 - Image 54

Adult Community

1 of 54

$764,900

Beds

2.0

Baths

2,303

Sq.Ft.

129 Sailcloth Way

Chester, MD

Courtesy of RE/MAX EXECUTIVE

266 Peregrine Drive Chester, MD MLS# MDQA2016140 - Image 1

266 Peregrine Drive Chester, MD MLS# MDQA2016140 - Image 2

266 Peregrine Drive Chester, MD MLS# MDQA2016140 - Image 3

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266 Peregrine Drive Chester, MD MLS# MDQA2016140 - Image 73

Adult Community

1 of 73

OPEN HOUSE: Sunday 4/19 12:00 PM - 2:00 PM

$720,000

Beds

3.0

Baths

2,870

Sq.Ft.

266 Peregrine Drive

Chester, MD

Courtesy of RE/MAX EXECUTIVE

111 Marshgrass Way # 22 Chester, MD MLS# MDQA2016122 - Image 1

111 Marshgrass Way # 22 Chester, MD MLS# MDQA2016122 - Image 2

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Adult Community

1 of 102

$529,900

Beds

2.1

Baths

1,900

Sq.Ft.

111 Marshgrass Way # 22

Chester, MD

Courtesy of LONG & FOSTER REAL ESTATE, INC.

110 Boatswain Way # 3034 Chester, MD MLS# MDQA2016092 - Image 1

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110 Boatswain Way # 3034 Chester, MD MLS# MDQA2016092 - Image 43

110 Boatswain Way # 3034 Chester, MD MLS# MDQA2016092 - Image 44

Adult Community

1 of 44

$949,990

Beds

2.1

Baths

2,602

Sq.Ft.

110 Boatswain Way # 3034

Chester, MD

Courtesy of KOVO REALTY

110 Boatswain Way # 3033 Chester, MD MLS# MDQA2016094 - Image 1

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110 Boatswain Way # 3033 Chester, MD MLS# MDQA2016094 - Image 51

110 Boatswain Way # 3033 Chester, MD MLS# MDQA2016094 - Image 52

Adult Community

1 of 52

$699,990

Beds

2.1

Baths

1,900

Sq.Ft.

110 Boatswain Way # 3033

Chester, MD

Courtesy of KOVO REALTY

110 Boatswain Way # 3032 Chester, MD MLS# MDQA2016096 - Image 1

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110 Boatswain Way # 3032 Chester, MD MLS# MDQA2016096 - Image 52

Adult Community

1 of 52

$699,990

Beds

2.1

Baths

1,900

Sq.Ft.

110 Boatswain Way # 3032

Chester, MD

Courtesy of KOVO REALTY

110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078 - Image 1

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110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078 - Image 43

110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078 - Image 44

Adult Community

1 of 44

$749,990

Beds

2.1

Baths

2,602

Sq.Ft.

110 Boatswain Way # 3021

Chester, MD

Courtesy of KOVO REALTY

110 Boatswain Way # 3031 Chester, MD MLS# MDQA2016080 - Image 1

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110 Boatswain Way # 3031 Chester, MD MLS# MDQA2016080 - Image 44

Adult Community

1 of 44

$849,990

Beds

2.1

Baths

2,602

Sq.Ft.

110 Boatswain Way # 3031

Chester, MD

Courtesy of KOVO REALTY

About Chester

Listings in Chester, MD: 108
Estimated median home price: $649,990

Chester MD Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Chester, Maryland real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Chester, MD.

Homes for Sale by Price in Chester, MD

Price	Count
$0 - 100K	2
$100K - 200K	1
$200K - 300K	8
$300K - 400K	10
$400K - 500K	13
$500K - 600K	16
$600K - 700K	13
$700K - 800K	17
$800K - 900K	7
$900K - 1M	10
$1M - Max	11

Homes for Sale by Type in Chester, MD

Property Type	Count
Single Family	46
Townhouse	0
Condo	58
Commercial	0
Rental	15
Lots and Land	4
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 4/19/2026)

Find Properties in Chester, MD

Chester, MD Information

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21619

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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Chester Maryland Homes for Sale

About Chester

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Homes for Sale by Price in Chester, MD

Homes for Sale by Type in Chester, MD

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