Chester Maryland Homes for Sale

28 total properties

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205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 1

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 2

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 3

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 4

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 5

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 6

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 7

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 8

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 9

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205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 11

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 12

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 13

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 14

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 15

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 16

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 17

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 18

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 19

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 20

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 21

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 22

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 23

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 24

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 25

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 26

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 27

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 28

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 29

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 30

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 31

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205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 34

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 35

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 36

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 37

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 38

205 Riverside Drive Chester, MD MLS# MDQA2017690 - Image 39

Virtual Tour

1 of 39

$699,000

Beds

2.0

Baths

1,524

Sq.Ft.

205 Riverside Drive

Chester, MD

Courtesy of ENGEL & VOLKERS ANNAPOLIS

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 1

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 2

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 3

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 4

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 5

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 6

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 7

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 8

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 9

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2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 11

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 12

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 13

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 14

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 15

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 16

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 17

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 18

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2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 20

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 21

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2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 23

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 24

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 25

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 26

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 27

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 28

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2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 39

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 40

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 41

2703 Sherman Drive Chester, MD MLS# MDQA2018980 - Image 42

1 of 42

$699,000

Beds

2.1

Baths

1,560

Sq.Ft.

2703 Sherman Drive

Chester, MD

Courtesy of ROSENDALE REALTY

2627 Cecil Drive Chester, MD MLS# MDQA2019148 - Image 1

2627 Cecil Drive Chester, MD MLS# MDQA2019148 - Image 2

2627 Cecil Drive Chester, MD MLS# MDQA2019148 - Image 3

2627 Cecil Drive Chester, MD MLS# MDQA2019148 - Image 4

2627 Cecil Drive Chester, MD MLS# MDQA2019148 - Image 5

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2627 Cecil Drive Chester, MD MLS# MDQA2019148 - Image 7

2627 Cecil Drive Chester, MD MLS# MDQA2019148 - Image 8

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2627 Cecil Drive Chester, MD MLS# MDQA2019148 - Image 11

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2627 Cecil Drive Chester, MD MLS# MDQA2019148 - Image 13

2627 Cecil Drive Chester, MD MLS# MDQA2019148 - Image 14

2627 Cecil Drive Chester, MD MLS# MDQA2019148 - Image 15

2627 Cecil Drive Chester, MD MLS# MDQA2019148 - Image 16

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2627 Cecil Drive Chester, MD MLS# MDQA2019148 - Image 18

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2627 Cecil Drive Chester, MD MLS# MDQA2019148 - Image 44

2627 Cecil Drive Chester, MD MLS# MDQA2019148 - Image 45

Recently Listed with Virtual Tour

1 of 45

$699,000

Beds

2.0

Baths

1,584

Sq.Ft.

2627 Cecil Drive

Chester, MD

Courtesy of LONG & FOSTER REAL ESTATE, INC.

THE TIME TO SELL IS NOW!

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 1

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 2

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 3

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830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 6

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830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 8

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 9

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 10

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 11

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 12

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 13

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 14

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 15

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 16

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 17

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 18

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 19

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 20

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 21

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 22

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 23

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830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 25

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 26

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830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 28

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 29

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 30

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 31

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 32

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 33

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 34

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 35

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 36

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 37

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 38

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 39

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 40

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 41

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 42

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 43

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 44

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 45

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 46

830 Warbler Way # 2833 Chester, MD MLS# MDQA2018800 - Image 47

Adult Community

1 of 47

$689,990

Beds

2.1

Baths

1,900

Sq.Ft.

830 Warbler Way # 2833

Chester, MD

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY - OP

111 Marshgrass Way # 21 Chester, MD MLS# MDQA2016714 - Image 1

111 Marshgrass Way # 21 Chester, MD MLS# MDQA2016714 - Image 2

111 Marshgrass Way # 21 Chester, MD MLS# MDQA2016714 - Image 3

111 Marshgrass Way # 21 Chester, MD MLS# MDQA2016714 - Image 4

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111 Marshgrass Way # 21 Chester, MD MLS# MDQA2016714 - Image 55

111 Marshgrass Way # 21 Chester, MD MLS# MDQA2016714 - Image 56

111 Marshgrass Way # 21 Chester, MD MLS# MDQA2016714 - Image 57

Adult Community

1 of 57

$680,000

Beds

2.1

Baths

2,602

Sq.Ft.

111 Marshgrass Way # 21

Chester, MD

Courtesy of SAMSON PROPERTIES

190 Harrier Way # 24 Chester, MD MLS# MDQA2019194 - Image 1

190 Harrier Way # 24 Chester, MD MLS# MDQA2019194 - Image 2

190 Harrier Way # 24 Chester, MD MLS# MDQA2019194 - Image 3

190 Harrier Way # 24 Chester, MD MLS# MDQA2019194 - Image 4

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190 Harrier Way # 24 Chester, MD MLS# MDQA2019194 - Image 9

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190 Harrier Way # 24 Chester, MD MLS# MDQA2019194 - Image 11

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190 Harrier Way # 24 Chester, MD MLS# MDQA2019194 - Image 50

190 Harrier Way # 24 Chester, MD MLS# MDQA2019194 - Image 51

190 Harrier Way # 24 Chester, MD MLS# MDQA2019194 - Image 52

Recently Listed

1 of 52

$675,000

Beds

2.1

Baths

2,602

Sq.Ft.

190 Harrier Way # 24

Chester, MD

Courtesy of COLDWELL BANKER REALTY

Lot 6 Norman Court Chester, MD MLS# MDQA2008126 - Image 1

Lot 6 Norman Court Chester, MD MLS# MDQA2008126 - Image 2

Lot 6 Norman Court Chester, MD MLS# MDQA2008126 - Image 3

Lot 6 Norman Court Chester, MD MLS# MDQA2008126 - Image 4

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New Construction

1 of 26

$674,900

Beds

2.1

Baths

Lot 6 Norman Court

Chester, MD

Courtesy of KELLER WILLIAMS FLAGSHIP

228 Bayberry Drive Chester, MD MLS# MDQA2018728 - Image 1

228 Bayberry Drive Chester, MD MLS# MDQA2018728 - Image 2

228 Bayberry Drive Chester, MD MLS# MDQA2018728 - Image 3

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228 Bayberry Drive Chester, MD MLS# MDQA2018728 - Image 57

Adult Community

1 of 57

$665,000

Beds

2.1

Baths

1,993

Sq.Ft.

228 Bayberry Drive

Chester, MD

Courtesy of LONG & FOSTER REAL ESTATE, INC.

118 Broadwater Drive Chester, MD MLS# MDQA2018202 - Image 1

118 Broadwater Drive Chester, MD MLS# MDQA2018202 - Image 2

118 Broadwater Drive Chester, MD MLS# MDQA2018202 - Image 3

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118 Broadwater Drive Chester, MD MLS# MDQA2018202 - Image 24

118 Broadwater Drive Chester, MD MLS# MDQA2018202 - Image 25

118 Broadwater Drive Chester, MD MLS# MDQA2018202 - Image 26

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118 Broadwater Drive Chester, MD MLS# MDQA2018202 - Image 45

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118 Broadwater Drive Chester, MD MLS# MDQA2018202 - Image 47

118 Broadwater Drive Chester, MD MLS# MDQA2018202 - Image 48

Adult Community

1 of 48

$645,000

Beds

2.0

Baths

2,473

Sq.Ft.

118 Broadwater Drive

Chester, MD

Courtesy of RE/MAX EXECUTIVE

1351 Calvert Road Chester, MD MLS# MDQA2018764 - Image 1

1351 Calvert Road Chester, MD MLS# MDQA2018764 - Image 2

1351 Calvert Road Chester, MD MLS# MDQA2018764 - Image 3

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1351 Calvert Road Chester, MD MLS# MDQA2018764 - Image 52

1351 Calvert Road Chester, MD MLS# MDQA2018764 - Image 53

1 of 53

$645,000

Beds

2.1

Baths

2,700

Sq.Ft.

1351 Calvert Road

Chester, MD

Courtesy of ENGEL & VOLKERS ANNAPOLIS

102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 1

102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 2

102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 3

102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 4

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102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 54

102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 55

102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 56

Adult Community

1 of 56

$619,990

Beds

2.1

Baths

2,003

Sq.Ft.

102 Boatswain Way # 2911

Chester, MD

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY - OP

102 Boatswain Way # 2912 Chester, MD MLS# MDQA2018092 - Image 1

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102 Boatswain Way # 2912 Chester, MD MLS# MDQA2018092 - Image 47

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102 Boatswain Way # 2912 Chester, MD MLS# MDQA2018092 - Image 54

102 Boatswain Way # 2912 Chester, MD MLS# MDQA2018092 - Image 55

102 Boatswain Way # 2912 Chester, MD MLS# MDQA2018092 - Image 56

Adult Community

1 of 56

$609,990

Beds

2.1

Baths

2,003

Sq.Ft.

102 Boatswain Way # 2912

Chester, MD

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY - OP

1616 Postal Road Chester, MD MLS# MDQA2018784 - Image 1

1616 Postal Road Chester, MD MLS# MDQA2018784 - Image 2

1616 Postal Road Chester, MD MLS# MDQA2018784 - Image 3

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1616 Postal Road Chester, MD MLS# MDQA2018784 - Image 43

1616 Postal Road Chester, MD MLS# MDQA2018784 - Image 44

Virtual Tour

1 of 44

$600,000

Beds

2.1

Baths

2,818

Sq.Ft.

1616 Postal Road

Chester, MD

Courtesy of COLDWELL BANKER REALTY

1616 Postal Road Chester, MD MLS# MDQA2018908 - Image 1

1616 Postal Road Chester, MD MLS# MDQA2018908 - Image 2

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1616 Postal Road Chester, MD MLS# MDQA2018908 - Image 44

1616 Postal Road Chester, MD MLS# MDQA2018908 - Image 45

1 of 45

$600,000

1616 Postal Road

Chester, MD

Courtesy of COLDWELL BANKER REALTY

102 Boatswain Way # 2912 Chester, MD MLS# MDQA2016670 - Image 1

102 Boatswain Way # 2912 Chester, MD MLS# MDQA2016670 - Image 2

102 Boatswain Way # 2912 Chester, MD MLS# MDQA2016670 - Image 3

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102 Boatswain Way # 2912 Chester, MD MLS# MDQA2016670 - Image 62

102 Boatswain Way # 2912 Chester, MD MLS# MDQA2016670 - Image 63

Adult Community

1 of 63

$599,990

Beds

2.1

Baths

2,003

Sq.Ft.

102 Boatswain Way # 2912

Chester, MD

Courtesy of KOVO REALTY

315 Bentons Pleasure Road Chester, MD MLS# MDQA2017854 - Image 1

315 Bentons Pleasure Road Chester, MD MLS# MDQA2017854 - Image 2

315 Bentons Pleasure Road Chester, MD MLS# MDQA2017854 - Image 3

315 Bentons Pleasure Road Chester, MD MLS# MDQA2017854 - Image 4

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315 Bentons Pleasure Road Chester, MD MLS# MDQA2017854 - Image 13

315 Bentons Pleasure Road Chester, MD MLS# MDQA2017854 - Image 14

315 Bentons Pleasure Road Chester, MD MLS# MDQA2017854 - Image 15

315 Bentons Pleasure Road Chester, MD MLS# MDQA2017854 - Image 16

315 Bentons Pleasure Road Chester, MD MLS# MDQA2017854 - Image 17

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1 of 65

$599,900

Beds

2.0

Baths

1,688

Sq.Ft.

315 Bentons Pleasure Road

Chester, MD

Courtesy of DOUGLAS REALTY LLC

1012 Auckland Way Chester, MD MLS# MDQA2018742 - Image 1

1012 Auckland Way Chester, MD MLS# MDQA2018742 - Image 2

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Virtual Tour

1 of 37

$599,900

Beds

3.1

Baths

2,076

Sq.Ft.

1012 Auckland Way

Chester, MD

Courtesy of REDFIN CORP

231 Dominion Road Chester, MD MLS# MDQA2018862 - Image 1

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231 Dominion Road Chester, MD MLS# MDQA2018862 - Image 3

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231 Dominion Road Chester, MD MLS# MDQA2018862 - Image 44

Virtual Tour

1 of 44

$599,000

Beds

3.0

Baths

1,852

Sq.Ft.

231 Dominion Road

Chester, MD

Courtesy of LONG & FOSTER REAL ESTATE, INC.

231 Dominion Road Chester, MD MLS# MDQA2018864 - Image 1

231 Dominion Road Chester, MD MLS# MDQA2018864 - Image 2

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231 Dominion Road Chester, MD MLS# MDQA2018864 - Image 43

231 Dominion Road Chester, MD MLS# MDQA2018864 - Image 44

Virtual Tour

1 of 44

$599,000

Beds

0.0

Baths

231 Dominion Road

Chester, MD

Courtesy of LONG & FOSTER REAL ESTATE, INC.

1000 Herons Nest Way # 43 Chester, MD MLS# MDQA2017608 - Image 1

1000 Herons Nest Way # 43 Chester, MD MLS# MDQA2017608 - Image 2

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1000 Herons Nest Way # 43 Chester, MD MLS# MDQA2017608 - Image 50

Adult Community with Virtual Tour

1 of 50

$595,000

Beds

2.1

Baths

1,832

Sq.Ft.

1000 Herons Nest Way # 43

Chester, MD

Courtesy of COLDWELL BANKER REALTY

About Chester

Listings in Chester, MD: 106
Estimated median home price: $600,000

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	3
$200K - 300K	5
$300K - 400K	15
$400K - 500K	13
$500K - 600K	16
$600K - 700K	11
$700K - 800K	14
$800K - 900K	10
$900K - 1M	10
$1M - Max	7

Homes for Sale by Type in Chester, MD

Property Type	Count
Single Family	46
Townhouse	2
Condo	53
Commercial	1
Rental	19
Lots and Land	3
Condo/Town/CoOp	0
CoOp	0
Multi Family	1
Mobile Home	0
Farms	0

(Data as of 11/2/2026)

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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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