Chester Maryland Homes for Sale

30 total properties

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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 61

315 Bentons Pleasure Road Chester, MD MLS# MDQA2017854 - Image 62

315 Bentons Pleasure Road Chester, MD MLS# MDQA2017854 - Image 63

315 Bentons Pleasure Road Chester, MD MLS# MDQA2017854 - Image 64

315 Bentons Pleasure Road Chester, MD MLS# MDQA2017854 - Image 65

1 of 65

$599,900

Beds

2.0

Baths

1,688

Sq.Ft.

315 Bentons Pleasure Road

Chester, MD

Courtesy of DOUGLAS REALTY LLC

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 8

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102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 11

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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

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2017928 - Image 1

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2017928 - Image 2

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2017928 - Image 3

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110 Boatswain Way # 3042 Chester, MD MLS# MDQA2017928 - Image 44

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2017928 - Image 45

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2017928 - Image 46

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2017928 - Image 47

Adult Community

1 of 47

$699,990

Beds

2.1

Baths

1,900

Sq.Ft.

110 Boatswain Way # 3042

Chester, MD

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY - OP

THE TIME TO SELL IS NOW!

121 Merlin Drive Chester, MD MLS# MDQA2017900 - Image 1

121 Merlin Drive Chester, MD MLS# MDQA2017900 - Image 2

121 Merlin Drive Chester, MD MLS# MDQA2017900 - Image 3

121 Merlin Drive Chester, MD MLS# MDQA2017900 - Image 4

121 Merlin Drive Chester, MD MLS# MDQA2017900 - Image 5

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121 Merlin Drive Chester, MD MLS# MDQA2017900 - Image 85

121 Merlin Drive Chester, MD MLS# MDQA2017900 - Image 86

Adult Community with Virtual Tour

1 of 86

$697,900

Beds

2.0

Baths

2,118

Sq.Ft.

121 Merlin Drive

Chester, MD

Courtesy of COLDWELL BANKER REALTY

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

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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

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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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

132 Wheelhouse Way # 11 Chester, MD MLS# MDQA2017364 - Image 1

132 Wheelhouse Way # 11 Chester, MD MLS# MDQA2017364 - Image 2

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132 Wheelhouse Way # 11 Chester, MD MLS# MDQA2017364 - Image 25

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132 Wheelhouse Way # 11 Chester, MD MLS# MDQA2017364 - Image 27

132 Wheelhouse Way # 11 Chester, MD MLS# MDQA2017364 - Image 28

132 Wheelhouse Way # 11 Chester, MD MLS# MDQA2017364 - Image 29

Adult Community with Virtual Tour

1 of 29

$699,000

Beds

2.1

Baths

2,003

Sq.Ft.

132 Wheelhouse Way # 11

Chester, MD

Courtesy of REAL BROKER, LLC

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

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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

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

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

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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

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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Lot 6 Norman Court Chester, MD MLS# MDQA2008126 - Image 26

New Construction

1 of 26

$674,900

Beds

2.1

Baths

Lot 6 Norman Court

Chester, MD

Courtesy of KELLER WILLIAMS FLAGSHIP

About Chester

Listings in Chester, MD: 120
Estimated median home price: $655,000

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	2
$200K - 300K	4
$300K - 400K	14
$400K - 500K	17
$500K - 600K	16
$600K - 700K	15
$700K - 800K	15
$800K - 900K	12
$900K - 1M	14
$1M - Max	9

Homes for Sale by Type in Chester, MD

Property Type	Count
Single Family	55
Townhouse	1
Condo	59
Commercial	1
Rental	24
Lots and Land	3
Condo/Town/CoOp	0
CoOp	0
Multi Family	1
Mobile Home	0
Farms	0

(Data as of 10/27/2026)

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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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