Chester Maryland Homes for Sale

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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

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102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 6

102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 7

102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 8

102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 9

102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 10

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

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102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 13

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102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 24

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102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 39

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102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 44

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102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 46

102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 47

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102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 51

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102 Boatswain Way # 2911 Chester, MD MLS# MDQA2017980 - Image 53

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

Recently Listed

1 of 56

$629,990

Beds

2.1

Baths

2,003

Sq.Ft.

102 Boatswain Way # 2911

Chester, MD

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY - OP

169 Harrier Way Chester, MD MLS# MDQA2017938 - Image 1

Adult Community

1 of 1

$779,900

Beds

2.0

Baths

2,394

Sq.Ft.

169 Harrier Way

Chester, MD

Courtesy of CENTURY 21 NEW MILLENNIUM

102 Boatswain Way # 2921 Chester, MD MLS# MDQA2017954 - Image 1

102 Boatswain Way # 2921 Chester, MD MLS# MDQA2017954 - Image 2

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102 Boatswain Way # 2921 Chester, MD MLS# MDQA2017954 - Image 9

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102 Boatswain Way # 2921 Chester, MD MLS# MDQA2017954 - Image 45

102 Boatswain Way # 2921 Chester, MD MLS# MDQA2017954 - Image 46

102 Boatswain Way # 2921 Chester, MD MLS# MDQA2017954 - Image 47

102 Boatswain Way # 2921 Chester, MD MLS# MDQA2017954 - Image 48

102 Boatswain Way # 2921 Chester, MD MLS# MDQA2017954 - Image 49

102 Boatswain Way # 2921 Chester, MD MLS# MDQA2017954 - Image 50

102 Boatswain Way # 2921 Chester, MD MLS# MDQA2017954 - Image 51

Adult Community

1 of 51

$869,990

Beds

2.1

Baths

2,602

Sq.Ft.

102 Boatswain Way # 2921

Chester, MD

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY - OP

THE TIME TO SELL IS NOW!

102 Boatswain Way # 2933 Chester, MD MLS# MDQA2017956 - Image 1

102 Boatswain Way # 2933 Chester, MD MLS# MDQA2017956 - Image 2

102 Boatswain Way # 2933 Chester, MD MLS# MDQA2017956 - Image 3

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102 Boatswain Way # 2933 Chester, MD MLS# MDQA2017956 - Image 9

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102 Boatswain Way # 2933 Chester, MD MLS# MDQA2017956 - Image 41

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102 Boatswain Way # 2933 Chester, MD MLS# MDQA2017956 - Image 44

102 Boatswain Way # 2933 Chester, MD MLS# MDQA2017956 - Image 45

102 Boatswain Way # 2933 Chester, MD MLS# MDQA2017956 - Image 46

102 Boatswain Way # 2933 Chester, MD MLS# MDQA2017956 - Image 47

Adult Community

1 of 47

$829,990

Beds

2.1

Baths

1,900

Sq.Ft.

102 Boatswain Way # 2933

Chester, MD

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY - OP

723 Warbler Way Chester, MD MLS# MDQA2017962 - Image 1

723 Warbler Way Chester, MD MLS# MDQA2017962 - Image 2

723 Warbler Way Chester, MD MLS# MDQA2017962 - Image 3

723 Warbler Way Chester, MD MLS# MDQA2017962 - Image 4

723 Warbler Way Chester, MD MLS# MDQA2017962 - Image 5

723 Warbler Way Chester, MD MLS# MDQA2017962 - Image 6

723 Warbler Way Chester, MD MLS# MDQA2017962 - Image 7

723 Warbler Way Chester, MD MLS# MDQA2017962 - Image 8

723 Warbler Way Chester, MD MLS# MDQA2017962 - Image 9

723 Warbler Way Chester, MD MLS# MDQA2017962 - Image 10

723 Warbler Way Chester, MD MLS# MDQA2017962 - Image 11

723 Warbler Way Chester, MD MLS# MDQA2017962 - Image 12

723 Warbler Way Chester, MD MLS# MDQA2017962 - Image 13

723 Warbler Way Chester, MD MLS# MDQA2017962 - Image 14

Adult Community

1 of 14

$789,990

Beds

3.0

Baths

2,791

Sq.Ft.

723 Warbler Way

Chester, MD

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY - OP

715 Warbler Way Chester, MD MLS# MDQA2017966 - Image 1

715 Warbler Way Chester, MD MLS# MDQA2017966 - Image 2

715 Warbler Way Chester, MD MLS# MDQA2017966 - Image 3

715 Warbler Way Chester, MD MLS# MDQA2017966 - Image 4

715 Warbler Way Chester, MD MLS# MDQA2017966 - Image 5

715 Warbler Way Chester, MD MLS# MDQA2017966 - Image 6

715 Warbler Way Chester, MD MLS# MDQA2017966 - Image 7

715 Warbler Way Chester, MD MLS# MDQA2017966 - Image 8

715 Warbler Way Chester, MD MLS# MDQA2017966 - Image 9

715 Warbler Way Chester, MD MLS# MDQA2017966 - Image 10

715 Warbler Way Chester, MD MLS# MDQA2017966 - Image 11

715 Warbler Way Chester, MD MLS# MDQA2017966 - Image 12

715 Warbler Way Chester, MD MLS# MDQA2017966 - Image 13

715 Warbler Way Chester, MD MLS# MDQA2017966 - Image 14

Adult Community

1 of 14

$839,990

Beds

3.0

Baths

2,791

Sq.Ft.

715 Warbler Way

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

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2017928 - Image 4

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2017928 - Image 5

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2017928 - Image 6

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110 Boatswain Way # 3042 Chester, MD MLS# MDQA2017928 - Image 8

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2017928 - Image 9

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2017928 - Image 10

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110 Boatswain Way # 3042 Chester, MD MLS# MDQA2017928 - Image 39

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2017928 - Image 40

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2017928 - Image 41

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2017928 - Image 42

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2017928 - Image 43

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

OPEN HOUSE: Saturday 8/8 11:00 AM - 4:00 PM

$749,990

Beds

2.1

Baths

1,900

Sq.Ft.

110 Boatswain Way # 3042

Chester, MD

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY - OP

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 86

Adult Community with Virtual Tour

1 of 86

$719,900

Beds

2.0

Baths

2,118

Sq.Ft.

121 Merlin Drive

Chester, MD

Courtesy of COLDWELL BANKER REALTY

230 Switchgrass Way # 12 Chester, MD MLS# MDQA2017860 - Image 1

230 Switchgrass Way # 12 Chester, MD MLS# MDQA2017860 - Image 2

230 Switchgrass Way # 12 Chester, MD MLS# MDQA2017860 - Image 3

230 Switchgrass Way # 12 Chester, MD MLS# MDQA2017860 - Image 4

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230 Switchgrass Way # 12 Chester, MD MLS# MDQA2017860 - Image 7

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230 Switchgrass Way # 12 Chester, MD MLS# MDQA2017860 - Image 16

230 Switchgrass Way # 12 Chester, MD MLS# MDQA2017860 - Image 17

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230 Switchgrass Way # 12 Chester, MD MLS# MDQA2017860 - Image 21

230 Switchgrass Way # 12 Chester, MD MLS# MDQA2017860 - Image 22

230 Switchgrass Way # 12 Chester, MD MLS# MDQA2017860 - Image 23

Adult Community

1 of 23

$525,000

Beds

2.1

Baths

2,003

Sq.Ft.

230 Switchgrass Way # 12

Chester, MD

Courtesy of REAL BROKER, LLC - CHESTER

205 Anchor Lane Chester, MD MLS# MDQA2017856 - Image 1

205 Anchor Lane Chester, MD MLS# MDQA2017856 - Image 2

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1 of 48

OPEN HOUSE: Saturday 8/8 11:00 AM - 1:00 PM

$535,000

Beds

3.0

Baths

3,000

Sq.Ft.

205 Anchor Lane

Chester, MD

Courtesy of SAMSON PROPERTIES

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

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

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

1 of 65

$629,900

Beds

2.0

Baths

1,688

Sq.Ft.

315 Bentons Pleasure Road

Chester, MD

Courtesy of DOUGLAS REALTY LLC

114 Cedar Road Chester, MD MLS# MDQA2017822 - Image 1

114 Cedar Road Chester, MD MLS# MDQA2017822 - Image 2

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1 of 97

$375,000

Beds

2.0

Baths

3,128

Sq.Ft.

114 Cedar Road

Chester, MD

Courtesy of KELLER WILLIAMS LEGACY

6010 Bridgepointe Drive Chester, MD MLS# MDQA2017824 - Image 1

6010 Bridgepointe Drive Chester, MD MLS# MDQA2017824 - Image 2

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6010 Bridgepointe Drive Chester, MD MLS# MDQA2017824 - Image 55

Virtual Tour

1 of 55

OPEN HOUSE: Saturday 8/8 9:00 AM - 11:00 AM

$380,000

Beds

2.0

Baths

1,885

Sq.Ft.

6010 Bridgepointe Drive

Chester, MD

Courtesy of ROSENDALE REALTY

233 Peregrine Drive Chester, MD MLS# MDQA2017836 - Image 1

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233 Peregrine Drive Chester, MD MLS# MDQA2017836 - Image 62

233 Peregrine Drive Chester, MD MLS# MDQA2017836 - Image 63

Adult Community

1 of 63

$724,999

Beds

3.0

Baths

3,151

Sq.Ft.

233 Peregrine Drive

Chester, MD

Courtesy of ROSENDALE REALTY

1000 Herons Nest Way # 23 Chester, MD MLS# MDQA2017786 - Image 1

1000 Herons Nest Way # 23 Chester, MD MLS# MDQA2017786 - Image 2

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Adult Community

1 of 39

$490,000

Beds

2.1

Baths

1000 Herons Nest Way # 23

Chester, MD

Courtesy of SAMSON PROPERTIES

7013 Bridgepointe Drive Chester, MD MLS# MDQA2017430 - Image 1

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7013 Bridgepointe Drive Chester, MD MLS# MDQA2017430 - Image 3

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7013 Bridgepointe Drive Chester, MD MLS# MDQA2017430 - Image 18

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7013 Bridgepointe Drive Chester, MD MLS# MDQA2017430 - Image 47

7013 Bridgepointe Drive Chester, MD MLS# MDQA2017430 - Image 48

Virtual Tour

1 of 48

$355,000

Beds

2.1

Baths

1,635

Sq.Ft.

7013 Bridgepointe 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

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Virtual Tour

1 of 38

$749,000

Beds

2.0

Baths

1,524

Sq.Ft.

205 Riverside Drive

Chester, MD

Courtesy of ENGEL & VOLKERS ANNAPOLIS

124 Riverside Drive Chester, MD MLS# MDQA2017718 - Image 1

124 Riverside Drive Chester, MD MLS# MDQA2017718 - Image 2

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1 of 45

$499,000

Beds

2.1

Baths

1,979

Sq.Ft.

124 Riverside Drive

Chester, MD

Courtesy of DOUGLAS REALTY LLC

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 49

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

2645 Cox Neck Road Chester, MD MLS# MDQA2017640 - Image 1

2645 Cox Neck Road Chester, MD MLS# MDQA2017640 - Image 2

2645 Cox Neck Road Chester, MD MLS# MDQA2017640 - Image 3

2645 Cox Neck Road Chester, MD MLS# MDQA2017640 - Image 4

2645 Cox Neck Road Chester, MD MLS# MDQA2017640 - Image 5

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2645 Cox Neck Road Chester, MD MLS# MDQA2017640 - Image 7

2645 Cox Neck Road Chester, MD MLS# MDQA2017640 - Image 8

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2645 Cox Neck Road Chester, MD MLS# MDQA2017640 - Image 41

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2645 Cox Neck Road Chester, MD MLS# MDQA2017640 - Image 47

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2645 Cox Neck Road Chester, MD MLS# MDQA2017640 - Image 49

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2645 Cox Neck Road Chester, MD MLS# MDQA2017640 - Image 58

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2645 Cox Neck Road Chester, MD MLS# MDQA2017640 - Image 60

2645 Cox Neck Road Chester, MD MLS# MDQA2017640 - Image 61

Virtual Tour

1 of 61

OPEN HOUSE: Saturday 8/8 11:00 AM - 1:00 PM

$379,900

Beds

1.1

Baths

1,192

Sq.Ft.

2645 Cox Neck Road

Chester, MD

Courtesy of COMPASS

About Chester

Listings in Chester, MD: 114
Estimated median home price: $694,990

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	1
$100K - 200K	2
$200K - 300K	8
$300K - 400K	14
$400K - 500K	10
$500K - 600K	12
$600K - 700K	13
$700K - 800K	15
$800K - 900K	12
$900K - 1M	15
$1M - Max	12

Homes for Sale by Type in Chester, MD

Property Type	Count
Single Family	52
Townhouse	2
Condo	57
Commercial	0
Rental	12
Lots and Land	3
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 8/6/2026)

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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