Chester Maryland Homes for Sale

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320 Bayberry Drive Chester, MD MLS# MDQA2018158 - Image 1

320 Bayberry Drive Chester, MD MLS# MDQA2018158 - Image 2

320 Bayberry Drive Chester, MD MLS# MDQA2018158 - Image 3

Adult Community

1 of 3

$897,750

Beds

2.0

Baths

2,331

Sq.Ft.

320 Bayberry Drive

Chester, MD

Courtesy of MR. LISTER REALTY

Harley Lane # LOT 1 Chester, MD MLS# MDQA2018170 - Image 1

Harley Lane # LOT 1 Chester, MD MLS# MDQA2018170 - Image 2

Harley Lane # LOT 1 Chester, MD MLS# MDQA2018170 - Image 3

Harley Lane # LOT 1 Chester, MD MLS# MDQA2018170 - Image 4

Harley Lane # LOT 1 Chester, MD MLS# MDQA2018170 - Image 5

Recently Listed

1 of 5

$149,900

Studio

Beds

0.0

Baths

Harley Lane # LOT 1

Chester, MD

Courtesy of KEVIN DEY REALTY

Harley Lane # LOT 2 Chester, MD MLS# MDQA2018178 - Image 1

Harley Lane # LOT 2 Chester, MD MLS# MDQA2018178 - Image 2

Harley Lane # LOT 2 Chester, MD MLS# MDQA2018178 - Image 3

Harley Lane # LOT 2 Chester, MD MLS# MDQA2018178 - Image 4

Harley Lane # LOT 2 Chester, MD MLS# MDQA2018178 - Image 5

Recently Listed

1 of 5

$139,900

Studio

Beds

0.0

Baths

Harley Lane # LOT 2

Chester, MD

Courtesy of KEVIN DEY REALTY

THE TIME TO SELL IS NOW!

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 1

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 2

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 3

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 4

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 5

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 6

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 7

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 8

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 9

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 10

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 11

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 12

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 13

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 14

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 15

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 16

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 17

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 18

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 19

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 20

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 21

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 22

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 23

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 24

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 25

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 26

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 27

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 28

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 29

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 30

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 31

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 32

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 33

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 34

201 Switchgrass Way # 34 Chester, MD MLS# MDQA2018120 - Image 35

Adult Community with Virtual Tour

1 of 35

$859,500

Beds

2.1

Baths

2,602

Sq.Ft.

201 Switchgrass Way # 34

Chester, MD

Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY

313 Thomas White Boulevard Chester, MD MLS# MDQA2018144 - Image 1

313 Thomas White Boulevard Chester, MD MLS# MDQA2018144 - Image 2

313 Thomas White Boulevard Chester, MD MLS# MDQA2018144 - Image 3

313 Thomas White Boulevard Chester, MD MLS# MDQA2018144 - Image 4

313 Thomas White Boulevard Chester, MD MLS# MDQA2018144 - Image 5

313 Thomas White Boulevard Chester, MD MLS# MDQA2018144 - Image 6

313 Thomas White Boulevard Chester, MD MLS# MDQA2018144 - Image 7

313 Thomas White Boulevard Chester, MD MLS# MDQA2018144 - Image 8

313 Thomas White Boulevard Chester, MD MLS# MDQA2018144 - Image 9

313 Thomas White Boulevard Chester, MD MLS# MDQA2018144 - Image 10

313 Thomas White Boulevard Chester, MD MLS# MDQA2018144 - Image 11

313 Thomas White Boulevard Chester, MD MLS# MDQA2018144 - Image 12

313 Thomas White Boulevard Chester, MD MLS# MDQA2018144 - Image 13

313 Thomas White Boulevard Chester, MD MLS# MDQA2018144 - Image 14

313 Thomas White Boulevard Chester, MD MLS# MDQA2018144 - Image 15

313 Thomas White Boulevard Chester, MD MLS# MDQA2018144 - Image 16

313 Thomas White Boulevard Chester, MD MLS# MDQA2018144 - Image 17

313 Thomas White Boulevard Chester, MD MLS# MDQA2018144 - Image 18

313 Thomas White Boulevard Chester, MD MLS# MDQA2018144 - Image 19

313 Thomas White Boulevard Chester, MD MLS# MDQA2018144 - Image 20

1 of 20

OPEN HOUSE: Sunday 8/9 2:30 PM - 4:30 PM

$825,000

Beds

2.1

Baths

3,291

Sq.Ft.

313 Thomas White Boulevard

Chester, MD

Courtesy of MONUMENT SOTHEBY'S INTERNATIONAL REALTY

509 Teal Court # E Chester, MD MLS# MDQA2018174 - Image 1

509 Teal Court # E Chester, MD MLS# MDQA2018174 - Image 2

509 Teal Court # E Chester, MD MLS# MDQA2018174 - Image 3

509 Teal Court # E Chester, MD MLS# MDQA2018174 - Image 4

509 Teal Court # E Chester, MD MLS# MDQA2018174 - Image 5

1 of 5

$300,000

Beds

2.0

Baths

1,100

Sq.Ft.

509 Teal Court # E

Chester, MD

Courtesy of RE/MAX EXECUTIVE

209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 1

209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 2

209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 3

209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 4

209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 5

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209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 67

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209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 71

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209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 73

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209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 78

209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 79

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209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 93

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209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 95

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209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 98

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209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 101

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209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 106

209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 107

209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 108

209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 109

209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 110

209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 111

209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 112

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209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 115

209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 116

209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 117

209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 118

209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 119

209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 120

209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 121

209 Harrier Way Chester, MD MLS# MDQA2018154 - Image 122

Recently Listed with Virtual Tour

1 of 122

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

$747,900

Beds

3.0

Baths

3,142

Sq.Ft.

209 Harrier Way

Chester, MD

Courtesy of LONG & FOSTER REAL ESTATE, INC.

113 Bentons Pleasure Road Chester, MD MLS# MDQA2018142 - Image 1

113 Bentons Pleasure Road Chester, MD MLS# MDQA2018142 - Image 2

1 of 2

$868,000

Beds

2.1

Baths

3,168

Sq.Ft.

113 Bentons Pleasure Road

Chester, MD

Courtesy of CUMMINGS & CO. REALTORS

532 Cross Creek Court Chester, MD MLS# MDQA2017890 - Image 1

1 of 1

$555,000

Beds

2.1

Baths

2,486

Sq.Ft.

532 Cross Creek Court

Chester, MD

Courtesy of LONG & FOSTER REAL ESTATE, INC.

193 Spinnaker Way Chester, MD MLS# MDQA2018122 - Image 1

193 Spinnaker Way Chester, MD MLS# MDQA2018122 - Image 2

193 Spinnaker Way Chester, MD MLS# MDQA2018122 - Image 3

193 Spinnaker Way Chester, MD MLS# MDQA2018122 - Image 4

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193 Spinnaker Way Chester, MD MLS# MDQA2018122 - Image 7

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193 Spinnaker Way Chester, MD MLS# MDQA2018122 - Image 10

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193 Spinnaker Way Chester, MD MLS# MDQA2018122 - Image 13

193 Spinnaker Way Chester, MD MLS# MDQA2018122 - Image 14

193 Spinnaker Way Chester, MD MLS# MDQA2018122 - Image 15

193 Spinnaker Way Chester, MD MLS# MDQA2018122 - Image 16

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193 Spinnaker Way Chester, MD MLS# MDQA2018122 - Image 40

193 Spinnaker Way Chester, MD MLS# MDQA2018122 - Image 41

Recently Listed

1 of 41

$856,000

Beds

3.0

Baths

2,527

Sq.Ft.

193 Spinnaker Way

Chester, MD

Courtesy of LONG & FOSTER REAL ESTATE, INC.

1025 Dundee Court Chester, MD MLS# MDQA2018108 - Image 1

1025 Dundee Court Chester, MD MLS# MDQA2018108 - Image 2

1025 Dundee Court Chester, MD MLS# MDQA2018108 - Image 3

1025 Dundee Court Chester, MD MLS# MDQA2018108 - Image 4

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1025 Dundee Court Chester, MD MLS# MDQA2018108 - Image 50

1 of 50

OPEN HOUSE: Saturday 8/8 9:30 AM - 11:30 AM

$298,000

Beds

2.1

Baths

1,400

Sq.Ft.

1025 Dundee Court

Chester, MD

Courtesy of RE/MAX EXECUTIVE

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

102 Boatswain Way # 2912 Chester, MD MLS# MDQA2018092 - Image 2

102 Boatswain Way # 2912 Chester, MD MLS# MDQA2018092 - Image 3

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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

2702 Harrington Road Chester, MD MLS# MDQA2017816 - Image 1

2702 Harrington Road Chester, MD MLS# MDQA2017816 - Image 2

2702 Harrington Road Chester, MD MLS# MDQA2017816 - Image 3

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2702 Harrington Road Chester, MD MLS# MDQA2017816 - Image 26

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2702 Harrington Road Chester, MD MLS# MDQA2017816 - Image 80

2702 Harrington Road Chester, MD MLS# MDQA2017816 - Image 81

1 of 81

$689,000

Beds

2.0

Baths

2,075

Sq.Ft.

2702 Harrington Road

Chester, MD

Courtesy of ROSENDALE REALTY

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 1

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 2

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 3

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 4

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 5

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 6

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 7

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 8

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 9

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 10

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 11

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 12

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 13

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 14

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 15

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 16

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 17

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 18

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 19

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 20

302 Merganser Court # A Chester, MD MLS# MDQA2018076 - Image 21

Recently Listed

1 of 21

$299,900

Beds

2.0

Baths

1,073

Sq.Ft.

302 Merganser Court # A

Chester, MD

Courtesy of KELLER WILLIAMS FLAGSHIP

26-B Queen Anne Way Chester, MD MLS# MDQA2018040 - Image 1

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26-B Queen Anne Way Chester, MD MLS# MDQA2018040 - Image 41

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26-B Queen Anne Way Chester, MD MLS# MDQA2018040 - Image 43

26-B Queen Anne Way Chester, MD MLS# MDQA2018040 - Image 44

Recently Listed with Virtual Tour

1 of 44

$225,000

Beds

1.0

Baths

640

Sq.Ft.

26-B Queen Anne Way

Chester, MD

Courtesy of REALTY NAVIGATOR

134 Richard Ingle Way Chester, MD MLS# MDQA2017930 - Image 1

134 Richard Ingle Way Chester, MD MLS# MDQA2017930 - Image 2

134 Richard Ingle Way Chester, MD MLS# MDQA2017930 - Image 3

134 Richard Ingle Way Chester, MD MLS# MDQA2017930 - Image 4

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134 Richard Ingle Way Chester, MD MLS# MDQA2017930 - Image 63

Recently Listed with Virtual Tour

1 of 63

$749,000

Beds

3.1

Baths

2,185

Sq.Ft.

134 Richard Ingle Way

Chester, MD

Courtesy of REDFIN CORP

102 Boatswain Way # 2932 Chester, MD MLS# MDQA2018008 - Image 1

102 Boatswain Way # 2932 Chester, MD MLS# MDQA2018008 - Image 2

102 Boatswain Way # 2932 Chester, MD MLS# MDQA2018008 - Image 3

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102 Boatswain Way # 2932 Chester, MD MLS# MDQA2018008 - Image 45

102 Boatswain Way # 2932 Chester, MD MLS# MDQA2018008 - Image 46

102 Boatswain Way # 2932 Chester, MD MLS# MDQA2018008 - Image 47

Recently Listed

1 of 47

$829,990

Beds

2.1

Baths

1,900

Sq.Ft.

102 Boatswain Way # 2932

Chester, MD

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY - OP

2810 Harvest Court Chester, MD MLS# MDQA2017934 - Image 1

2810 Harvest Court Chester, MD MLS# MDQA2017934 - Image 2

2810 Harvest Court Chester, MD MLS# MDQA2017934 - Image 3

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2810 Harvest Court Chester, MD MLS# MDQA2017934 - Image 77

Virtual Tour

1 of 77

$895,000

Beds

3.0

Baths

2,579

Sq.Ft.

2810 Harvest Court

Chester, MD

Courtesy of BLACKWELL REAL ESTATE, LLC

1609 Crab Alley Drive Chester, MD MLS# MDQA2017988 - Image 1

1 of 1

$345,000

Beds

1.1

Baths

1,080

Sq.Ft.

1609 Crab Alley Drive

Chester, MD

Courtesy of PAUL WESLEY REAL ESTATE

2004 Bridgepointe Drive Chester, MD MLS# MDQA2017932 - Image 1

2004 Bridgepointe Drive Chester, MD MLS# MDQA2017932 - Image 2

2004 Bridgepointe Drive Chester, MD MLS# MDQA2017932 - Image 3

2004 Bridgepointe Drive Chester, MD MLS# MDQA2017932 - Image 4

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2004 Bridgepointe Drive Chester, MD MLS# MDQA2017932 - Image 30

2004 Bridgepointe Drive Chester, MD MLS# MDQA2017932 - Image 31

2004 Bridgepointe Drive Chester, MD MLS# MDQA2017932 - Image 32

Recently Listed

1 of 32

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

$374,900

Beds

2.0

Baths

1,524

Sq.Ft.

2004 Bridgepointe Drive

Chester, MD

Courtesy of RE/MAX EXECUTIVE

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

Find Properties by Zip

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

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Chester Maryland Homes for Sale

About Chester

Listings in Chester, MD

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Chester, MD Information

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