Chester Maryland Homes for Sale

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126 Claiborne Street Chester, MD MLS# MDQA2017106 - Image 1

1 of 1

OPEN HOUSE: Sunday 5/3 11:00 AM - 1:00 PM

$787,900

Beds

2.1

Baths

2,160

Sq.Ft.

126 Claiborne Street

Chester, MD

Courtesy of SAMSON PROPERTIES

1848 Harbor Drive Chester, MD MLS# MDQA2017062 - Image 1

1848 Harbor Drive Chester, MD MLS# MDQA2017062 - Image 2

1848 Harbor Drive Chester, MD MLS# MDQA2017062 - Image 3

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1848 Harbor Drive Chester, MD MLS# MDQA2017062 - Image 7

1848 Harbor Drive Chester, MD MLS# MDQA2017062 - Image 8

1848 Harbor Drive Chester, MD MLS# MDQA2017062 - Image 9

1848 Harbor Drive Chester, MD MLS# MDQA2017062 - Image 10

1848 Harbor Drive Chester, MD MLS# MDQA2017062 - Image 11

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1848 Harbor Drive Chester, MD MLS# MDQA2017062 - Image 13

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1848 Harbor Drive Chester, MD MLS# MDQA2017062 - Image 16

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1848 Harbor Drive Chester, MD MLS# MDQA2017062 - Image 36

1848 Harbor Drive Chester, MD MLS# MDQA2017062 - Image 37

1848 Harbor Drive Chester, MD MLS# MDQA2017062 - Image 38

Recently Listed

1 of 38

$495,000

Beds

2.0

Baths

1,804

Sq.Ft.

1848 Harbor Drive

Chester, MD

Courtesy of EXP REALTY, LLC

1906 Stevens Drive Chester, MD MLS# MDQA2017056 - Image 1

1906 Stevens Drive Chester, MD MLS# MDQA2017056 - Image 2

1 of 2

$464,000

Beds

2.0

Baths

2,016

Sq.Ft.

1906 Stevens Drive

Chester, MD

Courtesy of RE/MAX EXECUTIVE

THE TIME TO SELL IS NOW!

200 Schooner Way Chester, MD MLS# MDQA2016718 - Image 1

200 Schooner Way Chester, MD MLS# MDQA2016718 - Image 2

200 Schooner Way Chester, MD MLS# MDQA2016718 - Image 3

200 Schooner Way Chester, MD MLS# MDQA2016718 - Image 4

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200 Schooner Way Chester, MD MLS# MDQA2016718 - Image 9

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200 Schooner Way Chester, MD MLS# MDQA2016718 - Image 11

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200 Schooner Way Chester, MD MLS# MDQA2016718 - Image 13

200 Schooner Way Chester, MD MLS# MDQA2016718 - Image 14

200 Schooner Way Chester, MD MLS# MDQA2016718 - Image 15

200 Schooner Way Chester, MD MLS# MDQA2016718 - Image 16

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200 Schooner Way Chester, MD MLS# MDQA2016718 - Image 18

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200 Schooner Way Chester, MD MLS# MDQA2016718 - Image 39

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200 Schooner Way Chester, MD MLS# MDQA2016718 - Image 41

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200 Schooner Way Chester, MD MLS# MDQA2016718 - Image 46

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200 Schooner Way Chester, MD MLS# MDQA2016718 - Image 51

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200 Schooner Way Chester, MD MLS# MDQA2016718 - Image 62

200 Schooner Way Chester, MD MLS# MDQA2016718 - Image 63

200 Schooner Way Chester, MD MLS# MDQA2016718 - Image 64

Recently Listed

1 of 64

$550,000

Beds

3.1

Baths

2,100

Sq.Ft.

200 Schooner Way

Chester, MD

Courtesy of LONG & FOSTER REAL ESTATE, INC.

134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 1

134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 2

134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 3

134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 4

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134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 7

134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 8

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134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 10

134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 11

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134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 13

134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 14

134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 15

134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 16

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134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 20

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134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 23

134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 24

134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 25

134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 26

134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 27

134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 28

134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 29

134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 30

134 Mchenny Court Chester, MD MLS# MDQA2017004 - Image 31

Recently Listed

1 of 31

$615,000

Beds

2.1

Baths

1,839

Sq.Ft.

134 Mchenny Court

Chester, MD

Courtesy of COLDWELL BANKER REALTY

1921 Harbor Drive Chester, MD MLS# MDQA2017018 - Image 1

1921 Harbor Drive Chester, MD MLS# MDQA2017018 - Image 2

1921 Harbor Drive Chester, MD MLS# MDQA2017018 - Image 3

1921 Harbor Drive Chester, MD MLS# MDQA2017018 - Image 4

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1921 Harbor Drive Chester, MD MLS# MDQA2017018 - Image 7

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1921 Harbor Drive Chester, MD MLS# MDQA2017018 - Image 33

1921 Harbor Drive Chester, MD MLS# MDQA2017018 - Image 34

1921 Harbor Drive Chester, MD MLS# MDQA2017018 - Image 35

New Construction

1 of 35

$519,900

Beds

2.1

Baths

2,000

Sq.Ft.

1921 Harbor Drive

Chester, MD

Courtesy of COLDWELL BANKER WATERMAN REALTY

1914 Anchorage Drive Chester, MD MLS# MDQA2017002 - Image 1

1914 Anchorage Drive Chester, MD MLS# MDQA2017002 - Image 2

1914 Anchorage Drive Chester, MD MLS# MDQA2017002 - Image 3

1914 Anchorage Drive Chester, MD MLS# MDQA2017002 - Image 4

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1914 Anchorage Drive Chester, MD MLS# MDQA2017002 - Image 36

1914 Anchorage Drive Chester, MD MLS# MDQA2017002 - Image 37

1914 Anchorage Drive Chester, MD MLS# MDQA2017002 - Image 38

Recently Listed

1 of 38

$299,900

Beds

2.0

Baths

1,800

Sq.Ft.

1914 Anchorage Drive

Chester, MD

Courtesy of CENTURY 21 DOWNTOWN

1700 Saint Marys Road Chester, MD MLS# MDQA2017012 - Image 1

1700 Saint Marys Road Chester, MD MLS# MDQA2017012 - Image 2

1700 Saint Marys Road Chester, MD MLS# MDQA2017012 - Image 3

1700 Saint Marys Road Chester, MD MLS# MDQA2017012 - Image 4

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1700 Saint Marys Road Chester, MD MLS# MDQA2017012 - Image 38

1700 Saint Marys Road Chester, MD MLS# MDQA2017012 - Image 39

1700 Saint Marys Road Chester, MD MLS# MDQA2017012 - Image 40

1700 Saint Marys Road Chester, MD MLS# MDQA2017012 - Image 41

Virtual Tour

1 of 41

$675,000

Beds

2.0

Baths

1,898

Sq.Ft.

1700 Saint Marys Road

Chester, MD

Courtesy of COLDWELL BANKER REALTY

1 Queen Victoria Court Chester, MD MLS# MDQA2016768 - Image 1

1 Queen Victoria Court Chester, MD MLS# MDQA2016768 - Image 2

1 Queen Victoria Court Chester, MD MLS# MDQA2016768 - Image 3

1 Queen Victoria Court Chester, MD MLS# MDQA2016768 - Image 4

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1 Queen Victoria Court Chester, MD MLS# MDQA2016768 - Image 40

1 Queen Victoria Court Chester, MD MLS# MDQA2016768 - Image 41

Recently Listed

1 of 41

$389,900

Beds

2.0

Baths

1,260

Sq.Ft.

1 Queen Victoria Court

Chester, MD

Courtesy of DOUGLAS REALTY LLC

200 Newtown Road Chester, MD MLS# MDQA2016754 - Image 1

200 Newtown Road Chester, MD MLS# MDQA2016754 - Image 2

200 Newtown Road Chester, MD MLS# MDQA2016754 - Image 3

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200 Newtown Road Chester, MD MLS# MDQA2016754 - Image 50

Virtual Tour

1 of 50

$445,000

Beds

2.1

Baths

1,296

Sq.Ft.

200 Newtown Road

Chester, MD

Courtesy of SAMSON PROPERTIES

126 Watermans Cove Lane Chester, MD MLS# MDQA2016908 - Image 1

126 Watermans Cove Lane Chester, MD MLS# MDQA2016908 - Image 2

126 Watermans Cove Lane Chester, MD MLS# MDQA2016908 - Image 3

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126 Watermans Cove Lane Chester, MD MLS# MDQA2016908 - Image 43

126 Watermans Cove Lane Chester, MD MLS# MDQA2016908 - Image 44

126 Watermans Cove Lane Chester, MD MLS# MDQA2016908 - Image 45

126 Watermans Cove Lane Chester, MD MLS# MDQA2016908 - Image 46

126 Watermans Cove Lane Chester, MD MLS# MDQA2016908 - Image 47

126 Watermans Cove Lane Chester, MD MLS# MDQA2016908 - Image 48

Recently Listed

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$579,000

Beds

3.0

Baths

1,536

Sq.Ft.

126 Watermans Cove Lane

Chester, MD

Courtesy of COLDWELL BANKER REALTY

114 Merganser Court Chester, MD MLS# MDQA2016968 - Image 1

114 Merganser Court Chester, MD MLS# MDQA2016968 - Image 2

114 Merganser Court Chester, MD MLS# MDQA2016968 - Image 3

114 Merganser Court Chester, MD MLS# MDQA2016968 - Image 4

114 Merganser Court Chester, MD MLS# MDQA2016968 - Image 5

114 Merganser Court Chester, MD MLS# MDQA2016968 - Image 6

114 Merganser Court Chester, MD MLS# MDQA2016968 - Image 7

114 Merganser Court Chester, MD MLS# MDQA2016968 - Image 8

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114 Merganser Court Chester, MD MLS# MDQA2016968 - Image 13

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114 Merganser Court Chester, MD MLS# MDQA2016968 - Image 19

114 Merganser Court Chester, MD MLS# MDQA2016968 - Image 20

Recently Listed

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$299,500

Beds

2.0

Baths

1,069

Sq.Ft.

114 Merganser Court

Chester, MD

Courtesy of BENSON & MANGOLD, LLC

1604 Midway Road Chester, MD MLS# MDQA2016844 - Image 1

1604 Midway Road Chester, MD MLS# MDQA2016844 - Image 2

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1604 Midway Road Chester, MD MLS# MDQA2016844 - Image 72

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1 of 73

$795,000

Beds

3.0

Baths

2,972

Sq.Ft.

1604 Midway Road

Chester, MD

Courtesy of WILSON REALTY & STAGING LLC

208 Blenny Lane Chester, MD MLS# MDQA2016002 - Image 1

208 Blenny Lane Chester, MD MLS# MDQA2016002 - Image 2

208 Blenny Lane Chester, MD MLS# MDQA2016002 - Image 3

208 Blenny Lane Chester, MD MLS# MDQA2016002 - Image 4

208 Blenny Lane Chester, MD MLS# MDQA2016002 - Image 5

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208 Blenny Lane Chester, MD MLS# MDQA2016002 - Image 34

Recently Listed

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OPEN HOUSE: Saturday 5/2 10:00 AM - 12:00 PM

$459,000

Beds

2.2

Baths

1,899

Sq.Ft.

208 Blenny Lane

Chester, MD

Courtesy of RE/MAX EXECUTIVE

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

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111 Marshgrass Way # 21 Chester, MD MLS# MDQA2016714 - Image 46

111 Marshgrass Way # 21 Chester, MD MLS# MDQA2016714 - Image 47

Recently Listed with Virtual Tour

1 of 47

$680,000

Beds

2.1

Baths

2,602

Sq.Ft.

111 Marshgrass Way # 21

Chester, MD

Courtesy of SAMSON PROPERTIES

29 Queen Mary Court Chester, MD MLS# MDQA2016898 - Image 1

29 Queen Mary Court Chester, MD MLS# MDQA2016898 - Image 2

29 Queen Mary Court Chester, MD MLS# MDQA2016898 - Image 3

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29 Queen Mary Court Chester, MD MLS# MDQA2016898 - Image 68

Recently Listed

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$599,000

Beds

2.1

Baths

1,425

Sq.Ft.

29 Queen Mary Court

Chester, MD

Courtesy of JORGE A. ZEA

1000 Herons Nest Way # 22 Chester, MD MLS# MDQA2016820 - Image 1

1000 Herons Nest Way # 22 Chester, MD MLS# MDQA2016820 - Image 2

1000 Herons Nest Way # 22 Chester, MD MLS# MDQA2016820 - Image 3

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1000 Herons Nest Way # 22 Chester, MD MLS# MDQA2016820 - Image 55

1000 Herons Nest Way # 22 Chester, MD MLS# MDQA2016820 - Image 56

Adult Community with Virtual Tour

1 of 56

$488,000

Beds

2.1

Baths

1,900

Sq.Ft.

1000 Herons Nest Way # 22

Chester, MD

Courtesy of RE/MAX EXECUTIVE

1000 Herons Nest Way # 402 Chester, MD MLS# MDQA2016710 - Image 1

1000 Herons Nest Way # 402 Chester, MD MLS# MDQA2016710 - Image 2

1000 Herons Nest Way # 402 Chester, MD MLS# MDQA2016710 - Image 3

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1000 Herons Nest Way # 402 Chester, MD MLS# MDQA2016710 - Image 52

1000 Herons Nest Way # 402 Chester, MD MLS# MDQA2016710 - Image 53

Adult Community

1 of 53

$599,000

Beds

2.1

Baths

1,900

Sq.Ft.

1000 Herons Nest Way # 402

Chester, MD

Courtesy of RE/MAX UNITED REAL ESTATE

111 Marshgrass Way # 43 Chester, MD MLS# MDQA2016724 - Image 1

111 Marshgrass Way # 43 Chester, MD MLS# MDQA2016724 - Image 2

111 Marshgrass Way # 43 Chester, MD MLS# MDQA2016724 - Image 3

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111 Marshgrass Way # 43 Chester, MD MLS# MDQA2016724 - Image 14

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Adult Community

1 of 61

$765,000

Beds

2.1

Baths

111 Marshgrass Way # 43

Chester, MD

Courtesy of COLDWELL BANKER REALTY

2008 Bridgepointe Drive Chester, MD MLS# MDQA2016728 - Image 1

2008 Bridgepointe Drive Chester, MD MLS# MDQA2016728 - Image 2

2008 Bridgepointe Drive Chester, MD MLS# MDQA2016728 - Image 3

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2008 Bridgepointe Drive Chester, MD MLS# MDQA2016728 - Image 41

Virtual Tour

1 of 41

$380,000

Beds

2.0

Baths

1,804

Sq.Ft.

2008 Bridgepointe Drive

Chester, MD

Courtesy of RE/MAX EXECUTIVE

About Chester

Listings in Chester, MD: 109
Estimated median home price: $659,990

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	8
$400K - 500K	13
$500K - 600K	16
$600K - 700K	14
$700K - 800K	18
$800K - 900K	7
$900K - 1M	11
$1M - Max	11

Homes for Sale by Type in Chester, MD

Property Type	Count
Single Family	49
Townhouse	1
Condo	55
Commercial	0
Rental	12
Lots and Land	4
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 5/1/2026)

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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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