Chester Maryland Homes for Sale

68 total properties

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Harbor Drive Chester, MD MLS# MDQA2015496 - Image 1

Harbor Drive Chester, MD MLS# MDQA2015496 - Image 2

Harbor Drive Chester, MD MLS# MDQA2015496 - Image 3

Harbor Drive Chester, MD MLS# MDQA2015496 - Image 4

Harbor Drive Chester, MD MLS# MDQA2015496 - Image 5

Harbor Drive Chester, MD MLS# MDQA2015496 - Image 6

Harbor Drive Chester, MD MLS# MDQA2015496 - Image 7

Harbor Drive Chester, MD MLS# MDQA2015496 - Image 8

Harbor Drive Chester, MD MLS# MDQA2015496 - Image 9

Harbor Drive Chester, MD MLS# MDQA2015496 - Image 10

Harbor Drive Chester, MD MLS# MDQA2015496 - Image 11

Harbor Drive Chester, MD MLS# MDQA2015496 - Image 12

New Construction

1 of 12

$499,900

Beds

2.0

Baths

1,250

Sq.Ft.

Harbor Drive

Chester, MD

Courtesy of COLDWELL BANKER WATERMAN REALTY

1906 Harbor Drive Chester, MD MLS# MDQA2015604 - Image 1

1906 Harbor Drive Chester, MD MLS# MDQA2015604 - Image 2

1906 Harbor Drive Chester, MD MLS# MDQA2015604 - Image 3

1 of 3

$499,900

Beds

2.0

Baths

1,750

Sq.Ft.

1906 Harbor Drive

Chester, MD

Courtesy of FIVE STAR REAL ESTATE

170 Harrier Way # 11 Chester, MD MLS# MDQA2012944 - Image 1

170 Harrier Way # 11 Chester, MD MLS# MDQA2012944 - Image 2

170 Harrier Way # 11 Chester, MD MLS# MDQA2012944 - Image 3

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170 Harrier Way # 11 Chester, MD MLS# MDQA2012944 - Image 73

170 Harrier Way # 11 Chester, MD MLS# MDQA2012944 - Image 74

Adult Community with Virtual Tour

1 of 74

$499,000

Beds

2.1

Baths

2,003

Sq.Ft.

170 Harrier Way # 11

Chester, MD

Courtesy of REDFIN CORP

THE TIME TO SELL IS NOW!

1000 Herons Nest Way # 32 Chester, MD MLS# MDQA2013002 - Image 1

1000 Herons Nest Way # 32 Chester, MD MLS# MDQA2013002 - Image 2

1000 Herons Nest Way # 32 Chester, MD MLS# MDQA2013002 - Image 3

1000 Herons Nest Way # 32 Chester, MD MLS# MDQA2013002 - Image 4

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1000 Herons Nest Way # 32 Chester, MD MLS# MDQA2013002 - Image 17

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1000 Herons Nest Way # 32 Chester, MD MLS# MDQA2013002 - Image 21

1000 Herons Nest Way # 32 Chester, MD MLS# MDQA2013002 - Image 22

1000 Herons Nest Way # 32 Chester, MD MLS# MDQA2013002 - Image 23

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1000 Herons Nest Way # 32 Chester, MD MLS# MDQA2013002 - Image 25

1000 Herons Nest Way # 32 Chester, MD MLS# MDQA2013002 - Image 26

1000 Herons Nest Way # 32 Chester, MD MLS# MDQA2013002 - Image 27

1000 Herons Nest Way # 32 Chester, MD MLS# MDQA2013002 - Image 28

Adult Community

1 of 28

$499,000

Beds

2.0

Baths

1,900

Sq.Ft.

1000 Herons Nest Way # 32

Chester, MD

Courtesy of RE/MAX EXECUTIVE

170 Harrier Way # 22 Chester, MD MLS# MDQA2012922 - Image 1

170 Harrier Way # 22 Chester, MD MLS# MDQA2012922 - Image 2

170 Harrier Way # 22 Chester, MD MLS# MDQA2012922 - Image 3

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170 Harrier Way # 22 Chester, MD MLS# MDQA2012922 - Image 61

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170 Harrier Way # 22 Chester, MD MLS# MDQA2012922 - Image 77

170 Harrier Way # 22 Chester, MD MLS# MDQA2012922 - Image 78

170 Harrier Way # 22 Chester, MD MLS# MDQA2012922 - Image 79

Adult Community

1 of 79

$499,000

Beds

2.1

Baths

1,900

Sq.Ft.

170 Harrier Way # 22

Chester, MD

Courtesy of KELLER WILLIAMS SELECT REALTORS OF ANNAPOLIS

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 1

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 2

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 3

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 4

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 5

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 6

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 7

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 8

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 9

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 10

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 11

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 12

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 13

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 14

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 15

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 16

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 17

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 18

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1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 20

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 21

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1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 37

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 38

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 39

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 40

1916 Stevens Drive Chester, MD MLS# MDQA2015554 - Image 41

1 of 41

$495,000

Beds

2.0

Baths

1,728

Sq.Ft.

1916 Stevens Drive

Chester, MD

Courtesy of COLDWELL BANKER REALTY

15 Queen Anne Way # E Chester, MD MLS# MDQA2015752 - Image 1

15 Queen Anne Way # E Chester, MD MLS# MDQA2015752 - Image 2

15 Queen Anne Way # E Chester, MD MLS# MDQA2015752 - Image 3

15 Queen Anne Way # E Chester, MD MLS# MDQA2015752 - Image 4

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15 Queen Anne Way # E Chester, MD MLS# MDQA2015752 - Image 13

15 Queen Anne Way # E Chester, MD MLS# MDQA2015752 - Image 14

15 Queen Anne Way # E Chester, MD MLS# MDQA2015752 - Image 15

1 of 15

OPEN HOUSE: Saturday 1/3 1:00 PM - 3:00 PM

$480,000

Beds

2.1

Baths

1,680

Sq.Ft.

15 Queen Anne Way # E

Chester, MD

Courtesy of RE/MAX EXECUTIVE

34 Queen Anne Way Chester, MD MLS# MDQA2013486 - Image 1

34 Queen Anne Way Chester, MD MLS# MDQA2013486 - Image 2

34 Queen Anne Way Chester, MD MLS# MDQA2013486 - Image 3

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34 Queen Anne Way Chester, MD MLS# MDQA2013486 - Image 57

Virtual Tour

1 of 57

$469,000

Beds

2.1

Baths

1,104

Sq.Ft.

34 Queen Anne Way

Chester, MD

Courtesy of TAYLOR PROPERTIES

1401 Calvert Road Chester, MD MLS# MDQA2014504 - Image 1

1401 Calvert Road Chester, MD MLS# MDQA2014504 - Image 2

1401 Calvert Road Chester, MD MLS# MDQA2014504 - Image 3

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1401 Calvert Road Chester, MD MLS# MDQA2014504 - Image 32

1401 Calvert Road Chester, MD MLS# MDQA2014504 - Image 33

1401 Calvert Road Chester, MD MLS# MDQA2014504 - Image 34

1 of 34

$454,900

Beds

2.0

Baths

1,444

Sq.Ft.

1401 Calvert Road

Chester, MD

Courtesy of COLDWELL BANKER WATERMAN REALTY

1340 Queen Anne Drive Chester, MD MLS# MDQA2011168 - Image 1

1340 Queen Anne Drive Chester, MD MLS# MDQA2011168 - Image 2

1340 Queen Anne Drive Chester, MD MLS# MDQA2011168 - Image 3

1340 Queen Anne Drive Chester, MD MLS# MDQA2011168 - Image 4

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1340 Queen Anne Drive Chester, MD MLS# MDQA2011168 - Image 26

1340 Queen Anne Drive Chester, MD MLS# MDQA2011168 - Image 27

1 of 27

$449,900

Beds

2.0

Baths

1,248

Sq.Ft.

1340 Queen Anne Drive

Chester, MD

Courtesy of RE/MAX EXECUTIVE

1701 Bayside Drive Chester, MD MLS# MDQA2015672 - Image 1

1701 Bayside Drive Chester, MD MLS# MDQA2015672 - Image 2

1701 Bayside Drive Chester, MD MLS# MDQA2015672 - Image 3

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1701 Bayside Drive Chester, MD MLS# MDQA2015672 - Image 43

1701 Bayside Drive Chester, MD MLS# MDQA2015672 - Image 44

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1701 Bayside Drive Chester, MD MLS# MDQA2015672 - Image 46

1701 Bayside Drive Chester, MD MLS# MDQA2015672 - Image 47

Virtual Tour

1 of 47

$435,000

Beds

2.0

Baths

1,980

Sq.Ft.

1701 Bayside Drive

Chester, MD

Courtesy of THE KW COLLECTIVE

807 Auckland Way Chester, MD MLS# MDQA2015692 - Image 1

807 Auckland Way Chester, MD MLS# MDQA2015692 - Image 2

807 Auckland Way Chester, MD MLS# MDQA2015692 - Image 3

807 Auckland Way Chester, MD MLS# MDQA2015692 - Image 4

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807 Auckland Way Chester, MD MLS# MDQA2015692 - Image 47

1 of 47

$425,000

Beds

3.1

Baths

2,100

Sq.Ft.

807 Auckland Way

Chester, MD

Courtesy of REAL BROKER, LLC

1407 Calvert Road Chester, MD MLS# MDQA2015514 - Image 1

1 of 1

$409,900

Beds

1.1

Baths

1,693

Sq.Ft.

1407 Calvert Road

Chester, MD

Courtesy of ROSENDALE REALTY

1839 Harbor Drive Chester, MD MLS# MDQA2014832 - Image 1

1839 Harbor Drive Chester, MD MLS# MDQA2014832 - Image 2

1839 Harbor Drive Chester, MD MLS# MDQA2014832 - Image 3

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1839 Harbor Drive Chester, MD MLS# MDQA2014832 - Image 23

1 of 23

$365,000

Beds

2.0

Baths

2,035

Sq.Ft.

1839 Harbor Drive

Chester, MD

Courtesy of TAYLOR PROPERTIES

54 Queen Caroline Court Chester, MD MLS# MDQA2015236 - Image 1

54 Queen Caroline Court Chester, MD MLS# MDQA2015236 - Image 2

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1 of 40

$349,000

Beds

2.0

Baths

1,280

Sq.Ft.

54 Queen Caroline Court

Chester, MD

Courtesy of LONG & FOSTER REAL ESTATE, INC.

206 Ringneck Court # 78 Chester, MD MLS# MDQA2015644 - Image 1

206 Ringneck Court # 78 Chester, MD MLS# MDQA2015644 - Image 2

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206 Ringneck Court # 78 Chester, MD MLS# MDQA2015644 - Image 23

1 of 23

$349,000

Beds

2.1

Baths

1,747

Sq.Ft.

206 Ringneck Court # 78

Chester, MD

Courtesy of RE/MAX EXECUTIVE

30 Queen Mary Court Chester, MD MLS# MDQA2015054 - Image 1

30 Queen Mary Court Chester, MD MLS# MDQA2015054 - Image 2

30 Queen Mary Court Chester, MD MLS# MDQA2015054 - Image 3

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Virtual Tour

1 of 60

$339,900

Beds

2.1

Baths

1,440

Sq.Ft.

30 Queen Mary Court

Chester, MD

Courtesy of DOUGLAS REALTY LLC

206 Blenny Lane Chester, MD MLS# MDQA2015760 - Image 1

1 of 1

$339,900

Beds

2.2

Baths

1,899

Sq.Ft.

206 Blenny Lane

Chester, MD

Courtesy of EXP REALTY, LLC

10 Queen Elizabeth Court Chester, MD MLS# MDQA2015650 - Image 1

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10 Queen Elizabeth Court Chester, MD MLS# MDQA2015650 - Image 3

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10 Queen Elizabeth Court Chester, MD MLS# MDQA2015650 - Image 19

1 of 19

$330,000

Beds

1.0

Baths

724

Sq.Ft.

10 Queen Elizabeth Court

Chester, MD

Courtesy of LONG & FOSTER REAL ESTATE, INC.

1870 Harbor Drive Chester, MD MLS# MDQA2015064 - Image 1

1870 Harbor Drive Chester, MD MLS# MDQA2015064 - Image 2

1870 Harbor Drive Chester, MD MLS# MDQA2015064 - Image 3

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1870 Harbor Drive Chester, MD MLS# MDQA2015064 - Image 34

Virtual Tour

1 of 34

$320,000

Beds

1.0

Baths

832

Sq.Ft.

1870 Harbor Drive

Chester, MD

Courtesy of RE/MAX EXECUTIVE

About Chester

Listings in Chester, MD: 78
Estimated median home price: $552,900

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	3
$100K - 200K	0
$200K - 300K	4
$300K - 400K	8
$400K - 500K	15
$500K - 600K	14
$600K - 700K	10
$700K - 800K	9
$800K - 900K	5
$900K - 1M	1
$1M - Max	9

Homes for Sale by Type in Chester, MD

Property Type	Count
Single Family	37
Townhouse	0
Condo	38
Commercial	0
Rental	8
Lots and Land	3
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 12/28/2025)

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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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Chester Maryland Homes for Sale

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