Chester Maryland Homes for Sale

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102 Boatswain Way # 2911 Chester, MD MLS# MDQA2016668 - Image 1

102 Boatswain Way # 2911 Chester, MD MLS# MDQA2016668 - Image 2

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102 Boatswain Way # 2911 Chester, MD MLS# MDQA2016668 - Image 59

102 Boatswain Way # 2911 Chester, MD MLS# MDQA2016668 - Image 60

102 Boatswain Way # 2911 Chester, MD MLS# MDQA2016668 - Image 61

102 Boatswain Way # 2911 Chester, MD MLS# MDQA2016668 - Image 62

102 Boatswain Way # 2911 Chester, MD MLS# MDQA2016668 - Image 63

Adult Community

1 of 63

$629,990

Beds

2.1

Baths

2,003

Sq.Ft.

102 Boatswain Way # 2911

Chester, MD

Courtesy of KOVO REALTY

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

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

102 Boatswain Way # 2912 Chester, MD MLS# MDQA2016670 - Image 3

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102 Boatswain Way # 2912 Chester, MD MLS# MDQA2016670 - Image 59

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102 Boatswain Way # 2912 Chester, MD MLS# MDQA2016670 - Image 61

102 Boatswain Way # 2912 Chester, MD MLS# MDQA2016670 - Image 62

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

249 Warbler Way Chester, MD MLS# MDQA2016488 - Image 1

249 Warbler Way Chester, MD MLS# MDQA2016488 - Image 2

249 Warbler Way Chester, MD MLS# MDQA2016488 - Image 3

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249 Warbler Way Chester, MD MLS# MDQA2016488 - Image 49

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249 Warbler Way Chester, MD MLS# MDQA2016488 - Image 51

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249 Warbler Way Chester, MD MLS# MDQA2016488 - Image 67

249 Warbler Way Chester, MD MLS# MDQA2016488 - Image 68

Adult Community

1 of 68

$679,000

Beds

2.0

Baths

2,025

Sq.Ft.

249 Warbler Way

Chester, MD

Courtesy of RE/MAX EXECUTIVE

THE TIME TO SELL IS NOW!

1872 Harbor Drive Chester, MD MLS# MDQA2016514 - Image 1

1872 Harbor Drive Chester, MD MLS# MDQA2016514 - Image 2

1872 Harbor Drive Chester, MD MLS# MDQA2016514 - Image 3

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1872 Harbor Drive Chester, MD MLS# MDQA2016514 - Image 23

1 of 23

$455,000

Beds

2.0

Baths

1,486

Sq.Ft.

1872 Harbor Drive

Chester, MD

Courtesy of CROSS STREET REALTORS LLC

1025 Dundee Court Chester, MD MLS# MDQA2016050 - Image 1

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1025 Dundee Court Chester, MD MLS# MDQA2016050 - Image 47

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1025 Dundee Court Chester, MD MLS# MDQA2016050 - Image 53

1 of 53

OPEN HOUSE: Saturday 6/20 8:00 AM - 10:00 AM

$324,900

Beds

2.1

Baths

1,400

Sq.Ft.

1025 Dundee Court

Chester, MD

Courtesy of RE/MAX EXECUTIVE

34-E Queen Anne Way Chester, MD MLS# MDQA2016464 - Image 1

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34-E Queen Anne Way Chester, MD MLS# MDQA2016464 - Image 52

Virtual Tour

1 of 52

$529,000

Beds

2.1

Baths

1,586

Sq.Ft.

34-E Queen Anne Way

Chester, MD

Courtesy of TAYLOR PROPERTIES

8-F Queen Victoria Way Chester, MD MLS# MDQA2016442 - Image 1

8-F Queen Victoria Way Chester, MD MLS# MDQA2016442 - Image 2

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8-F Queen Victoria Way Chester, MD MLS# MDQA2016442 - Image 29

8-F Queen Victoria Way Chester, MD MLS# MDQA2016442 - Image 30

Virtual Tour

1 of 30

$240,000

Beds

1.0

Baths

724

Sq.Ft.

8-F Queen Victoria Way

Chester, MD

Courtesy of LONG & FOSTER REAL ESTATE, INC.

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 1

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 2

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 3

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 4

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110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 51

110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358 - Image 52

Adult Community

1 of 52

$749,990

Beds

2.1

Baths

1,900

Sq.Ft.

110 Boatswain Way # 3042

Chester, MD

Courtesy of KOVO REALTY

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 1

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110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 51

110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360 - Image 52

Adult Community

1 of 52

$799,990

Beds

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Baths

1,900

Sq.Ft.

110 Boatswain Way # 3043

Chester, MD

Courtesy of KOVO REALTY

1868 Roberta Drive Chester, MD MLS# MDQA2016194 - Image 1

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1 of 42

$725,000

Beds

3.1

Baths

3,250

Sq.Ft.

1868 Roberta Drive

Chester, MD

Courtesy of COLDWELL BANKER REALTY

266 Peregrine Drive Chester, MD MLS# MDQA2016140 - Image 1

266 Peregrine Drive Chester, MD MLS# MDQA2016140 - Image 2

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266 Peregrine Drive Chester, MD MLS# MDQA2016140 - Image 73

Adult Community

1 of 73

$707,000

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3.0

Baths

2,870

Sq.Ft.

266 Peregrine Drive

Chester, MD

Courtesy of RE/MAX EXECUTIVE

110 Boatswain Way # 3033 Chester, MD MLS# MDQA2016094 - Image 1

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110 Boatswain Way # 3033 Chester, MD MLS# MDQA2016094 - Image 52

Adult Community

1 of 52

$699,990

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2.1

Baths

1,900

Sq.Ft.

110 Boatswain Way # 3033

Chester, MD

Courtesy of KOVO REALTY

110 Boatswain Way # 3032 Chester, MD MLS# MDQA2016096 - Image 1

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110 Boatswain Way # 3032 Chester, MD MLS# MDQA2016096 - Image 51

110 Boatswain Way # 3032 Chester, MD MLS# MDQA2016096 - Image 52

Adult Community

1 of 52

$689,990

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2.1

Baths

1,900

Sq.Ft.

110 Boatswain Way # 3032

Chester, MD

Courtesy of KOVO REALTY

110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078 - Image 1

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110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078 - Image 27

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110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078 - Image 29

110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078 - Image 30

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110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078 - Image 32

110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078 - Image 33

110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078 - Image 34

110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078 - Image 35

110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078 - Image 36

110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078 - Image 37

110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078 - Image 38

110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078 - Image 39

110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078 - Image 40

110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078 - Image 41

110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078 - Image 42

110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078 - Image 43

110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078 - Image 44

Adult Community

1 of 44

$749,990

Beds

2.1

Baths

2,602

Sq.Ft.

110 Boatswain Way # 3021

Chester, MD

Courtesy of KOVO REALTY

3-D Queen Victoria Court Chester, MD MLS# MDQA2016014 - Image 1

3-D Queen Victoria Court Chester, MD MLS# MDQA2016014 - Image 2

3-D Queen Victoria Court Chester, MD MLS# MDQA2016014 - Image 3

3-D Queen Victoria Court Chester, MD MLS# MDQA2016014 - Image 4

3-D Queen Victoria Court Chester, MD MLS# MDQA2016014 - Image 5

3-D Queen Victoria Court Chester, MD MLS# MDQA2016014 - Image 6

3-D Queen Victoria Court Chester, MD MLS# MDQA2016014 - Image 7

3-D Queen Victoria Court Chester, MD MLS# MDQA2016014 - Image 8

3-D Queen Victoria Court Chester, MD MLS# MDQA2016014 - Image 9

1 of 9

$269,000

Beds

1.0

Baths

724

Sq.Ft.

3-D Queen Victoria Court

Chester, MD

Courtesy of COLDWELL BANKER REALTY

176 Flagstaff Way # 2433 Chester, MD MLS# MDQA2015874 - Image 1

176 Flagstaff Way # 2433 Chester, MD MLS# MDQA2015874 - Image 2

176 Flagstaff Way # 2433 Chester, MD MLS# MDQA2015874 - Image 3

176 Flagstaff Way # 2433 Chester, MD MLS# MDQA2015874 - Image 4

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176 Flagstaff Way # 2433 Chester, MD MLS# MDQA2015874 - Image 27

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176 Flagstaff Way # 2433 Chester, MD MLS# MDQA2015874 - Image 37

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176 Flagstaff Way # 2433 Chester, MD MLS# MDQA2015874 - Image 39

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176 Flagstaff Way # 2433 Chester, MD MLS# MDQA2015874 - Image 41

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176 Flagstaff Way # 2433 Chester, MD MLS# MDQA2015874 - Image 50

176 Flagstaff Way # 2433 Chester, MD MLS# MDQA2015874 - Image 51

176 Flagstaff Way # 2433 Chester, MD MLS# MDQA2015874 - Image 52

Adult Community

1 of 52

$799,990

Beds

2.1

Baths

1,900

Sq.Ft.

176 Flagstaff Way # 2433

Chester, MD

Courtesy of KOVO 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

1906 Harbor Drive Chester, MD MLS# MDQA2015604 - Image 4

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1906 Harbor Drive Chester, MD MLS# MDQA2015604 - Image 41

1906 Harbor Drive Chester, MD MLS# MDQA2015604 - Image 42

1906 Harbor Drive Chester, MD MLS# MDQA2015604 - Image 43

1906 Harbor Drive Chester, MD MLS# MDQA2015604 - Image 44

1 of 44

$449,900

Beds

2.0

Baths

1,750

Sq.Ft.

1906 Harbor Drive

Chester, MD

Courtesy of FIVE STAR REAL ESTATE

176 Flagstaff Way # 2411 Chester, MD MLS# MDQA2015804 - Image 1

176 Flagstaff Way # 2411 Chester, MD MLS# MDQA2015804 - Image 2

176 Flagstaff Way # 2411 Chester, MD MLS# MDQA2015804 - Image 3

176 Flagstaff Way # 2411 Chester, MD MLS# MDQA2015804 - Image 4

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176 Flagstaff Way # 2411 Chester, MD MLS# MDQA2015804 - Image 63

Adult Community

1 of 63

$599,990

Beds

2.1

Baths

2,003

Sq.Ft.

176 Flagstaff Way # 2411

Chester, MD

Courtesy of KOVO REALTY

176 Flagstaff Way # 2412 Chester, MD MLS# MDQA2015806 - Image 1

176 Flagstaff Way # 2412 Chester, MD MLS# MDQA2015806 - Image 2

176 Flagstaff Way # 2412 Chester, MD MLS# MDQA2015806 - Image 3

176 Flagstaff Way # 2412 Chester, MD MLS# MDQA2015806 - Image 4

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176 Flagstaff Way # 2412 Chester, MD MLS# MDQA2015806 - Image 16

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176 Flagstaff Way # 2412 Chester, MD MLS# MDQA2015806 - Image 63

Adult Community

1 of 63

$659,990

Beds

2.1

Baths

2,003

Sq.Ft.

176 Flagstaff Way # 2412

Chester, MD

Courtesy of KOVO REALTY

4000 Herons Nest Way # 22 Chester, MD MLS# MDQA2015800 - Image 1

4000 Herons Nest Way # 22 Chester, MD MLS# MDQA2015800 - Image 2

4000 Herons Nest Way # 22 Chester, MD MLS# MDQA2015800 - Image 3

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4000 Herons Nest Way # 22 Chester, MD MLS# MDQA2015800 - Image 17

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4000 Herons Nest Way # 22 Chester, MD MLS# MDQA2015800 - Image 69

4000 Herons Nest Way # 22 Chester, MD MLS# MDQA2015800 - Image 70

Adult Community with Virtual Tour

1 of 70

$560,000

Beds

2.1

Baths

1,900

Sq.Ft.

4000 Herons Nest Way # 22

Chester, MD

Courtesy of RE/MAX LEADING EDGE

About Chester

Listings in Chester, MD: 106
Estimated median home price: $679,500

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	5
$300K - 400K	11
$400K - 500K	11
$500K - 600K	15
$600K - 700K	13
$700K - 800K	15
$800K - 900K	9
$900K - 1M	11
$1M - Max	13

Homes for Sale by Type in Chester, MD

Property Type	Count
Single Family	49
Townhouse	3
Condo	51
Commercial	0
Rental	13
Lots and Land	3
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 6/19/2026)

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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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