View 110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078
$749,990
3

Beds

2.1

Baths

2,602

Sq.Ft.

110 Boatswain Way # 3021

Chester, MD

Bright
Courtesy of KOVO REALTY
View 1868 Roberta Drive Chester, MD MLS# MDQA2016194
$749,500
5

Beds

3.1

Baths

3,250

Sq.Ft.

1868 Roberta Drive

Chester, MD

Bright
Courtesy of COLDWELL BANKER REALTY
View 630 Warbler Way # 2221 Chester, MD MLS# MDQA2014800
$724,900
2

Beds

2.1

Baths

2,602

Sq.Ft.

630 Warbler Way # 2221

Chester, MD

Bright
Courtesy of KOVO REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 266 Peregrine Drive Chester, MD MLS# MDQA2016140
  • Adult Community
1 of 73
$720,000
4

Beds

3.0

Baths

2,870

Sq.Ft.

266 Peregrine Drive

Chester, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View 630 Warbler Way # 2224 Chester, MD MLS# MDQA2014898
$714,990
2

Beds

2.1

Baths

2,602

Sq.Ft.

630 Warbler Way # 2224

Chester, MD

Bright
Courtesy of KOVO REALTY
View 110 Boatswain Way # 3033 Chester, MD MLS# MDQA2016094
$699,990
2

Beds

2.1

Baths

1,900

Sq.Ft.

110 Boatswain Way # 3033

Chester, MD

Bright
Courtesy of KOVO REALTY
View 110 Boatswain Way # 3032 Chester, MD MLS# MDQA2016096
$699,990
2

Beds

2.1

Baths

1,900

Sq.Ft.

110 Boatswain Way # 3032

Chester, MD

Bright
Courtesy of KOVO REALTY
View 1715 Little Creek Road Chester, MD MLS# MDQA2008168
$698,900
2

Beds

2.0

Baths

1,726

Sq.Ft.

1715 Little Creek Road

Chester, MD

Bright
Courtesy of BEAM REALTY GROUP, INC.
View 111 Marshgrass Way # 21 Chester, MD MLS# MDQA2016714
$680,000
3

Beds

2.1

Baths

2,602

Sq.Ft.

111 Marshgrass Way # 21

Chester, MD

Bright
Courtesy of SAMSON PROPERTIES
View 249 Warbler Way Chester, MD MLS# MDQA2016488
  • Adult Community
1 of 68
$679,000
2

Beds

2.0

Baths

2,025

Sq.Ft.

249 Warbler Way

Chester, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View 230 Switchgrass Way # 21 Chester, MD MLS# MDQA2016166
  • Adult Community with Virtual Tour
1 of 106
$675,000
3

Beds

2.1

Baths

2,602

Sq.Ft.

230 Switchgrass Way # 21

Chester, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View Lot 6 Norman Court Chester, MD MLS# MDQA2008126
  • New Construction
1 of 26
$674,900
4

Beds

2.1

Baths

Lot 6 Norman Court

Chester, MD

Bright
Courtesy of KELLER WILLIAMS FLAGSHIP
View 176 Flagstaff Way # 2412 Chester, MD MLS# MDQA2015806
$659,990
2

Beds

2.1

Baths

2,003

Sq.Ft.

176 Flagstaff Way # 2412

Chester, MD

Bright
Courtesy of KOVO REALTY
View 102 Boatswain Way # 2911 Chester, MD MLS# MDQA2016668
$649,990
2

Beds

2.1

Baths

2,003

Sq.Ft.

102 Boatswain Way # 2911

Chester, MD

Bright
Courtesy of KOVO REALTY
View 102 Boatswain Way # 2912 Chester, MD MLS# MDQA2016670
$649,990
2

Beds

2.1

Baths

2,003

Sq.Ft.

102 Boatswain Way # 2912

Chester, MD

Bright
Courtesy of KOVO REALTY
View 200 Harrier Way # 21 Chester, MD MLS# MDQA2014528
  • Adult Community
1 of 44
$649,900
3

Beds

2.1

Baths

2,600

Sq.Ft.

200 Harrier Way # 21

Chester, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 630 Warbler Way # 2232 Chester, MD MLS# MDQA2015436
$644,990
2

Beds

2.1

Baths

1,900

Sq.Ft.

630 Warbler Way # 2232

Chester, MD

Bright
Courtesy of KOVO REALTY
View 630 Warbler Way # 2233 Chester, MD MLS# MDQA2015438
$644,990
2

Beds

2.1

Baths

1,900

Sq.Ft.

630 Warbler Way # 2233

Chester, MD

Bright
Courtesy of KOVO REALTY
View 176 Flagstaff Way # 2411 Chester, MD MLS# MDQA2015804
$599,990
2

Beds

2.1

Baths

2,003

Sq.Ft.

176 Flagstaff Way # 2411

Chester, MD

Bright
Courtesy of KOVO REALTY
View 1000 Herons Nest Way # 402 Chester, MD MLS# MDQA2016710
$599,000
2

Beds

2.1

Baths

1,900

Sq.Ft.

1000 Herons Nest Way # 402

Chester, MD

Bright
Courtesy of RE/MAX UNITED REAL ESTATE

About Chester

Listings in Chester, MD

107

Estimated median home price

$649,990
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

PriceCount
$0 - 100K2
$100K - 200K1
$200K - 300K8
$300K - 400K10
$400K - 500K12
$500K - 600K16
$600K - 700K13
$700K - 800K17
$800K - 900K7
$900K - 1M10
$1M - Max11

Homes for Sale by Type in Chester, MD

Property TypeCount
Single Family45
Townhouse0
Condo58
Commercial0
Rental15
Lots and Land4
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 4/20/2026)

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 ReciprocitySM 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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