View 176 Flagstaff Way # 2424 Chester, MD MLS# MDQA2015838
$935,990
3

Beds

2.1

Baths

2,602

Sq.Ft.

176 Flagstaff Way # 2424

Chester, MD

Bright
Courtesy of KOVO REALTY
View 311 Kingfisher Lane Chester, MD MLS# MDQA2015840
  • Adult Community
1 of 40
$899,990
5

Beds

4.1

Baths

3,225

Sq.Ft.

311 Kingfisher Lane

Chester, MD

Bright
Courtesy of KOVO REALTY
View 110 Kinglet Court Chester, MD MLS# MDQA2015794
  • Adult Community
1 of 40
$889,990
5

Beds

4.1

Baths

3,225

Sq.Ft.

110 Kinglet Court

Chester, MD

Bright
Courtesy of KOVO REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 719 Warbler Way Chester, MD MLS# MDQA2016506
  • Adult Community
1 of 38
$889,990
4

Beds

3.0

Baths

2,791

Sq.Ft.

719 Warbler Way

Chester, MD

Bright
Courtesy of KOVO REALTY
View 102 Boatswain Way # 2921 Chester, MD MLS# MDQA2016674
$889,990
3

Beds

2.1

Baths

2,602

Sq.Ft.

102 Boatswain Way # 2921

Chester, MD

Bright
Courtesy of KOVO REALTY
View 110 Boatswain Way # 3031 Chester, MD MLS# MDQA2016080
$849,990
3

Beds

2.1

Baths

2,602

Sq.Ft.

110 Boatswain Way # 3031

Chester, MD

Bright
Courtesy of KOVO REALTY
View 102 Boatswain Way # 2933 Chester, MD MLS# MDQA2016914
$849,990
2

Beds

2.1

Baths

1,900

Sq.Ft.

102 Boatswain Way # 2933

Chester, MD

Bright
Courtesy of KOVO REALTY
View 255 Redstart Drive Chester, MD MLS# MDQA2016024
  • Adult Community
1 of 37
$829,990
4

Beds

3.0

Baths

2,791

Sq.Ft.

255 Redstart Drive

Chester, MD

Bright
Courtesy of KOVO REALTY
View 176 Flagstaff Way # 2433 Chester, MD MLS# MDQA2015874
$799,990
2

Beds

2.1

Baths

1,900

Sq.Ft.

176 Flagstaff Way # 2433

Chester, MD

Bright
Courtesy of KOVO REALTY
View 259 Redstart Drive Chester, MD MLS# MDQA2015878
  • Adult Community
1 of 37
$799,990
4

Beds

3.0

Baths

2,791

Sq.Ft.

259 Redstart Drive

Chester, MD

Bright
Courtesy of KOVO REALTY
View 110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358
$799,990
2

Beds

2.1

Baths

1,900

Sq.Ft.

110 Boatswain Way # 3042

Chester, MD

Bright
Courtesy of KOVO REALTY
View 110 Boatswain Way # 3043 Chester, MD MLS# MDQA2016360
$799,990
2

Beds

2.1

Baths

1,900

Sq.Ft.

110 Boatswain Way # 3043

Chester, MD

Bright
Courtesy of KOVO REALTY
View 132 Wheelhouse Way # 11 Chester, MD MLS# MDQA2016856
  • Recently Listed with Virtual Tour
1 of 75
$799,900
2

Beds

2.1

Baths

2,003

Sq.Ft.

132 Wheelhouse Way # 11

Chester, MD

Bright
Courtesy of REAL BROKER, LLC
View 528 Warbler Way Chester, MD MLS# MDQA2015904
  • Adult Community with Virtual Tour
1 of 29
$799,500
4

Beds

3.0

Baths

2,791

Sq.Ft.

528 Warbler Way

Chester, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View 1604 Midway Road Chester, MD MLS# MDQA2016844
  • Recently Listed
1 of 73
$795,000
4

Beds

3.0

Baths

2,972

Sq.Ft.

1604 Midway Road

Chester, MD

Bright
Courtesy of WILSON REALTY & STAGING LLC
View 539 Warbler Way Chester, MD MLS# MDQA2016406
  • Adult Community
1 of 59
$789,990
3

Beds

3.0

Baths

2,789

Sq.Ft.

539 Warbler Way

Chester, MD

Bright
Courtesy of KOVO REALTY
View 169 Harrier Way Chester, MD MLS# MDQA2016630
  • Adult Community
1 of 89
$779,900
3

Beds

2.0

Baths

2,394

Sq.Ft.

169 Harrier Way

Chester, MD

Bright
Courtesy of CENTURY 21 REDWOOD REALTY
View 111 Marshgrass Way # 43 Chester, MD MLS# MDQA2016724
$765,000
2

Beds

2.1

Baths

111 Marshgrass Way # 43

Chester, MD

Bright
Courtesy of COLDWELL BANKER REALTY
View 129 Sailcloth Way Chester, MD MLS# MDQA2016176
  • Adult Community
1 of 54
$764,900
3

Beds

2.0

Baths

2,303

Sq.Ft.

129 Sailcloth Way

Chester, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View 2000 Herons Nest Way # 401 Chester, MD MLS# MDQA2016336
  • Adult Community with Virtual Tour
1 of 113
$750,000
3

Beds

2.1

Baths

2,602

Sq.Ft.

2000 Herons Nest Way # 401

Chester, MD

Bright
Courtesy of REAL BROKER, LLC

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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