View 141 Redstart Drive Chester, MD MLS# MDQA2015792
  • Adult Community
1 of 54
$899,990
3

Beds

3.0

Baths

2,789

Sq.Ft.

141 Redstart Drive

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
View 110 Boatswain Way # 3031 Chester, MD MLS# MDQA2016080
$889,990
3

Beds

2.1

Baths

2,602

Sq.Ft.

110 Boatswain Way # 3031

Chester, MD

Bright
Courtesy of KOVO REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358
$859,990
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
$859,990
2

Beds

2.1

Baths

1,900

Sq.Ft.

110 Boatswain Way # 3043

Chester, MD

Bright
Courtesy of KOVO REALTY
View 176 Flagstaff Way # 2433 Chester, MD MLS# MDQA2015874
$829,990
2

Beds

2.1

Baths

1,900

Sq.Ft.

176 Flagstaff Way # 2433

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 539 Warbler Way Chester, MD MLS# MDQA2016406
  • Recently Listed
1 of 59
$829,990
3

Beds

3.0

Baths

2,789

Sq.Ft.

539 Warbler Way

Chester, MD

Bright
Courtesy of KOVO REALTY
View 202 Mchenny Court Chester, MD MLS# MDQA2015440
  • Virtual Tour
1 of 63
$825,000
3

Beds

2.1

Baths

2,520

Sq.Ft.

202 Mchenny Court

Chester, MD

Bright
Courtesy of COLDWELL BANKER REALTY
View 135 Nauset Lane Chester, MD MLS# MDQA2015026
  • Adult Community with Virtual Tour
1 of 81
$814,900
3

Beds

3.0

Baths

2,399

Sq.Ft.

135 Nauset Lane

Chester, MD

Bright
Courtesy of REAL BROKER, LLC - ANNAPOLIS
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 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 110 Boatswain Way # 3021 Chester, MD MLS# MDQA2016078
$789,990
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
  • Recently Listed
1 of 42
$769,500
5

Beds

3.1

Baths

3,250

Sq.Ft.

1868 Roberta Drive

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 110 Boatswain Way # 3033 Chester, MD MLS# MDQA2016094
$759,990
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
$759,990
2

Beds

2.1

Baths

1,900

Sq.Ft.

110 Boatswain Way # 3032

Chester, MD

Bright
Courtesy of KOVO REALTY
View 266 Peregrine Drive Chester, MD MLS# MDQA2016140
  • Adult Community
1 of 70
$750,000
4

Beds

3.0

Baths

2,870

Sq.Ft.

266 Peregrine Drive

Chester, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View 113 Kirwans Landing Lane Chester, MD MLS# MDQA2016316
$750,000
4

Beds

3.0

Baths

2,140

Sq.Ft.

113 Kirwans Landing Lane

Chester, MD

Bright
Courtesy of CUMMINGS & CO. REALTORS
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

About Chester

Listings in Chester, MD

95

Estimated median home price

$599,990
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 - 200K0
$200K - 300K6
$300K - 400K10
$400K - 500K16
$500K - 600K14
$600K - 700K9
$700K - 800K11
$800K - 900K10
$900K - 1M6
$1M - Max11

Homes for Sale by Type in Chester, MD

Property TypeCount
Single Family43
Townhouse1
Condo48
Commercial0
Rental10
Lots and Land3
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 3/11/2026)

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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