View 1704 Bayside Drive Chester, MD MLS# MDQA2015660
$1,100,000
3

Beds

2.1

Baths

1,830

Sq.Ft.

1704 Bayside Drive

Chester, MD

Bright
Courtesy of COTTAGE STREET REALTY LLC
View 127 Flycatcher Way Chester, MD MLS# MDQA2015632
  • Adult Community
1 of 49
$1,100,000
2

Beds

2.0

Baths

1,993

Sq.Ft.

127 Flycatcher Way

Chester, MD

Bright
Courtesy of KOVO REALTY
View 123 Flycatcher Way Chester, MD MLS# MDQA2015634
  • Adult Community
1 of 47
$1,300,000
3

Beds

3.0

Baths

2,789

Sq.Ft.

123 Flycatcher Way

Chester, MD

Bright
Courtesy of KOVO REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 117 Flycatcher Way Chester, MD MLS# MDQA2015636
  • Adult Community
1 of 49
$1,400,000
3

Beds

3.1

Baths

2,930

Sq.Ft.

117 Flycatcher Way

Chester, MD

Bright
Courtesy of KOVO REALTY
View 111 Flycatcher Way Chester, MD MLS# MDQA2015638
  • Adult Community
1 of 48
$1,400,000
5

Beds

4.1

Baths

3,225

Sq.Ft.

111 Flycatcher Way

Chester, MD

Bright
Courtesy of KOVO REALTY
View 1916 Stevens Drive Chester, MD MLS# MDQA2015554
$489,000
3

Beds

2.0

Baths

1,728

Sq.Ft.

1916 Stevens Drive

Chester, MD

Bright
Courtesy of COLDWELL BANKER REALTY
View 203 Riverside Drive Chester, MD MLS# MDQA2014798
  • New Construction
1 of 68
$1,099,900
5

Beds

3.1

Baths

3,036

Sq.Ft.

203 Riverside Drive

Chester, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 112 Chessie Court Chester, MD MLS# MDQA2015532
$519,900
3

Beds

2.1

Baths

2,066

Sq.Ft.

112 Chessie Court

Chester, MD

Bright
Courtesy of CHANEY HOMES, LLC
View Harbor Drive Chester, MD MLS# MDQA2015496
  • New Construction
1 of 12
$519,900
Studio

Beds

0.0

Baths

1,250

Sq.Ft.

Harbor Drive

Chester, MD

Bright
Courtesy of COLDWELL BANKER WATERMAN 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 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 3000 Herons Nest Way # 11 Chester, MD MLS# MDQA2015222
  • Adult Community with Virtual Tour
1 of 66
$555,800
2

Beds

2.1

Baths

2,003

Sq.Ft.

3000 Herons Nest Way # 11

Chester, MD

Bright
Courtesy of COLDWELL BANKER REALTY
View 132 Wheelhouse Way Chester, MD MLS# MDQA2015138
  • Adult Community
1 of 68
$1,249,990
2

Beds

2.1

Baths

1,900

Sq.Ft.

132 Wheelhouse Way

Chester, MD

Bright
Courtesy of KOVO REALTY
View 1870 Harbor Drive Chester, MD MLS# MDQA2015064
  • Virtual Tour
1 of 34
$320,000
2

Beds

1.0

Baths

832

Sq.Ft.

1870 Harbor Drive

Chester, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View 135 Nauset Lane Chester, MD MLS# MDQA2015026
  • Adult Community with Virtual Tour
1 of 81
$814,900
3

Beds

3.0

Baths

2,795

Sq.Ft.

135 Nauset Lane

Chester, MD

Bright
Courtesy of REAL BROKER, LLC - ANNAPOLIS
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 630 Warbler Way # 2223 Chester, MD MLS# MDQA2014900
$574,900
2

Beds

2.1

Baths

1,900

Sq.Ft.

630 Warbler Way # 2223

Chester, MD

Bright
Courtesy of KOVO REALTY
View 141 Switchgrass Way # 34 Chester, MD MLS# MDQA2014868
  • Adult Community with Virtual Tour
1 of 61
$684,950
3

Beds

2.1

Baths

2,600

Sq.Ft.

141 Switchgrass Way # 34

Chester, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View 635 Dominion Road Chester, MD MLS# MDQA2014836
  • Virtual Tour
1 of 50
$895,000
3

Beds

3.2

Baths

2,818

Sq.Ft.

635 Dominion Road

Chester, MD

Bright
Courtesy of COLDWELL BANKER REALTY

About Chester

Listings in Chester, MD

99

Estimated median home price

$644,990
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 - 300K7
$300K - 400K10
$400K - 500K16
$500K - 600K14
$600K - 700K9
$700K - 800K12
$800K - 900K11
$900K - 1M7
$1M - Max11

Homes for Sale by Type in Chester, MD

Property TypeCount
Single Family45
Townhouse1
Condo50
Commercial0
Rental10
Lots and Land3
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 3/16/2026)

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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