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 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 111 Marshgrass Way # 22 Chester, MD MLS# MDQA2016122
  • Adult Community
1 of 102
$529,900
2

Beds

2.1

Baths

1,900

Sq.Ft.

111 Marshgrass Way # 22

Chester, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
The time to sell is now! THE TIME TO SELL IS NOW!
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 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 3 Queen Victoria Court Chester, MD MLS# MDQA2016014
$269,000
1

Beds

1.0

Baths

724

Sq.Ft.

3 Queen Victoria Court

Chester, MD

Bright
Courtesy of COLDWELL BANKER REALTY
View 1363 Calvert Road Chester, MD MLS# MDQA2015954
  • Virtual Tour
1 of 35
$501,200
3

Beds

2.0

Baths

1,400

Sq.Ft.

1363 Calvert Road

Chester, MD

Bright
Courtesy of REVOL REAL ESTATE, LLC
View 204 Ringneck Court Chester, MD MLS# MDQA2015908
$324,900
3

Beds

3.1

Baths

1,747

Sq.Ft.

204 Ringneck Court

Chester, MD

Bright
Courtesy of CUMMINGS & CO. REALTORS
View 1906 Harbor Drive Chester, MD MLS# MDQA2015604
$474,900
4

Beds

2.0

Baths

1,750

Sq.Ft.

1906 Harbor Drive

Chester, MD

Bright
Courtesy of FIVE STAR REAL ESTATE
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 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 4000 Herons Nest Way # 22 Chester, MD MLS# MDQA2015800
  • Adult Community with Virtual Tour
1 of 70
$560,000
2

Beds

2.1

Baths

1,900

Sq.Ft.

4000 Herons Nest Way # 22

Chester, MD

Bright
Courtesy of RE/MAX LEADING EDGE
View 54 Queen Caroline Court Chester, MD MLS# MDQA2015236
    1 of 40
    OPEN HOUSE: Sunday 5/3 11:30 AM - 1:30 PM
    $339,000
    2

    Beds

    2.1

    Baths

    1,280

    Sq.Ft.

    54 Queen Caroline Court

    Chester, MD

    Bright
    Courtesy of LONG & FOSTER REAL ESTATE, INC.
    View Newtown Road Chester, MD MLS# MDQA2015734
    $230,000
    Studio

    Beds

    0.0

    Baths

    Newtown Road

    Chester, MD

    Bright
    Courtesy of DOUGLAS REALTY LLC
    View 807 Auckland Way Chester, MD MLS# MDQA2015692
      1 of 47
      OPEN HOUSE: Sunday 5/3 12:00 PM - 2:00 PM
      $425,000
      3

      Beds

      3.1

      Baths

      2,100

      Sq.Ft.

      807 Auckland Way

      Chester, MD

      Bright
      Courtesy of REAL BROKER, LLC
      View 1916 Stevens Drive Chester, MD MLS# MDQA2015554
        1 of 41
        OPEN HOUSE: Sunday 5/3 12:00 PM - 2:00 PM
        $475,000
        3

        Beds

        2.1

        Baths

        1,728

        Sq.Ft.

        1916 Stevens Drive

        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
        $539,000
        2

        Beds

        2.1

        Baths

        2,003

        Sq.Ft.

        3000 Herons Nest Way # 11

        Chester, MD

        Bright
        Courtesy of COLDWELL BANKER REALTY

        About Chester

        Listings in Chester, MD

        111

        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 - 500K13
        $500K - 600K16
        $600K - 700K14
        $700K - 800K18
        $800K - 900K7
        $900K - 1M11
        $1M - Max11

        Homes for Sale by Type in Chester, MD

        Property TypeCount
        Single Family49
        Townhouse1
        Condo57
        Commercial0
        Rental12
        Lots and Land4
        Condo/Town/CoOp0
        CoOp0
        Multi Family0
        Mobile Home0
        Farms0

        (Data as of 5/2/2026)

        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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