View 102 Boatswain Way # 2933 Chester, MD MLS# MDQA2016914
$829,990
2

Beds

2.1

Baths

1,900

Sq.Ft.

102 Boatswain Way # 2933

Chester, MD

Bright
Courtesy of KOVO REALTY
View 135 Nauset Lane Chester, MD MLS# MDQA2015026
  • Adult Community with Virtual Tour
1 of 81
$799,999
3

Beds

3.0

Baths

2,795

Sq.Ft.

135 Nauset Lane

Chester, MD

Bright
Courtesy of REAL BROKER, LLC - ANNAPOLIS
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
The time to sell is now! THE TIME TO SELL IS NOW!
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 723 Warbler Way Chester, MD MLS# MDQA2017706
  • Recently Listed
1 of 38
$799,990
4

Beds

3.0

Baths

2,791

Sq.Ft.

723 Warbler Way

Chester, MD

Bright
Courtesy of KOVO REALTY
View 134 Richard Ingle Way Chester, MD MLS# MDQA2017486
  • Recently Listed
1 of 66
$780,000
4

Beds

3.1

Baths

2,185

Sq.Ft.

134 Richard Ingle Way

Chester, MD

Bright
Courtesy of KELLER WILLIAMS REALTY CENTRAL-DELAWARE
View 126 Claiborne Street Chester, MD MLS# MDQA2017106
    1 of 44
    OPEN HOUSE: Saturday 6/20 10:00 AM - 12:00 PM
    $775,000
    3

    Beds

    2.1

    Baths

    2,276

    Sq.Ft.

    126 Claiborne Street

    Chester, MD

    Bright
    Courtesy of SAMSON PROPERTIES
    View 711 Warbler Way Chester, MD MLS# MDQA2017038
    • Adult Community
    1 of 38
    $769,990
    4

    Beds

    3.0

    Baths

    2,791

    Sq.Ft.

    711 Warbler Way

    Chester, MD

    Bright
    Courtesy of KOVO 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 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 110 Boatswain Way # 3042 Chester, MD MLS# MDQA2016358
    $749,990
    2

    Beds

    2.1

    Baths

    1,900

    Sq.Ft.

    110 Boatswain Way # 3042

    Chester, MD

    Bright
    Courtesy of KOVO REALTY
    View 212 Switchgrass Way # 34 Chester, MD MLS# MDQA2017250
    • Adult Community
    1 of 40
    OPEN HOUSE: Saturday 6/20 12:00 PM - 4:00 PM
    $749,950
    3

    Beds

    2.1

    Baths

    212 Switchgrass Way # 34

    Chester, MD

    Bright
    Courtesy of RE/MAX EXECUTIVE
    View 630 Warbler Way # 2224 Chester, MD MLS# MDQA2014898
    $739,990
    2

    Beds

    2.1

    Baths

    2,602

    Sq.Ft.

    630 Warbler Way # 2224

    Chester, MD

    Bright
    Courtesy of KOVO REALTY
    View 132 Wheelhouse Way # 11 Chester, MD MLS# MDQA2017364
    • Adult Community with Virtual Tour
    1 of 29
    $729,999
    2

    Beds

    2.1

    Baths

    2,003

    Sq.Ft.

    132 Wheelhouse Way # 11

    Chester, MD

    Bright
    Courtesy of REAL BROKER, LLC
    View 1868 Roberta Drive Chester, MD MLS# MDQA2016194
    $725,000
    5

    Beds

    3.1

    Baths

    3,250

    Sq.Ft.

    1868 Roberta Drive

    Chester, MD

    Bright
    Courtesy of COLDWELL BANKER REALTY
    View 266 Peregrine Drive Chester, MD MLS# MDQA2016140
    • Adult Community
    1 of 73
    $707,000
    4

    Beds

    3.0

    Baths

    2,870

    Sq.Ft.

    266 Peregrine Drive

    Chester, MD

    Bright
    Courtesy of RE/MAX EXECUTIVE
    View 2000 Herons Nest Way # 401 Chester, MD MLS# MDQA2017542
    • Recently Listed with Virtual Tour
    1 of 36
    OPEN HOUSE: Sunday 6/21 1:00 PM - 3:00 PM
    $700,000
    3

    Beds

    2.1

    Baths

    2,602

    Sq.Ft.

    2000 Herons Nest Way # 401

    Chester, MD

    Bright
    Courtesy of REAL BROKER, LLC
    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 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 110 Boatswain Way # 3032 Chester, MD MLS# MDQA2016096
    $689,990
    2

    Beds

    2.1

    Baths

    1,900

    Sq.Ft.

    110 Boatswain Way # 3032

    Chester, MD

    Bright
    Courtesy of KOVO REALTY

    About Chester

    Listings in Chester, MD

    106

    Estimated median home price

    $679,500
    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 - 300K5
    $300K - 400K11
    $400K - 500K11
    $500K - 600K15
    $600K - 700K13
    $700K - 800K15
    $800K - 900K9
    $900K - 1M11
    $1M - Max13

    Homes for Sale by Type in Chester, MD

    Property TypeCount
    Single Family49
    Townhouse3
    Condo51
    Commercial0
    Rental13
    Lots and Land3
    Condo/Town/CoOp0
    CoOp0
    Multi Family0
    Mobile Home0
    Farms0

    (Data as of 6/19/2026)

    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.

    © 2026 BrightMLS. All Rights Reserved.