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Chester, MD Homes for Sale | Realty.com
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70 listings
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Homes for Sale in Chester, MD

Homes for Sale in Chester, MD

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24 of 70 Listings
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Homes for Sale in Chester, MD

24 of 70 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 406 Dominion Rd — photo3Active

    $199,900

    3 bd · 2 ba · 1,080 sqft

    406 Dominion Rd, Chester, MD

    Daniel J. Demers · Sell Your Home Services

  2. 1905-1907 Keister Dr — photo17Active

    $280,000

    3 bd · 1 ba · 0 sqft

    1905-1907 Keister Dr, Chester, MD

    Gregory A Bennett Jr. · Five Star Real Estate

  3. 2627 Cecil Dr — photo45Active

    $699,000

    3 bd · 2 ba · 1,584 sqft

    2627 Cecil Dr, Chester, MD

    Linda L Austin · Long & Foster Real Estate, Inc.

  4. 1837 Harbor — photo33Active

    $396,900

    3 bd · 2 ba · 1,116 sqft

    1837 Harbor, Chester, MD

    Norma L Coursey · Benson & Mangold, LLC

  5. 227 Gibson Cir — photo50Active

    $559,900

    3 bd · 3 ba · 2,062 sqft

    227 Gibson Cir, Chester, MD

    Pamela Doll · RE/MAX Executive

  6. 107 Widgeon Way — photo30Active

    $349,900

    3 bd · 3 ba · 1,899 sqft

    107 Widgeon Way, Chester, MD

    Carol L Tinnin · RE/MAX Leading Edge

  7. 101 Bufflehead Ct — photo26Active

    $275,000

    2 bd · 2 ba · 1,069 sqft

    101 Bufflehead Ct, Chester, MD

    Kevin McDermott · The KW Collective

  8. 2703 Sherman Dr — photo42Active

    $699,000

    3 bd · 3 ba · 1,560 sqft

    2703 Sherman Dr, Chester, MD

    Tammy D Rosendale · Rosendale Realty

  9. 1-F Queen Victoria Ct — photo26Active

    $400,000

    2 bd · 2 ba · 1,260 sqft

    1-F Queen Victoria Ct, Chester, MD

    Doris Williams · Douglas Realty LLC

  10. 100 Schooner Way — photo42Active

    $545,000

    3 bd · 3 ba · 2,100 sqft

    100 Schooner Way, Chester, MD

    Lauren Matera · LPT Realty, LLC

  11. 107 Lee Rd — photoPrice Reduced20Active

    $308,000

    3 bd · 1 ba · 960 sqft

    107 Lee Rd, Chester, MD

    Verria Hairston · Open Door Brokerage, LLC

  12. 830 Warbler Way #2843 — photo47Active

    $789,990

    2 bd · 3 ba · 1,900 sqft

    830 Warbler Way #2843, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  13. 1509 Calvert Rd — photo53Active

    $1,350,000

    4 bd · 3 ba · 3,680 sqft

    1509 Calvert Rd, Chester, MD

    Jimmy J White Jr. · Long & Foster Real Estate, Inc.

  14. 205 Dominion Ln — photo22Active

    $300,000

    3 bd · 2 ba · 1,160 sqft

    205 Dominion Ln, Chester, MD

    Jonathan C Nicholls · EXP Realty, LLC

  15. 8-E Piney Narrows Rd — photo16Active

    $40,000

    0 bd · 0 ba · 830 sqft

    8-E Piney Narrows Rd, Chester, MD

    Kaitlyn C Collins · Benson & Mangold, LLC

  16. 168 Redstart Dr — photoPrice Reduced50Active

    $749,900

    2 bd · 3 ba · 2,014 sqft

    168 Redstart Dr, Chester, MD

    Carol L Tinnin · RE/MAX Leading Edge

  17. 111 Marshgrass Way #43 — photo36Active

    $744,900

    2 bd · 3 ba · 1,900 sqft

    111 Marshgrass Way #43, Chester, MD

    Jimmy J White Jr. · Long & Foster Real Estate, Inc.

  18. 231 Dominion Rd — photo44Active

    $599,000

    5 bd · 3 ba · 1,852 sqft

    231 Dominion Rd, Chester, MD

    Dane P Ways · Long & Foster Real Estate, Inc.

  19. 129 Wheelhouse Way #21 — photo60Active

    $1,399,000

    3 bd · 3 ba · 2,601 sqft

    129 Wheelhouse Way #21, Chester, MD

    Christina L Eury · Rise Real Estate, LLC

  20. 630 Warbler Way #12 — photo44Active

    $549,950

    2 bd · 3 ba · 2,000 sqft

    630 Warbler Way #12, Chester, MD

    Ralph S. Kennedy · RE/MAX Executive

  21. 114 Kinglet Ct — photo25Active

    $999,990

    3 bd · 3 ba · 2,772 sqft

    114 Kinglet Ct, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  22. 7-B Queen Victoria Way #B — photo39Active

    $499,000

    2 bd · 3 ba · 1,680 sqft

    7-B Queen Victoria Way #B, Chester, MD

    Christina Sousa · RE/MAX Allegiance

  23. 118 Kinglet Ct — photo25Active

    $969,990

    2 bd · 3 ba · 2,010 sqft

    118 Kinglet Ct, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  24. 162 Kirwans Landing Ln — photoPrice Reduced64Active

    $1,160,000

    5 bd · 3 ba · 3,000 sqft

    162 Kirwans Landing Ln, Chester, MD

    Jessica DuLaney · Next Step Realty

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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. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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Listing data & MLS disclosures

Bright MLS
The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Realty.com participates, and is provided by BRIGHT through a licensing agreement. 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 Closed or are no longer being offered for sale.
Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-11-01 13:34:03 UTC
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #01-6355

    Call Thomas

    Nearby areas

    ZIP codes

    • 21223 (308)
    • 21224 (288)
    • 21230 (265)
    • 21217 (220)
    • 21213 (173)
    • 21216 (164)
    • 21401 (136)
    • 21222 (135)

    Cities

    • Baltimore (2,156)
    • Annapolis (304)
    • Glen Burnie (174)
    • Easton (128)
    • Pasadena (121)
    • Stevensville (86)
    • Chestertown (61)
    • Dundalk (61)

    Chester, MD community profile

    Area
    22.5 sq. mi.

    Source: HJN community data

    Chester housing market

    October 2026 · This period is still settling

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 14 sales · as of Oct 30, 2026

    Homes on the market · MLS, as of Oct 25, 2026–Oct 30, 2026

    Median list price
    $545,000
    Homes for sale
    57
    Median days on market
    33 days

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

    Median home size
    1,728 sq. ft.