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Homes Under $500K in Chester, MD
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28 listings
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Homes Under $500K in Chester, MD

Homes Under $500K in Chester, MD

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24 of 28 Listings
Map

Homes Under $500K in Chester, MD

24 of 28 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 406 Dominion Rd — photoNew3Active

    $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 — photoNew17Active

    $280,000

    3 bd · 1 ba · 0 sqft

    1905-1907 Keister Dr, Chester, MD

    Gregory A Bennett Jr. · Five Star Real Estate

  3. 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

  4. 101 Bufflehead Ct — photo26Active

    $275,000

    2 bd · 2 ba · 1,069 sqft

    101 Bufflehead Ct, Chester, MD

    Kevin McDermott · The KW Collective

  5. 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

  6. 107 Lee Rd — photoPrice Reduced20Active

    $308,000

    3 bd · 1 ba · 960 sqft

    107 Lee Rd, Chester, MD

    Verria Hairston · Open Door Brokerage, LLC

  7. 205 Dominion Ln — photo22Active

    $300,000

    3 bd · 2 ba · 1,160 sqft

    205 Dominion Ln, Chester, MD

    Jonathan C Nicholls · EXP Realty, LLC

  8. 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

  9. 117 Wright Rd — photoPrice Reduced61Active

    $399,999

    3 bd · 2 ba · 1,337 sqft

    117 Wright Rd, Chester, MD

    Diane Superczynski · Douglas Realty LLC

  10. 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

  11. 510 Auckland Way — photo31Active

    $410,000

    3 bd · 3 ba · 1,899 sqft

    510 Auckland Way, Chester, MD

    Dawn Haskins Smith · Engel & Volkers Annapolis

  12. 512 Auckland Way — photo51Active

    $375,000

    3 bd · 4 ba · 1,899 sqft

    512 Auckland Way, Chester, MD

    Lawrence Doyle · Long & Foster Real Estate, Inc.

  13. 53-E Queen Caroline Ct — photo38Active

    $329,000

    2 bd · 3 ba · 1,440 sqft

    53-E Queen Caroline Ct, Chester, MD

    Tammy Studebaker · EXP Realty, LLC

  14. 6005 Bridgepointe Dr — photoPrice Reduced54Active

    $324,000

    3 bd · 3 ba · 1,302 sqft

    6005 Bridgepointe Dr, Chester, MD

    Megan E Rosendale · Rosendale Realty

  15. 326 Castle Marina Rd — photoPrice Reduced83Active

    $499,000

    5 bd · 4 ba · 3,552 sqft

    326 Castle Marina Rd, Chester, MD

    Virginia Elizabeth Dauses · Coldwell Banker Waterman Realty

  16. 108 Blenny Ln — photoPrice Reduced37Active

    $364,900

    3 bd · 3 ba · 1,899 sqft

    108 Blenny Ln, Chester, MD

    Carol L Tinnin · RE/MAX Leading Edge

  17. 230 Switchgrass Way #12 — photoPrice Reduced23Active

    $499,000

    2 bd · 3 ba · 2,003 sqft

    230 Switchgrass Way #12, Chester, MD

    David J. Moore · Real Broker, LLC - Chester

  18. 21-F Queen Victoria Way — photo38Active

    $472,500

    3 bd · 3 ba · 1,620 sqft

    21-F Queen Victoria Way, Chester, MD

    Jennifer Anne Thomas · RE/MAX Executive

  19. 807 Auckland Way — photo48Active

    $425,500

    3 bd · 4 ba · 2,100 sqft

    807 Auckland Way, Chester, MD

    David J. Moore · Real Broker, LLC - Chester

  20. 106 Bodys Neck Rd — photoPrice Reduced48Active

    $429,900

    3 bd · 3 ba · 1,595 sqft

    106 Bodys Neck Rd, Chester, MD

    William Warren Longest Jr. · Realty Navigator

  21. 5011 Bridgepointe Dr — photoPrice Reduced46Active

    $315,000

    3 bd · 3 ba · 1,302 sqft

    5011 Bridgepointe Dr, Chester, MD

    Nickolaus B Waldner · Keller Williams Realty Centre

  22. 45-G Queen Neva Ct — photoPrice Reduced40Active

    $318,500

    2 bd · 3 ba · 1,312 sqft

    45-G Queen Neva Ct, Chester, MD

    John V Freeman · Coldwell Banker Realty

  23. 54F Queen Caroline Ct — photoPrice Reduced46Active

    $349,900

    3 bd · 3 ba · 1,440 sqft

    54F Queen Caroline Ct, Chester, MD

    Lawrence Doyle · Long & Foster Real Estate, Inc.

  24. 1000 Herons Nest Way #22 — photoPrice Reduced56Active

    $485,000

    2 bd · 3 ba · 1,900 sqft

    1000 Herons Nest Way #22, Chester, MD

    Ralph S. Kennedy · RE/MAX Executive

12
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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: 2026-10-29 23:05:19 UTC
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #01-6355

    Call Thomas

    Chester housing market

    September 2026

    Chester 12-month median sale price trend

    Selling at 99.0% of asking price

    Buyers here are paying below asking. MLS · 16 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 29, 2026

    Median sale price
    $491,023$280,000–$689,000 typical range
    Price per sq. ft.
    $285
    Sales
    25
    Paid in cash
    52.0%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

    Median list price
    $554,500
    Homes for sale
    46
    Median days on market
    22 days

    Price trend · Assessor repeat sales, as of Sep 30, 2026

    Year-over-year
    -5.9%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 2026

    Median home size
    1,728 sq. ft.

    Chester, MD community profile

    Area
    22.5 sq. mi.

    Source: HJN community data