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Homes Under $500K in Chester, MD
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3 bedsNew constructionWith a pool

Homes Under $500K in Chester, MD

Homes Under $500K in Chester, MD

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19 Listings
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Homes Under $500K in Chester, MD

19 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 1868 Roberta Dr — photo48Active

    $400,000

    5 bd · 4 ba · 3,250 sqft

    1868 Roberta Dr, Chester, MD

    Carley R. Cooper · Alex Cooper Auctioneers, Inc.

  2. 108 Blenny Ln — photo26Active

    $389,900

    3 bd · 3 ba · 1,899 sqft

    108 Blenny Ln, Chester, MD

    Carol L Tinnin · RE/MAX Leading Edge

  3. 2004 Bridgepointe Dr — photoPrice Reduced32Active

    $374,900

    3 bd · 2 ba · 1,524 sqft

    2004 Bridgepointe Dr, Chester, MD

    Sheryl Marie Carmody · RE/MAX Executive

  4. 6010 Bridgepointe Dr — photoPrice Reduced55Active

    $374,900

    3 bd · 2 ba · 1,885 sqft

    6010 Bridgepointe Dr, Chester, MD

    April L Heim · Rosendale Realty

  5. 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

  6. 106 Bodys Neck Rd — photo48Active

    $435,000

    3 bd · 3 ba · 1,595 sqft

    106 Bodys Neck Rd, Chester, MD

    William Warren Longest Jr. · Realty Navigator

  7. 6005 Bridgepointe Dr — photoPrice Reduced38Active

    $349,000

    3 bd · 3 ba · 1,302 sqft

    6005 Bridgepointe Dr, Chester, MD

    Megan E Rosendale · Rosendale Realty

  8. 5011 Bridgepointe Dr — photoPrice Reduced46Active

    $354,900

    3 bd · 3 ba · 1,302 sqft

    5011 Bridgepointe Dr, Chester, MD

    Nickolaus B Waldner · Keller Williams Realty Centre

  9. 45-G Queen Neva Ct — photo40Active

    $349,500

    2 bd · 3 ba · 1,312 sqft

    45-G Queen Neva Ct, Chester, MD

    John V Freeman · Coldwell Banker Realty

  10. 54-D Queen Caroline Ct — photoPrice Reduced38Active

    $309,900

    3 bd · 3 ba · 1,440 sqft

    54-D Queen Caroline Ct, Chester, MD

    Michelle DiDonato · Island Realty, LLC

  11. 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.

  12. 114 Merganser Ct — photoPrice Reduced27Active

    $287,500

    2 bd · 2 ba · 1,069 sqft

    114 Merganser Ct, Chester, MD

    Beverly A Sloane · Benson & Mangold, LLC

  13. 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

  14. 8-F Queen Victoria Way — photoPrice Reduced30Active

    $240,000

    1 bd · 1 ba · 724 sqft

    8-F Queen Victoria Way, Chester, MD

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

  15. 208 Blenny Ln — photoPrice Reduced32Active

    $374,900

    4 bd · 4 ba · 1,899 sqft

    208 Blenny Ln, Chester, MD

    Pamela B Ackermann · RE/MAX Executive

  16. 4000 Herons Nest Way #22 — photoPrice Reduced70Active

    $499,000

    2 bd · 3 ba · 1,900 sqft

    4000 Herons Nest Way #22, Chester, MD

    Carol L Tinnin · RE/MAX Leading Edge

  17. 3000 Herons Nest Way #11 — photoPrice Reduced66Active

    $479,000

    2 bd · 3 ba · 2,003 sqft

    3000 Herons Nest Way #11, Chester, MD

    John V Freeman · Coldwell Banker Realty

  18. 1405 Little Creek Rd — photo2Active

    $19,500

    2 bd · 1 ba · 764 sqft

    1405 Little Creek Rd, Chester, MD

    Dustin Parker · The Parker Group

  19. 1340 Queen Anne Dr — photoPrice Reduced27Active

    $439,900

    3 bd · 2 ba · 1,248 sqft

    1340 Queen Anne Dr, Chester, MD

    Darlene L Winegardner · RE/MAX Executive

Explore Chester homes

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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: 2026-09-02 19:42:45 UTC
    • New construction
    • With a pool

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #01-6355

    Call Thomas

    Chester, MD community profile

    Area
    22.5 sq. mi.

    Source: HJN community data

    Chester housing market

    August 2026 · This period is still settling

    Chester 12-month median sale price trend

    Selling at 99.4% of asking price

    Buyers here are paying below asking. MLS · 15 sales · as of Aug 26, 2026

    Homes that sold · County records, as of Aug 14, 2026

    Median sale price
    $567,500$387,500–$843,750 typical range
    Price per sq. ft.
    $317
    Sales
    11
    Paid in cash
    54.6%

    Homes on the market · MLS, as of Aug 26, 2026–Aug 31, 2026

    Median list price
    $564,450
    Homes for sale
    46
    Median days on market
    17 days

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    -8.8%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

    Median home size
    1,728 sq. ft.