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Homes Under $500K in Chester, MD
11 listings

Homes Under $500K in Chester, MD

Homes Under $500K in Chester, MD

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11 Listings
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Homes Under $500K in Chester, MD

11 Listings

  1. 7-B Queen Victoria Way #B — photo39Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

$499,000

2 bd · 3 ba · 1,680 sqft

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

Christina Sousa · RE/MAX Allegiance

  • 510 Auckland Way — photo31Active

    $410,000

    3 bd · 3 ba · 1,899 sqft

    510 Auckland Way, Chester, MD

    Dawn Haskins Smith · Engel & Volkers Annapolis

  • 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.

  • 108 Blenny Ln — photoPrice Reduced37Active

    $369,900

    3 bd · 3 ba · 1,899 sqft

    108 Blenny Ln, Chester, MD

    Carol L Tinnin · RE/MAX Leading Edge

  • 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

  • 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

  • 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

  • 54-D Queen Caroline Ct — photoPrice Reduced43Active

    $299,900

    3 bd · 3 ba · 1,440 sqft

    54-D Queen Caroline Ct, Chester, MD

    Michelle DiDonato · Island Realty, LLC

  • 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

  • 4000 Herons Nest Way #22 — photoPrice Reduced70Active

    $492,500

    2 bd · 3 ba · 1,900 sqft

    4000 Herons Nest Way #22, Chester, MD

    Carol L Tinnin · RE/MAX Leading Edge

  • 3000 Herons Nest Way #11 — photoPrice Reduced66Active

    $498,400

    2 bd · 3 ba · 2,003 sqft

    3000 Herons Nest Way #11, Chester, MD

    John V Freeman · Coldwell Banker Realty

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    L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

    Equal Housing OpportunityEqual Housing Lender

    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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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #01-6355

    Call Thomas

    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: 2026-10-05 18:00:34 UTC

    Chester, MD community profile

    Area
    22.5 sq. mi.

    Source: HJN community data

    Chester housing market

    September 2026 · This period is still settling

    Chester 12-month median sale price trend

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 15 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 18, 2026

    Median sale price
    $400,000$284,250–$656,750 typical range
    Price per sq. ft.
    $278
    Sales
    14
    Paid in cash
    57.1%

    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
    21 days

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

    Year-over-year
    -23.4%

    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.