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

Homes Under $500K in Chester, VA

Homes Under $500K in Chester, VA

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24 of 102 Listings
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Homes Under $500K in Chester, VA

24 of 102 Listings

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Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas
  1. 2342 Buena Vista Blvd — photoNew33Active

    $265,000

    3 bd · 2 ba · 1,248 sqft

    2342 Buena Vista Blvd, Chester, VA

    Nicole Smith · Open Gate Realty Group

  2. 4504 Edenton Pl — photo32Active

    $365,000

    3 bd · 2 ba · 1,766 sqft

    4504 Edenton Pl, Chester, VA

    Jennifer McCray · Real Broker LLC

  3. 4820 Cedar Cliff Rd — photoNew47Active

    $395,000

    4 bd · 3 ba · 1,925 sqft

    4820 Cedar Cliff Rd, Chester, VA

    Rebby Castro-Imobisa · Real Broker LLC

  4. 12541 Winfree St — photoNew54Active

    $430,000

    4 bd · 3 ba · 2,760 sqft

    12541 Winfree St, Chester, VA

    Kasey Shumaker · Douglas Elliman Real Estate

  5. 5112 Weatherby Dr — photoNew38Active

    $339,500

    3 bd · 3 ba · 1,864 sqft

    5112 Weatherby Dr, Chester, VA

    Mike Hogan · The Hogan Group Real Estate

  6. 501 Green Orchard Dr — photoNew37Active

    $414,999

    3 bd · 3 ba · 1,872 sqft

    501 Green Orchard Dr, Chester, VA

    Monier Monier · United Real Estate Richmond

  7. 2723 Goyne Ter — photoNew33Active

    $280,000

    2 bd · 3 ba · 1,320 sqft

    2723 Goyne Ter, Chester, VA

    Kimberly Holmes · Boss Moves Real Estate

  8. 12418 Percival St — photo25Active

    $350,000

    3 bd · 3 ba · 1,420 sqft

    12418 Percival St, Chester, VA

    Justine Rice · Liz Moore & Associates

  9. 14519 Sonnenburg Dr — photo26Active

    $365,000

    3 bd · 2 ba · 1,804 sqft

    14519 Sonnenburg Dr, Chester, VA

    Giovanni SantaAna · Move4Free Realty, LLC

  10. 5712 Stephens Point Ct — photo48Active

    $495,000

    4 bd · 3 ba · 2,701 sqft

    5712 Stephens Point Ct, Chester, VA

    Sarah Jefferson · Compass

  11. 2211 Osborne Rd — photo42Active

    $495,000

    4 bd · 2 ba · 1,770 sqft

    2211 Osborne Rd, Chester, VA

    Nicole Reed · Real Broker LLC

  12. 13406 Greenham Ct — photo17Active

    $415,000

    4 bd · 3 ba · 2,008 sqft

    13406 Greenham Ct, Chester, VA

    Teresa Price · Samson Properties

  13. 13306 Castlewellan Dr — photo24Active

    $482,000

    4 bd · 4 ba · 2,749 sqft

    13306 Castlewellan Dr, Chester, VA

    Verria Hairston · Opendoor Brokerage LLC

  14. 12001 Rubystone Dr — photo40Active

    $377,990

    3 bd · 4 ba · 2,146 sqft

    12001 Rubystone Dr, Chester, VA

    Janickal Hanson · KW Metro Center

  15. 3231 Ludgate Rd — photo34Active

    $350,000

    3 bd · 3 ba · 1,882 sqft

    3231 Ludgate Rd, Chester, VA

    Justine Rice · Liz Moore & Associates

  16. 11419 Dunmore Mill Ct — photo28Active

    $369,900

    3 bd · 3 ba · 1,868 sqft

    11419 Dunmore Mill Ct, Chester, VA

    Chris Haskins · EXP Realty, LLC

  17. 1713 Mainsail Ln — photo26Active

    $445,000

    3 bd · 3 ba · 1,695 sqft

    1713 Mainsail Ln, Chester, VA

    James Strum · Long & Foster REALTORS

  18. 4229 Greenbriar Dr — photo35Active

    $319,000

    3 bd · 2 ba · 1,286 sqft

    4229 Greenbriar Dr, Chester, VA

    Brett Harris · Harris & Assoc, Inc

  19. 4818 Stavely Rd — photo36Active

    $444,900

    3 bd · 2 ba · 1,604 sqft

    4818 Stavely Rd, Chester, VA

    Maria Andrea Febres · Spring Hill Real Estate

  20. 11609 Wilton Dr — photo23Active

    $325,000

    2 bd · 2 ba · 1,300 sqft

    11609 Wilton Dr, Chester, VA

    Debbie Reynolds · Keller Williams Realty

  21. 4325 Poplar Village Dr — photo36Active

    $500,000

    4 bd · 2 ba · 2,258 sqft

    4325 Poplar Village Dr, Chester, VA

    James Strum · Long & Foster REALTORS

  22. 14306 Bermuda Ave — photo21Active

    $349,000

    4 bd · 3 ba · 1,770 sqft

    14306 Bermuda Ave, Chester, VA

    Jasmine Douglas · Next Level Real Estate Group LLC

  23. 11500 Kralan Dr — photo47Active

    $480,000

    4 bd · 3 ba · 2,217 sqft

    11500 Kralan Dr, Chester, VA

    Eric Dunkum · Harris & Assoc, Inc

  24. 16003 Edgewood Dr — photo15Active

    $229,000

    3 bd · 1 ba · 864 sqft

    16003 Edgewood Dr, Chester, VA

    Jill Woodlief · Ingram & Assoc Chester

12…5

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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: 2026-08-28 22:52:56 UTC
Central Virginia Regional MLS
IDX information is provided by the Central Virginia Regional Multiple Listing Service, LLC, from a copyrighted compilation of Listings. All CVR MLS information provided is deemed reliable but is not guaranteed accurate.The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.
The compilation of Listings and each individual Listing are ©2026 Central Virginia Regional Multiple Listing Service, LLC®. All Rights Reserved. Last Updated: 2026-09-02 23:10:08 UTC
    • New construction
    • With a pool

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #0225245042

    Call Thomas

    Chester, VA community profile

    Area
    50 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 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 43 sales · as of Aug 28, 2026

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

    Median sale price
    $401,600$350,675–$502,500 typical range
    Price per sq. ft.
    $195
    Sales
    39
    Paid in cash
    15.4%

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

    Median list price
    $447,475
    Homes for sale
    110

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

    Year-over-year
    -1.3%

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

    Median home size
    2,096 sq. ft.