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Chester, VA Homes for Sale | Realty.com
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29 listings
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3 bedsWith a pool

Homes for Sale in Chester, VA

Homes for Sale in Chester, VA

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24 of 29 Listings
Map

Homes for Sale in Chester, VA

24 of 29 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas
  1. 4321 Lilking Ct — photo39Active

    $509,000

    3 bd · 3 ba · 3,010 sqft

    4321 Lilking Ct, Chester, VA

    Nicholas Thurman · CapCenter

  2. 14500 Happy Hill — photo58Active

    $627,500

    5 bd · 3 ba · 3,598 sqft

    14500 Happy Hill, Chester, VA

    Michael Conway · Real Broker LLC

  3. 11913 Helmway Ct — photo78Active

    $650,000

    4 bd · 3 ba · 3,290 sqft

    11913 Helmway Ct, Chester, VA

    Tracy McGuire · The Steele Group

  4. 1769 Outrigger Dr — photoPrice Reduced36Active

    $495,000

    4 bd · 3 ba · 2,248 sqft

    1769 Outrigger Dr, Chester, VA

    Jeremy Cecchettini · Real Broker LLC

  5. 12621 Green Garden Ter — photo45Active

    $465,000

    5 bd · 3 ba · 2,516 sqft

    12621 Green Garden Ter, Chester, VA

    Matthew Henry · KW Metro Center

  6. 5640 Teterling Ct — photo47Active

    $525,000

    4 bd · 3 ba · 3,559 sqft

    5640 Teterling Ct, Chester, VA

    Ronda Bradley-Gallagher · Bradley Real Estate, LLC

  7. 4611 Dunkirk Dr — photoPrice Reduced40Active

    $350,000

    4 bd · 2 ba · 2,429 sqft

    4611 Dunkirk Dr, Chester, VA

    Kristin Murphy · Real Broker LLC

  8. 14119 Kentwood Forest Dr — photo32Active

    $399,950

    4 bd · 3 ba · 2,250 sqft

    14119 Kentwood Forest Dr, Chester, VA

    Kelly Rivers · United Real Estate Richmond

  9. 11425 Claimont Mill Dr — photo42Active

    $337,000

    3 bd · 3 ba · 1,644 sqft

    11425 Claimont Mill Dr, Chester, VA

    Tucker Greer · Shaheen Ruth Martin & Fonville

  10. 554 Greymont Ln — photo32Active

    $549,950

    4 bd · 3 ba · 2,948 sqft

    554 Greymont Ln, Chester, VA

    Tiffany Wake · Long & Foster REALTORS

  11. 1799 Outrigger Dr — photo39Active

    $545,000

    3 bd · 3 ba · 2,164 sqft

    1799 Outrigger Dr, Chester, VA

    Tracy Girard · Real Broker LLC

  12. 2403 Bermuda Ave — photo62Active

    $1,150,000

    4 bd · 4 ba · 4,802 sqft

    2403 Bermuda Ave, Chester, VA

    James Nay · River City Elite Properties - Real Broker

  13. 612 Green Garden Cir — photoPrice Reduced35Active

    $421,999

    3 bd · 2 ba · 2,208 sqft

    612 Green Garden Cir, Chester, VA

    Anthony Burch · United Real Estate Richmond

  14. 5112 Weatherby Dr — photoPrice Reduced38Active

    $334,500

    3 bd · 3 ba · 1,864 sqft

    5112 Weatherby Dr, Chester, VA

    Mike Hogan · The Hogan Group Real Estate

  15. 13446 Bradley Bridge Rd — photoPrice Reduced75Active

    $1,780,000

    5 bd · 5 ba · 4,444 sqft

    13446 Bradley Bridge Rd, Chester, VA

    Kristin Krupp · Shaheen Ruth Martin & Fonville

  16. 13406 Greenham Ct — photoPrice ReducedOpen house Sun, Oct 11 · 12:00 PM17Active

    $399,999

    4 bd · 3 ba · 2,008 sqft

    13406 Greenham Ct, Chester, VA

    Teresa Price · Samson Properties

  17. 13601 Green Spire Cir — photoPrice Reduced51Active

    $499,950

    5 bd · 4 ba · 3,100 sqft

    13601 Green Spire Cir, Chester, VA

    Katrina Davis-Young · 757 Realty

  18. 14201 Sonnenburg Dr — photo61Active

    $389,950

    4 bd · 2 ba · 1,626 sqft

    14201 Sonnenburg Dr, Chester, VA

    Jane Chambers · Virginia Capital Realty

  19. 2526 Channelmark Pl — photoPrice Reduced50Active

    $660,000

    5 bd · 3 ba · 3,341 sqft

    2526 Channelmark Pl, Chester, VA

    Libby Gatewood · Parr & Abernathy Realty, Inc.

  20. 12019 Winbolt Dr — photo5Active

    $735,000

    5 bd · 4 ba · 4,258 sqft

    12019 Winbolt Dr, Chester, VA

    LaTanya Wagstaff · Call It Closed International I

  21. 12218 Winbolt Dr — photoPrice Reduced36Active

    $464,000

    4 bd · 3 ba · 2,560 sqft

    12218 Winbolt Dr, Chester, VA

    Richard Sena · Redfin Corporation

  22. 11813 Middlecoff Dr — photoPrice Reduced39Active

    $844,999

    6 bd · 5 ba · 4,310 sqft

    11813 Middlecoff Dr, Chester, VA

    Dianne Mann · Hardy Realty & Auction

  23. 1501 Bluewater Ter — photo47Active

    $1,100,000

    7 bd · 6 ba · 6,513 sqft

    1501 Bluewater Ter, Chester, VA

    Deborah Reynolds · Keller Williams Realty

  24. 11556 Claimont Mill Dr — photoPrice Reduced41Active

    $352,000

    3 bd · 3 ba · 1,848 sqft

    11556 Claimont Mill Dr, Chester, VA

    Nicole Reed · Real Broker LLC

12

Explore Chester homes

By price

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  • Homes Under $500K
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Nearby areas

ZIP codes

  • 23112 (199)
  • 23832 (148)
  • 23803 (145)
  • 23223 (126)
  • 23120 (118)
  • 23860 (117)
  • 23111 (116)
  • 23234 (116)

Cities

  • Richmond (647)
  • Henrico (455)
  • Chesterfield (379)
  • Midlothian (312)
  • Glen Allen (155)
  • Mechanicsville (152)
  • Petersburg (145)
  • Moseley (112)

Listing data & MLS disclosures

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: 2026-10-10 19:12:53 UTC

Chester, VA community profile

Area
50 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 · 46 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 24, 2026

Median sale price
$395,155$330,000–$440,500 typical range
Price per sq. ft.
$183
Sales
40
Paid in cash
20.0%

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

Median list price
$436,500
Homes for sale
137

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

Year-over-year
-4.0%

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

Median home size
2,089 sq. ft.
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #0225245042

    Call Thomas