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3 bedsNew constructionWith a pool
467 listings

Homes Under $500K in Chesapeake, VA

Homes Under $500K in Chesapeake, VA

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24 of 467 Listings
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Homes Under $500K in Chesapeake, VA

24 of 467 Listings

  1. 216 Stubbs Drive — photoNew37Active

$459,900

4 bd · 2 ba · 1,992 sqft

216 Stubbs Drive, Chesapeake, VA

The Bryant Group

  • 518 Silk Tree Lane — photoNew49Active

    $449,900

    3 bd · 3 ba · 2,366 sqft

    518 Silk Tree Lane, Chesapeake, VA

    RHOAD & CO.

  • 4337 Sunray Avenue — photoNew47Active

    $500,000

    4 bd · 3 ba · 2,076 sqft

    4337 Sunray Avenue, Chesapeake, VA

    The Agency

  • 4116 Emberhill Lane — photoNew44Active

    $435,000

    5 bd · 2 ba · 1,978 sqft

    4116 Emberhill Lane, Chesapeake, VA

    World Class Realty

  • 4141 3rd Street — photoNew23Active

    $319,500

    3 bd · 2 ba · 1,154 sqft

    4141 3rd Street, Chesapeake, VA

    CoastalVA Realty Inc.

  • 2716 Thomas Street — photoNew42Active

    $415,000

    4 bd · 3 ba · 2,412 sqft

    2716 Thomas Street, Chesapeake, VA

    Own Real Estate LLC

  • 904 McKinley Avenue — photoNew31Active

    $299,900

    3 bd · 2 ba · 1,168 sqft

    904 McKinley Avenue, Chesapeake, VA

    World Class Realty

  • 416 Mishannock Way — photoNew46Active

    $474,900

    4 bd · 3 ba · 1,862 sqft

    416 Mishannock Way, Chesapeake, VA

    Barn Door Homes

  • 1505 Waitsel Drive — photoNew45Active

    $310,000

    2 bd · 2 ba · 1,327 sqft

    1505 Waitsel Drive, Chesapeake, VA

    Redfin Corporation

  • 1437 Glendale Avenue — photoNew30Active

    $360,000

    4 bd · 2 ba · 1,380 sqft

    1437 Glendale Avenue, Chesapeake, VA

    Real Broker LLC

  • 813 Mullen Road — photoNew16Active

    $439,900

    4 bd · 3 ba · 1,800 sqft

    813 Mullen Road, Chesapeake, VA

    The Real Estate Group

  • 930 Railroad Avenue — photoNew8Active

    $399,900

    3 bd · 3 ba · 1,436 sqft

    930 Railroad Avenue, Chesapeake, VA

    BHHS RW Towne Realty

  • 2900 Rodgers Street — photoNew30Active

    $330,000

    4 bd · 2 ba · 1,450 sqft

    2900 Rodgers Street, Chesapeake, VA

    A Better Way Realty Inc.

  • 509 Dinwiddie Court — photoNew49Active

    $490,000

    3 bd · 2 ba · 1,906 sqft

    509 Dinwiddie Court, Chesapeake, VA

    The Real Estate Group

  • 2630 Cecilia Terrace — photoNew38Active

    $474,900

    4 bd · 3 ba · 1,875 sqft

    2630 Cecilia Terrace, Chesapeake, VA

    RE/MAX Prime

  • 3904 Starboard Road — photoNew26Active

    $360,000

    3 bd · 2 ba · 1,323 sqft

    3904 Starboard Road, Chesapeake, VA

    Iron Valley Real Estate Prestige

  • 2456 Whitman Street — photoNew46Active

    $279,900

    2 bd · 3 ba · 1,314 sqft

    2456 Whitman Street, Chesapeake, VA

    Swell Real Estate Co

  • 1125 Sir Gawaine Drive — photoNew42Active

    $360,000

    4 bd · 3 ba · 1,950 sqft

    1125 Sir Gawaine Drive, Chesapeake, VA

    Creed Realty

  • 2432 Youngman Road — photoNew33Active

    $262,500

    2 bd · 1 ba · 825 sqft

    2432 Youngman Road, Chesapeake, VA

    RE/MAX Edge

  • 216 Astra Lane — photoNew24Active

    $299,900

    3 bd · 3 ba · 1,239 sqft

    216 Astra Lane, Chesapeake, VA

    Boyd Realty Partners

  • 905 Railroad Avenue — photoNew30Active

    $399,900

    3 bd · 3 ba · 1,654 sqft

    905 Railroad Avenue, Chesapeake, VA

    BHHS RW Towne Realty

  • 1403 Elder Avenue — photoNew38Active

    $450,000

    5 bd · 3 ba · 2,159 sqft

    1403 Elder Avenue, Chesapeake, VA

    Real Broker LLC

  • 1221 Commerce Avenue — photoNew29Active

    $279,725

    3 bd · 3 ba · 1,280 sqft

    1221 Commerce Avenue, Chesapeake, VA

    Own Real Estate LLC

  • 3301 Settlement Court — photoNew27Active

    $275,000

    2 bd · 2 ba · 1,274 sqft

    3301 Settlement Court, Chesapeake, VA

    Real Broker LLC

  • 12…20

    About Homes Under $500K in Chesapeake, VA

    Homes Under $500K in Chesapeake, VA: 467 active listings as of October 17, 2026, 23:55 UTC.

    Property types among these 467 listings, by the property type each listing’s MLS reports, spelled as the MLS spells it. Types with fewer than 5 listings, and listings whose MLS reports no type, are not shown, so the shares can total less than 100%.
    Property typeListingsShare
    Single Family Residence29463.0%
    Condominium12426.6%

    Homes Under $500K in nearby cities

    • Homes Under $500K in Virginia Beach
    • Homes Under $500K in Norfolk
    • Homes Under $500K in Suffolk
    • Homes Under $500K in Smithfield

    Explore Chesapeake 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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    Your Chesapeake agent

    TG

    Tiffany Gelzinis

    The Gelzinis Group/REAL

    Lic. #0225217891

    Call Tiffany

    Your Chesapeake agent

    TG

    Tiffany Gelzinis

    The Gelzinis Group/REAL

    Lic. #0225217891

    Call Tiffany

    Listing data & MLS disclosures

    Real Estate Information Network (REIN)
    © 2026 REIN Inc. Information Deemed Reliable but Not Guaranteed. The listings data displayed on this medium comes in part from the Real Estate Information Network, Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent. © 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW. REIN updates its listings on a daily basis. Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions. Some or all of the listings (or listings Data) represented in this application have been enhanced with Data not provided by REIN. This application does not include information on all of the properties available for sale at this time.

    Chesapeake, VA community profile

    Population
    256,189
    Median income
    $93,979
    Housing units
    94,442
    People per sq. mi.
    718.2
    Area
    356.7 sq. mi.

    Source: HJN community data

    Chesapeake housing market

    September 2026 · This period is still settling

    Chesapeake 12-month median sale price trend

    Homes that sold · County records, as of Sep 23, 2026

    Median sale price
    $379,900$300,000–$535,000 typical range
    Price per sq. ft.
    $217
    Sales
    297
    Paid in cash
    19.5%

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

    Median list price
    $367,500
    Homes for sale
    14

    · Assessor repeat sales, as of Sep 30, 2026

    Price trend
    Year-over-year
    -1.8%

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

    Median home size
    1,938 sq. ft.
    Homes Under $500K in Chesapeake, VA