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3 bedsNew constructionWith a pool
Homes Under $500K in Chesapeake, VA
461 listings

Homes Under $500K in Chesapeake, VA

Homes Under $500K in Chesapeake, VA

Show Map
24 of 461 Listings
Map

Homes Under $500K in Chesapeake, VA

24 of 461 Listings

  1. 708 Sail Fish Quay — photoNew1Active

Your Chesapeake agent

TG

Tiffany Gelzinis

The Gelzinis Group/REAL

Lic. #0225217891

Call Tiffany

$239,900

2 bd · 2 ba · 1,236 sqft

708 Sail Fish Quay, Chesapeake, VA

EXIT Realty Central

  • 713 Sutherland Drive — photoNew38Active

    $310,000

    3 bd · 3 ba · 1,516 sqft

    713 Sutherland Drive, Chesapeake, VA

    BHHS RW Towne Realty

  • 2901 Bainbridge Boulevard — photoNew47Active

    $300,000

    3 bd · 1 ba · 1,492 sqft

    2901 Bainbridge Boulevard, Chesapeake, VA

    1st Class Real Estate Integrity

  • 4356 Pickney Lane — photoNew36Active

    $340,000

    3 bd · 3 ba · 1,760 sqft

    4356 Pickney Lane, Chesapeake, VA

    Serhant

  • 901 Summerfield Crescent — photoNew50Active

    $475,000

    4 bd · 3 ba · 2,248 sqft

    901 Summerfield Crescent, Chesapeake, VA

    Cape & Coast Real Estate Group LLC

  • 1821 Volvo Parkway — photoNew22Active

    $370,000

    2 bd · 3 ba · 1,334 sqft

    1821 Volvo Parkway, Chesapeake, VA

    CENTURY 21 Nachman Realty

  • NewActive

    $490,000

    4 bd · 7 ba · 1,923 sqft

    753 Helmsdale Way, Chesapeake, VA

    COVA Home Realty

  • 907 Railroad Avenue — photoNew30Active

    $399,900

    3 bd · 3 ba · 1,654 sqft

    907 Railroad Avenue, Chesapeake, VA

    BHHS RW Towne Realty

  • 401 Henley Court — photoNew12Active

    $229,900

    2 bd · 3 ba · 1,275 sqft

    401 Henley Court, Chesapeake, VA

    Creed Realty

  • 1318 Bainbridge Boulevard — photoNew43Active

    $489,900

    4 bd · 3 ba · 2,176 sqft

    1318 Bainbridge Boulevard, Chesapeake, VA

    BHHS RW Towne Realty

  • 1507 Linden Avenue — photoNew16Active

    $309,900

    3 bd · 2 ba · 1,212 sqft

    1507 Linden Avenue, Chesapeake, VA

    RE/MAX Prime

  • 176 Driftwood Drive — photoNew40Active

    $470,000

    4 bd · 3 ba · 1,778 sqft

    176 Driftwood Drive, Chesapeake, VA

    ReWard Real Estate LLC

  • 500 Judah Way — photoNew27Active

    $270,000

    2 bd · 2 ba · 1,215 sqft

    500 Judah Way, Chesapeake, VA

    Compass Rose Realty

  • 1644 Songbird Lane — photoNew13Active

    $489,900

    4 bd · 4 ba · 2,235 sqft

    1644 Songbird Lane, Chesapeake, VA

    Wainwright Real Estate

  • 1640 Songbird Lane — photoNew13Active

    $499,900

    4 bd · 4 ba · 2,312 sqft

    1640 Songbird Lane, Chesapeake, VA

    Wainwright Real Estate

  • 302 Gale Avenue — photoNew40Active

    $389,900

    3 bd · 3 ba · 1,680 sqft

    302 Gale Avenue, Chesapeake, VA

    JP Realty and Associates

  • 2309 Drum Creek Road — photoNew50Active

    $439,900

    4 bd · 2 ba · 1,771 sqft

    2309 Drum Creek Road, Chesapeake, VA

    Atlantic Sothebys Int'l Realty

  • 2039 Mango Street — photoNew14Active

    $347,900

    2 bd · 3 ba · 1,495 sqft

    2039 Mango Street, Chesapeake, VA

    Corinth Realty LLC

  • 5 Lydney Circle — photoNew29Active

    $320,000

    3 bd · 3 ba · 1,428 sqft

    5 Lydney Circle, Chesapeake, VA

    Real Broker LLC

  • 1648 Songbird Lane — photoNew13Active

    $499,900

    4 bd · 4 ba · 2,235 sqft

    1648 Songbird Lane, Chesapeake, VA

    Wainwright Real Estate

  • 2312 Campostella Road — photoNew3Active

    $161,000

    2 bd · 1 ba · 612 sqft

    2312 Campostella Road, Chesapeake, VA

    JDK Ventures LLC

  • 3004 Kilbride Drive — photoNew21Active

    $290,000

    3 bd · 1 ba · 950 sqft

    3004 Kilbride Drive, Chesapeake, VA

    Own Real Estate LLC

  • 2121 Speedy Avenue — photoNew41Active

    $390,000

    4 bd · 3 ba · 1,543 sqft

    2121 Speedy Avenue, Chesapeake, VA

    BHHS RW Towne Realty

  • 3316 Kindlewood Crescent — photoNew40Active

    $498,250

    4 bd · 3 ba · 2,594 sqft

    3316 Kindlewood Crescent, Chesapeake, VA

    BHHS RW Towne Realty

  • 12…20

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    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 4, 2026

    Median sale price
    $389,950$305,000–$555,000 typical range
    Price per sq. ft.
    $218
    Sales
    76
    Paid in cash
    13.2%

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

    Median list price
    $367,500
    Homes for sale
    14

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

    Year-over-year
    0.8%

    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.