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3 beds
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New construction
With a pool
Homes Under $500K in Chesapeake, VA
445 listings

Homes Under $500K in Chesapeake, VA

Homes Under $500K in Chesapeake, VA

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24 of 445 Listings
Map

Homes Under $500K in Chesapeake, VA

24 of 445 Listings

  1. 404 Redbrick Dr — photoNew29

Your Chesapeake agent

TG

Tiffany Gelzinis

The Gelzinis Group/REAL

Lic. #0225217891

Call Tiffany
Active

$465,000

4 bd · 3 ba · 2,010 sqft

404 Redbrick Dr, Chesapeake, VA

  • 4117 Hawksley Dr — photoNew34Active

    $409,900

    4 bd · 2 ba · 1,864 sqft

    4117 Hawksley Dr, Chesapeake, VA

  • 1901 Kelly Rn — photoNew46Active

    $435,000

    4 bd · 2 ba · 1,932 sqft

    1901 Kelly Rn, Chesapeake, VA

  • 2205 Hilton Ct — photoNew38Active

    $329,900

    4 bd · 2 ba · 1,920 sqft

    2205 Hilton Ct, Chesapeake, VA

  • 916 Redstart Ave — photoNew43Active

    $375,000

    3 bd · 2 ba · 1,744 sqft

    916 Redstart Ave, Chesapeake, VA

  • 701 D St — photoNew4Active

    $247,500

    6 bd · 2 ba · 2,962 sqft

    701 D St, Chesapeake, VA

  • 1216 Club Point Dr — photoNew18Active

    $380,000

    3 bd · 2 ba · 1,528 sqft

    1216 Club Point Dr, Chesapeake, VA

  • 1214 Holly Ave — photoNew29Active

    $199,000

    3 bd · 1 ba · 1,155 sqft

    1214 Holly Ave, Chesapeake, VA

  • 4704 Mahogany Rn — photoNew48Active

    $447,340

    4 bd · 3 ba · 2,880 sqft

    4704 Mahogany Rn, Chesapeake, VA

  • 9 Colonial Way — photoNew37Active

    $265,000

    3 bd · 1 ba · 1,280 sqft

    9 Colonial Way, Chesapeake, VA

  • 1307 Perry St — photoNew18Active

    $252,000

    4 bd · 2 ba · 1,659 sqft

    1307 Perry St, Chesapeake, VA

  • 2209 Hilton Ct — photoNew15Active

    $307,000

    3 bd · 2 ba · 1,777 sqft

    2209 Hilton Ct, Chesapeake, VA

  • 1604 Myrtle Ave — photoNew50Active

    $339,000

    4 bd · 2 ba · 1,584 sqft

    1604 Myrtle Ave, Chesapeake, VA

  • 4332 Hillingdon Bnd 106 — photo29Active

    $246,640

    2 bd · 2 ba · 1,370 sqft

    4332 Hillingdon Bnd 106, Chesapeake, VA

  • 313 Holyoke Ln — photo30Active

    $283,999

    2 bd · 2 ba · 1,352 sqft

    313 Holyoke Ln, Chesapeake, VA

  • 700 Nottoway River Ct D — photo31Active

    $265,000

    2 bd · 2 ba · 1,490 sqft

    700 Nottoway River Ct D, Chesapeake, VA

  • 2615 Cedar Rd — photo28Active

    $409,000

    4 bd · 2 ba · 1,642 sqft

    2615 Cedar Rd, Chesapeake, VA

  • 3705 Davis Ave — photo40Active

    $499,900

    5 bd · 3 ba · 2,550 sqft

    3705 Davis Ave, Chesapeake, VA

  • 4706 Mahogany Rn — photo20Active

    $457,195

    4 bd · 2 ba · 2,614 sqft

    4706 Mahogany Rn, Chesapeake, VA

  • 614 Butterwick Court — photo38Active

    $245,000

    2 bd · 2 ba · 1,254 sqft

    614 Butterwick Court, Chesapeake, VA

  • 1100 Dane St — photo37Active

    $424,900

    3 bd · 2 ba · 1,664 sqft

    1100 Dane St, Chesapeake, VA

  • 3117 Kenelm Dr — photo42Active

    $325,000

    3 bd · 2 ba · 1,388 sqft

    3117 Kenelm Dr, Chesapeake, VA

  • 719 Creekside Cres — photo21Active

    $310,000

    3 bd · 2 ba · 1,400 sqft

    719 Creekside Cres, Chesapeake, VA

  • 1308 Sunnybrook Ter — photo32Active

    $365,000

    4 bd · 3 ba · 2,200 sqft

    1308 Sunnybrook Ter, Chesapeake, VA

  • 12…19

    Explore Chesapeake homes

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    • With a pool
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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

    August 2026 · This period is still settling

    Chesapeake 12-month median sale price trend

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 325 sales · as of Aug 31, 2026

    Homes that sold · County records, as of Aug 17, 2026

    Median sale price
    $415,000$300,000–$591,250 typical range
    Price per sq. ft.
    $216
    Sales
    208
    Paid in cash
    17.3%

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

    Median list price
    $489,500
    Homes for sale
    851
    Median days on market
    19 days

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

    Year-over-year
    -1.1%

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

    Median home size
    1,938 sq. ft.