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3 bedsNew constructionWith a pool
5 Bedroom Homes in Chesapeake, VA
147 listings

5 Bedroom Homes in Chesapeake, VA

5 Bedroom Homes in Chesapeake, VA

Show Map
24 of 147 Listings
Map

5 Bedroom Homes in Chesapeake, VA

24 of 147 Listings

  1. 402 Undershot Ct Ct — photoNew50

Your Chesapeake agent

TG

Tiffany Gelzinis

The Gelzinis Group/REAL

Lic. #0225217891

Call Tiffany
Active

$565,000

5 bd · 2 ba · 2,800 sqft

402 Undershot Ct Ct, Chesapeake, VA

  • 803 Gresham Way — photoNew28Active

    $625,000

    5 bd · 3 ba · 3,670 sqft

    803 Gresham Way, Chesapeake, VA

  • 622 Ambrose St — photoNew18Active

    $625,000

    5 bd · 3 ba · 2,600 sqft

    622 Ambrose St, Chesapeake, VA

  • 1453 Whittamore Rd — photoNew39Active

    $699,900

    5 bd · 3 ba · 2,660 sqft

    1453 Whittamore Rd, Chesapeake, VA

  • 212 Kwanzan Ct — photoNew24Active

    $793,267

    5 bd · 3 ba · 2,888 sqft

    212 Kwanzan Ct, Chesapeake, VA

  • 2949 Prince Of Wales Dr — photoNew44Active

    $539,000

    5 bd · 2 ba · 3,138 sqft

    2949 Prince Of Wales Dr, Chesapeake, VA

  • NewActive

    $395,000

    5 bd · 2 ba · 3,333 sqft

    3861 Ahoy Dr Dr, Chesapeake, VA

  • 900 Golden Cypress Ct — photoNew49Active

    $425,000

    5 bd · 2 ba · 1,787 sqft

    900 Golden Cypress Ct, Chesapeake, VA

  • 212 Tinker St — photo26Active

    $674,990

    5 bd · 3 ba · 2,718 sqft

    212 Tinker St, Chesapeake, VA

  • Lot 18 Tbd Flax Mill Way — photo1Active

    $767,500

    5 bd · 3 ba · 2,994 sqft

    Lot 18 Tbd Flax Mill Way, Chesapeake, VA

  • 429 Warrick Rd — photo48Active

    $725,000

    5 bd · 4 ba · 3,159 sqft

    429 Warrick Rd, Chesapeake, VA

  • 1432 Rivers Edge Trce — photo50Active

    $530,000

    5 bd · 3 ba · 3,450 sqft

    1432 Rivers Edge Trce, Chesapeake, VA

  • 1813A Hoover Ave — photo33Active

    $434,900

    5 bd · 2 ba · 1,862 sqft

    1813A Hoover Ave, Chesapeake, VA

  • 1201 Richwood Ave — photo37Active

    $575,000

    5 bd · 3 ba · 2,412 sqft

    1201 Richwood Ave, Chesapeake, VA

  • 804 Wakedale Arch — photo35Active

    $719,900

    5 bd · 4 ba · 3,720 sqft

    804 Wakedale Arch, Chesapeake, VA

  • 3705 Davis Ave — photo40Active

    $499,900

    5 bd · 3 ba · 2,550 sqft

    3705 Davis Ave, Chesapeake, VA

  • 3708 Riverwood Cres — photo33Active

    $775,000

    5 bd · 2 ba · 2,978 sqft

    3708 Riverwood Cres, Chesapeake, VA

  • 2722 Gum Rd — photo41Active

    $650,000

    5 bd · 3 ba · 3,112 sqft

    2722 Gum Rd, Chesapeake, VA

  • 952 Checkerspot Way — photo49Active

    $685,000

    5 bd · 2 ba · 2,954 sqft

    952 Checkerspot Way, Chesapeake, VA

  • 813 Satinwood Ct — photo47Active

    $725,000

    5 bd · 3 ba · 3,100 sqft

    813 Satinwood Ct, Chesapeake, VA

  • 1910 Hallmark Way — photo25Active

    $998,895

    5 bd · 3 ba · 3,988 sqft

    1910 Hallmark Way, Chesapeake, VA

  • 3405 Anita Cir — photo34Active

    $540,000

    5 bd · 3 ba · 3,164 sqft

    3405 Anita Cir, Chesapeake, VA

  • 412 Harper Ct — photo46Active

    $575,000

    5 bd · 3 ba · 2,853 sqft

    412 Harper Ct, Chesapeake, VA

  • 1052 Stockleybridge Dr — photo50Active

    $747,995

    5 bd · 3 ba · 3,126 sqft

    1052 Stockleybridge Dr, Chesapeake, VA

  • 12…7

    Explore Chesapeake homes

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    • New construction
    • 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.