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3 bedsNew constructionWith a pool
5 Bedroom Homes in Chesapeake, VA — Page 5
124 listings

5 Bedroom Homes in Chesapeake, VA

5 Bedroom Homes in Chesapeake, VA

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24 of 124 Listings
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5 Bedroom Homes in Chesapeake, VA

24 of 124 Listings

  1. 2202 Wilmington Avenue — photo5Active

Your Chesapeake agent

TG

Tiffany Gelzinis

The Gelzinis Group/REAL

Lic. #0225217891

Call Tiffany

$632,735

5 bd · 3 ba · 2,620 sqft

2202 Wilmington Avenue, Chesapeake, VA

RHOAD & CO.

  • 208 Leicester Court — photo42Active

    $795,000

    5 bd · 3 ba · 4,160 sqft

    208 Leicester Court, Chesapeake, VA

    Davis & Reed Realty

  • 810 Hedgerow Court — photo50Active

    $679,900

    5 bd · 3 ba · 3,200 sqft

    810 Hedgerow Court, Chesapeake, VA

    BHHS RW Towne Realty

  • 806 Falls Creek Drive — photo49Active

    $669,900

    5 bd · 3 ba · 3,383 sqft

    806 Falls Creek Drive, Chesapeake, VA

    RE/MAX Allegiance

  • 785 Caddie Street — photo38Active

    $599,000

    5 bd · 3 ba · 2,600 sqft

    785 Caddie Street, Chesapeake, VA

    BHHS RW Towne Realty

  • 1417 Gust Lane — photo35Active

    $314,000

    5 bd · 4 ba · 2,354 sqft

    1417 Gust Lane, Chesapeake, VA

    BHHS RW Towne Realty

  • 700 Canoe Street — photo32Active

    $500,000

    5 bd · 3 ba · 3,166 sqft

    700 Canoe Street, Chesapeake, VA

    Keller Williams Coastal VA Norfolk

  • 2861 Raccoon Trail — photo3Active

    $1,069,417

    5 bd · 4 ba · 3,570 sqft

    2861 Raccoon Trail, Chesapeake, VA

    AtCoastal Realty

  • 1533 Sanderson Road — photo3Active

    $997,724

    5 bd · 5 ba · 3,585 sqft

    1533 Sanderson Road, Chesapeake, VA

    AtCoastal Realty

  • 2116 Cedar Road — photo38Active

    $644,900

    5 bd · 3 ba · 2,500 sqft

    2116 Cedar Road, Chesapeake, VA

    EXP Realty LLC

  • 2857 Raccoon Trail — photo4Active

    $894,595

    5 bd · 3 ba · 3,026 sqft

    2857 Raccoon Trail, Chesapeake, VA

    AtCoastal Realty

  • 707 River Gate Court — photo50Active

    $674,900

    5 bd · 3 ba · 3,036 sqft

    707 River Gate Court, Chesapeake, VA

    CENTURY 21 Nachman Realty

  • 112 Station Road — photo48Active

    $725,000

    5 bd · 3 ba · 4,200 sqft

    112 Station Road, Chesapeake, VA

    The Real Estate Group

  • 4205 Nautilus Avenue — photo41Active

    $349,800

    5 bd · 2 ba · 2,150 sqft

    4205 Nautilus Avenue, Chesapeake, VA

    Redfin Corporation

  • 5036 Queen Street — photo35Active

    $525,000

    5 bd · 4 ba · 2,302 sqft

    5036 Queen Street, Chesapeake, VA

    ONYX Realty Professionals LLC

  • 5041 Queen Street — photo35Active

    $525,000

    5 bd · 4 ba · 2,302 sqft

    5041 Queen Street, Chesapeake, VA

    ONYX Realty Professionals LLC

  • 2832 Martins Point Way — photo19Active

    $1,257,400

    5 bd · 4 ba · 3,600 sqft

    2832 Martins Point Way, Chesapeake, VA

    Howard Hanna Real Estate Svcs.

  • 2032 Charwood Drive — photo30Active

    $765,425

    5 bd · 4 ba · 3,089 sqft

    2032 Charwood Drive, Chesapeake, VA

    Dragas Companies Realty Inc

  • 2039 Charwood Drive — photo29Active

    $745,425

    5 bd · 4 ba · 3,089 sqft

    2039 Charwood Drive, Chesapeake, VA

    Dragas Companies Realty Inc

  • 150 Hessian Loop — photo45Active

    $899,900

    5 bd · 4 ba · 3,393 sqft

    150 Hessian Loop, Chesapeake, VA

    Swell Realty Co

  • 517 Woodards Ford Road — photo50Active

    $1,695,000

    5 bd · 5 ba · 6,073 sqft

    517 Woodards Ford Road, Chesapeake, VA

    Cottage Street Realty LLC

  • 915 Harbour North Drive — photo6Active

    $268,000

    5 bd · 3 ba · 1,916 sqft

    915 Harbour North Drive, Chesapeake, VA

    XRealty.NET LLC

  • 404 Vespasian Circle — photo39Active

    $749,900

    5 bd · 3 ba · 3,446 sqft

    404 Vespasian Circle, Chesapeake, VA

    LPT Realty LLC

  • 915 Shelter Rock Lane — photo50Active

    $750,000

    5 bd · 4 ba · 3,647 sqft

    915 Shelter Rock Lane, Chesapeake, VA

    Garrett Realty Partners

  • 1…456

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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 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

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

    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.