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

5 Bedroom Homes in Chesapeake, VA

5 Bedroom Homes in Chesapeake, VA

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24 of 131 Listings
Map

5 Bedroom Homes in Chesapeake, VA

24 of 131 Listings

  1. 320 Oak Lake Ter — photoNew47

Your Chesapeake agent

TG

Tiffany Gelzinis

The Gelzinis Group/REAL

Lic. #0225217891

Call Tiffany
Active

$430,000

5 bd · 2 ba · 2,300 sqft

320 Oak Lake Ter, Chesapeake, VA

  • MM Carter (5 Bed) — photoNew22Active

    $565,900

    5 bd · 4 ba · 2,441 sqft

    MM Carter (5 Bed), Chesapeake, VA

  • 641 Ravenwoods Dr — photo48Active

    $1,519,000

    5 bd · 4 ba · 6,848 sqft

    641 Ravenwoods Dr, Chesapeake, VA

  • 2624 Powell Cir — photo44Active

    $415,000

    5 bd · 3 ba · 2,256 sqft

    2624 Powell Cir, Chesapeake, VA

  • 2209 Beeblossom Ln — photo46Active

    $695,000

    5 bd · 2 ba · 3,200 sqft

    2209 Beeblossom Ln, Chesapeake, VA

  • 1520 Jimmy Ln — photo21Active

    $724,990

    5 bd · 3 ba · 3,010 sqft

    1520 Jimmy Ln, Chesapeake, VA

  • 3201 Letcher Court Ct — photo50Active

    $585,588

    5 bd · 2 ba · 3,150 sqft

    3201 Letcher Court Ct, Chesapeake, VA

  • 389 Scotland Lane — photo31Active

    $665,900

    5 bd · 3 ba · 3,100 sqft

    389 Scotland Lane, Chesapeake, VA

  • 1120 Kathleen Ln — photo50Active

    $1,500,000

    5 bd · 3 ba · 7,155 sqft

    1120 Kathleen Ln, Chesapeake, VA

  • 940 Sydenham Blvd — photo47Active

    $724,900

    5 bd · 3 ba · 3,315 sqft

    940 Sydenham Blvd, Chesapeake, VA

  • 1125 George Olah Dr — photo50Active

    $700,000

    5 bd · 3 ba · 2,900 sqft

    1125 George Olah Dr, Chesapeake, VA

  • 1010 Cuervo Ct — photo50Active

    $615,000

    5 bd · 3 ba · 3,000 sqft

    1010 Cuervo Ct, Chesapeake, VA

  • MM Bellhaven-Multi-Gen — photo33Active

    $800,000

    5 bd · 3 ba · 3,240 sqft

    MM Bellhaven-Multi-Gen, Chesapeake, VA

  • 1432 Pine Grove Ln — photo42Active

    $645,500

    5 bd · 3 ba · 3,256 sqft

    1432 Pine Grove Ln, Chesapeake, VA

  • 705 Creekwood Dr — photo39Active

    $595,000

    5 bd · 4 ba · 3,000 sqft

    705 Creekwood Dr, Chesapeake, VA

  • 1040 Drumcastle Ln — photo45Active

    $950,000

    5 bd · 3 ba · 4,253 sqft

    1040 Drumcastle Ln, Chesapeake, VA

  • 1152 Crystalwood Cir — photo47Active

    $529,900

    5 bd · 2 ba · 3,000 sqft

    1152 Crystalwood Cir, Chesapeake, VA

  • 3649 Kathys Way — photo49Active

    $624,900

    5 bd · 3 ba · 2,662 sqft

    3649 Kathys Way, Chesapeake, VA

  • 4624 Westborough Dr — photo29Active

    $497,500

    5 bd · 3 ba · 3,590 sqft

    4624 Westborough Dr, Chesapeake, VA

  • 816 Poquoson Xing — photo46Active

    $688,900

    5 bd · 3 ba · 3,650 sqft

    816 Poquoson Xing, Chesapeake, VA

  • 2044 Hallmark Way — photo50Active

    $995,000

    5 bd · 3 ba · 4,246 sqft

    2044 Hallmark Way, Chesapeake, VA

  • MM Ashbee — photo38Active

    $725,000

    5 bd · 3 ba · 2,752 sqft

    MM Ashbee, Chesapeake, VA

  • 901 Railroad Ave — photo31Active

    $446,500

    5 bd · 2 ba · 1,862 sqft

    901 Railroad Ave, Chesapeake, VA

  • 3504 Riverwood Cres — photo50Active

    $849,900

    5 bd · 4 ba · 4,670 sqft

    3504 Riverwood Cres, Chesapeake, VA

  • 12…6

    Explore Chesapeake homes

    By price

    • Under $300K
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    By bedrooms

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    • 5 beds

    By type

    • Single family
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    By feature

    • 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 · 268 sales · as of Aug 28, 2026

    Homes that sold · County records, as of Aug 12, 2026

    Median sale price
    $415,000$285,000–$599,500 typical range
    Price per sq. ft.
    $220
    Sales
    159
    Paid in cash
    19.5%

    Homes on the market · MLS, as of Aug 28, 2026–Aug 31, 2026

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

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

    Year-over-year
    -0.5%

    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.