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Chesapeake, VA Homes for Sale | Realty.com
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3 bedsNew constructionWith a pool

Homes for Sale in Chesapeake, VA

Homes for Sale in Chesapeake, VA

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24 of 901 Listings
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Homes for Sale in Chesapeake, VA

24 of 901 Listings

Your Chesapeake agent

TG

Tiffany Gelzinis

The Gelzinis Group/REAL

Lic. #0225217891

Call Tiffany
  1. 4509 Winnie Drive — photoNew50Active

    $735,000

    5 bd · 4 ba · 4,524 sqft

    4509 Winnie Drive, Chesapeake, VA

    Keller Williams Realty Twn Ctr

  2. 2032 Charwood Drive — photoNew30Active

    $765,425

    5 bd · 4 ba · 3,089 sqft

    2032 Charwood Drive, Chesapeake, VA

    Dragas Companies Realty Inc

  3. 1229 Waters Road — photoNew48Active

    $600,000

    4 bd · 3 ba · 2,211 sqft

    1229 Waters Road, Chesapeake, VA

    Howard Hanna Real Estate Svcs.

  4. 2044 Charwood Drive — photoNew27Active

    $776,315

    4 bd · 4 ba · 3,555 sqft

    2044 Charwood Drive, Chesapeake, VA

    Dragas Companies Realty Inc

  5. 2644 Westwood Ave — photoNew32Active

    $223,000

    3 bd · 2 ba · 1,260 sqft

    2644 Westwood Ave, Chesapeake, VA

    Derek Greene · The Greene Realty Group

  6. 4009 Santa Maria Drive — photoNew34Active

    $395,000

    3 bd · 2 ba · 1,578 sqft

    4009 Santa Maria Drive, Chesapeake, VA

    Southside Real Estate

  7. 2610 Cayce Court — photoNew17Active

    $229,900

    3 bd · 1 ba · 825 sqft

    2610 Cayce Court, Chesapeake, VA

    The Real Estate Group

  8. 1217 Spruce Lane — photoNew4Active

    $515,000

    3 bd · 3 ba · 2,240 sqft

    1217 Spruce Lane, Chesapeake, VA

    EXIT Realty Central

  9. 2039 Charwood Drive — photoNew29Active

    $745,425

    5 bd · 4 ba · 3,089 sqft

    2039 Charwood Drive, Chesapeake, VA

    Dragas Companies Realty Inc

  10. 4908 Apricot Way — photoNew22Active

    $387,900

    3 bd · 3 ba · 1,642 sqft

    4908 Apricot Way, Chesapeake, VA

    Corinth Realty LLC

  11. 4009 San Salvador Drive — photoNew28Active

    $375,000

    3 bd · 2 ba · 1,771 sqft

    4009 San Salvador Drive, Chesapeake, VA

    Creed Realty

  12. 1849 Cedar Road — photoNew2Active

    $325,000

    2 bd · 1 ba · 1,096 sqft

    1849 Cedar Road, Chesapeake, VA

    Green Tree Real Estate Inc

  13. Bellhaven-Multi-Gen — photoNew33Active

    $800,000

    5 bd · 4 ba · 3,240 sqft

    Bellhaven-Multi-Gen, Chesapeake, VA

    BHHS RW Towne Realty

  14. 720 Hunters Quay — photoNew50Active

    $299,000

    3 bd · 3 ba · 1,448 sqft

    720 Hunters Quay, Chesapeake, VA

    LPT Realty LLC

  15. 2369 Old Greenbrier Road — photo27Active

    $260,000

    2 bd · 2 ba · 1,352 sqft

    2369 Old Greenbrier Road, Chesapeake, VA

    World Class Realty & Prop Mgmt

  16. 428 San Roman Drive — photo21Active

    $330,000

    3 bd · 3 ba · 1,528 sqft

    428 San Roman Drive, Chesapeake, VA

    The Real Estate Group

  17. 2033 Charwood Drive — photo29Active

    $624,305

    4 bd · 3 ba · 2,518 sqft

    2033 Charwood Drive, Chesapeake, VA

    Dragas Companies Realty Inc

  18. 145 Sinclair Lane — photo49Active

    $650,000

    5 bd · 3 ba · 3,436 sqft

    145 Sinclair Lane, Chesapeake, VA

    Focus Realty LLC

  19. 1217 Club House Drive — photo48Active

    $600,000

    4 bd · 3 ba · 2,493 sqft

    1217 Club House Drive, Chesapeake, VA

    The Agency

  20. 1540 Eldwick Drive #104 — photo5Active

    $320,130

    2 bd · 2 ba · 1,355 sqft

    1540 Eldwick Drive #104, Chesapeake, VA

    Dragas Companies Realty Inc

  21. 1540 Eldwick Drive #206 — photo5Active

    $295,130

    2 bd · 2 ba · 1,355 sqft

    1540 Eldwick Drive #206, Chesapeake, VA

    Dragas Companies Realty Inc

  22. 1540 Eldwick Drive #307 — photo31Active

    $325,130

    2 bd · 2 ba · 1,386 sqft

    1540 Eldwick Drive #307, Chesapeake, VA

    Dragas Companies Realty Inc

  23. 728 Morely Lane — photo12Active

    $623,360

    4 bd · 3 ba · 2,652 sqft

    728 Morely Lane, Chesapeake, VA

    Dragas Companies Realty Inc

  24. 4025 Ahoy Drive — photo37Active

    $449,900

    4 bd · 3 ba · 2,180 sqft

    4025 Ahoy Drive, Chesapeake, VA

    Redefy Real Estate

12…38

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Listing data & MLS disclosures

Central Virginia Regional MLS
IDX information is provided by the Central Virginia Regional Multiple Listing Service, LLC, from a copyrighted compilation of Listings. All CVR MLS information provided is deemed reliable but is not guaranteed accurate.The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.
The compilation of Listings and each individual Listing are ©2026 Central Virginia Regional Multiple Listing Service, LLC®. All Rights Reserved. Last Updated: 2026-10-26 15:34:38 UTC
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

Chesapeake 12-month median sale price trend

Homes that sold · County records, as of Sep 30, 2026

Median sale price
$389,900$300,000–$540,000 typical range
Price per sq. ft.
$217
Sales
385
Paid in cash
20.5%

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
0.4%

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.
  • Waterfront Homes
  • Your Chesapeake agent

    TG

    Tiffany Gelzinis

    The Gelzinis Group/REAL

    Lic. #0225217891

    Call Tiffany

    Nearby areas

    ZIP codes

    • 23434 (326)
    • 23322 (290)
    • 23451 (247)
    • 23435 (226)
    • 23320 (216)
    • 23456 (210)
    • 23462 (165)
    • 23464 (160)

    Cities

    • Virginia Beach (1,306)
    • Norfolk (712)
    • Suffolk (587)
    • Hampton (485)
    • Portsmouth (337)
  • Newport News (260)
  • Smithfield (107)
  • Carrollton (59)