Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings

Registered offenders on the map

Save search

Registered offenders on the map

Safety & registry resources

Review official public-safety information for any area from these government sources:

  • U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
  • FBI: state sex-offender registry directory
Chesapeake, VA Homes for Sale — Page 30 | Realty.com
Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings
  • Commercial

Registered offenders on the map

Save search
3 bedsNew construction
902 listings
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
With a pool

Homes for Sale in Chesapeake, VA

Homes for Sale in Chesapeake, VA

Hide Map
24 of 902 Listings
Map

Homes for Sale in Chesapeake, VA

24 of 902 Listings

Your Chesapeake agent

TG

Tiffany Gelzinis

The Gelzinis Group/REAL

Lic. #0225217891

Call Tiffany
  1. 109 Ballahack Rd — photo46Active

    $916,000

    3 bd · 2 ba · 2,734 sqft

    109 Ballahack Rd, Chesapeake, VA

  2. 1915 Canning Pl — photo48Active

    $468,900

    3 bd · 2 ba · 1,982 sqft

    1915 Canning Pl, Chesapeake, VA

  3. 2164 Edwin Dr — photo25Active

    $577,740

    3 bd · 3 ba · 2,642 sqft

    2164 Edwin Dr, Chesapeake, VA

  4. 2462 Leytonstone Dr — photo23Active

    $314,900

    3 bd · 2 ba · 1,870 sqft

    2462 Leytonstone Dr, Chesapeake, VA

  5. 700 Canoe St — photo32Active

    $500,000

    5 bd · 3 ba · 3,166 sqft

    700 Canoe St, Chesapeake, VA

  6. 2806 Baldwin Dr — photo32Active

    $284,000

    2 bd · 2 ba · 1,314 sqft

    2806 Baldwin Dr, Chesapeake, VA

  7. 4309 East Rd — photo42Active

    $440,000

    3 bd · 1 ba · 1,341 sqft

    4309 East Rd, Chesapeake, VA

  8. 1806 Beckwood Cmn — photo20Active

    $277,000

    3 bd · 2 ba · 1,275 sqft

    1806 Beckwood Cmn, Chesapeake, VA

  9. 2861 Raccoon Trl — photo3Active

    $1,069,417

    5 bd · 4 ba · 3,570 sqft

    2861 Raccoon Trl, Chesapeake, VA

  10. 1533 Sanderson Rd — photo3Active

    $997,724

    5 bd · 4 ba · 3,585 sqft

    1533 Sanderson Rd, Chesapeake, VA

  11. 858 Waters Rd — photo34Active

    $525,000

    4 bd · 2 ba · 1,736 sqft

    858 Waters Rd, Chesapeake, VA

  12. 2116 Cedar Rd — photo38Active

    $647,499

    5 bd · 3 ba · 2,500 sqft

    2116 Cedar Rd, Chesapeake, VA

  13. 1910 Bexley Ln — photo45Active

    $570,000

    4 bd · 2 ba · 2,530 sqft

    1910 Bexley Ln, Chesapeake, VA

  14. 4308 Galston Ct — photo49Active

    $565,000

    5 bd · 2 ba · 3,229 sqft

    4308 Galston Ct, Chesapeake, VA

  15. 421 Plummer Dr — photo18Active

    $440,000

    6 bd · 3 ba · 2,657 sqft

    421 Plummer Dr, Chesapeake, VA

  16. 2217 Nantucket Ave — photo50Active

    $649,900

    4 bd · 2 ba · 2,913 sqft

    2217 Nantucket Ave, Chesapeake, VA

  17. 145 Sinclair Ln — photo50Active

    $719,900

    5 bd · 3 ba · 3,436 sqft

    145 Sinclair Ln, Chesapeake, VA

  18. 2116 Sanderson Rd — photo3Active

    $988,613

    4 bd · 3 ba · 3,424 sqft

    2116 Sanderson Rd, Chesapeake, VA

  19. 2857 Raccoon Trl — photo4Active

    $894,595

    5 bd · 3 ba · 3,026 sqft

    2857 Raccoon Trl, Chesapeake, VA

  20. 2720 Deerfield Cres — photo50Active

    $539,999

    4 bd · 2 ba · 2,574 sqft

    2720 Deerfield Cres, Chesapeake, VA

  21. 2415 Fieldsway Dr — photo30Active

    $373,000

    3 bd · 2 ba · 1,750 sqft

    2415 Fieldsway Dr, Chesapeake, VA

  22. 4316 Hillingdon Bnd 305 — photo45Active

    $220,000

    2 bd · 2 ba · 1,362 sqft

    4316 Hillingdon Bnd 305, Chesapeake, VA

  23. 316 Esplanade Pl — photo22Active

    $315,000

    2 bd · 2 ba · 1,352 sqft

    316 Esplanade Pl, Chesapeake, VA

  24. 300 San Roman Dr — photo41Active

    $295,000

    2 bd · 1 ba · 1,136 sqft

    300 San Roman Dr, Chesapeake, VA

1…293031…38

Explore Chesapeake homes

By price

  • Under $300K
  • Under $500K
  • Under $700K
  • Luxury

By bedrooms

  • 2 beds
  • 3 beds
  • 4 beds
  • 5 beds

By type

  • Single family
  • Townhomes
  • Condos
  • Manufactured homes
  • Multi-family homes
  • Co-ops
Realty.com

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

Equal Housing OpportunityEqual Housing Lender

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

© 2026 Realty.com. All rights reserved.·Privacy·Terms·California Privacy Rights·Accessibility·Licensing

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.
  • By feature

    • New construction
    • With a pool

    Your Chesapeake agent

    TG

    Tiffany Gelzinis

    The Gelzinis Group/REAL

    Lic. #0225217891

    Call Tiffany

    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
    -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.

    Nearby areas

    ZIP codes

    • 23434 (285)
    • 23451 (260)
    • 23322 (239)
    • 23320 (223)
    • 23456 (204)
    • 23462 (162)
    • 23321 (158)
    • 23435 (157)

    Cities

    • Virginia Beach (1,245)
    • Norfolk (718)
    • Hampton (502)
    • Suffolk (469)
    • Portsmouth (336)
    • Newport News (266)
    • Smithfield (89)
    • Carrollton (54)