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

Save search

Map layers

Safety

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
Homes Under $300K in Chesapeake, VA
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

135 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
Save search
3 bedsNew constructionWith a pool

Homes Under $300K in Chesapeake, VA

Homes Under $300K in Chesapeake, VA

Hide Map
24 of 135 Listings
Map

Homes Under $300K in Chesapeake, VA

24 of 135 Listings

Your Chesapeake agent

TG

Tiffany Gelzinis

The Gelzinis Group/REAL

Lic. #0225217891

Call Tiffany
  1. 904 McKinley Avenue — photoNew31Active

    $299,900

    3 bd · 2 ba · 1,168 sqft

    904 McKinley Avenue, Chesapeake, VA

    World Class Realty

  2. 216 Astra Lane — photo24Active

    $299,900

    3 bd · 3 ba · 1,239 sqft

    216 Astra Lane, Chesapeake, VA

    Boyd Realty Partners

  3. 2456 Whitman Street — photo46Active

    $279,900

    2 bd · 3 ba · 1,314 sqft

    2456 Whitman Street, Chesapeake, VA

    Swell Real Estate Co

  4. 2432 Youngman Road — photo33Active

    $262,500

    2 bd · 1 ba · 825 sqft

    2432 Youngman Road, Chesapeake, VA

    RE/MAX Edge

  5. 1221 Commerce Avenue — photo29Active

    $279,725

    3 bd · 3 ba · 1,280 sqft

    1221 Commerce Avenue, Chesapeake, VA

    Own Real Estate LLC

  6. 3301 Settlement Court — photo27Active

    $275,000

    2 bd · 2 ba · 1,274 sqft

    3301 Settlement Court, Chesapeake, VA

    Real Broker LLC

  7. 2112 Willow Point Arch — photo25Active

    $240,000

    2 bd · 2 ba · 1,244 sqft

    2112 Willow Point Arch, Chesapeake, VA

    BHHS RW Towne Realty

  8. 710 Rue Marseille — photo12Active

    $233,500

    2 bd · 2 ba · 1,105 sqft

    710 Rue Marseille, Chesapeake, VA

    Iron Valley Real Est Norfolk

  9. 710 B Street — photo15Active

    $197,500

    3 bd · 2 ba · 1,372 sqft

    710 B Street, Chesapeake, VA

    Benham Real Estate LLC

  10. 1021 Roundtable Court — photo18Active

    $260,000

    3 bd · 2 ba · 1,496 sqft

    1021 Roundtable Court, Chesapeake, VA

    Iron Valley Real Estate HR

  11. 1054 Wickford Court — photo1Active

    $255,000

    2 bd · 1 ba · 920 sqft

    1054 Wickford Court, Chesapeake, VA

    RE/MAX Alliance

  12. 708 Sail Fish Quay — photo1Active

    $239,900

    2 bd · 2 ba · 1,236 sqft

    708 Sail Fish Quay, Chesapeake, VA

    EXIT Realty Central

  13. 1514 Orchard Grove Drive — photo28Active

    $269,900

    2 bd · 2 ba · 1,383 sqft

    1514 Orchard Grove Drive, Chesapeake, VA

    Realty Specialists

  14. 2901 Bainbridge Boulevard — photo47Active

    $300,000

    3 bd · 1 ba · 1,492 sqft

    2901 Bainbridge Boulevard, Chesapeake, VA

    1st Class Real Estate Integrity

  15. 500 Judah Way — photo27Active

    $270,000

    2 bd · 2 ba · 1,215 sqft

    500 Judah Way, Chesapeake, VA

    Compass Rose Realty

  16. 401 Henley Court — photo12Active

    $229,900

    2 bd · 3 ba · 1,275 sqft

    401 Henley Court, Chesapeake, VA

    Creed Realty

  17. 3004 Kilbride Drive — photo24Active

    $290,000

    3 bd · 1 ba · 950 sqft

    3004 Kilbride Drive, Chesapeake, VA

    Own Real Estate LLC

  18. 1313 Willow Avenue — photo25Active

    $299,900

    3 bd · 1 ba · 1,380 sqft

    1313 Willow Avenue, Chesapeake, VA

    Vylla Home

  19. 3616 Clover Meadows Drive — photo18Active

    $155,000

    2 bd · 1 ba · 851 sqft

    3616 Clover Meadows Drive, Chesapeake, VA

    Keller Williams Coastal Virginia Chesapeake

  20. 708 Nottaway Drive — photo31Active

    $289,900

    2 bd · 3 ba · 1,404 sqft

    708 Nottaway Drive, Chesapeake, VA

    1st Class Real Estate Integrity

  21. 1940 Candlelight Drive — photo28Active

    $240,000

    2 bd · 3 ba · 1,257 sqft

    1940 Candlelight Drive, Chesapeake, VA

    RE/MAX Alliance

  22. 3212 Clover Road E — photo14Active

    $185,000

    2 bd · 2 ba · 1,020 sqft

    3212 Clover Road E, Chesapeake, VA

    Royal Emerald Realty Group

  23. 540 Fernwood Farms Road — photo1Active

    $99,000

    2 bd · 1 ba · 740 sqft

    540 Fernwood Farms Road, Chesapeake, VA

    EXIT Realty Central

  24. 733 Wickford Drive — photo1Active

    $225,000

    3 bd · 2 ba · 1,280 sqft

    733 Wickford Drive, Chesapeake, VA

    LPT Realty LLC

12…6

About Homes Under $300K in Chesapeake, VA

Homes Under $300K in Chesapeake, VA: 135 active listings as of October 18, 2026, 11:54 UTC.

Property types among these 135 listings, by the property type each listing’s MLS reports, spelled as the MLS spells it. Types with fewer than 5 listings, and listings whose MLS reports no type, are not shown, so the shares can total less than 100%.
Property typeListingsShare
Single Family Residence6749.6%
Condominium4533.3%

Explore Chesapeake homes

By price

  • Homes Under $300K
  • Homes Under $400K
  • Homes Under $500K
  • Homes Under $600K
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.
  • Homes Under $700K

    By bedrooms

    • 2 Bedroom Homes
    • 3 Bedroom Homes
    • 4 Bedroom Homes
    • 5 Bedroom Homes

    By type

    • Single-Family Homes
    • Condos

    By feature

    • New Construction Homes
    • Homes with a Pool
    • Waterfront Homes

    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

    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.