Chesapeake Real Estate
Welcome home to Chesapeake! As Virginia’s second most populous city, Chesapeake is a mix of rural and suburban living, located in Hampton Roads just south of the James River. The sections of Chesapeake are so distinctive, you will feel as if you’re in an entirely separate place in each of them yet all under one umbrella.
Magnificently manicured Riverwalk is inviting and in the Oscar Smith school zone, which boasts an International Baccalaureate Diploma Program at its high school.
Chesapeake was rated the 21st best city in the U.S. by Bloomberg Businessweek in 2011. Its highly ranked schools serve more than 40,000 students. Outdoor parks and trail areas scattered all over the city provide the backdrop for picnics and daytime retreats. Established neighborhoods are filled with residents who take great pride in their yards. With lots of activities, light traffic, easy parking and access to major highways, Chesapeake is a great option to call home!
Magnificently manicured Riverwalk is inviting and in the Oscar Smith school zone, which boasts an International Baccalaureate Diploma Program at its high school.
Chesapeake was rated the 21st best city in the U.S. by Bloomberg Businessweek in 2011. Its highly ranked schools serve more than 40,000 students. Outdoor parks and trail areas scattered all over the city provide the backdrop for picnics and daytime retreats. Established neighborhoods are filled with residents who take great pride in their yards. With lots of activities, light traffic, easy parking and access to major highways, Chesapeake is a great option to call home!
Most Popular
1112 Sir Gawaine DR
$430,000
Most Expensive
4112 Mingo TRL
$2,495,000
Least Expensive
2053 Iowa ST
$95000
Chesapeake Listings Summary
Chesapeake - Town vs. County Stats
Avg Price in Chesapeake: $520,900 / County Avg $524,400
99%
Avg Taxes in Chesapeake: $4,700 / County Avg $4,700
100%
Avg Sq. Ft. in Chesapeake: 2,259 / County Avg 2,269
100%
Avg Price per/sqft in Chesapeake:$231 / County Avg $231
100%
Avg Walkscore in Chesapeake: 14 / County Avg 11
127%
Avg Year Built in Chesapeake: 1997 / County Avg 1997
100%
Avg Days on Website in Chesapeake: 49 / County Avg 49
100%
Chesapeake Real Estate Market Health
New Listings
Foreclosures
Short Sales
| Areas in Chesapeake VA |
|---|
| 134 - Chesapeake |
| Central Chesapeake |
| South Chesapeake |
| West Chesapeake |
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All MLS listings are © 2026 Central Virginia Regional Multiple Listing Service, LLC. All
All or a portion of the multiple listing information is provided by the Williamsburg Multiple Listing Service, LLC, from a copyrighted compilation of listings. All WMLS information provided is deemed reliable but is not guaranteed accurate. The compilation of listings and each individual listing are ©2026 Central Virginia Regional Multiple Listing Service, LLC. All rights reserved.
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Last Updated: September 26, 2026 9:45 AM UTC
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