Room to spread out, strong schools and quick access to Norfolk and Virginia Beach. Chesapeake is suburban living with a country edge.
Chesapeake · Southside
Overview
Chesapeake is a large independent city in Southside Hampton Roads, formed in 1963 from the City of South Norfolk and Norfolk County. Buyers choose it for newer neighborhoods, larger lots, Chesapeake Public Schools, and central access to Norfolk, Virginia Beach and Portsmouth. The real estate tax rate is $1.01 per $100 of assessed value.
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Neighborhoods
A central area along the Intracoastal Waterway, site of the 1775 Battle of Great Bridge and home to Great Bridge High and Middle.
A semi-rural southern area with larger lots and newer subdivisions, served by Hickory High and Middle.
A growing area near the Intracoastal Waterway with a mix of established homes and new construction.
Chesapeake’s main commercial hub near I-64, with shopping, dining and nearby residential neighborhoods.
The city’s western section near Portsmouth and Suffolk, with residential communities, shopping and waterfront neighborhoods.
The historic former City of South Norfolk, which merged with Norfolk County in 1963 to create Chesapeake.
An established, centrally located area close to the Norfolk and Virginia Beach lines.
Schools
| School | Virginia rank |
|---|---|
| Grassfield High | 9th of 331 |
| Hickory High | 16th of 331 |
| Great Bridge High | 71st of 331 |
| Western Branch High | 82nd of 331 |
| Hickory Middle | 22nd of 416 |
| Great Bridge Middle | 24th of 416 |
| Hugo A. Owens Middle | 59th of 416 |
| Greenbrier Middle | 92nd of 416 |
| Jolliff Middle | 104th of 416 |
| Western Branch Middle | 109th of 416 |
SchoolDigger 2026 statewide rankings (source). Zones follow addresses; confirm with Chesapeake Public Schools.
Commute
| To | Off-peak |
|---|---|
| Norfolk Naval Shipyard (Portsmouth) | ~15–25 min |
| Downtown Norfolk | ~20 min |
| Naval Station Norfolk | ~25–30 min |
| NAS Oceana | ~25–30 min |
| NSA Northwest Annex | ~25–30 min |
| Yorktown (via I-664 / MMMBT) | ~50–60 min |
| Yorktown (via I-64 / HRBT) | ~50–60 min |
Approximate off-peak drive times; rush hour and tunnel traffic add time. PCSing? See our military relocation guide.
Living here
More than 112,000 acres of swamp forest with boardwalks, trails and Lake Drummond.
An 8.3-mile paved trail for walking, biking and horseback riding along the old Route 17.
A waterfront park marking the 1775 Battle of Great Bridge, with a replica causeway and history path.
A city park and campground in southern Chesapeake for hiking, fishing and paddling.
A large central park with a dog park and room for festivals and events.
A riverfront park with a dog park, boat ramp and waterfront views.
Get a value based on what actually sold near you this season, from a local team that knows the neighborhoods.
Questions
Chesapeake is an independent city, not part of any county. It was formed in 1963 when the City of South Norfolk merged with Norfolk County. At about 341 square miles, it is one of the largest cities by area in the country, which is why so much of it still feels open.
Chesapeake Public Schools serves the whole city. On SchoolDigger’s 2026 Virginia rankings, Grassfield High ranked 9th and Hickory High 16th of 331 high schools. Hickory Middle and Great Bridge Middle ranked 22nd and 24th of 416 middle schools.
Chesapeake’s real estate tax rate is $1.01 per $100 of assessed value. On a home assessed at $375,000, that comes to about $3,787.50 a year, or roughly $316 a month. Rates are set each spring with the city budget, so confirm the current rate before closing.
From much of Chesapeake, Norfolk Naval Shipyard in Portsmouth is about 15 to 25 minutes away off-peak. Naval Station Norfolk is closer to 25 to 30 minutes. Traffic at the High Rise Bridge and on I-64 and I-464 can add time at rush hour.
Some parts of Chesapeake sit near rivers, the Intracoastal Waterway and low-lying land, and lenders generally require flood insurance for homes in FEMA high-risk zones. Check the FEMA flood map for any address you are considering. Chesapeake is a Class 7 Community Rating System community, which gives eligible NFIP policies a 15% discount.
More in the Southside
Key Areas
Figures were checked in October 2026. Tax rates, school rankings and drive times change; confirm them for a specific address before you buy.
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