Chesapeake combines quiet neighborhoods, top-rated schools, and a central Hampton Roads location — making it one of the most desirable cities for families and professionals alike.

Best Places to Live in Chesapeake, VA

Why Buy in Chesapeake, VA?

Chesapeake offers the space and suburban feel many buyers are looking for — without sacrificing convenience. With highly rated schools, large homes, and easy access to nearby cities, it’s a smart choice for growing families and commuters alike.

Highlights:

One of the safest and fastest-growing cities in Hampton Roads
Excellent public schools, especially in Grassfield, Great Bridge, and Hickory
Family-oriented, with parks, trails, and newer homes
Ideal for commuters — with quick access to I-64, I-464, and I-168
Great for new construction buyers and those needing space

Chesapeake, VA Top Neighborhoods

Grassfield

Best For: Families, school-focused buyers
Highlights: Newer homes, highly ranked schools, parks and sports fields

Great Bridge

Best For: Commuters, families, traditional neighborhoods
Highlights: Central location, top schools, mix of home styles

Hickory

Best For: Buyers looking for space and privacy
Highlights: Large lots, semi-rural, newer construction, great schools

Greenbrier

Best For: Shopping, accessibility, townhomes and condos
Highlights: Walkability, proximity to Greenbrier Mall, newer developments

Western Branch

Best For: Commuters to Portsmouth/Suffolk, affordability
Highlights: Quiet neighborhoods, established homes, good schools

Not sure where to live?

Not sure which part of Hampton Roads fits your goals? Tell us what matters most – schools, commute, or price – and we’ll guide you to the right fit.