Market Overview
Chesapeake is pricier ($380K median vs $350K), a difference of about $30K. Chesterfield moves faster, with homes averaging 17 days on market compared to 22 in Chesapeake. Chesterfield offers a lower entry point at $150K–$900K.
Chesapeake
VA
Chesterfield
VA
Median Price
$380K
$350K
Avg Days on Market
22 days
17 days
Price Range
$175K–$1M
$150K–$900K
Top Neighborhoods
Great Bridge, Greenbrier, Hickory, Western Branch
Midlothian, Brandermill, Woodlake, Moseley
Schools
Chesapeake has a 79% average SOL pass rate; Chesterfield has 79% (2024 state assessment data). Public schools in Chesapeake include Grassfield High School and Hickory High School; in Chesterfield, Cosby High School and Clover Hill High School. See Chesapeake schools | See Chesterfield schools
Chesapeake
VA
Chesterfield
VA
Avg Pass Rate
79%
79%
Public schools
Grassfield High School, Hickory High School, Oscar F. Smith High School
Cosby High School, Clover Hill High School, Midlothian High School
Pass Rate
Commute
Chesterfield is closer to downtown at ~20 minutes vs ~20 minutes. Neither city has direct Metro access. Major highway access: Chesapeake (I-64, I-464, I-264), Chesterfield (I-95, I-295, Rt 1).
Chesapeake
VA
Chesterfield
VA
Drive to Downtown
~20 min
~20 min
Metro Stations
No Metro access
No Metro access
Metro Lines
N/A
N/A
Major Highways
I-64, I-464, I-264, Rt 168, Rt 17
I-95, I-295, Rt 1, Rt 10, Rt 360
Commuter Rail
None
None
VA
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Frequently Asked Questions
Is Chesapeake or Chesterfield more affordable?
Chesterfield is more affordable with a median home price of $350K, compared to $380K in Chesapeake. Both cities offer a wide range of housing options, from condos and townhomes to single-family homes. Chesapeake prices range from $175K–$1M. Chesterfield prices range from $150K–$900K.
What are the public-school pass rates in Chesapeake and Chesterfield?
Chesapeake public schools have a 79% average SOL pass rate; Chesterfield has 79% (2024 state assessment data). Public schools in Chesapeake include Grassfield High School and Hickory High School; in Chesterfield, Cosby High School and Clover Hill High School. Pass rates reflect district-wide assessment results; check the specific assigned schools for any address.
Which is easier to commute from, Chesapeake or Chesterfield?
Chesterfield has the shorter commute to downtown at ~20 minutes vs ~20 minutes. Chesapeake has no direct Metro access. Chesterfield has no direct Metro access.
How do Chesapeake and Chesterfield compare?
Chesapeake is a sprawling Hampton Roads city offering spacious homes, public schools, and access to the Great Dismal Swamp. Chesterfield County is one of the fastest-growing counties in the Richmond metro, offering new construction, public schools, and affordable homes south of the James River. The right choice depends on your priorities: budget, commute length, home types, and neighborhood feel. smover can connect you with a verified agent in either city.
Market data verified by smover using real transaction records. School data from Virginia DOE, Maryland MSDE, and DC OSSE public reports. Property tax rates from Virginia Dept. of Taxation (2024). Walkability scores from Walk Score (2024). Crime data from FBI UCR and Virginia State Police (2023). Commute times are approximate rush-hour estimates. Updated June 2026.