Market Overview
Chesapeake is pricier ($380K median vs $370K), a difference of about $10K. Chesapeake moves faster, with homes averaging 22 days on market compared to 28 in Williamsburg. Williamsburg offers a lower entry point at $150K–$1.5M.
Chesapeake
VA
Williamsburg
VA
Median Price
$380K
$370K
Avg Days on Market
22 days
28 days
Price Range
$175K–$1M
$150K–$1.5M
Top Neighborhoods
Great Bridge, Greenbrier, Hickory, Western Branch
Colonial Williamsburg, Kingsmill, New Town, Ford's Colony
Schools
Williamsburg leads on school quality with a 84% average pass rate (rated Strong) compared to 79% in Chesapeake. Top schools in Chesapeake include Grassfield High School and Hickory High School. In Williamsburg, families look to Lafayette High School and Warhill High School. See Chesapeake schools | See Williamsburg schools
Chesapeake
VA
Williamsburg
VA
Quality Tier
Strong
Strong
Avg Pass Rate
79%
84%
Top Schools
Grassfield High School, Hickory High School, Oscar F. Smith High School
Lafayette High School, Warhill High School, Berkeley Middle School
Pass Rate
Commute
Chesapeake is closer to downtown at ~20 minutes vs ~25 minutes. Neither city has direct Metro access. Major highway access: Chesapeake (I-64, I-464, I-264), Williamsburg (I-64, Rt 60, Rt 199).
Chesapeake
VA
Williamsburg
VA
Drive to Downtown
~20 min
~25 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-64, Rt 60, Rt 199
Commuter Rail
None
None
Walkability
Williamsburg is more walkable with a Walk Score of 35 (Car-Dependent), compared to 18 in Chesapeake. Transit scores: Chesapeake (8) vs Williamsburg (10). Walkability varies significantly by neighborhood. Urban corridors like Great Bridge and Colonial Williamsburg score much higher than suburban areas.
Chesapeake
VA
Williamsburg
VA
Walk Score
Transit Score
8
10
Bike Score
22
42
Safety
Chesapeake is rated "Safe" with a total crime rate 13% below Virginia average. Williamsburg is rated "Average" (Near Virginia average). Both cities compare favorably to the Virginia state average. Crime rates vary by neighborhood, so check specific areas when house hunting.
Chesapeake
VA
Williamsburg
VA
Safety Rating
Violent Crime
1.2/1K
1.2/1K
Property Crime
13.5/1K
15.2/1K
vs Virginia Avg
13% below Virginia average
Near Virginia average
VA
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Frequently Asked Questions
Is Chesapeake or Williamsburg more affordable?
Williamsburg is more affordable with a median home price of $370K, 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. Williamsburg prices range from $150K–$1.5M.
Which has better schools, Chesapeake or Williamsburg?
Williamsburg has stronger schools overall, with a 84% average pass rate compared to 79% in Chesapeake. Top schools in Chesapeake include Grassfield High School and Hickory High School. In Williamsburg, standout schools include Lafayette High School and Warhill High School. School quality varies by neighborhood, so check specific school zones when evaluating homes.
Which is easier to commute from, Chesapeake or Williamsburg?
Chesapeake has the shorter commute to downtown at ~20 minutes vs ~25 minutes. Chesapeake has no direct Metro access. Williamsburg has no direct Metro access.
Is Chesapeake or Williamsburg better for families?
Both cities are popular with families. Chesapeake is a sprawling Hampton Roads city offering spacious homes, excellent schools, and access to the Great Dismal Swamp. Williamsburg blends colonial history with modern living. The best choice depends on your priorities: budget, school quality, commute length, and neighborhood feel. smover can help you find a verified agent in either city who specializes in family-friendly neighborhoods.
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 March 2026.