Market Overview
Williamsburg is pricier ($370K median vs $350K), a difference of about $20K. Chesterfield moves faster, with homes averaging 17 days on market compared to 28 in Williamsburg. Chesterfield offers a lower entry point at $150K–$900K.
Chesterfield
VA
Williamsburg
VA
Median Price
$350K
$370K
Avg Days on Market
17 days
28 days
Price Range
$150K–$900K
$150K–$1.5M
Top Neighborhoods
Midlothian, Brandermill, Woodlake, Moseley
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 Chesterfield. Top schools in Chesterfield include Cosby High School and Clover Hill High School. In Williamsburg, families look to Lafayette High School and Warhill High School. See Chesterfield schools | See Williamsburg schools
Chesterfield
VA
Williamsburg
VA
Quality Tier
Strong
Strong
Avg Pass Rate
79%
84%
Top Schools
Cosby High School, Clover Hill High School, Midlothian High School
Lafayette High School, Warhill High School, Berkeley Middle School
Pass Rate
Commute
Chesterfield is closer to downtown at ~20 minutes vs ~25 minutes. Neither city has direct Metro access. Major highway access: Chesterfield (I-95, I-295, Rt 1), Williamsburg (I-64, Rt 60, Rt 199).
Chesterfield
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-95, I-295, Rt 1, Rt 10, Rt 360
I-64, Rt 60, Rt 199
Commuter Rail
None
None
VA
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Frequently Asked Questions
Is Chesterfield or Williamsburg more affordable?
Chesterfield is more affordable with a median home price of $350K, compared to $370K in Williamsburg. Both cities offer a wide range of housing options, from condos and townhomes to single-family homes. Chesterfield prices range from $150K–$900K. Williamsburg prices range from $150K–$1.5M.
Which has better schools, Chesterfield or Williamsburg?
Williamsburg has stronger schools overall, with a 84% average pass rate compared to 79% in Chesterfield. Top schools in Chesterfield include Cosby High School and Clover Hill 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, Chesterfield or Williamsburg?
Chesterfield has the shorter commute to downtown at ~20 minutes vs ~25 minutes. Chesterfield has no direct Metro access. Williamsburg has no direct Metro access.
Is Chesterfield or Williamsburg better for families?
Both cities are popular with families. Chesterfield County is one of the fastest-growing counties in the Richmond metro, offering new construction, strong schools, and affordable homes south of the James River. 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.