Market Overview
Williamsburg is pricier ($370K median vs $310K), a difference of about $60K. Winchester moves faster, with homes averaging 25 days on market compared to 28 in Williamsburg. Winchester offers a lower entry point at $150K–$700K.
Williamsburg
VA
Winchester
VA
Median Price
$370K
$310K
Avg Days on Market
28 days
25 days
Price Range
$150K–$1.5M
$150K–$700K
Top Neighborhoods
Colonial Williamsburg, Kingsmill, New Town, Ford's Colony
Old Town, Stonewall Industrial, Kernstown, Meadow Branch
Schools
Williamsburg has a 84% average SOL pass rate; Winchester has 75% (2024 state assessment data). Public schools in Williamsburg include Lafayette High School and Warhill High School; in Winchester, John Handley High School and Daniel Morgan Middle School. See Williamsburg schools | See Winchester schools
Williamsburg
VA
Winchester
VA
Avg Pass Rate
84%
75%
Public schools
Lafayette High School, Warhill High School, Berkeley Middle School
John Handley High School, Daniel Morgan Middle School, Quarles Elementary
Pass Rate
Commute
Winchester is closer to downtown at ~10 minutes vs ~25 minutes. Neither city has direct Metro access. Major highway access: Williamsburg (I-64, Rt 60, Rt 199), Winchester (I-81, Rt 7, Rt 11).
Williamsburg
VA
Winchester
VA
Drive to Downtown
~25 min
~10 min
Metro Stations
No Metro access
No Metro access
Metro Lines
N/A
N/A
Major Highways
I-64, Rt 60, Rt 199
I-81, Rt 7, Rt 11, Rt 50, Rt 522
Commuter Rail
None
None
VA
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Frequently Asked Questions
Is Williamsburg or Winchester more affordable?
Winchester is more affordable with a median home price of $310K, compared to $370K in Williamsburg. Both cities offer a wide range of housing options, from condos and townhomes to single-family homes. Williamsburg prices range from $150K–$1.5M. Winchester prices range from $150K–$700K.
What are the public-school pass rates in Williamsburg and Winchester?
Williamsburg public schools have a 84% average SOL pass rate; Winchester has 75% (2024 state assessment data). Public schools in Williamsburg include Lafayette High School and Warhill High School; in Winchester, John Handley High School and Daniel Morgan Middle School. Pass rates reflect district-wide assessment results; check the specific assigned schools for any address.
Which is easier to commute from, Williamsburg or Winchester?
Winchester has the shorter commute to downtown at ~10 minutes vs ~25 minutes. Williamsburg has no direct Metro access. Winchester has no direct Metro access.
How do Williamsburg and Winchester compare?
Williamsburg blends colonial history with modern living. Winchester is a historic Shenandoah Valley city known for apple orchards, Civil War heritage, and a revitalized downtown. 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.