Market Overview
Williamsburg's median sold price is $510K with homes averaging 46 days on market; Winchester is at $404K and 45 days (12-month settled sales in smover's records, through Aug 2026). Williamsburg is pricier ($510K median vs $404K), a difference of about $106K. Winchester moves faster, with homes averaging 45 days on market compared to 46 in Williamsburg. Winchester offers a lower entry point at $150K–$700K.
Williamsburg
VA
Winchester
VA
Median Sold Price
12 months through Aug 2026
$510K
$404K
Avg Days on Market
12 months through Aug 2026
46 days
45 days
Price Range
$150K–$1.5M
$150K–$700K
Notable 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
These are district-wide assessment results. Verify current school assignments, boundaries, and programs with each local district for a specific address.
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 sold price of $404K, compared to $510K in Williamsburg (12-month settled sales in smover's records, through Aug 2026). 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 lets you compare agent profiles and available transaction records in either city.
Median sold prices and days on market are 12-month aggregates of settled sales in smover's records, through Aug 2026. 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 September 2026.