Market Overview
Annapolis is pricier ($510K median vs $310K), a difference of about $200K. Both cities average 25 days on market. Winchester offers a lower entry point at $150K–$700K.
Annapolis
MD
Winchester
VA
Median Price
$510K
$310K
Avg Days on Market
25 days
25 days
Price Range
$200K–$3M+
$150K–$700K
Top Neighborhoods
Downtown Annapolis, Eastport, West Annapolis, Parole
Old Town, Stonewall Industrial, Kernstown, Meadow Branch
Schools
Annapolis has a 80% average SOL pass rate; Winchester has 75% (2024 state assessment data). Public schools in Annapolis include Annapolis High School and Broadneck High School; in Winchester, John Handley High School and Daniel Morgan Middle School. See Annapolis schools | See Winchester schools
Annapolis
MD
Winchester
VA
Avg Pass Rate
80%
75%
Public schools
Annapolis High School, Broadneck High School, Annapolis Middle School
John Handley High School, Daniel Morgan Middle School, Quarles Elementary
Pass Rate
Commute
Winchester is closer to downtown at ~10 minutes vs ~45 minutes. Neither city has direct Metro access. Major highway access: Annapolis (Rt 50, Rt 2, I-97), Winchester (I-81, Rt 7, Rt 11).
Annapolis
MD
Winchester
VA
Drive to Downtown
~45 min
~10 min
Metro Stations
No Metro access
No Metro access
Metro Lines
N/A
N/A
Major Highways
Rt 50, Rt 2, I-97
I-81, Rt 7, Rt 11, Rt 50, Rt 522
Commuter Rail
None
None
MD
Find agents in Annapolis
Browse verified agents with real sales data in Annapolis.
View agentsVA
Find agents in Winchester
Browse verified agents with real sales data in Winchester.
View agentsRelated Comparisons
See how other nearby cities stack up.
Frequently Asked Questions
Is Annapolis or Winchester more affordable?
Winchester is more affordable with a median home price of $310K, compared to $510K in Annapolis. Both cities offer a wide range of housing options, from condos and townhomes to single-family homes. Annapolis prices range from $200K–$3M+. Winchester prices range from $150K–$700K.
What are the public-school pass rates in Annapolis and Winchester?
Annapolis public schools have a 80% average SOL pass rate; Winchester has 75% (2024 state assessment data). Public schools in Annapolis include Annapolis High School and Broadneck 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, Annapolis or Winchester?
Winchester has the shorter commute to downtown at ~10 minutes vs ~45 minutes. Annapolis has no direct Metro access. Winchester has no direct Metro access.
How do Annapolis and Winchester compare?
Annapolis is Maryland's capital and the home of the U. 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.