Market Overview
Leesburg is pricier ($870K median vs $380K), a difference of about $490K. Both cities average 22 days on market. Chesapeake offers a lower entry point at $175K–$1M.
Chesapeake
VA
Leesburg
VA
Median Price
$380K
$870K
Avg Days on Market
22 days
22 days
Price Range
$175K–$1M
$150K–$5.8M
Notable Neighborhoods
Great Bridge, Greenbrier, Hickory, Western Branch
Lansdowne, Raspberry Falls, Beacon Hill, Edwards Ferry Road
Schools
Chesapeake has a 79% average SOL pass rate; Leesburg has 88% (2024 state assessment data). Public schools in Chesapeake include Grassfield High School and Hickory High School; in Leesburg, Tuscarora High School and Heritage High School. See Chesapeake schools | See Leesburg schools
Chesapeake
VA
Leesburg
VA
Avg Pass Rate
79%
88%
Public schools
Grassfield High School, Hickory High School, Oscar F. Smith High School
Tuscarora High School, Heritage High School, Smart's Mill Middle School
These are district-wide assessment results. Verify current school assignments, boundaries, and programs with each local district for a specific address.
Commute
Chesapeake is closer to downtown at ~20 minutes vs ~50 minutes. Neither city has direct Metro access. Major highway access: Chesapeake (I-64, I-464, I-264), Leesburg (Rt 7, Rt 15, Dulles Greenway).
Chesapeake
VA
Leesburg
VA
Drive to Downtown
~20 min
~50 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
Rt 7, Rt 15, Dulles Greenway
Commuter Rail
None
None
Walkability
Leesburg is more walkable with a Walk Score of 38 (Car-Dependent), compared to 18 in Chesapeake. Transit scores: Chesapeake (8) vs Leesburg (10). Walkability varies significantly by neighborhood. Urban corridors like Great Bridge and Lansdowne score much higher than suburban areas.
Chesapeake
VA
Leesburg
VA
Walk Score
Transit Score
8
10
Bike Score
22
42
Reported Crime Data
The cited public datasets report city-level violent- and property-crime rates for Chesapeake and Leesburg. These historical figures do not describe a specific address or predict an individual's experience. Review the source period and local agency information for current context.
Chesapeake
VA
Leesburg
VA
Reported Violent Crime
1.2/1K
0.5/1K
Reported Property Crime
13.5/1K
7.8/1K
VA
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Frequently Asked Questions
Is Chesapeake or Leesburg more affordable?
Chesapeake is more affordable with a median home price of $380K, compared to $870K in Leesburg. Both cities offer a wide range of housing options, from condos and townhomes to single-family homes. Chesapeake prices range from $175K–$1M. Leesburg prices range from $150K–$5.8M.
What are the public-school pass rates in Chesapeake and Leesburg?
Chesapeake public schools have a 79% average SOL pass rate; Leesburg has 88% (2024 state assessment data). Public schools in Chesapeake include Grassfield High School and Hickory High School; in Leesburg, Tuscarora High School and Heritage High School. Pass rates reflect district-wide assessment results; check the specific assigned schools for any address.
Which is easier to commute from, Chesapeake or Leesburg?
Chesapeake has the shorter commute to downtown at ~20 minutes vs ~50 minutes. Chesapeake has no direct Metro access. Leesburg has no direct Metro access.
How do Chesapeake and Leesburg compare?
Chesapeake is a sprawling Hampton Roads city offering spacious homes, public schools, and access to the Great Dismal Swamp. Leesburg blends colonial history with modern amenities. 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.
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 September 2026.