Market Overview
Leesburg is pricier ($870K median vs $350K), a difference of about $520K. Chesterfield moves faster, with homes averaging 17 days on market compared to 22 in Leesburg. Chesterfield offers a lower entry point at $150K–$900K.
Chesterfield
VA
Leesburg
VA
Median Price
$350K
$870K
Avg Days on Market
17 days
22 days
Price Range
$150K–$900K
$150K–$5.8M
Top Neighborhoods
Midlothian, Brandermill, Woodlake, Moseley
Lansdowne, Raspberry Falls, Beacon Hill, Edwards Ferry Road
Schools
Leesburg leads on school quality with a 88% average pass rate (rated Excellent) compared to 79% in Chesterfield. Top schools in Chesterfield include Cosby High School and Clover Hill High School. In Leesburg, families look to Tuscarora High School and Heritage High School. See Chesterfield schools | See Leesburg schools
Chesterfield
VA
Leesburg
VA
Quality Tier
Strong
Excellent
Avg Pass Rate
79%
88%
Top Schools
Cosby High School, Clover Hill High School, Midlothian High School
Tuscarora High School, Heritage High School, Smart's Mill Middle School
Pass Rate
Commute
Chesterfield is closer to downtown at ~20 minutes vs ~50 minutes. Neither city has direct Metro access. Major highway access: Chesterfield (I-95, I-295, Rt 1), Leesburg (Rt 7, Rt 15, Dulles Greenway).
Chesterfield
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-95, I-295, Rt 1, Rt 10, Rt 360
Rt 7, Rt 15, Dulles Greenway
Commuter Rail
None
None
VA
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Frequently Asked Questions
Is Chesterfield or Leesburg more affordable?
Chesterfield is more affordable with a median home price of $350K, compared to $870K in Leesburg. Both cities offer a wide range of housing options, from condos and townhomes to single-family homes. Chesterfield prices range from $150K–$900K. Leesburg prices range from $150K–$5.8M.
Which has better schools, Chesterfield or Leesburg?
Leesburg has stronger schools overall, with a 88% average pass rate compared to 79% in Chesterfield. Top schools in Chesterfield include Cosby High School and Clover Hill High School. In Leesburg, standout schools include Tuscarora High School and Heritage High School. School quality varies by neighborhood, so check specific school zones when evaluating homes.
Which is easier to commute from, Chesterfield or Leesburg?
Chesterfield has the shorter commute to downtown at ~20 minutes vs ~50 minutes. Chesterfield has no direct Metro access. Leesburg has no direct Metro access.
Is Chesterfield or Leesburg 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. Leesburg blends colonial history with modern amenities. 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.