Market Overview
Annapolis's median sold price is $620K with homes averaging 36 days on market; Chesterfield is at $400K and 37 days (12-month settled sales in smover's records, through Aug 2026). Annapolis is pricier ($620K median vs $400K), a difference of about $220K. Annapolis moves faster, with homes averaging 36 days on market compared to 37 in Chesterfield. Chesterfield offers a lower entry point at $150K–$900K.
Annapolis
MD
Chesterfield
VA
Median Sold Price
12 months through Aug 2026
$620K
$400K
Avg Days on Market
12 months through Aug 2026
36 days
37 days
Price Range
$200K–$3M+
$150K–$900K
Notable Neighborhoods
Downtown Annapolis, Eastport, West Annapolis, Parole
Midlothian, Brandermill, Woodlake, Moseley
Schools
Annapolis has a 80% average SOL pass rate; Chesterfield has 79% (2024 state assessment data). Public schools in Annapolis include Annapolis High School and Broadneck High School; in Chesterfield, Cosby High School and Clover Hill High School. See Annapolis schools | See Chesterfield schools
Annapolis
MD
Chesterfield
VA
Avg Pass Rate
80%
79%
Public schools
Annapolis High School, Broadneck High School, Annapolis Middle School
Cosby High School, Clover Hill High School, Midlothian High School
These are district-wide assessment results. Verify current school assignments, boundaries, and programs with each local district for a specific address.
Commute
Chesterfield is closer to downtown at ~20 minutes vs ~45 minutes. Neither city has direct Metro access. Major highway access: Annapolis (Rt 50, Rt 2, I-97), Chesterfield (I-95, I-295, Rt 1).
Annapolis
MD
Chesterfield
VA
Drive to Downtown
~45 min
~20 min
Metro Stations
No Metro access
No Metro access
Metro Lines
N/A
N/A
Major Highways
Rt 50, Rt 2, I-97
I-95, I-295, Rt 1, Rt 10, Rt 360
Commuter Rail
None
None
MD
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Frequently Asked Questions
Is Annapolis or Chesterfield more affordable?
Chesterfield is more affordable with a median sold price of $400K, compared to $620K in Annapolis (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. Annapolis prices range from $200K–$3M+. Chesterfield prices range from $150K–$900K.
What are the public-school pass rates in Annapolis and Chesterfield?
Annapolis public schools have a 80% average SOL pass rate; Chesterfield has 79% (2024 state assessment data). Public schools in Annapolis include Annapolis High School and Broadneck High School; in Chesterfield, Cosby High School and Clover Hill High School. Pass rates reflect district-wide assessment results; check the specific assigned schools for any address.
Which is easier to commute from, Annapolis or Chesterfield?
Chesterfield has the shorter commute to downtown at ~20 minutes vs ~45 minutes. Annapolis has no direct Metro access. Chesterfield has no direct Metro access.
How do Annapolis and Chesterfield compare?
Annapolis is Maryland's capital and the home of the U. Chesterfield County is one of the fastest-growing counties in the Richmond metro, with new construction and a range of housing prices south of the James River. 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.