Market Overview
Annapolis is pricier ($510K median vs $350K), a difference of about $160K. Chesterfield moves faster, with homes averaging 17 days on market compared to 25 in Annapolis. Chesterfield offers a lower entry point at $150K–$900K.
Annapolis
MD
Chesterfield
VA
Median Price
$510K
$350K
Avg Days on Market
25 days
17 days
Price Range
$200K–$3M+
$150K–$900K
Top Neighborhoods
Downtown Annapolis, Eastport, West Annapolis, Parole
Midlothian, Brandermill, Woodlake, Moseley
Schools
Annapolis leads on school quality with a 80% average pass rate (rated Strong) compared to 79% in Chesterfield. Top schools in Annapolis include Annapolis High School and Broadneck High School. In Chesterfield, families look to Cosby High School and Clover Hill High School. See Annapolis schools | See Chesterfield schools
Annapolis
MD
Chesterfield
VA
Quality Tier
Strong
Strong
Avg Pass Rate
80%
79%
Top Schools
Annapolis High School, Broadneck High School, Annapolis Middle School
Cosby High School, Clover Hill High School, Midlothian High School
Pass Rate
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
Find agents in Annapolis
Browse verified agents with real sales data in Annapolis.
View top agentsVA
Find agents in Chesterfield
Browse verified agents with real sales data in Chesterfield.
View top agentsRelated Comparisons
See how other nearby cities stack up.
Frequently Asked Questions
Is Annapolis or Chesterfield more affordable?
Chesterfield is more affordable with a median home price of $350K, 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+. Chesterfield prices range from $150K–$900K.
Which has better schools, Annapolis or Chesterfield?
Annapolis has stronger schools overall, with a 80% average pass rate compared to 79% in Chesterfield. Top schools in Annapolis include Annapolis High School and Broadneck High School. In Chesterfield, standout schools include Cosby High School and Clover Hill High School. School quality varies by neighborhood, so check specific school zones when evaluating homes.
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.
Is Annapolis or Chesterfield better for families?
Both cities are popular with families. Annapolis is Maryland's capital and the home of the U. 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. 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.