Market Overview
Annapolis is pricier ($510K median vs $380K), a difference of about $130K. Chesapeake moves faster, with homes averaging 22 days on market compared to 25 in Annapolis. Chesapeake offers a lower entry point at $175K–$1M.
Annapolis
MD
Chesapeake
VA
Median Price
$510K
$380K
Avg Days on Market
25 days
22 days
Price Range
$200K–$3M+
$175K–$1M
Top Neighborhoods
Downtown Annapolis, Eastport, West Annapolis, Parole
Great Bridge, Greenbrier, Hickory, Western Branch
Schools
Annapolis leads on school quality with a 80% average pass rate (rated Strong) compared to 79% in Chesapeake. Top schools in Annapolis include Annapolis High School and Broadneck High School. In Chesapeake, families look to Grassfield High School and Hickory High School. See Annapolis schools | See Chesapeake schools
Annapolis
MD
Chesapeake
VA
Quality Tier
Strong
Strong
Avg Pass Rate
80%
79%
Top Schools
Annapolis High School, Broadneck High School, Annapolis Middle School
Grassfield High School, Hickory High School, Oscar F. Smith High School
Pass Rate
Commute
Chesapeake 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), Chesapeake (I-64, I-464, I-264).
Annapolis
MD
Chesapeake
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-64, I-464, I-264, Rt 168, Rt 17
Commuter Rail
None
None
Walkability
Annapolis is more walkable with a Walk Score of 45 (Car-Dependent), compared to 18 in Chesapeake. Transit scores: Annapolis (18) vs Chesapeake (8). Walkability varies significantly by neighborhood. Urban corridors like Downtown Annapolis and Great Bridge score much higher than suburban areas.
Annapolis
MD
Chesapeake
VA
Walk Score
Transit Score
18
8
Bike Score
52
22
Safety
Chesapeake is rated "Safe" with a total crime rate 13% below Virginia average. Annapolis is rated "Below Average" (34% above Virginia average). Both cities compare favorably to broader regional trends. Crime rates vary by neighborhood, so check specific areas when house hunting.
Annapolis
MD
Chesapeake
VA
Safety Rating
Violent Crime
2.2/1K
1.2/1K
Property Crime
20.5/1K
13.5/1K
vs Virginia Avg
34% above Virginia average
13% below Virginia average
MD
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Frequently Asked Questions
Is Annapolis or Chesapeake more affordable?
Chesapeake is more affordable with a median home price of $380K, 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+. Chesapeake prices range from $175K–$1M.
Which has better schools, Annapolis or Chesapeake?
Annapolis has stronger schools overall, with a 80% average pass rate compared to 79% in Chesapeake. Top schools in Annapolis include Annapolis High School and Broadneck High School. In Chesapeake, standout schools include Grassfield High School and Hickory High School. School quality varies by neighborhood, so check specific school zones when evaluating homes.
Which is easier to commute from, Annapolis or Chesapeake?
Chesapeake has the shorter commute to downtown at ~20 minutes vs ~45 minutes. Annapolis has no direct Metro access. Chesapeake has no direct Metro access.
Is Annapolis or Chesapeake better for families?
Both cities are popular with families. Annapolis is Maryland's capital and the home of the U. Chesapeake is a sprawling Hampton Roads city offering spacious homes, excellent schools, and access to the Great Dismal Swamp. 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.