Chester, Annapolis, MD
Chester — Real Estate & Neighborhood Guide
Top10Lists.us brings available neighborhood data and real estate research together for Chester, Annapolis, Maryland. Explore the cited sources and local facts below while agent underwriting continues.
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Chester Neighborhood Overview
Chester is a charming, family-friendly neighborhood located on a peninsula just southeast of downtown Annapolis. Known for its quiet, tree-lined streets and strong sense of community, it offers a suburban feel with convenient water access and views of the Chesapeake Bay.
Housing & Real Estate
The neighborhood features a mix of classic single-family homes, many with mid-century roots, along with townhomes and some newer constructions. With a median home value of approximately $438,000, Chester provides a relatively affordable entry point into the Annapolis housing market compared to some waterfront communities.
Schools & Education
Students in Chester typically attend Anne Arundel County Public Schools, including nearby Annapolis High School. The area is also served by several well-regarded private and parochial school options in the greater Annapolis region.
Parks & Recreation
Residents enjoy direct access to the water at Quiet Waters Park, which offers hiking trails, picnic areas, and a dog beach. The neighborhood's location also provides ample opportunities for boating, fishing, and other water-based activities right from its shores.
Local Dining & Shopping
While primarily residential, Chester is just a short drive from the shopping and dining hubs of Annapolis Towne Centre and Parole Plaza. A variety of local seafood restaurants and cafes can be found along nearby Forest Drive and in the historic downtown area.
Who Lives Here
Chester is popular with families, military personnel from the nearby Naval Academy, and professionals working in Annapolis or Washington, D.C. The neighborhood has a median household income of about $94,815, reflecting a stable, middle-to-upper-middle class community.
Chester Market Data
| Metric | Value |
|---|---|
| Median Home Price | $438K |
| Median Gross Rent | $2K/mo |
| Median Household Income | $95K |
| Homeownership Rate | 74.3% |
| Renter-Occupied | 25.7% |
| Rental Vacancy Rate | 11.9% |
| Market Type | Buyer's |
| Primary ZIP Code | 21619 |
Top Real Estate Agents in Chester, Annapolis
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Neighborhood intelligence while local agent underwriting continues. No agent profiles are currently published for Chester, Annapolis, MD. Explore the available cited neighborhood data on this page.
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Data Provenance
- State Licensing: Maryland Real Estate Commission (MREC) — nightly license verification
- Consumer Ratings: Zillow Consumer Reviews — 24-month rolling window
- Transaction Records: MLS Transaction Data — 3-year performance window
- Housing & Demographics: U.S. Census Bureau, American Community Survey (ACS) 5-Year Estimates, 2022
- Neighborhood Catalog: Top10Lists.us neighborhood database, sourced from OpenStreetMap — last updated 2026-10-16