Chester MD Real Estate & Homes for Sale

Quick Answer

Is Chester good for homebuyers? Chester is a water-oriented Kent Island community known for its marinas, the scenic Cross Island Trail, and convenient shopping along the US-50/301 corridor. Home options range from waterfront estates to townhomes and condos, all within minutes of the Bay Bridge for easy access to Annapolis and beyond.

Who’s it best for?

Boaters, anglers, commuters to Annapolis/Baltimore/D.C., and buyers seeking waterfront or low-maintenance living.

Vibe in one line

Laid-back island living with marina views, trails, and quick bridge access to the city.

Updated · 6–8 min read

Key Facts

County: Queen Anne's

ZIP Code: 21619

Landmarks/Trails: Cross Island Trail; Kent Narrows/Chester marinas; Chesapeake Heritage & Visitor Center

Main Routes: US-50/301; MD-18; local marina roads

Property Types

  • Marina-adjacent condos/townhomes — Lock-and-leave options near docks and dining.
  • Single-family — Ranchers/colonials with renovations common.
  • Micro-neighborhoods to watch — Kent Narrows, Bayside, Queen Anne Colony (vicinity).
  • Water-amenity lifestyle — Community beaches/piers, kayak launches, and marina access.
  • Water-privileged or waterfront — Community beaches/piers and select deep-water frontage—verify depth/exposure.

Popular Searches

  • Water-view condos — Near marinas and Narrows.
  • Homes with slip access — Check HOA/marina policies.
  • Kent Narrows homes — Inventory varies; verify HOA/amenities.
  • Bayside homes — Inventory varies; verify HOA/amenities.
  • Queen Anne Colony (vicinity) homes — Inventory varies; verify HOA/amenities.
  • Homes near marinas/ramps — Verify water depth/exposure and permits.
  • New listings this week — See current listings · Book a tour.

Local Highlights

  • Kent Narrows Waterfront: Seafood restaurants, marinas, and lively nightlife along the Kent Narrows channel. (Kent Narrows)
  • Chesapeake Bay Environmental Center (CBEC): 510-acre preserve with trails, birding, kayaking, and environmental education programs. (CBEC)
  • Terrapin Nature Park: Bayfront park with sandy beach, walking trails, and Chesapeake Bay Bridge views. (Queen Anne’s County Parks)
  • Cross Island Trail: Scenic paved trail connecting Terrapin Park to Kent Narrows, ideal for walking and biking. (TrailLink)
  • Ferry Point Park: Boardwalks, shoreline access, and views at the Kent Narrows Environmental Center. (Queen Anne’s County Parks)
  • Queenstown Premium Outlets: Nearby outlet shopping with national brands and seasonal deals. (Queenstown Outlets)
  • Chester River & Bay Access: Public boat ramps and marinas serving boaters and anglers. (Google Maps)
  • Kent Narrows Public Landing & Boat Ramp: County-maintained ramp with fishing, crabbing, and kayak access. (Queen Anne’s County Parks)
  • Matapeake Beach & Clubhouse (Stevensville): Bayfront swimming beach with pier and dog-friendly trail. (Queen Anne’s County Parks)
  • Schools: Served by Queen Anne’s County Public Schools—confirm boundaries by address. (QACPS Locator)
  • Dining & Local Flavor: Waterfront seafood, crab houses, and dock bars—browse current options via Yelp, TripAdvisor, Google Maps.

Transit & Commute

  • Highways: Immediate access to US-50/301
  • Boating: Marinas and waterfront dining at Kent Narrows

Schools

  • Kent Island High School — QACPS
  • Matapeake Middle — QACPS

FAQ

  • Is Chester part of Kent Island? Yes—eastern side near Kent Narrows.
  • Typical drive times (off-peak)? Annapolis: 20–30 min; Baltimore: 40–60 min (bridge dependent); BWI: 35–50 min
  • Bay Bridge commute tips? Travel off-peak when possible; check bridge alerts during weekends and rush hours.
  • Is Chester good for commuters? Yes—multiple corridors and transit options; verify typical times at your hour and route.
  • Which schools serve Chester? Assignments vary by address—verify with the district boundary tools before you tour.
  • Are there walkable parks or trails? Yes—most neighborhoods are within a short drive to local parks/trails; proximity varies by pocket.
  • Are HOA or condo fees common? In many planned communities and condo clusters—compare amenities, rules, and fees before buying.
  • How competitive is the market right now? Updated, well-located homes can draw strong interest; set alerts and be ready to tour quickly.
  • Any inspection or insurance considerations? Older homes may need system updates; water-adjacent pockets can involve flood/surge coverage—verify per property.
  • What price ranges are typical? Varies by property type and micro-area; review recent comps and set real-time alerts for your budget.
  • Which communities have beaches or boat ramps? Several HOAs offer beaches/ramps and nearby marinas; confirm access, fees, and any waitlists.
  • Bay Bridge timing tips? Travel off-peak when possible and check alerts during rush hours and summer weekends.
  • Are there public marinas and waterfront dining at Kent Narrows? Yes—Kent Narrows offers multiple marinas and restaurants; amenities vary by operator/HOA (verify slips and fees with each property/association).
  • Is bridge traffic a factor from Chester? Yes—allow extra time during peak/seasonal periods; see MDTA advisories (Source: https://mdta.maryland.gov/blog-category/bay-bridge-traffic-advisories).
  • How do I confirm school assignments for Chester addresses? Check Queen Anne’s County Public Schools attendance zones (Source: https://www.qacps.org/wp-content/uploads/2022/02/6-Elementary-School-Zones.pdf).

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Written by Lifetime Client Group

Trusted Maryland real estate experts helping buyers and sellers make smart moves.

School and business data provided by Attom Data.

MD

Chester

Welcome to Chester, our local agent will provide you a professional market report and accurate local info. Please contact us at anytime.
$803,200
Average Sales Price
$700,000
Median Sales Price
111
Total Listings
4,245
Population Data provided by Attom Data

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RECENTLY SOLD LISTINGS

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Single Family Home

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14.3%

listing detail

Average Median
Bathrooms 2.98 3
Bedrooms 2.93 3
Year Built 2007 2017
Lot Size 0.47 Acres 7,405 Sqft
Taxes $4,550 $3,795
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demographics

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Population:

4.2K

Density:

833.7

Households:

1.7K

Gender

49%
Male
51%
Female
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