A Quiet Escape with Easy Access

Chester strikes the perfect balance between calm and convenience. With quick access to Route 50, it’s ideal for commuters, second-home seekers, or anyone wanting to be near the water without sacrificing proximity to major cities.

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Outdoor Paradise

Chester is surrounded by water, with access to the Chester River, Eastern Bay, and a network of creeks and inlets. Boaters, paddleboarders, and anglers love the marinas, boat ramps, and quiet coves. The Cross Island Trail winds through town, offering scenic biking and walking routes through forests, wetlands, and waterfront views.

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Real Estate and Neighborhoods

Chester features a variety of housing options — from luxury waterfront estates in Queen’s Landing and Marling Farms to modern condos and cozy single-family homes near shopping and dining. Many homes feature docks, water views, and access to neighborhood amenities like pools and clubhouses.

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Things to Do in Chester

• Fisherman’s Inn & Crab Deck – A Kent Island staple for fresh seafood and waterfront dining

• Terrapin Nature Park – A serene bayfront park with sandy beaches and trails

• Kent Narrows – Just minutes away, this lively area offers nightlife, restaurants, and boating action

• Queenstown Premium Outlets – Shopping just a short drive from town

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Local Vibe

Chester has a small-town feel with strong community spirit. You’ll find local farmers markets, food truck nights, and holiday events throughout the year — all set against the backdrop of the Chesapeake Bay.

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Whether you're moving full-time or searching for a weekend getaway, Chester, Maryland is a place where the pace slows down and the views open up.

Let GetTheDaisy.com guide you to your next home on Kent Island.