$590,111Average Value$295Average Price per Sq Ft80Homes For Sale
A central spot on Kent Island
Sandwiched between the Chester River and Chesapeake Bay in the heart of Kent Island, the Chester area comprises residential suburbs with close proximity to Highway 50. “It is known for its maritime feel—endless views of water, marinas and local establishments, lining the shoreline,” says Jennifer Heilman, the marketing manager for K. Hovnanian Homes. The area also sits 17 miles from Annapolis, Maryland’s capital city and the home of the United States Naval Academy. With access to both nature and modern conveniences, Chester caters to the laid-back coastal lifestyle without sacrificing convenience.
Sandwiched between the Chester River and Chesapeake Bay in the heart of Kent Island, the Chester area comprises residential suburbs with close proximity to Highway 50.
Downtown Annapolis is a historic city with many shops, events, and tourism.
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Taking off from the Castle Marina
Chester offers a range of parks and recreational activities, both on land and water. Terrapin Nature Park features walking paths, tidal marshes and Chesapeake Bay views. Hikers and cyclists can hit the Cross Island Trail for a paved walkway across Kent Island. Boats take off from Castle Marina to fish and sail along the surrounding waterways. For indoor exercise, Club One Fitness and Aerobics has gym facilities, an aquatic center and group workout classes for members.
Boats take off from Castle Marina to fish and sail along the surrounding waterways.
Terrapin Nature Park features walking paths, tidal marshes and Chesapeake Bay views.
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Luxury condos, suburban streets and waterfront estates
Buyers will find a mix of single-family homes, condos and townhouses on the market. Ranch-style homes and colonials sit alongside New Traditional builds throughout the neighborhood. Properties south of Highway 50 were typically built in the mid-to-late 20th century, while newer communities have been constructed in the northern sector of town throughout the past decade. These more contemporary parts of Chester tend to have brick sidewalks and freshly paved roads, organized into a uniformed grid. The smallest single-family houses sell as low as $125,000, and homes on the water with private docks and sprawling yards can reach $1.5 million. The properties may require additional flood insurance. The smallest condos start in the $200,000 range, and luxury units in new complexes often surpass $1 million.
New luxury condos close to the waterfront in Chester, MD can sell for up to a million dollars.
Waterfront properties in Chester, MD offer a private lifestyle on the Chesapeake Bay.
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Indulging in the Annual Crab Feast
Kent Island host a variety of annual events to bring the community together. The island celebrates the day it was founded in May of 1631 with a parade, historical exhibits and local vendors. Residents can make the quick trip across the Chesapeake Bay Bridge for the Annapolis Baygrass Music Festival, which spotlights bluegrass and jam bands. The Annual Crab Feast at the Kent Island Yacht Club is another tradition with live music and fresh Maryland blue crabs.
St Patricks Day Parade in Annapolis, MD is an annual celebration of the Irish culture.
Chester residents can attend local events like The Maryland Polar Bear Plunge that takes place every winter at the Sandy Point State Park.
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Shopping off Highway 50 and bayside dining in Kent Narrows
Most shopping and dining choices are concentrated in plazas off Highway 50. Safeway, Walgreens and Target are a few of the big-box stores with locations in the neighborhood. Restaurants range from fast and casual options to independently owned classics. Though the Pour House Pub operates by the Castle Marina, most waterfront dining options are just east in Kent Narrows. “Famous restaurants include The Jetty, which features live music most weekends, Bridges and Fisherman’s Inn,” Heilman says.
Indulge in fresh seafood from the Chesapeake bay at the Fisherman's Inn in Chester, MD.
Catch scenic views of the Chesapeake while enjoying a drink or meal at The Jetty in Chester, MD.
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Queen Annes County Public Schools
Prekindergarten through second graders can enroll at Kent Island Elementary, which earns a B on Niche. Bayside Elementary scores an A-minus for third through fifth grade. Stevensville Middle earns a B-plus, and Kent Island High has an A-minus. High schoolers can participate in dozens of clubs and extracurricular activities, from cornhole to the literary magazine.
Stevensville Middle School is a public school serving grades 6-8 in Chester, MD.
Kent Island Elementary School is a public school serving grades pre-k - 5 in Chester, MD.
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Transportation options in Chester
Highway 50 serves as Chester’s main thoroughfare and leads to Annapolis, 17 miles away. The road also contains the Chesapeake Bay Bridge, which Heilman says “is the gateway to Annapolis, Baltimore and Washington, D.C.” Queen Anne’s County buses offer public transportation and connect with neighboring towns. The BWI International Airport is about 30 miles away.
Written By
Grace Pitney
Photography Contributed By
Jesse Son
Video By
Ellie Brown
Interested in learning more about homes in this area?
Reach out to
Melissa Kesner-Fultz,
an experienced agent in this area.
GreatSchools:
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On average, homes in Chester, MD sell after 50 days on the market compared to the national average of 50 days. The median sale price for homes in Chester, MD over the last 12 months is $565,000, up 4% from the median home sale price over the previous 12 months.
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Property Id: 1348539SENIOR APTS 62+ Two-bedroom, one bath on first flooravailable to see July 9th. Appliances included. Small petsallowed. Close to all your needs. Call today .
Experience luxurious, maintenance-free living at K. Hovnanian’s Four Seasons at Kent Island—an active 55+ community on Maryland’s Eastern Shore. This 2-bedroom, 2.5-bath penthouse condo offers sweeping views of the Chester River and refined coastal living. The open floor plan features a gourmet kitchen with quartz countertops, premium appliances, and a large center island, flowing into a
Courtney ChipourasTTR Sotheby's International Realty
Welcome to this charming single-family home in the heart of coveted Four Seasons. Built in 2024, this delightful '55 or better' residence offers two bedrooms and two bathrooms within 2,147 square feet of living space, perfect for anyone seeking comfort and convenience.Key property features include a modern, open design with soaring ceilings ranging 10-13'- throughout the home! Enjoy the
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