$591,404Average Value$294Average Price per Sq Ft59Homes 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
Jim Davidson,
an experienced agent in this area.
GreatSchools:
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On average, homes in Chester, MD sell after 100 days on the market compared to the national average of 53 days. The median sale price for homes in Chester, MD over the last 12 months is $627,400, up 9% from the median home sale price over the previous 12 months.
**OPEN HOUSE Sunday, 1/11/26 from 11 - 1PM ** New Listing! Four Seasons @ Kent Island - 55+ Community - Turnkey & Lovely 2nd Floor Condo in Elevator Building with 1 Car Garage plus 1 Car Outdoor Parking and Private, Secure Indoor Storage Area. This Chester Model offers 1900 sf with pond view and winter water views of Macum Creek. Enter to find an expansive, open floor plan featuring a beautiful
This stunning Taylor home offers an inviting open floor plan designed for both comfort and functionality. Featuring 2 bedrooms, 2.5 baths, and a spacious 3-car garage, this home perfectly blends everyday ease with elevated style. Highlights include a dedicated home office, a cozy screened patio for outdoor relaxation, and a dramatic 2-story stone fireplace that serves as the heart of the great
Introducing the Kerr with a projected settlement date of January 2026. This home offers 3 bedrooms, 3 baths, and a spacious 3-car garage. Notable features include a home office, a screened patio, and a striking 1-story fireplace. The kitchen is beautifully appointed with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lights, and a tile backsplash,
If you’ve ever dreamed of waking up and feeling like you’re on vacation—but with the comforts of home—welcome to 135 Nauset Lane.Tucked into a quiet corner of Kent Island’s Four Seasons community, this home isn’t just beautiful—it’s part of a lifestyle that’s hard to find and even harder to leave. The sellers were first drawn here by the energy of the community and the resort-style
NO HOA! Beautifully maintained 2017-built home offering 3 bedrooms and 2.5 baths. Features a fenced yard for kids and pets, screened porch, large yard with concrete pad, and small storage shed. Temperature-controlled concrete crawl space, new sump pump, and septic contract for easy, worry-free living. Conveniently located near shopping and everything Kent Island has to offer.
**OPEN HOUSE Sunday, 1/11/26 from 11 - 1PM ** New Listing! Four Seasons @ Kent Island - 55+ Community - Turnkey & Lovely 2nd Floor Condo in Elevator Building with 1 Car Garage plus 1 Car Outdoor Parking and Private, Secure Indoor Storage Area. This Chester Model offers 1900 sf with pond view and winter water views of Macum Creek. Enter to find an expansive, open floor plan featuring a beautiful
Super Cute Condo in popular Queen's Landing with views of the pond from your private back patio. Laundry in unit and 2 storage closets on patio along with convenient parking. Community features pool, tennis, fitness, walking paths, and access to cross island trail as well as restaurants and local marinas.
Modernized single-level living in the desirable Harbor View community! This beautifully refreshed 3BR/2BA rancher offers a sleek, turnkey lifestyle on Kent Island. The bright interior is highlighted by brand-new luxury vinyl plank (LVP) flooring and a stunning kitchen featuring premium stone countertops and a suite of stainless steel appliances. The primary bedroom provides a private retreat with
WATERFRONT!!! Price reduction! Super rental as a full-time residence or as a weekend or holiday getaway! Watch the sun rise over the Chester River! It offers one bedroom and one bath, 724 square feet, with a living room adjoining the compact, well laid-out kitchen. A patio for relaxing moments is entered from a sliding glass door on the waterside. Minutes from the Bay Bridge, you can be in this
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