$594,175Average Value$301Average Price per Sq Ft84Homes 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
Biana Arentz,
an experienced agent in this area.
GreatSchools:
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On average, homes in Chester, MD sell after 303 days on the market compared to the national average of 58 days. The median sale price for homes in Chester, MD over the last 12 months is $644,990, up 11% from the median home sale price over the previous 12 months.
Waterfront Living in Kirwan’s Landing! Set on 1.4 beautifully landscaped acres, this designer-renovated five-bedroom residence with pool and private pier blends elevated coastal style with resort-inspired outdoor living. The outdoor setting feels like a private resort, featuring an oversized saltwater pool with a newly hardscaped stone deck, mature landscaping, fruit trees, and peaceful water
Escape the ordinary in this one-of-a-kind waterfront masterpiece on Cox Creek. Designed for those who refuse to settle for "cookie-cutter," this residence seamlessly blends sophisticated daily living with an unparalleled entertaining layout. The ground-level "Party Zone" is a showstopper, featuring a full bar and lounge with dual garage doors that open directly to a private oasis complete with a
Samantha GrimesChesapeake Real Estate Associates, LLC
Welcome to 200 Newtown Road, a charming home perfectly suited for those looking to enjoy Eastern Shore living. The inviting front porch offers the perfect spot to relax and unwind, while the screened porch provides additional space to enjoy the outdoors in comfort. Inside, you’ll find a generously sized kitchen with room for a table for six, ideal for everyday living and entertaining. A sliding
Welcome home to this beautifully maintained three-bedroom, two-and-a-half-bath home in the sought-after waterfront community of Gibson’s Grant, where lifestyle and a prime Kent Island location come together effortlessly. A welcoming front porch sets the tone, leading into an open-concept main level designed for both everyday living and entertaining. The spacious living room with propane fireplace
Four Seasons @ Kent Island - 55+ Community - Turn-key & 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 white Kitchen with quartz counters, propane gas cooktop
Welcome home to Queens Landing. One bedroom condo with open concept kitchen and living room. The spacious bedroom has plenty of closet space and access to a gated private courtyard with locked storage area. Laundry closet is conveniently situated off the bedroom. Move in ready with fresh paint throughout, new LVP floors in the living areas, and new carpet in the bedroom. Queens Landing is a
Price improvement! Motivated sellers. This custom built home offers the perfect opportunity to live just minutes away from the Chesapeake Bay Bridge and Route 50, offering partial water views and a layout designed for both everyday living and effortless entertaining. The main level features 12 foot ceilings and oversized 6 foot windows that create bright, open living spaces. A vaulted morning
Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom home in the Waterman’s Cove community in Chester. Nestled on a quiet street along scenic Cox Creek, this charming property offers the perfect blend of comfort, style, and convenience. An inviting front porch welcomes you home, while water views greet you upon arrival and can also be enjoyed from the spacious rear composite deck, built
Waterfront Living in Kirwan’s Landing! Set on 1.4 beautifully landscaped acres, this designer-renovated five-bedroom residence with pool and private pier blends elevated coastal style with resort-inspired outdoor living. The outdoor setting feels like a private resort, featuring an oversized saltwater pool with a newly hardscaped stone deck, mature landscaping, fruit trees, and peaceful water
Open airy floorplan on the first floor with private patio. Large gourmet kitchen and dining area, great for entertaining. Wonderful home office for your telecommuting needs. Sumptuous owner’s suite with spa bath . Fantastic great room with large windows for your viewing pleasure. Large secondary bedroom with opt. door to access patio. Pricing is inclusive of an average location premium.
Extra Suite perfect for overnight guests. Private home office off foyer for working from home. Spacious great room with slider to covered patio. Stylish kitchen with island and large pantry. Luxurious primary suite with triple windows. Relaxing primary bath with split vanities and walk-in closet. Convenient 3-car tandem garage for additional storage space.
Extra Suite with full bath for overnight guests. Private home office off foyer for working from home. Spacious great room with adjacent dining area. Beautiful kitchen with large center island. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with optional freestanding tub. Convenient 3-car tandem garage for additional storage.
Formal dining room off foyer for entertaining guests. Stylish kitchen with plenty of cabinet space and large island. Open and airy great room with slider to covered patio. Luxurious primary suite with triple windows. Private primary bath with optional freestanding tub. Convenient 2-car garage with storage space.
Private home office off foyer for working from home. Formal dining room off foyer for entertaining guests. Open and airy floorplan with spacious great room. Striking kitchen with large center island. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with optional freestanding tub. Convenient 3-car tandem garage for additional storage.
Secluded bedroom 2 and bath off foyer for overnight guests.Stylish home office off foyer for working from home.Open & airy great room with adjacent dining area.Striking kitchen with island & tons of cabinet space.Luxurious primary suite with oversized walk-in closet.Palatial primary bath with roomy shower.Convenient 3-car tandem garage for additional storage.
Awesome water front living on Cox Creek! This wonderful, spacious Home is a must see on Kent Islands in popular Bentons Pleasure Neighborhood! HUGE GREAT ROOM AND PRIMARY BEDROOM/BATH ADDITION! Wonderful open concept kitchen/ dining room & great room combo w/stone fireplace, handsome built-in book cases, Brazilian cherry hardwood floors, recessed lighting, custom wet bar, wine cooler and water
Property Id: 2256460SENIOR APTS 62+ AT VILLAGE AT CHESTER. ALL APTS ARE TWO BR, ONE BA. ALL APPLIANCES INCLUDED. PETS ALLOWED. STORAGE SPACE COMES WITH LEASE. ONE YEAR LEASE. ELECTRIC AND CABLE ARE TENANTS BILLS. CLOSE TO ALL YOUR NEEDS. AVAILABLE 06/01/2026.CALL TODAY TO ANSWER ANY QUESTIONS YOU HAVE.BLYTHE LARRIMORE OSM
Your dream retreat awaits in this stunning luxury condo, where modern elegance meets breathtaking natural beauty. Total Turnkey! This exquisite residence features two spacious bedrooms, each with its own en-suite bath, and an additional half bath for guests. The thoughtfully designed office boasts custom built-in cabinets, providing both functionality and style.--Step into the heart of the home,
1 bedroom 1 bath apartment, second floor with balcony. Freshley painted, new LVP flooring. Reserved parking for 1 vehicle, overflow parking for one other vehicle. Water & sewer, trash removal and parking included. Small pets under 35lbs welcomed on a case-by-case basis. Secure building.
Beautiful, four-bedroom, ranch-style home on level lot with spacious, fenced backyard. Kitchen has stainless steel appliances and granite counters/island. Hardwood floors. Energy efficiency improvements include a fully encapsulated, insulated crawlspace and R49 attic insulation. Quiet street. One small dog considered on case-by-case-basis, additional fee and deposit will apply. AVAILABLE JUNE 1,
Spacious well maintained unit. Security entrance, close to shopping with easy access to Rt. 50 and easy distance to Easton or Annapolis. Large living area, large bedrooms, large kitchen. Use owner lease.
Fully renovated 3-bedroom, 1.5-bath home in a prime location just minutes from the Bay Bridge, perfect for enjoying spring and summer on the island. This home features a completely updated interior with a new kitchen, appliances, bathrooms, flooring, paint, and fixtures, offering a fresh, modern feel throughout. The open and airy layout is filled with natural light, creating a bright and inviting
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