$606,091Average Value$306Average Price per Sq Ft87Homes 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
Matthew Wyble,
an experienced agent in this area.
GreatSchools:
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On average, homes in Chester, MD sell after 375 days on the market compared to the national average of 55 days. The median sale price for homes in Chester, MD over the last 12 months is $669,200, up 13% from the median home sale price over the previous 12 months.
Open House Sunday, Aug 30 from 12-2PM - Bayside In Kent Island Located in the Popular Community of Bayside just minutes from the Bay Bridge and all Kent Island has to offer! This lovely End Unit Townhome with Garage is very well maintained and in move in condition. It features 3 levels above ground. Enter at ground level which includes Garage, Foyer, Laundry and a bright and sunny 1st floor
BACK on the MARKET. GREAT OPPORTUNITY at THIS PRICE.This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wildlife in all seasons. Easy walk to Kayak launch and creek. With nearly 2000 square feet of open living space this home has a great layout for entertaining family and friends. The spacious great room, adjacent to the dining area
OPEN SATURDAY 12-3PM. Kent Island Living at Its Best! Welcome to this stunning colonial-style home nestled in the desirable Clayborne Woods community in Chester. Offering 2,332 square feet of thoughtfully designed living space, this beautifully maintained residence blends elegance with modern updates and everyday comfort. From the inviting covered front porch with newly replaced fiberglass
Four Seasons @ Kent Island - 55+ Community - Reduced! * 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
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
Open House Sunday, Aug 30 from 12-2PM - Bayside In Kent Island Located in the Popular Community of Bayside just minutes from the Bay Bridge and all Kent Island has to offer! This lovely End Unit Townhome with Garage is very well maintained and in move in condition. It features 3 levels above ground. Enter at ground level which includes Garage, Foyer, Laundry and a bright and sunny 1st floor
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.
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
Kent Island Waterfront on Cox Creek!! Public Sewer available, road frontage is 45ft. This is a flag lot with opening on the waterfront of 108 ft. This property does not have a pier, so please do not go on pier. This is the perfect lot to build your dream home. The natural environment has wildlife and waterfowl and as well as good fishing and crabbing. If you want a piece of the shore-life this is
Seller is offering up to $9,000 toward the buyer's interest rate buydown or closing costs. That's real money applied at settlement, and on a home already carrying over $50,000 in owner improvements, it's the kind of combination that doesn't sit long.This is a renovated end-unit townhome with three bedrooms and three and a half baths in Bayside, an established waterfront community along
Nestled in the heart of Kent Island, this charming 3 Bedroom, 2 Full Bathroom townhome with Bonus Room, offers the perfect blend of comfort, convenience, and peaceful surroundings. Located in the desirable Bridgepointe community, this home features major updates including a newer roof, HVAC system, and water heater providing peace of mind for years to come. Enjoy a private backyard setting that
This is What You Have Been Looking For + More! You'll love this Gorgeous 2600 sf Condo in Four Seasons @ Kent Island, a Premiere 55+ Community! This is a rare and quality offering of this modern and bright 2nd Floor end unit condo in a resort style, waterfront community. This is the largest condo model built here by K.Hovnanian called The Severn with 3 Bedrooms and 2.5 Baths. It is being offered
Make your new home on Kent Island at The Promenade at Red Apple Town Center, and you will have found the ideal setting that combines the best of city and beach living. With easy access to Route 50 and just a short drive from Annapolis, Easton, and Centreville, adventure is always right around the corner.When you’re not exploring the surrounding area, at home you’ll enjoy premium interior finishes
Apartment #C-Upstairs all on one level 4-bedroom, 2 bath unit, just painted and new LVP flooring & carpet added. Plenty of parking in building lot. Easy access to Rt 50, close to shopping, restaurants. Trash, parking, grounds maintenance and water sewer included in rent. One pet under 35lbs allowed with pet rent.
1500 square feet, 3 bedrooms, 1.5 baths. Large rooms. Kitchen with pantry and full dining area. New carpet and laminate flooring. Secured entrance. Townhouse-style apartment (living space downstairs, bedrooms upstairs) located on the second and third floors of the Chester Centre building.
Welcome to Kent Island living at its finest! This beautifully maintained end-unit townhome offers the perfect blend of coastal charm and modern comfort. The upper level features two spacious primary bedroom suites, each with its own private full bathroom, providing an ideal layout for homeowners and guests alike. Enjoy peaceful mornings and relaxing evenings from one of two private exterior decks
1500 square feet, 3 bedrooms, 1.5 baths. Large rooms. Kitchen with pantry and full dining area. New carpet and laminate flooring. Secured entrance. Townhouse-style apartment (living space downstairs, bedrooms upstairs) located on the second and third floors of the Chester Centre building.
Highly sought after first-floor condo shows like a model home. Love Where You Live! Experience resort-style living that blends comfort, luxury, and convenience—just steps from the waterfront. Enjoy peaceful mornings without the disruption of construction nearby. Move-in ready and meticulously maintained, featuring numerous upgrades throughout. Step inside to an open, light-filled layout enhanced
Craving a WATERFRONT rental with pier, 15,000 lb boat lift, jet-ski lift, nearly 200 feet of shoreline, & sandy beach area on .4 acres just 5 mins from Bay Bridge? Welcome home! Enjoy this 6-Month WATERFRONT playground! Nearly 200' of shoreline with Private, sandy beach, 120' Pier with Boat Lift AND Jet-ski lift, panoramic views of coveted Cox Creek. With generous water depth, ideal location with
Come see this freshly renovated waterview unit in Queens Landing! More photos to come, kitchen and bathrooms are being renovated. Enjoy Chester River views from all angles! The spacious first floor with a half bath has plenty of room for living, dining and whatever else you desire. The upper level features two bedrooms each with their own waterview balcony and full bathroom (one in the hall and
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