$601,287Average Value$304Average Price per Sq Ft94Homes 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
Barbara McPhail,
an experienced agent in this area.
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On average, homes in Chester, MD sell after 301 days on the market compared to the national average of 57 days. The median sale price for homes in Chester, MD over the last 12 months is $665,000, up 18% from the median home sale price over the previous 12 months.
Two separate living quarters, each with unobstructed views and up to date amenities. Discover a captivating blend of traditional charm and vintage coastal in the primary 3-bedroom, 2-bathroom residence, recently updated in spring 2026 (some work still in progress) enhancing its already impressive appeal. Nestled in a serene rural setting, this home boasts picturesque views along the banks of Cox
Welcome to 1000 Herons Nest Way #23, an exceptional former model home located in the first phase of condominiums within the highly desirable Four Seasons at Kent Island. This beautiful 2-bedroom, 2.5-bath residence combines designer finishes, thoughtful upgrades, and a peaceful natural setting to create the perfect low-maintenance retreat. From the moment you enter, you'll appreciate the bright,
Experience the ease of elegant one-level living in this exceptional home, located in one of Maryland's premier 55+ active adult communities on the Chesapeake Bay.Designed for both comfort and style, this beautifully appointed residence features a three-car tandem garage with an EV charger, a spacious screened porch, a cozy gas fireplace, upgraded trim and designer feature walls. Thoughtful
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
Four Seasons @ Kent Island - 55+ Community - Price Improvement + Seller to Credit $4000 towards Capital Contribution Fee * 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
Welcome to 2645 Cox Neck Road, a move-in ready home in the desirable Harbor View Community of Chester. Offering 3 bedrooms, 1.5 baths, and situated on a spacious .34-acre lot, this well-maintained property combines comfort, convenience, and exceptional value at $399,500. Inside, you'll find a bright and inviting floor plan featuring a kitchen with a stylish tile backsplash, ample cabinetry, and
Price improvement and ready to move in! 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
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
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 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.
Efficient kitchen with gray cabinetry, quartz countertops, & matte black finishes.Open concept living areas featuring a vaulted ceiling, stained beams, & cozy fireplace.Lavish primary suite & plus bath with generous walk-in closet.Private Extra Suite perfect for overnight guests.Formal home office provides a quiet area for studying or reading.Versatile screened patio for
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
Property Id: 2730520Two Rooms for rent for 1,400 each or 2800 for the whole house in a beautiful townhome in Chester Maryland.There is a pond outback with fountain. It is a 3 story end unit next to a lighthouse. Two bedroom house with two full private bathrooms on the third floor in each bedroom, on the second floor there's the kitchen, a deck, a living room, a rec room and 1/2 bathroom.
Property Id: 2619180Office space available approximately 875 square feet. Features two separate offices plus common area, Two individual private bath rooms . This is a second floor office with outside entry but no elevator. A shared kitchenette is also available for your use. NO CAM nor utility charges. Building is well maintained and office staff available during the week to answer any
Welcome to your ideal rental! This one bedroom one bath apartment has been recently renovated. It is located off of Main Street in Chester. Close to shopping restaurants and the Kent Island Trail.
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
AVAILABLE FOR RENT JULY 1ST-- RARE RENTAL in sought- after water-oriented Four Seasons- Ready to "try-on" coveted 'Four Seasons'? Treat yourself to this STUNNING beauty- Boasting soaring ceilings, flooded with natural light, spacious, open-floor plan nearly 2200 SF, with generously-sized primary suite & spa-like bath with walk-in-closet, double sinks & walk-in-shower. 2nd bedroom & bath across
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
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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