A Local's Guide To Living In Four Seasons at Kent Island

Written By Malcolm Lawson

For those aged 55+ who are seeking an active lifestyle in retirement, there are few better options than Four Seasons at Kent Island. This resort-style community is located on Kent Island in the Chesapeake Bay, Maryland. It allows you to experience island life in luxury, surrounded by other people who are looking for exactly the same.

The Active Lifestyle Concept

The founder of this community, Kevork S. Hovnanian, was one of the first people to implement the idea of an active lifestyle community back in the early 1970s. He used his homebuilding company to create the first Four Seasons in Lakewood, New Jersey. The community combined beautiful homes with exceptional amenities — a concept that is replicated at Four Seasons on Kent Island.

About Kent Island

Kent Island 55 and over communities

Although it’s only a short distance from the shore across the Kent Narrows and about 4 miles across the water to Sandy Point State Park near Annapolis, Kent Island allows you to fully experience island living. It is the largest island in the Chesapeake Bay and consists of the cities of Stevensville and Chester. The combined population of the two cities is around 11,000, although Chester is by far the smaller.

Read our full article about Living On Kent Island.

Four Seasons at Kent Island Home Models

The more than 150 homes at Four Seasons are all recent constructions. The single-family homes come in three different collections, called the River Series, the Bay Series, and the Island Series. The following 4 are available models right now.

The Kerr Series: 2,773 sq ft 2 stories 3 beds 3 baths 3 garages

The Tuscaloosa Series: 3,218 sq ft 2 stories 5 beds 4.5 baths 3 garages


The Jenkins II Series: 2,019 sq ft 1 story 2 beds 2 baths 2 garages

The Franklin Series: 2,963 sq ft 1 story 3 beds 3.5 baths 2 garages

There are also four condominium buildings on the waterfront which start at $429,990 . These come in three models, ranging from 1,900 square feet to 2,602 square feet. They have two or three bedrooms, two and a half bathrooms, and a one-car garage.

Condos at Four Seasons at Kent Island


The following homes are previously built models which are only available for resale now.

The River Series starts at $403,990 and has homes in three-floor plans, ranging from 1,689 square feet to 1,993 square feet. All the homes have two bedrooms and an attached two-car garage. You can choose to have two or two and a half bathrooms.

Four Seasons at Kent Island Model Homes For Sale

The Bay Series homes start at $434,990 and are slightly larger at 2,000 square feet to 2,862 square feet. There are five-floor plans, each with two or three bedrooms and two or three bathrooms. Again, you have an attached garage for two cars.

Four Seasons At Kent Island Homes For Sale

The largest homes are part of the Island Series which starts at $505,990. The six different floor plans range from 2,440 square feet to 3,494 square feet. You can choose between two or three bedrooms, two to four bathrooms, and 9- or 10-foot-high ceilings. In addition to the two-car garage, these homes feature a master suite on the first floor, granite kitchen countertops, and ceramic tiles in the bathrooms.

Four Seasons at Kent Island New Construction Homes


Four Seasons at Kent Island Amenities 

  • Golf Courses Near By
  • Tennis & Pickleball Courts
  • Indoor Pool
  • Outdoor Pool
  • water aerobics
  • Clubhouse
  • Fitness Center
  • Yoga & Zoomba Sessions
  • Demonstration Kitchen
  • Dog Park
  • Kayaking
  • Walking Paths
  • Card Room

Four Seasons at Kent Island Amenities

By living at Four Seasons, you gain much more than just a property. For one thing, there are numerous outdoor activities to try. You can play in one of the many golf courses or tennis, bocce, and pickleball courts. You can also swim in the pools — Four Seasons has both an indoor and an outdoor pool, making it easy to stay active no matter the time of year. Around the outdoor pool, there are tiki huts where you can relax at any time.

The community also has an expansive 24,000-square-foot clubhouse called Chester House. It features a fitness center and multi-purpose rooms for various types of activities and meetings.

Now is the time to get in the best shape of your life. The onsite lifestyle director can help you with whatever your fitness goals. For a guided practice, join a yoga session, Zumba class, water aerobics, or another activity. There’s always plenty on the calendar to choose from.

In addition to all these sports facilities, you’ll have the chance to increase your skills and knowledge in various aspects of your life. For instance, there’s a demonstration kitchen that the community uses to invite local chefs to teach residents to prepare new dishes. You can also use the space to cook with a group of friends or neighbors — perhaps even to hold a competition.

Another way to expand your mind is to visit the onsite library. You’ll find a wide array of books on all kinds of topics. It’s the perfect place to start a book club to share your favorite reads and receive new recommendations.

Socializing with Other Residents

Four Seasons at Kent Island makes it easy to meet new people with similar interests and maintain an active social life. All the residents have also lived a life of hard work — and have decided that now’s the time to relax and enjoy all the luxuries a 55+ community has to offer. You can play sports together, share a backyard barbecue, invite neighbors over to your home for a dinner party, or just chat on the outdoor terrace.

You’ll have plenty of opportunities to meet people. As well as the fitness activities, the community organizes games of cards, mahjong, and billiards. Plus, the year always ends with holiday parties and festivities.

Things to Do Nearby

There are plenty of things to do within the vicinity of Four Seasons and elsewhere on Kent Island.

Trails and Nature

Cross Island Trail Kent Island Maryland

The Four Seasons community connects you with walking and biking trails on the island. On the trails, you’ll pass through woodland, farms, and fields — there’s a real countryside feel.

One option is the 6.5-mile-long Cross Island Trail, which runs all the way across the island from east to west. Another, covering the entire lower section of the island, is 7-mile South Island Trail. It begins at Matapeake State Park and takes you all the way to Romancoke Pier, passing parallel to Route 8. The trail is paved all the way, making for a smooth ride on a bike. If you want to find other people to walk with, you can join the Four Season walking club.

For more nature, head to Terrapin Nature Park, which is just a few minutes from Four Seasons. Or, if you’re a dog owner, check out the dog park at Matapeake Clubhouse and Public Beach, which also has an outdoor amphitheater and swimming beach. It’s the perfect place for picnics!


Set just steps away from the waterfront, Four Seasons is the perfect option if you want to live life on the water. Whether you’re already an avid boater or you have no experience, this is your chance to discover a passion for all kinds of aquatic activities from sailing to fishing. There are even canoe and kayak launches at the Four Seasons community.

If you prefer to be up in the air than on the water, you’re still in luck. There are two recreational airports on the island: Bay Bridge Airport and Kentmorr Airpark, both in Stevensville.

Dining and Shopping

You’ll have easy access to restaurants and shops on the waterfront, which makes Four Seasons feel like a small town. For greater shopping needs, you can find many shopping centers elsewhere on the island. There are a couple in Stevensville and around four more in Chester. The closest are Kent Island Shopping Center and Kent Towne Market, each of which are less than a mile away.

Finally, wine-lovers will be happy to hear that Kent Island is home to the award-winning Cascia Vineyards, a family-run winery. However, if wine is not your drink of choice, there’s also Blackwater Distilling, which makes rye whiskey, rum, and vodka — there’s something for everyone!

A Historical Island

Kent Island is one of the most significant historical locations in the area. Not only is it one of the oldest permanent English settlements in the country, it was the first settlement in Maryland.

There are historic sites across the island. In Stevensville Historic District, there are around 100 historic structures, some of which are on the National Register of Historic Places. Once a month, starting in April, you can attend special events in the historic downtown.

You can find many well-preserved 19th-century buildings as you’re driving along the Chesapeake Country Scenic Byway and by hiking or biking the part of the American Discovery Trail that covers Kent Island.

Highlights include the old Stevensville post office, the Christ Episcopal Church, and Stevensville Train Depot. Make sure to also pass by Cray House, which dates back to 1809. It’s one of the few surviving buildings that feature a post-and-plank construction. Finally, pay a visit to Historic Kent Manor Inn if you want to try regional food, including a champagne brunch buffet.

Convenient Location

One more great thing about Kent Island is its proximity to both Washington DC and Baltimore. Whenever you’re craving the big city, you can reach either in just a 45-minute drive. Annapolis is nearer still — just take the U.S. Route 50/U.S. Route 301 over the Chesapeake Bay Bridge to cross the Delmarva Peninsula. This will bring you to Central Maryland and then it’s just 15 minutes to reach Annapolis.

Other ways to reach the mainland are the Kent Narrows Bridge (which also carries the US 50/301) and Old Kent Narrows Bridge (Maryland 18 into Grasonville), which is a drawbridge. Plus, if you’re ever without your own means of transport, you can take advantage of the commuter buses. These run every day of the week and go to both Annapolis and Washington DC.

Buying a Home In Four Seasons at Kent Island

Start living your life to the full with a house or condo at Four Seasons. As a 55+ community specialist, I can advise you on the best community in the area and help you negotiate the best deal possible.  I have lived on Kent Island for the past 25 years and helped numerous clients of mine purchase new and resale homes in the many 55 and over communities in the area. 

Annapolis Maryland Real Estate Agent

Sorry we are experiencing system issues. Please try again.