Choosing your Chesapeake 55+ active community
Heron Point in Chestertown, Maryland, makes the most of its beautiful property overlooking the Chester River.
Not everyone looking for a home or selling a home on the Eastern Shore is seeking bigger, better, more. For many, the Eastern Shore offers a charming place to downshift, downsize, and consider their next chapter—and often their real estate interests are focused on exploring the convenience, community, and right-sized ease of active adult communities.
Designed for adults 55 and over, these communities combine independence with low-maintenance living, thoughtful amenities, and a dynamic social life. Whether it’s a cottage, condo, or single-level home, these neighborhoods offer a variety of housing choices for retirees seeking comfort, connection, and convenience. There are several throughout Kent, Queen Anne’s and Talbot Counties, and many of them provide a great way to experience the region’s amenities—waterfront access and docks, walkability to the Eastern Shore’s vibrant small towns—within an easy drive of Annapolis, Baltimore and Washington, D.C.
PICK YOUR COUNTY
Just across the Bay Bridge in Kent Island, Four Seasons at Kent Island in Queen Anne’s County is a resort-style community with a clubhouse, indoor and outdoor pools, walking trails, and stunning Chesapeake Bay views. Its amenities include a 450-foot fishing pier, kayak launch, walking and biking trails, and proximity to local shops and restaurants
Talbot County has several 55+ active adult communities to explore. Easton Club East is located just outside of historic Easton and a quick drive from the boating meccas of St. Michaels and Oxford. This community offers tennis courts, a fitness center, and plenty of group activities. Londonderry on the Tred Avon is a 55+ active adult community sited along the banks of the scenic Tred Avon River in Talbot County, Maryland. Residents enjoy direct water access, walking trails, and tranquil views that reflect the natural beauty of the Eastern Shore.
In Kent County, those seeking a community with ongoing care options should explore Heron Point. Combining waterfront living with cultural charm, Heron Point’s cottages and facilities are located along the scenic Chester River in a quiet neighborhood adjacent to historic downtown Chestertown. Heron Point provides easy access to walking trails, kayaking, and vibrant community life. This continuing care retirement community blends natural beauty with small-town appeal, offering a unique alternative for independent seniors seeking connection, wellness, and a sense of place.
Kent Island’s Four Seasons community provides residents with year-round activities, excursions, and community gatherings.
SIZE
One of the big differences between 50+ active communities on the Eastern Shore is size. Some are large and lively, with hundreds of homes and frequent social gatherings. Others are more intimate and low-key. For example, Four Seasons at Kent Island offers a vibrant calendar of events and waterfront amenities, while smaller communities like Londonderry may appeal to those seeking peace and privacy. Consider whether you want the energy of a large neighborhood or the tranquility of a close-knit group of neighbors.
Easton Club East’s extensive, manicured grounds include a pocket park where residents can relax and unwind.
AMENITIES
Amenities are a major draw for 55+ active adult communities on Maryland’s Eastern Shore, offering residents a blend of recreation, wellness, and social connection. Most communities feature beautifully maintained clubhouses and community centers that host everything from neighborhood gatherings to educational seminars.
Residents often enjoy access to indoor and outdoor pools, fitness centers, and scenic walking trails, ideal for staying active while enjoying the region’s natural beauty. Sports enthusiasts can take advantage of pickleball and tennis courts, while others may gravitate toward gardening clubs, arts and crafts studios, woodworking shops, or book discussion groups.
Ask about membership fees, usage restrictions, and what’s included in your HOA dues. Some communities like Easton Club East have robust programming and active resident boards, while others allow you to shape your own retirement experience.
HOAs
More about HOAs. Most of the region’s active adult communities are governed by a Homeowners Association (HOA), which helps maintain common areas and enforce neighborhood guidelines. This can be beneficial—but it's important to understand the rules. HOAs may set limits on exterior decorations, pet ownership, or street parking. They also typically require monthly or quarterly dues, which should be factored into your long-term budget.
Retirement is a major life milestone, and choosing where to spend it matters. Whether you’re drawn to Kent Island’s scenic views, Easton’s cultural offerings, or the historic charm of Chestertown, there’s a community to match your goals and lifestyle. Ready to learn more? Don’t hesitate to reach out!
