Welcome to Four Seasons at Kent Island, a premier 55+ waterfront community offering luxury, lifestyle, and leisure. This beautifully maintained 3rd floor Chester model features 2 spacious bedrooms plus a den/office, 2.5 baths, and serene pond views with a fountain—creating a picturesque, peaceful setting in every season. Inside, enjoy a light-filled open-concept floorplan with a gourmet kitchen boasting high-end appliances, a cozy living area with a modern fireplace, and oversized bedroom windows offering year-round peek-a-boo views of the Chester River. Elegant French doors open to a versatile den/office, while double sliding glass doors lead to a private, covered balcony where you can sip morning coffee and watch deer, herons, egrets, or distant sailboats drift by. Thoughtful upgrades include custom coastal-toned paint, walk-in closet organizers, built-in drawers in the primary suite, and a spacious laundry room with cabinetry. Additional conveniences include a dedicated climate-controlled storage closet on the first floor, an attached one-car garage with Gladiator cabinets, a ceiling fan on the balcony, and an energy-efficient interior location for lower utility costs—all with weather-free access to the interior mail room. Enjoy resort-style amenities such as an indoor lap pool, a stunning outdoor beach-entry infinity pool overlooking the Chester River, a well-equipped clubhouse with a gym, gathering rooms, a book-share library, and a game room. Explore miles of scenic walking and biking trails—including direct access to the 6.5-mile Cross Island Trail—and take advantage of the kayak/paddleboard launch and storage, tennis, bocce, and pickleball courts, multiple outdoor fire pits (wood-burning on the inland sandy beach and gas on the patio), and a vibrant calendar of community events, clubs, food trucks, and socials. Ideally located near Annapolis, Washington D.C., BWI Airport, and the charming towns of St. Michaels, Chestertown, and Tilghman Island—this is Eastern Shore living at its finest.