Welcome to 424 Winterberry Drivea beautifully maintained 3-bedroom, 3-bathroom Ranch nestled in a vibrant 55+ community in the heart of Middletown. With 2,650 square feet of thoughtfully designed living space, this home offers the perfect blend of comfort, style, and LOW-MAINTENANCE LIVING. Step inside and be greeted by BRAND-NEW LUXURY VINYL PLANK FLOORING that flows seamlessly throughout the main level, paired with FRESH PAINT that creates a bright and inviting atmosphere. The heart of the home - the kitchen, features Corian countertops, stainless steel appliances, a breakfast bar, recessed lighting, and two pantries, including a spacious walk-in. Also on the main level you will find 3 bedrooms, a home office and 2 full bathrooms. The master suite features a WALK-IN CLOSET and an ensuite bath. Downstairs, the expansive FINISHED BASEMENT includes a great room and a partially constructed train room perfect for a train enthusiast or to be used as a craft/hobbie room. Also on the lower level is a massive storage room. Enjoy peace of mind with recent upgrades such as a NEWER WATER HEATER, NEW SUMP PUMP, and a backup generator. The outdoor space invites you to relax on the deck, complete with a gas hookup for grilling (no tanks needed!), all while enjoying the benefits of a professionally maintained lawn, thanks to the HOAs comprehensive services including grass cutting, trash pickup, and snow removal. A built-in irrigation system and Ring doorbell add even more convenience. As a resident of this welcoming community, you'll also enjoy access to premium amenities like a community pool, tennis courts, bocce ball, a lively clubhouse & some absolutely beautiful walking trails. Whether you're looking to downsize in style or simply enjoy the ease of a well-appointed home, 424 Winterberry Drive offers the lifestyle you've been dreaming of. Be sure to schedule your tour today!