Welcome to 5066 Cheshire Glen Road — a beautifully maintained, original-owner home in The Villas at Canandaigua, a well-regarded HOA community offering maintenance-free living and access to outstanding clubhouse amenities! This thoughtfully designed property features 2 bedrooms, 2 full bathrooms, a bright four-season sunroom, a versatile office/bonus room, first-floor laundry, and a spacious primary bedroom with a private full bath, double sinks, and a large walk-in closet. Arch windows throughout lead to an abundance of natural sunlight, complemented by cathedral ceilings that enhance the open, airy feel of the home. The open layout seamlessly connects the kitchen, dining, living room, sunroom, and bonus room — ideal for both daily living and entertaining. Additional highlights include a cozy gas fireplace, a welcoming front patio with views of the clubhouse and neighborhood, a 2-car attached garage, a large dry attic for extra storage, a newer furnace (2023), and a tankless hot water heater (2020). Ideally located in The Villas, just a short walk to the central clubhouse, which offers residents an outdoor heated pool, fitness room, library, billiards room, entertainment area, showers, kitchen, and a lively calendar of year-round activities. With shopping, dining, the picturesque downtown Canandaigua, and Canandaigua Lake just minutes away — plus a nearby farmstand — this home offers the ultimate in convenience and vibrant local charm. Seize the chance to embrace a carefree, active lifestyle in this welcoming community — the perfect place to enjoy your next chapter!