Welcome to The Cloisters, one of Winter Park's established and sought-after lakefront communities, ideally between Park Avenue and Lake Osceola. Rarely available and perched on the top floor, this elegantly remodeled residence features a private, oversized screened-in balcony with a custom awning, an open-air retreat seldom found in this floor plan, where most balconies were enclosed at the time of construction. The outdoor space offers tranquil views of the heated pool, putting green, manicured gardens and Lake Osceola, creating an elevated setting for year-round enjoyment. Inside, custom decorator finishes define every detail. The kitchen features bespoke cabinetry and granite countertops, while both baths have been thoughtfully remodeled, the hall bath with a new tub and glass enclosure, and the primary bath with a walk-in shower and glass enclosure, each complemented by custom vanities and refined tile flooring. The home also offers new engineered hardwood flooring in the main living areas and plush carpet in both bedrooms. The primary suite provides functional elegance with custom built-ins for storage and display, as well as a built-in desk with additional cabinetry in the vestibule, framed by dual closets that lead to the en-suite bath. The second bedroom is privately situated and ideal for use as a study or guest room, with optional shared access from the primary suite. Additional highlights include an assigned covered parking space outfitted with one of the building's few electric vehicle charging stations, ample guest parking nearby and community dock access with boat slips leased through a resident lottery system. Residents also enjoy two fitness centers with dry saunas and a renovated social gathering space with a kitchen and bath, ideal for hosting private events. Just steps from the dining, shopping and cultural vibrancy of Park Avenue, and in proximity to Rollins College, this original-owner residence delivers an exceptional blend of lifestyle, location and enduring design.