This beautifully maintained 5-bedroom, 5-bath home in the 5-Star Windsor Hills Resort combines one of the community's most desirable 5-bedroom floor plans with extensive mechanical and interior updates and an established short-term vacation rental setup just minutes from Walt Disney World. Designed with large families and vacationing groups in mind, the open layout provides exceptional flow, multiple gathering areas, and excellent bedroom separation. Major improvements add significant appeal, including a 2022 roof with 30-year architectural shingles, 2023 saltwater pool system, 2023 WiFi-controlled pool heater, brand-new 2026 WiFi-capable water heater, new toilets added in 2026, and dual HVAC systems with major components replaced in 2016 and newer coils installed within the last two years. Nest thermostats provide added convenience and efficiency. Inside, upgraded bath vanities with solid-surface counters and wood-laminate hickory flooring in all bedrooms enhance both the appearance and durability of the home. The open main level offers a spacious dining area, separate breakfast room, kitchen bar seating, granite countertops, stainless steel appliances, and a large living area designed for gathering. Two first-floor ensuite bedrooms plus an additional queen bedroom with an adjacent bath provide convenient main-level accommodations. Upstairs, two Disney-themed junior suites, each with its own bathroom, create a fun and memorable space for younger guests. The converted garage game room with air hockey and pool tables provides another dedicated entertainment area. Outside, the screened lanai features a private heated saltwater pool and spa, privacy screening, and a mature hedge that creates a secluded place to relax after a day at the parks. The updated saltwater system and WiFi-controlled pool heater add convenience for both owners and guests. Windsor Hills Resort offers an impressive collection of amenities including a clubhouse, lagoon-style pool, tennis courts, racquetball court, basketball court, marketplace, theater, game room, fitness center, playgrounds, putting greens, and 24-hour guarded security. Its proximity to Walt Disney World continues to make Windsor Hills especially attractive to vacation-home buyers and short-term rental investors. For buyers looking for an investment property, the seller is willing to transfer future bookings, providing the opportunity for income continuity following the sale. With its desirable floor plan, extensive updates, private pool and spa, themed bedrooms, game room, and prime Windsor Hills location, this home offers an exceptional combination of guest appeal and investment potential.