One or more photo(s) has been virtually staged. Opportunities like this are rare. Perfectly suited for multi-generational living, mother-in-law suite potential, or rental income, this versatile POOL home sits on an oversized lot with no HOA in one of Central Florida’s most desirable locations — Winter Park. The flexible floor plan allows for comfortable separation of living spaces, making it ideal for extended family, guests, or income-producing arrangements, while still maintaining a natural sense of connection throughout the home. All major high-ticket items have already been taken care of, offering true peace of mind for years to come. Updates include a newer roof 2022, new AC system 2025, new water heater 2025, energy-efficient double-pane windows 2025, resurfaced pool with a new pool pump 2025, fresh interior and exterior paint 2025, and new quality flooring throughout. The updated kitchen features 42-inch shaker cabinetry with soft-close drawers, generous storage, and new appliances, creating a functional and inviting space for daily living and entertaining. Step outside to your private outdoor retreat—ideal for gatherings, relaxation, or future enhancements. The location truly elevates this property. Just minutes from Rollins College, Full Sail University, AdventHealth Winter Park Hospital, and the Cady Way / Gateway Trail. Everyday conveniences are nearby, including Sprouts Farmers Market, Publix, Costco, boutique shopping, cafés, and fine dining along Park Avenue and Baldwin Park. Quick access to major highways ensures easy connectivity throughout Central Florida. Zoned for highly regarded Winter Park schools and surrounded by consistent buyer demand, this home offers a compelling combination of versatility, extensive upgrades, and a prestigious address. Call for your private tour today!