Opportunities like this are rare-an oversized .28-acre Harbour Island sanctuary with a beautifully finished main residence and a private guest casita, all wrapped in a sun-filled courtyard design that captures skyline views while preserving complete privacy. Step inside to a dramatic 20-ft living room volume, warm wood flooring, and effortless flow to the courtyard and pool-your daily invitation to unwind. The kitchen blends function and style with gas cooking, a center island, and abundant cabinetry, opening seamlessly to the family room. The formal dining room enjoys a serene courtyard fountain view, perfect for intimate gatherings. The first-floor primary suite is a retreat of its own, with French doors opening to the courtyard. The primary retreat also features dual custom- organized closets and an ensuite bath complete with dual vanities, a deep soaking tub, walk-in shower, and private water closet. Upstairs, three additional bedrooms offer flexibility for guests, family, or a dedicated home office. Thoughtful updates throughout include marble flooring and Dolomite countertops in the kitchen, refreshed secondary baths, and newer flooring. The detached guest casita elevates the property further-ideal for extended family, visiting guests, or a private studio-complete with new flooring, Dolomite counters, a new refrigerator, and a fully remodeled bath. Recent enhancements bring peace of mind and modern luxury: a NEW 2023 custom tile roof, NEW 2023 pool and equipment, 3 NEW 2023 HVAC systems, NEW irrigation, and refreshed landscaping. All within Harbour Island's coveted 24-hour gated community-steps from Water Street, Sparkman Wharf, LifeTime Fitness, Tampa's Riverwalk, and minutes to Bayshore, Downtown, I-275, and the Selmon Expressway. Designed for the buyer who knows the difference, demands the best, and invests in a lifestyle worthy of Harbour Island's finest. Secure your private viewing before it's too late!