1444 Winchester Avenue E Luxury meets country charm within this Exceptional 3.02-Acre gated estate in LaBelle, Florida! Welcome to this rare multi-residence property offering over 5000 Sq ft of living space across the main home, guest house, and garage apartment. The two-story main home features cathedral ceilings, a beautiful eat in kitchen with stainless steel appliances and a stunning floor to ceiling fireplace. Eating dinner in the formal dining room with the beautiful views from the surrounding windows will make family dinners unforgettable. Step into a breathtaking master suite designed for both comfort and style. This spacious retreat features a private bathroom with a separate soaking tub and shower, custom-designed closet with ample storage, built-ins, and useful finishes to keep your wardrobe organized and accessible. The suite also boasts a dual-sided fireplace, thoughtfully engineered to open to both the bedroom and the living room, creating a warm, inviting atmosphere and a seamless flow between spaces. The 2 story Guest house features a full kitchen, large family room, 2 bedrooms and downstairs bath. The extra apartment provides 1 bedroom, 1 bath, and a full kitchen above a 3-car garage with workshop/gym. Enjoy resort-style outdoor living with a saltwater pool, triple waterfall, and screened lanai connecting to the main house with a paver walk way. Nestled on the property is a charming shed-style building, perfect as a home office, creative studio, or "she shed." Its cozy yet functional layout offers a private retreat, ideal for focused work, hobbies, or quiet relaxation. With its quaint design and versatile space, it adds both character and utility to the property, providing a peaceful escape right in your backyard. The property is fully fenced with dual electric gates, surrounded by beautiful mature oak trees, and includes a 3 bay pole barn with separate areas for different animals near by. The large fenced in side yard is suitable for horses. Perfect for multi-generational living, entertaining, or income potential, this estate combines privacy, luxury, and versatility in one of LaBelle's most desirable Communities "The Ranchettes"!