18143 WINDING OAKS BOULEVARD STUNNING POOL HOME. LUXURY UPDATES. JUST OVER ¾ ACRE. You will not want to go anywhere else once you arrive at 18143 Winding Oaks Blvd where over $87, 000 in updates and upgrades avail. This home makes an impression before you even step out of your car. From the expansive 10 car driveway to the meticulously maintained landscape, accented with vibrant pops of color from the flowers and plants welcoming you home. A private mailbox and a classic black lamppost at the front of the yard add a timeless charm that truly sets the tone for the home. The exterior was painted in 2020, with additional enhancements completed in 2026, including painting the driveway, walkway, pool deck, and garage, further elevating the home’s curb appeal. The expansive primary suite features a true ensuite that offers a flexible sitting area ideal for a reading nook or home office, double closets plus direct access to the pool via glass sliding doors. Primary bathroom remodeled features walk-in shower with frameless glass, river rock flooring, floor to ceiling tile, and jetted garden tub. The home features formal dining and formal living room with glass sliders out to the lanai. Along with a spacious kitchen with breakfast area and open concept to the great room with built-in fireplace. Solar-heated saltwater pool with extensive upgrades, including full resurfacing with premium PebbleTec finish, updated tile, new stainless-steel ladder and pool skimmer repair. Enhanced with a replaced skimmer, updated plumbing, refreshed pool deck, and convenient outdoor shower for a polished, resort-style outdoor experience. Oversized pie-shaped homesite just under an acre, featuring a large chain-link fenced area with additional open yard space beyond. No fence restrictions allow for added flexibility. Items Worthy of Mention; Water heater (2026), Whole home water softener system installed (2024), Both bathrooms updated, Luxury vinyl plank flooring throughout the entire home, New kitchen with top-of-the-line GE Café Series (2021), Large laundry room with cabinets, granite counters and upgraded utility sink, gutters and downspouts, garage door opener replacement (2022), garage door neoprene rollers, springs, components and hardware replacement (2024), well water for irrigation system with the well pump and tank system replaced (2021), full interior painting (2019), HVAC system replaced (2015), roof replaced (2015). Spacious 3-car garage (766 sq ft) featuring a painted floor with decorative flake finish, freshly painted interior, smooth ceilings with popcorn removed, multiple garage door openers, rear access door, additional refrigerator, and a dedicated wall AC unit for climate control. Autumn Oaks is a community of executive-style homes set on expansive homesites, where each home is uniquely designed, offering a lush, private feel with a tennis court in a prime location. Upgrade sheet available upon request. Conveniently located near Gulf waters, golf, nature parks, and major roadways, offering the perfect balance of lifestyle and accessibility. HOA fee is $435 per year.