Under contract-accepting backup offers. RARE OPPORTUNITY in the highly desirable Winters Landing community - golf cart accessible to downtown Winter Garden and steps to the tree-shaded, 22 mile long West Orange Trail! Upon entering this David Weekly-designed home, you'll be captivated by the inviting nature of this single-story property loaded with upgrades. No stone has been left unturned, including crown molding, five-inch baseboards, plantation shutters, upgraded wood window casings, newer light and fan fixtures, and a wood shiplap accent wall. The home features an updated roof (2020), new water heater (2025), updated dark oak laminate flooring throughout, water softener system, 3-car garage, and an oversized lot (.29 acres), giving you plenty of elbow room between neighbors! All 3,290 square feet of living space was thoughtfully designed and is perfect for entertaining, with the open yet split floor plan providing balance and accessibility. The gourmet kitchen will delight your inner chef with its elevated materials: stainless steel appliances (including a new range), cabinetry with detailed molding, granite countertops, built-in double oven, breakfast bar and convenient eat-in dining space. The kitchen is positioned beautifully to the sun-drenched living room with its large-scale windows and wood-burning fireplace; plus, a double set of French doors that lead to the expansive screened and covered lanai overlooking the large backyard. The impressive primary suite offers a private sanctuary with its own access to the lanai, sitting area, deep walk-in closet, and spa-like bathroom featuring a jacuzzi tub, separate walk-in shower, and dual vanities. On the other side of the house sits a generous, multipurpose flex space that cushions the three sizeable guest bedrooms. Additional rooms include a spacious dining room, lounge area, and dedicated home office with French doors and built-in shelving. With easy access to the FL Turnpike, SR 429, and HWY 27, traveling and commuting is a breeze. Plus, Oakland Avenue Charter School is just across the street from the neighborhood, with highly rated Orange County Schools also nearby. This Oakland residence checks every box and is truly a special place to live. Discover the lifestyle you've been dreaming of; call today to schedule your private tour and make this home yours! *AT&T fiber optics network available here!