1411 EASTOVER LOOP Under contract-accepting backup offers. Discover an exceptional and rare offering in the prestigious OAKLAND PARK community, just a short GOLF CART ride from historic downtown Winter Garden—voted “#1 Community to Live In” by Orlando Style Magazine. This sophisticated, nearly 2, 000-square-foot duplex unit (1 of only 4) sits on .13 of an ACRE, faces a beautiful PARK, and features three bedrooms with a primary suite on the main floor, three-and-a-half baths, HARDWOOD flooring, plantation SHUTTERS, a welcoming front porch, a large screened-in back porch, and a striking metal roof. With an oversized two-car garage and a fully-FENCED side yard, this home is truly a hidden gem. Step inside to an inviting and meticulously designed interior where the kitchen shines with newer stainless-steel appliances, QUARTZ countertops, FARMHOUSE sink, a tile backsplash, and a spacious pantry. The main floor offers a serene primary suite with two walk-in closets, dual vanities, a garden tub, and separate shower. Just off of the primary suite is the screened-in patio—a perfect spot for morning coffee or evening relaxation. The living room, dining area, mudroom, powder room, and laundry complete the thoughtful layout on this level. Upstairs you’ll find two bedrooms with en-suite baths, complemented by a versatile LOFT ideal as a study nook or play area. The oversized two-car garage, boasting 20-foot ceilings and built-in storage, provides ample space for all your gear. Your guests can comfortably park behind the home in the driveway or along the street. A SOLID CONCRETE wall ensures privacy between the units, while the generously sized and lushly landscaped backyard, complete with market lights and up-lighting on the vines, creates a private oasis. Unwind with friends and family while enjoying a backyard barbecue, a cozy fire, or a relaxing football game under the stars. Venture to the LAKE-side walking trail just a few steps away, or lounge in the park with neighbors for an evening of fun. Recent UPGRADES include a 2022 full kitchen remodel, durable and high quality TimberTech decking on the front and back porches (2021), screen enclosure, custom accent walls in the upstairs bedrooms (2023), a revamped powder room and mudroom with built-in cabinetry (2023), refreshed interior paint (2021-2024), and a 2019 AC system with updated parts in 2024. HOA fee includes: exterior pressure washing of the home, sidewalks, and driveways, minor exterior maintenance, termite protection, exterior painting (2025), roof. This home offers the ideal blend of comfort and convenience, perfect for enjoying the vibrant lifestyle of Winter Garden. From charming boutiques and rooftop dining to the lively Farmers Market and Splash Park, downtown Winter Garden is a vibrant destination easily accessed via golf cart. Outdoor enthusiasts will love the 22 mile long West Orange Trail. This golf-cart-approved community offers year-round events, from golf cart parades to book clubs and social gatherings, making it an extraordinary place to call home. The WATERFRONT community features parks, playgrounds, two pools (including a resort style pool), a clubhouse, dog park, and spectacular sunset views. Don’t miss this rare opportunity to live in one of the area’s most sought-after neighborhoods, with easy access to interstate travel, shops, restaurants, golf courses, and world-renowned theme parks. This gem is one of the LOWEST priced entry points into the community and is ready to be embraced by its new owner!