One or more photo(s) has been virtually staged. Looking for a beautifully updated Craftsman style home with character on a lot that offers more than most? This Downtown Winter Garden property delivers. Imagine living in the city limits without the restrictions of an HOA! Situated on a rare .53-acre R-2 zoned lot in the golf cart district, this home is refreshed with updates and ready for your vision—whether that’s an addition, guest house, backyard oasis with luxury pool, lush gardens, or even a lot split (with city approval). Inside, you’ll find 2,200+ sq. ft. of living space designed for today’s lifestyle. Recent updates include: NEW ROOF (2025) Fresh interior paint (2025) Refinished 1st floor original hardwood flooring (2025) New luxury vinyl plank flooring (2025) New French door refrigerator (2025) New light fixtures in main living areas (2025) Deck updates with new railings, stairs, and stain (2025). The layout offers plenty of flexibility with multiple living areas, a spacious family room with wood-burning fireplace, custom kitchen featuring stainless appliances, 6 burner gas cooktop, and double ovens. The front sunroom is perfect for a home office or bonus space. Upstairs, the primary suite features hardwood floors, a huge walk-in closet, and a spacious en-suite bath with clawfoot tub and tiled shower. Step outside and enjoy the oversized fenced backyard with two wood decks, butterfly and vegetable gardens, and a 14,000-gallon above ground pool (2020). The attached 23x25 main deck is ideal for entertaining or relaxing outdoors. Additional features include dual HVAC systems (2019 & 2020), Rinnai tankless gas water heater (2023–24), updated electrical panels (2005 & 2020), termite tenting with transferable bond (2025), replumbed systems, and an oversized 2-car garage with new openers (2023 & 2025). An enclosed breezeway with Saltillo tile flooring and tongue-and-groove ceiling (2025) connects to the garage and attached storage building. Just a few short blocks to the West Orange Trail, Plant Street Market, the weekly Farmers Market, and Winter Garden’s charming restaurants, coffee shops, & boutiques—this location is truly second to none. More than just a home, this is a living piece of Winter Garden’s history—a unique blend of character, comfort, and community legacy. If you’ve been dreaming of timeless architecture, modern convenience, and a walkable lifestyle in one of Central Florida’s most beloved historic districts, your next chapter begins here. Sold as-is.