One or more photo(s) has been virtually staged. Historic Downtown Winter Garden Craftsman – Where Timeless Charm Meets Modern Living Discover a rare opportunity to own a beautifully preserved piece of Winter Garden history in the heart of the vibrant downtown golf cart district. This distinguished 1928 Craftsman-style home sits proudly on an expansive .53-acre, R-2 zoned lot—a rarity in this sought-after area—and offers a harmonious blend of original architectural character and thoughtful modern updates. Once owned by the Collie Biggers family, early pioneers of Winter Garden’s movie theatre legacy, the home has been lovingly cared for over the past 34 years by its current owners, fondly remembered as the faces behind the cherished local eatery "Downtown Brown’s." This deep-rooted local connection enhances the home’s legacy and makes it a true cornerstone of the community. Offering approximately 2,204 square feet of living space plus a charming ducted sunroom, this two-story gem welcomes you with historic details including refinished original hardwood floors (2025), glass doorknobs, custom built-ins, and vintage trim work. The formal living & dining rooms maintain their period elegance, while the spacious family room—complete with a wood-burning fireplace—was seamlessly added to accommodate today’s lifestyle. The heart of the home is a custom kitchen outfitted with timeless cabinetry, stainless appliances, double ovens, natural gas 6-burner cooktop with hood, and a new French door refrigerator (2025). New luxury vinyl plank flooring runs throughout the kitchen, family room, sunroom, and main-level powder bath, offering beauty and durability. Upstairs, a private primary suite features gleaming hardwood floors, a huge walk-in closet, convenient washer/dryer cubby, and a spacious en-suite bath with clawfoot tub and tiled shower—your personal retreat. Step outside to relax or entertain on the shaded 23x25 rear deck, recently updated with new railings, stairs, and stain finish (2025). Enjoy sunny Florida days in the 14,000-gallon above-ground pool (2020) or meander through lush butterfly and vegetable gardens across the tranquil, fully fenced backyard. Two additional wooden decks provide peaceful spots to unwind. The property also features: NEW ROOF(2025), Fresh interior paint throughout (2025) New light fixtures in main living areas (2025) Breezeway with Saltillo tile and tongue-and-groove ceiling (2025) Termite tented with transferable bond (2025) Dual HVAC systems (2019 & 2020) Electrical panel upgrades (2005 & 2020) Replumbed (~2004) and a Rinnai tankless gas water heater (2023-24). There's even a partial basement below the home with sump pump and water softener! Stow vehicles in the oversized 2-car garage with new openers (2023 & 2025) and tools and toys in the attached 12x12 shed. With its zoning and lot size, this home also presents exciting future development potential—including a possible lot split (subject to city variance; buyer to verify). 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.