One or more photo(s) has been virtually staged. New Lower Price! Downtown Winter Garden CraftsmanWhere 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 lota rarity in this sought after areaand offers a harmonious blend of original architectural character and thoughtful modern updates. Once owned by the Collie Biggers family, early pioneers of Winter Gardens 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 Browns." This deep rooted local connection enhances the homes 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 roomcomplete with a wood burning fireplacewas seamlessly added to accommodate todays 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 showeryour 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 potentialincluding 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 Gardens charming restaurants, coffee shops, & boutiquesthis location is truly second to none. More than just a home, this is a living piece of Winter Gardens historya unique blend of character, comfort, and community legacy. If youve been dreaming of timeless architecture, modern convenience, and a walkable lifestyle in one of Central Floridas most beloved historic districts, your next chapter begins here. Sold as is.