Welcome to this charming four-bedroom, three-bath home nestled in the highly sought-after community of Orwin Manor, Winter Park. Built in 1926, this historic gem boasts a brand-new roof and recent crawl space floor joist reinforcement in 2024, preserving its integrity with original wood flooring throughout. Zoned R2, this home features an in-law suite with a detached ADU (Accessory Dwelling Unit) including a private bathroom and entrance, ideal for extended family, rental income, or guest accommodations. Enjoy modern comforts with all-new windows, updated irrigation systems, and a freshly paved driveway. Additional upgrades include a new water heater, interior paint, granite kitchen countertops, and remodeled bathrooms. Conveniently located a short distance of Winter Park's Rollins College, the boat tour, art festivals, and the farmers market, plus a short stroll to local coffee shops. Easy access to I-4, 1792, Maitland, and downtown Orlando ensures you're connected to the best of Central Florida living. Don't miss the opportunity to own this historic yet modernized home in the heart of Winter Park. Schedule your showing today!