Discover timeless elegance in this beautiful 4-bedroom, 3.5+ bathroom historic property nestled in the sought-after Lake Cherokee neighborhood. A main house with original details from 1911 showcases 3 beds/2.5 baths over 3 stories, an updated open floor plan, upgraded metal roof & modernized HVAC, windows, electrical, and plumbing. The kitchen is a stunner, featuring quartz countertops, a gas range with leather vent hood, stainless appliances, custom cabinetry, built-in breakfast banquette, functional oversized island AND an additional island with bar height seating. Just off the kitchen, a laundry/mudroom and dog bed area is discreetly tucked out of sight. This residence blends classic character with contemporary comforts. Enjoy original hardwood flooring, plantation shutters, spacious living areas, inviting wraparound porches, and a sparkling swimming pool—perfect for gatherings and relaxation. The versatile carriage house built in 2009 presents an incredible opportunity for rental or Airbnb income through its R2A zoning and features an additional 1 bed/1bath, separate laundry area, and .5 pool bath . Added highlights include Ring doorbell security cameras, a gated entry with space to park a boat/RV hookup, and 3-car covered spots/ garage with epoxy floors. This home further PAYS FOR ITSELF* through potential property tax credits and a prime location that's walkable to work. Live near downtown Orlando's offices, dining, theater, parks, and top schools...this home is a rare find. Make an offer before it's gone! Features: Major renovation including new wraparound porch with long-lasting metal shingle roof, new kitchen/living area, new windows, spray foam insulation under the entire floor system, two new two-speed AC systems with humidity control and Nest thermostats, new plumbing throughout, new electrical throughout, new LED lighting (2015) Fully renovated master bath & guest bath with custom built ins (2020) Foundation piers adjusted and supplemented (2016) Spray foam insulation to the entire roofline (2011) Whole-house water filtration system (2012) Upgraded sprinkler system timer and rain gauge (2017) Automatic driveway gate (2019) Pool, guest house and garage added (2009) Replaced air handler for guest house (2020) 30 amp RV charging station (2020) Tankless (main house) & traditional (carriage house) water heaters (2021)