This home PAYS FOR ITSELF* details in the description. Discover timeless elegance in this beautiful 4-bedroom, 3.5+ bathroom historic property nestled in the sought-after Lake Cherokee neighborhood on the same block as infamous Honeymoon Row. This property has stories to tell and has been in the spotlight too—it was featured in printed publications and two TV commercials! A main house with original details from 1911 showcases 3 beds/2.5 baths plus Florida room 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 dining banquette that seats 8, 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. Enjoy restored hardwood flooring, two fireplaces, plantation shutters, spacious living areas, inviting wraparound porches, and a sparkling swimming pool—perfect for gatherings and relaxation. This residence blends classic character with contemporary comforts. 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 on this oversized 75’x190’ property include Ring doorbell security cameras, a gated entry with space to park a boat / RV 30-amp 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 includes 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 water heater in main house & traditional water heater in carriage house (2021) Refrigerator and washer/dryer in main house (2023)