**Multiple Offers - All offers to be submitted by 11/3/2024 at 6pm ** Historic charm & character meet modern style & function on this .39-acre lot in Orlando's desirable Lake Highland district. Built in 1925 by E.B. Hess—a prolific typewriter inventor—the property was selected for its elevated city location, earning the name “House on the Hill.” Extensively renovated, including a major 1995 update back to the studs, the residence preserved its cherished original features while expanding to include a rear primary suite, creating a 4-bedroom, 4 1/2-bath home. Now 4,017 living SF, the home retains its unique character w/ 7 original & 50 historic replication windows, wrought-iron balconies, a hidden Prohibition-era cabinet, & hand-glazed tiles on the living room floor, risers, & fireplace. The current owners, w/ a loving & meticulous approach, enhanced the property further w/ a new roof (2022), HVAC units (2017 & 2023), tankless water heaters, full re-plumbing (2018), window rehab (2017–2019), a solar system (2022), & an elevated pool & spa (2021). A walkway leads to a covered front stoop (new custom front doors will be installed soon), opening into a light-filled foyer & family room w/ fireplace & wide arched openings that create easy flow & flexible use between these spaces and the adjacent kitchen. Off a soft entry to the right are 2 fully renovated alternate bedroom suites with en-suite baths. The kitchen, updated in 2018, includes Thermador appliances, custom cabinetry, a gas range w/ custom vent hood, concrete & Silestone countertops, & a large island w/ ample seating & a copper farmhouse sink. French doors open to a covered outdoor living area, complete w/ electric screens, a pergola-covered deck, & an outdoor kitchen w/ a copper sink, marble countertops, ice maker, refrigerator, grill, & Alfa pizza oven overlooking the saltwater pool & spa, both heated & chilled for year-round enjoyment. The 4th bedroom, currently used as a pantry/prep area, could easily be converted back by adding a door for privacy and includes an en-suite bathroom doubling as a pool bath. The primary suite, split for optimal privacy, features lofty ceilings, French doors to the outside, a spacious bathroom w/ walk-in shower, clawfoot tub, double vanities, private water closet & 2 custom closets. A wide driveway & parking pad extend to the attached 2-car garage, connected to the home through a mudroom/laundry room. Additional interior spaces include a dining room w/ wet bar adjacent to the kitchen, a turret-window-bordered office, a cozy sitting area, & a private powder room for guests. Other amenities include a whole-house water softener, osmosis water system at the wet bar, a termite bond, & an EV charger in the garage. The most recent renovation opened the conditioned basement to the main living area, now a family favorite for activities like ping pong, board games, & reading. The extraordinary landscape includes plantings for honeybees & butterflies, a raised garden bed of vegetables & herbs, & fruit trees such as avocado, mango, banana, & fig. Environment-friendly features include a well-water irrigation system & solar, saving $150 monthly & offsetting roughly 2/3 of the electric bill. This exceptional home seamlessly blends timeless character w/ thoughtful modern updates & is ideally located near major roads, downtown Orlando, Winter Park, the airport, & Lake Highland Prep, offering a unique, inviting & convenient living experience.