**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.