One or more photo(s) has been virtually staged. This impeccably restored 1920s residence, inspired by the timeless designs of Italian architect Andrea Palladio, seamlessly blends historic charm with contemporary luxury. Set on a rare double lot shaded by mature Live Oaks and framed by picturesque brick streets, the home offers dual street access and has undergone a meticulous, full scale renovation. Every inch was thoughtfully reimagined both levels reconfigured to maximize functionality, natural light, and flow while original architectural details were carefully preserved. High ceilings contribute to the home's open, airy feel. The main residence features a flexible layout with three generously proportioned bedrooms and three and a half bathrooms. A detached, fully self contained one bedroom, one bath guest house complete with a private entrance and full kitchen offers ideal accommodations for guests, extended stays, or income generating opportunities. All three newly renovated bathrooms in the main home feature frameless glass walk in showers, elegant stone countertops, and premium fixtures. Major system upgrades include new plumbing, electrical, ductwork, and HVAC. Energy efficiency was a priority throughout, with features such as R 38 attic insulation, a tankless water heater, double pane Pella windows, and custom doors and hardware. The lanai, equipped with motorized shades, offers both privacy and convenience blending indoor comfort with outdoor elegance. At the heart of the home lies a chefs kitchen designed for both beauty and performance. Highlights include a custom island, integrated gas cooktop, Dacor double ovens, and bespoke cabinetry. A floor to ceiling sliding glass wall seamlessly connects the interior to a covered lanai and a newly rebuilt 16x32 saltwater pool 8 feet deep with updated piping and mechanicals, a feature that could not be replicated under todays building codes. The home includes three distinct living areas, a formal dining room, and a spacious eat in kitchen. A sunlit home office and a large laundry room with stone countertops, deep sink, and custom cabinetry add exceptional functionality. A centrally located powder room provides added convenience for guests. Upstairs, the expansive primary suite offers a spa inspired retreat. The luxurious bath includes a soaking tub, a walk in shower adorned with Italian Calacatta Gold porcelain tile, champagne gold fixtures, dual Kohler sinks, and Cambria quartz countertops. A custom walk in closet completes the suites refined ambiance. Two additional upstairs bedrooms each include en suite bathrooms, offering comfort and privacy for family or guests. Ideally situated just steps from Lake Lawsona and within walking distance of Lake Eola, Thornton Park, Orlando Health, the Orlando Arena, and the Dr. Phillips Center, the home provides effortless access to Orlandos most vibrant destinations. Nearby Winter Park adds to the appeal with its scenic parks, upscale boutiques, renowned art galleries, and acclaimed dining. Cultural institutions like the Morse Museum, Winter Park Historical Museum, and Central Park are also close at hand, along with the Winter Park Golf and Country Club and the Winter Park Chain of Lakes. With Michelin rated restaurants, a popular Sunday farmers market, SunRail access, and Orlando International Airport just minutes away, this exceptional home presents a rare opportunity to own a landmark property where architectural heritage, modern luxury, and urban convenience intersect.