Step into timeless elegance with this gorgeous 1925 estate home located on a charming brick-lined street in the highly sought-after Lake Cherokee District. Featuring 5 bedrooms, 4.5 bathrooms, and nearly 3,600 square feet of living space, this character-filled home includes a detached 1,009 SF guest house, a resort-style pool, and countless high-end upgrades throughout. The main home showcases a seamless blend of historic charm and modern luxury with formal living and dining rooms, hardwood floors, high ceilings, and both gas and wood-burning fireplaces. The chef's kitchen is a standout, featuring marble countertops, a commercial-grade 8-burner dual oven gas range, Miele coffee system with external milk container and cup drawer, glass rinser, pasta arm, and two full refrigerators. Upstairs, the primary suite offers a spacious sitting area, renovated en suite bath with dual vanities, walk-in shower, and multiple closets. Three additional bedrooms and two full baths complete the second floor, along with access to a laundry chute, floored attic, and fully insulated attic and crawlspace with closed-cell foam. Downstairs also includes a private office/den, half bath, and a basement equipped with a top-of-the-line sump pump, offering both function and peace of mind—especially since the home sits well above the flood line and has remained untouched by past flooding. Step outside into a true backyard oasis featuring a resort-style pool with water jets, a solar-heated outdoor shower, brand new pool pump, light, and filter, two covered lanais, and a generous fenced-in yard. The property also includes smart solar exterior lighting with customizable seasonal presets, a pool storage room, and an additional storage room at the rear of the home. The detached guest house offers privacy and flexibility with a bedroom, full bathroom, kitchenette, and living area—ideal for visitors, extended family, or rental potential. Additional upgrades include rain showers in all bathrooms, granite counters throughout, and a washer/dryer set with steam, shoe-wash, and dry-cleaning features.Zoned for top-rated Blankner K-8 and Boone High School, this exceptional home is located just minutes from Downtown Orlando, Waterford Lakes, UCF, Orlando International Airport (MCO), and major roads including E Colonial Dr and the 408. This is a rare opportunity to own a piece of Orlando history with every modern convenience.