This fairytale property is located in the gracious neighborhood surrounding Park Avenue known for homes of unique character & historic architecture. The main home was originally built in 1918 & has been thoughtfully renovated to modernize the home's function while maintaining the architectural integrity. It is located in the heart of Winter Park on a rare half acre, corner lot w/ charming views of the Winter Park Country Club & golf course. The semi-circular driveway that connects to both Webster & Old England provides convenience & enhances the curb appeal. Upon arrival, your guests will immediately appreciate the lush landscape, the dynamic & steeply pitched roof, overlapping, front-facing gables & charming, arched front door popular w/ Tudor style homes. Inside the foyer & through the arched doorway to the left, this home opens to an expansive, formal living space featuring cathedral style, volume ceilings ornamented w/stained, hand hewn oak, wood floors, tall windows, french doors overlooking the brick courtyard & an elegant, floor to ceiling, wood burning fireplace. To the right of the foyer are the formal dining & sitting rooms w/ long, rectangular windows clustered together offering an abundance of natural light to these richly detailed yet comfortable interior spaces. Towards the back, right side of the home, the spacious kitchen opens to an eat-in area, family room & stairs leading down to the basement wine storage. The kitchen features real wood cabinets, black granite counter tops, a sizable island w/seating for five, a Subzero refrigerator, Viking gas range & oven w/stainless steel vent hood, double-bowl, under-mount sinks, commercial style faucet, ice maker, prep sink, under counter microwave, a pantry & a large closet-style storage space allowing for easy access to your favorite serving pieces. The eat-in area & family rooms feature multiple sets of french doors through which you are provided beautiful views of the fountain at the center of the courtyard, pool & backyard haven. The layout of the main house includes a 3-way split plan w/ all bedrooms & bathrooms on the 2nd floor. The primary is located on the left side of the home and is accessed through a rear stairwell. This spacious suite is equipped w/ a walk-in closet, Juliet balcony & charming bathroom featuring a wood vanity, marble countertop & a shower/tub combination w/ floor to ceiling white subway tile. The two alternate bedrooms & bathrooms are accessed from the entry stairwell. The front, right alternate bedroom suite features a spiral staircase w/ loft. The rear, alternate bedroom suite is adjacent to the roof top deck. Both are rich w/ character showcasing wood floors, extensive millwork, renovated baths w/shower-tub combination, white subway tile, bead-board & pedestal sinks. The guest house was built in 1925 & is located on the far side of the courtyard. It includes a full kitchen, general living space, laundry room & half bathroom on the 1st floor as well as 2 bedrooms & 1 ½ bathrooms on the 2nd floor. This flexible space could be used in myriad ways. A rear, gated driveway w/ access from Old England is located at the NE corner of the property & is discretely hidden behind a jasmine covered wall. This is the first time this century that this Old Florida property w/ its storybook exterior architecture, majestic oaks & private courtyards that leaves you w/ a rare feeling of deep connection & an undeniable sense of place is being offered for sale.