A Jewel Box: Curated for a Life Well Lived. Penthouse 404 at The Alabama is a rare architectural gema two story residence that blends historic provenance w/ design forward luxury in the heart of Winter Parks most coveted lakefront setting. Created by combining two original top floor units, this expansive penthouse is the largest in the building & the only one w/ a private outdoor terrace. Originally constructed in 1921 as the Alabama Hotel, the Mediterranean Revival structure has been transformed into an intimate community of 19 private residences overlooking Lake Maitland w/ direct access to the Winter Park Chain of Lakes. Reimagined by Z Properties in 2019 w/ a full renovation, the home reflects thoughtful scale, bespoke craftsmanship & a sophisticated design vision. The dramatic entry foyer features extensive millwork paneling that conceals the bedroom suites & opens into a light filled great room w/ expansive lake facing windows & French doors that open to the signature terrace: a professionally landscaped outdoor retreat w/ turf grass, mist fans, lighting, irrigation & custom planters. At the heart of the home, the boldly composed kitchen balances sculptural form & high function. A sculptural block of black quartz anchors the island w/ seating, trimmed in gold metal cladding that echoes the gold countertops & full height backsplash. Sleek, dark wood, high gloss cabinetry conceals a panel ready Thermador suite, including double refrigerator columns & dishwasher. Lacquered finishes, under cabinet lighting, geometric black & white tile, designer fixtures, brass Lutron controls, linear HVAC diffusers, LED recessed lighting & in ceiling Sonos speakers complete the experience. What appears to be cabinetry is actually a hidden door leading to a den/family room at the rear of the homeoverlooking the lake & appointed w/ custom built ins, black sisal carpet & a moody grasscloth ceiling that mirrors the wall color & adds cinematic ambiance. Throughout, curated materials elevate each room: Venetian plaster, Schumacher wallpaper, signature lighting, oak chevron patterned hardwood floors & tailored sisal carpets. The main level includes two en suite bedrooms located just off the foyer. The primary suite offers a lacquered accent wall, boutique style closets & a spa quality bath w/ a custom vanity, dual undermount sinks, lucite & metal hardware, black quartz counters & full height mirrors w/ integrated lighting. A glass enclosed wet room w/ soaking tub & rain shower, Toto toilet & Venetian plaster walls completes the suite. A discreet laundry room & storage area are tucked away nearby. The secondary bedroom features a black vanity w/ gold hardware, black & white subway tile, gold sunburst mirror & a walk in frameless glass showerideal for guests or extended stays. Upstairs, a third en suite bedroom offers treetop & lake views, a mirrored gym wall & private bath featuring a black vanity w/ silver toned hardware, black quartz top, black penny tile floors & bold geometric tile that spans the shower & vanity wallcomplete w/ a tucked away water closet for added privacy. Additional features include Nest controlled dual HVAC, 80 gallon stainless water heater w/ booster, Everpure filtration, Jeld Wen impact rated windows & doors, Lutron controls & two reserved covered parking spaces. The Alabama offers a lakeside pool, renovated clubhouse, private dock & community boat slipsall just minutes from Park Avenue.