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Under contract-accepting backup offers. A Jewel Box: Curated for a Life Well Lived. Penthouse 404 at The Alabama is a rare architectural gem"”a two-story residence that blends historic provenance w/ design-forward luxury in the heart of Winter Park's 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 home"”overlooking 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 shower"”ideal 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 wall"”complete 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 slips"”all just minutes from Park Avenue.
| DAYS ON MARKET | 196 | LAST UPDATED | 12/9/2025 |
|---|---|---|---|
| TRACT | ALABAMA CONDO | YEAR BUILT | 1981 |
| COMMUNITY | 32789 - Winter Park | COUNTY | Orange |
| STATUS | Pending | PROPERTY TYPE(S) | Condo/Townhouse/Co-Op |
| Elementary School | Lakemont Elem |
|---|---|
| Jr. High School | Maitland Middle |
| High School | Winter Park High |
| ADDITIONAL DETAILS | |
| AIR | Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| AMENITIES | Insurance, Maintenance Grounds, Maintenance Structure, Pest Control, Security, Sewer, Trash, Water |
| APPLIANCES | Dishwasher, Disposal, Microwave, Range, Range Hood, Refrigerator |
| AREA | 32789 - Winter Park |
| CONSTRUCTION | Block, Frame, Stucco |
| EXTERIOR | Balcony, Lighting |
| HEAT | Electric, Heat Pump |
| INTERIOR | Built-in Features, Eat-in Kitchen, Elevator, Open Floorplan, Stone Counters, Walk-In Closet(s) |
| LOT DESCRIPTION | Landscaped, Paved, Waterfront |
| PARKING | Assigned, Covered, Guest |
| SEWER | Public Sewer |
| STORIES | 2 |
| STYLE | Historic, Mediterranean, Traditional |
| SUBDIVISION | ALABAMA CONDO |
| TAXES | 26498 |
| UTILITIES | Cable Available, Cable Connected, Electricity Connected, Sewer Connected, Water Connected |
| VIEW | Yes |
| VIEW DESCRIPTION | Lake, Water, Park/Greenbelt |
| WATER | Public |
| WATER ACCESS | LAKE MAITLAND |
| WATERFRONT | Yes |
| WATERFRONT DESCRIPTION | Lake Privileges |
MORTGAGE CALCULATOR
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Listing provided by Padgett McCormick, KELLY PRICE & COMPANY LLC, 407-645-4321
The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 12/18/25 6:33 AM PST.
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