$5,895,000
5 Bed
9 Bath
7,916 Sqft
0.70 Acre Lot

1400 Alabama Dr, Winter Park, Florida 32789

  • Residential Property Type
  • 7,916 Sqft Square Footage
  • Driveway Cars Garage
  • 1996 Year Built
Property Description

Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .71-acre corner lot in one of Winter Park’s most sought-after locations. This 7,916 SF property includes a main residence of over 7,100 SF, a detached guest house, and a poolside catering suite. The private covered boat dock is located just steps away, across the street, in the historic Kraft Azalea Garden, providing direct lake access with boat and personal watercraft storage on Lake Maitland, without the upkeep of a waterfront backyard. Inside, fresh neutral interiors and beautiful landscaping frame elegant arrival and living spaces. The thoughtful layout offers 5 bedrooms and 5 full plus 4 half baths, including a 550 SF guest house. Expansive entertaining areas flow seamlessly to a private courtyard with a heated pool and spa, covered dining, outdoor grill, wood-burning fireplace, and multiple terraces. Highlights include a grand primary suite with dual bathrooms and closets, a two-story wardrobe with an office in one of the primary closets, an impressive entertainment room, and a gourmet kitchen outfitted with Viking appliances, a newly replaced double oven, and a trash compactor. For large-scale entertaining, the detached pool house doubles as a catering suite with prep sink, refrigerator, and wall-to-wall storage. Built by renowned builder Charles Clayton, the home is a masterpiece of solid block construction and timeless detail featuring imported Parisian fireplaces, solid marble columns, both marble and travertine floors, and Venetian plaster walls. A new barrel tile roof (2023) adds lasting value and peace of mind. Ideally located across from Kraft Azalea Garden and near Rollins College, the estate offers a rare combination of waterfront tranquility and walkable access to Park Avenue’s world-class dining, boutiques, and museums. The Winter Park Racquet Club is also just a short golf cart ride away. This is an opportunity to acquire a legacy property at a fair value, with the heaviest aesthetic updates complete and future equity poised for growth.

Basic Details
Residential
For Sale
O6285791
$5,895,000
Park/Greenbelt,Water
5
9
4
7,916 Sqft
1996
0.70 Acre
Active
5
Single Family Residence
: Tile
1
Features
: Gunite, In Ground, Pool Sweep
: Central
: Central Air
: Other, Masonry, Electric
: Living Room, Wood Burning, Gas, Outside, Other, Primary Bedroom
: Covered, Patio
: Driveway, Garage Faces Rear, Circular Driveway, Garage Faces Side, Electric Vehicle Charging Station(s)
: Lighting, Sidewalk, Rain Gutters, Balcony, Courtyard, French Doors, Awning(s), Outdoor Grill
: Carpet, Travertine, Marble
: Walk-In Closet(s), High Ceilings, Primary Bedroom Main Floor, Solid Surface Counters, Thermostat, Split Bedroom, Window Treatments, Solid Wood Cabinets, Stone Counters, Crown Molding, Built-in Features, Coffered Ceiling(s), Wet Bar
: Laundry Room, Inside, Washer Hookup, Electric Dryer Hookup, Other
1
: Public Sewer
: Underground Utilities, Electricity Connected, BB/HS Internet Available, Cable Connected, Sewer Connected, Water Connected, Propane
: Lake Privileges
: Shutters, Window Treatments, Shades
: Contemporary, Other
Appliances
: Dishwasher, Range, Disposal, Electric Water Heater, Dryer, Refrigerator, Washer, Bar Fridge, Range Hood, Built-In Oven
Address Map
US
FL
Orange
Winter Park
J KRONENBERGER SUB
32789
ALABAMA
1400
DRIVE
W82° 39' 19.5''
N28° 36' 38.2''
Northwest
From N Orlando Ave. Take Webster Ave. to LEFT on Park Ave. RIGHT on E Stovin, RIGHT on Palmer Ave., LEFT on Alabama Dr. House in on the RIGHT.
32789 - Winter Park
R-1AA
Neighborhood
Lakemont Elem
Winter Park High
Maitland Middle
Additional Info
THE AGENCY ORLANDO
Rachel Peters, LLC
$0
$0
Additional Information
: Block, Stucco
: Slab
4
: Two
2025-02-28
6200000
2
LAKE MAITLAND
: Public
1
10175
Financial
41240.46
Listing Information
261207434
261019000
Cash,Conventional
Active
2025-10-05T17:10:10Z
Stellar
: None
2025-09-30T01:28:42Z
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Contact Agent
Contact Us
407-615-0866