Skip to content
1400 Alabama Dr.

1400 Alabama DriveWinter Park, FL, 32789

5beds
9baths
7,916sqft
Single Family Residence
Built in 1996
$5,400,000
Sold
Price per sqft
$682
Sold on
Feb 27, 2026
MLS #O6285791Updated Feb 27, 2026

About this property

Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .72-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 into a private courtyard with a heated pool and spa, covered dining, an outdoor grill, a 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 and designed by Marc-Michaels, 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. A rare opportunity to acquire a legacy property with major aesthetic updates already completed and future equity positioned for growth.

Interested in this property?
Gaby, Property Specialist
Speak to GabyProperty Specialist, SerhantGaby can share what this home sold for, and find you comparable properties still on the market.
+1 (407) 490-0475
No pressure. Your details stay private.

Property details

Property type
Single Family Residence
Street address
1400 Alabama Drive
City
Winter Park
State
FL
ZIP code
32789
Year built
1996
New construction
No
Faces
Northwest
Rooms
11
Building stories
2
Living area
7,916 sqft
Total building area
10,175 sqft
Architectural style
Contemporary, Other
Levels
Two

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at October 8, 2026 at 8:01 AM EDT

Price & sale history

EventPrice
SoldMLS #O6285791$5,400,000
Price reducedMLS #O6285791$5,895,000Change: −15.2%−$1,055,000
Listed for saleMLS #O6285791$6,950,000
SoldMLS #O4601223$3,599,482
History may be incomplete.
Explore nearby sales

Location

Recent sales nearby

1400 Alabama Dr.
Learn more about this propertyGet in touch for more information
We will use your details to respond to this request and may share them with a suitable real estate professional when needed. Marketing is optional.