1400 Alabama Drive, Winter Park, FL 32789
For Sale $5,895,000
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Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .71-acre corner lot in one of Winter Parks 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.
Built-in Features
Coffered Ceiling(s)
Crown Molding
High Ceilings
Primary Bedroom Main Floor
Solid Surface Counters
Solid Wood Cabinets
Split Bedroom
Stone Counters
Thermostat
Walk-In Closet(s)
Wet Bar
Window Treatments
Taxes: $41.00
Tax Year: 2024
Awning(s)
Balcony
Courtyard
French Doors
Lighting
Outdoor Grill
Rain Gutters
Sidewalk
Bar Fridge
Built-In Oven
Dishwasher
Disposal
Dryer
Electric Water Heater
Range
Range Hood
Refrigerator
Washer
Park/Greenbelt
Water
Lake Privileges
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Junior High: Maitland Middle
High School: Winter Park High
MLS Area: 32789 - Winter Park
Price per Square Feet: $744.69
Total Floors: 2
Water: Public
Construction: Block, Stucco
Date Listed: 2025-03-01 04:54:55
Pool: Yes
Pool Type: Gunite, In Ground, Pool Sweep
Private Spa: Yes
Windows: Shades, Shutters, Window Treatments
Parking: Circular Driveway, Driveway, Electric Vehicle Charging Station(S), Garage Faces Rear, Garage Faces Side
Garage Spaces: 4
Flooring: Carpet, Marble, Travertine
Roof: Tile
Heating: Central
Cooling: Central Air
Sewer: Public Sewer
Listing Courtesy Of: The Agency Orlando
rachel.peters@theagencyre.com
Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .71-acre corner lot in one of Winter Parks 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.
Property Details
Price: $5,895,000
Sq Ft: 7,916
($745 per sqft)
Bedrooms: 5
Bathrooms: 5
Partial Baths: 4
City: Winter Park
County: Orange
Type: Single Family Reside
Development: J Kronenberger Sub
Acres: 0.70
Year Built: 1996
Listing Number: O6285791
Status Code: A-Active
Taxes: $41.00
Tax Year: 2024
Garage:
4
Interior Features:
Built-in Features
Coffered Ceiling(s)
Crown Molding
High Ceilings
Primary Bedroom Main Floor
Solid Surface Counters
Solid Wood Cabinets
Split Bedroom
Stone Counters
Thermostat
Walk-In Closet(s)
Wet Bar
Window Treatments
Financial Information:
Taxes: $41.00
Tax Year: 2024
Exterior Features:
Awning(s)
Balcony
Courtyard
French Doors
Lighting
Outdoor Grill
Rain Gutters
Sidewalk
Equipment:
Bar Fridge
Built-In Oven
Dishwasher
Disposal
Dryer
Electric Water Heater
Range
Range Hood
Refrigerator
Washer
View:
Park/Greenbelt
Water
Waterfront Description:
Lake Privileges
School Information:
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Junior High: Maitland Middle
High School: Winter Park High
Additional Information:
MLS Area: 32789 - Winter Park
Price per Square Feet: $744.69
Total Floors: 2
Water: Public
Construction: Block, Stucco
Date Listed: 2025-03-01 04:54:55
Pool: Yes
Pool Type: Gunite, In Ground, Pool Sweep
Private Spa: Yes
Windows: Shades, Shutters, Window Treatments
Parking: Circular Driveway, Driveway, Electric Vehicle Charging Station(S), Garage Faces Rear, Garage Faces Side
Garage Spaces: 4
Flooring: Carpet, Marble, Travertine
Roof: Tile
Heating: Central
Cooling: Central Air
Sewer: Public Sewer
Map of 1400 Alabama Drive, Winter Park, FL 32789
Listing Courtesy Of: The Agency Orlando
rachel.peters@theagencyre.com