1400 ALABAMA DRIVE Winter Park, FL $ 5,895,000
1400 ALABAMA DRIVE
$ 5,895,000
Share Save

1400 ALABAMA DRIVE

Winter Park, FL, 32789
$ 5,895,000
Bedrooms5 Baths5.4 Sq 7,916

Monthly Estimate*

$ 36,777

1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 1
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 2
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 3
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 4
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 5
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 6
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 7
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 8
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 9
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 10
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 11
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 12
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 13
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 14
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 15
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 16
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 17
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 18
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 19
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 20
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 21
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 22
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 23
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 24
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 25
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 26
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 27
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 28
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 29
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 30
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 31
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 32
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 33
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 34
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 35
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 36
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 37
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 38
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 39
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 40
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 41
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 42
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 43
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 44
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 45
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 46
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 47
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 48
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 49
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 50
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 51
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 52
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 53
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 54
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 55
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 56
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 57
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 58
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 59
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 60
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 61
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 62
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 63
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 64
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 65
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 66
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 67
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 68
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 69
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 70
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 71
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 72
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 73
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 74
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 75
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 76
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 77
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 78
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 79
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 80
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 81
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 82
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 83
1400 ALABAMA DRIVE, Winter Park, FL 32789 - Image 84

Single Family Home for sale in Winter Park, FL

for $5,895,000 with 5 bedrooms and 5 full baths, 4 half baths. This 7,916 square foot home was built in 1996 on a lot size of 0.7.

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.

See more

Single Family Active

Price

$ 5,895,000

Bedrooms

5

Full Bath

5

Half Bath

4

Property Type

Single Family

Taxes

$ 41,240

Style

Contemporary Other

Lot Size

0.7

Year Built

1996

Town/City

Winter Park

County/Region

Orange

MLS | Web ID

O6285791

Features
General
Sewer Public Sewer
Heating Central
Cooling Central Air
Utilities BB/HS Internet Available Cable Connected Electricity Connected Propane Sewer Connected Underground Utilities Water Connected
Roof Tile
Appliances Bar Fridge Built-In Oven Dishwasher Disposal Dryer Electric Water Heater Range Range Hood Refrigerator Washer
Zoning R-1AA
Garage Spaces 4
Patio/Porch Features Covered Patio
Architectural Style Contemporary Other
Pool Features Gunite In Ground Pool Sweep
Security Features Security System
Construction Materials Block Stucco
Year Built 1996
View Park/Greenbelt Water
Levels Two
Property Subtype Single Family Residence
Tax Year 2024
Ownership Fee Simple
Waterfront Features Lake - Chain of Lakes
County Orange
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name J KRONENBERGER SUB
Facing Direction Northwest
Garage Y/N true
Total Rooms 11
Full Baths 5
Status Active
Directions 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.
High School Winter Park High
City WINTER PARK
Body of Water LAKE MAITLAND
Senior Community Y/N false
MLS Area 32789 - Winter Park
Lot Size Units Square Feet
Lot Size Square Feet 30423
Carport Y/N false
Listing Terms Cash Conventional
Spa Features Heated In Ground
Elementary School Lakemont Elem
Land Lease Y/N false
Tax Annual Amount 41240.46
Middle/Junior High School Maitland Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Building Area Units Square Feet
Living Area Units Square Feet
Builder Name Charles Clayton
Standard Status Active
Occupancy Type Tenant
Tax Lot 14
Legal Description J KRONENBERGER SUB G/56 LOTS 14 15 & 16BLK C & BOAT HOUSE LOTS 20-C & 21-C
Water View Lake - Chain of Lakes
Water Access Type Lake - Chain of Lakes
Minimum Lease 1 Week
Water Access Y/N true
Additional Rooms Den/Library/Office Inside Utility Media Room
ILS Under Air SQFT 500
Water View Y/N true
Flood Zone Code X AE
See more
Interior
Interior Amenities 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
Flooring Carpet Marble Travertine
Fireplace Features Gas Living Room Other Room Outside Master Bedroom Wood Burning
Total Stories 2
Air Conditioning Y/N true
Heating Y/N true
Window Features Shades Shutters Window Treatments
Fireplace Y/N true
Half Baths 4
Laundry Features Electric Dryer Hookup Inside Laundry Room Other Washer Hookup
Total Bedrooms 5
Total Baths 9
See more
Exterior
Exterior Amenities Awning(s) Balcony Courtyard French Doors Irrigation System Lighting Outdoor Grill Rain Gutters Sidewalk
Vegetation Mature Landscaping Trees/Landscaped
Fencing Electric Masonry Other
Parking Features Circular Driveway Driveway Electric Vehicle Charging Station(s) Garage Faces Rear Garage Faces Side
Water Source Public
Lot Size Area 30423
Foundation Details Slab
Spa true
Building Area Total 10175
Lot Size Acres 0.7
Road Surface Type Brick Paved
Private Pool true
Waterfront Y/N true
Covered Spaces 4
Builder Model Custom
See more
* Excluded Features
List By
The Agency Orlando

Broker

rachel.peters@theagencyre.com

Email

Affordability Calculator

$40,214
Per Month
91%
9%
0%
Monthly Principal & Interest
$36,777
Monthly Property Taxes
$3,437
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby
0 Elementary School
0 Middle School
Winter Park High High School High School
Pricing History
DatePricePrice ChangeDescription
12/19/2025$5,895,000 Listed Price

Map


See all

1400 ALABAMA DRIVE, Winter Park, FL, 32789 is a Single Family Home for sale at $5,895,000 with 7,916 sqft and a lot size of 0.7. 1400 ALABAMA DRIVE has 5 bedrooms, 5.4 baths, and was built in 1996. The property's zip code is 32789 which is in Winter Park, FL