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$5,895,000

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 5 Full Baths
  • 4 Partial Baths
  • 7,916 Sq. Ft.
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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.

Full Property Details for 1400 Alabama Dr

General

  • Price: $5,895,000
  • Taxes: $41,240 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6285791
  • Updated: 10/5/2025
  • Added to Site: 323 day(s) ago

Rental Information

  • Min. Lease: 1 Week

Interior

  • Number of Rooms: 11
  • 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
  • Fireplace: Yes
  • Fireplace(s): Gas, Living Room, Other Room, Outside, Master Bedroom, Wood Burning
  • Appliances: Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Range, Range Hood, Refrigerator, Washer
  • Flooring: Carpet, Marble, Travertine

Rooms

Bathrooms

  • Total Bathrooms: 9
  • Full Bathrooms: 5
  • Half Bathrooms: 4

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Electric Dryer Hookup, Inside, Laundry Room, Other, Washer Hookup

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Gunite, In Ground, Pool Sweep
  • Spa: Yes
  • Spa Description: Heated, In Ground
  • Security/Safety: Security System

Exterior

  • Exterior Features: Awning(s), Balcony, Courtyard, French Doors, Irrigation System, Lighting, Outdoor Grill, Rain Gutters, Sidewalk
  • Deck/Patio: Covered, Patio
  • Porch/Patio/Deck: Covered, Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 4
  • Covered Spaces: 4
  • Parking Features: Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Faces Rear, Garage Faces Side

Location

  • Area: 32789 - Winter Park
  • County: Orange
  • Development Name: 32789 - Winter Park
  • Subdivision: J KRONENBERGER SUB
  • Driving 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.
  • Direction Faces: Northwest

School Information

  • Elementary School: Lakemont Elem
  • Middle School: Maitland Middle
  • High School: Winter Park High

Community

  • Community Name: 32789 - Winter Park

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water District: LAKE MAITLAND
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable Connected, Electricity Connected, Propane, Sewer Connected, Underground Utilities, Water Connected

Structural Information

  • Architectural Info: Contemporary, Other
  • Architectural Style: Contemporary, Other
  • Builder: Charles Clayton
  • Exterior Const.: Block, Stucco
  • Roof: Tile
  • Windows: Shades, Shutters, Window Treatments
  • Stories/Levels: Two
  • Square Feet: 7,916
  • Sq. Ft. Source: Public Records
  • Year Built: 1996

Lot Features

  • Property View: Park/Greenbelt, Water
  • Lot Size (Acres): 0.7
  • Lot Size (Sq. Ft.): 30,423
  • Lot Size: 30423
  • Street/Road Desc.: Brick, Paved
  • Fencing (Description): Electric, Masonry, Other

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Access: Yes
  • Water Access Desc: Lake - Chain of Lakes
  • Water Extras: Yes
  • Water Front Name: LAKE MAITLAND
  • Water Front Desc.: Lake - Chain of Lakes

Financial Considerations

  • Tax Amount: $41,240.46
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: J KRONENBERGER SUB G/56 LOTS 14 15 & 16BLK C & BOAT HOUSE LOTS 20-C & 21-C
  • Flood Zone Info: X, AE
  • APN: 312130422003150
  • Property ID: 312130422003150
  • Block/Lot/Section: C

Listed by The Agency Orlando

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Listing agent

— 1400 Alabama Dr —

  • The Agency Orlando

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with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 1400 Alabama Dr

School District:Orange County School District
NameGradesDistance
Lakemont Elementary School
901 North Lakemont Avenue, Winter Park, FL 32792
K-51 mi
Maitland Middle School
701 North Thistle Lane, Maitland, FL 32751
6-81.6 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1400 Alabama Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/05/2025
Price Reduced
$5,895,000
-4.92%
MLS
7/20/2025
Price Reduced
$6,200,000
-4.62%
MLS
4/16/2025
Price Reduced
$6,500,000
-6.47%
MLS
2/28/2025
Listed
$6,950,000
—
MLS
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1400 Alabama Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$41,240
—
$2,743,161
3%
2024
$41,240
3%
$2,665,851
3%
2023
$39,862
6%
$2,588,205
6%
2021
$37,783
-1%
$2,434,918
-3%
2022
$38,140
1%
$2,507,966
4%
2021
$37,783
—
$2,401,300
2%
2019
$37,660
—
$2,347,312
2%
2018
$37,495
1%
$2,303,545
2%
2017
$37,212
2%
$2,256,166
2%
2016
$36,475
-2%
$2,209,761
1%
2015
$37,351
-1%
$2,194,400
1%
2014
$37,680
2%
$2,176,984
1%
2013
$36,925
—
$2,144,812
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by The Agency Orlando

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1400 Alabama Drive, Winter Park, FL 32789 (MLS# O6285791) is a Single Family property with 5 bedrooms, 5 full bathrooms and 4 partial bathrooms. 1400 Alabama Drive is currently listed for $5,895,000 and was received on February 28, 2025. Want to learn more about 1400 Alabama Drive? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

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