1400 Alabama Dr

Winter Park, FL 32789

$5,895,000
Price
5
Beds
7,916 Sq. Ft.
$745 / Sq. Ft.
7,916
Sq. Ft.
$745
per Sq. Ft.
a front view of a house with a yard
a view of a balcony with chairs and wooden floor
a living room with furniture and a chandelier
a living room with fireplace furniture and a chandelier
a living room with furniture chandelier and a large window
a living room with furniture chandelier and fireplace
a view of a dining room with furniture and wooden floor
a view of an entryway door and hallway
a living room with furniture a fireplace and a chandelier
a living room with furniture a fireplace and a chandelier
a bathroom with a granite countertop sink and a mirror
a kitchen with a sink and a clock
a view of an outdoor space with seating area
a kitchen with a sink a counter top space and stainless steel appliances
a front view of a house with a garden
a dining room with furniture and a floor to ceiling window
a living room with fireplace a flat screen tv and a large window
a spacious bedroom with bed and a chandelier
a spacious bedroom with a bed and a fireplace
a bedroom with a bed couch and window
a living room with furniture and large window
a view of lobby with chandelier
a view of walk in closet with clothes
a view of a big room with closet area
a view of an empty room
a view of a kitchen with a sink and dishwasher with white cabinets
a bathroom with a sink and a mirror
a view of a room with door and wooden floor
a view of walk in closet and bedroom
a living room with furniture a fireplace and a flat screen tv
a view of house with outdoor space and swimming pool
a view of a patio with table and chairs and potted plants
a view of a porch with furniture and backyard
a view of a house with swimming pool and sitting area
a view of a swimming pool with a patio
a view of a garden with plants
a view of a kitchen with white cabinets
a view of an entryway with wooden floor
a bathroom with a sink a toilet and a mirror
a front view of a house with garden
a view of a hallway with wooden floor and windows
a bedroom with a bed a chair and the potted plant
a bathroom with a tub a sink and shower
a view of staircase with lots of frames on wall and a window
an empty room with windows
a bed sitting in a room next to a window
a bathroom with a tub sink and mirror
a view of backyard with plants and outdoor seating
an empty room with windows
an empty room with a window
a bathroom with a sink toilet a mirror and shower
a front view of a house with garden
a backyard of a house with lots of green space
an aerial view of a house with a yard and trees
a view of a backyard of a house with a lake view
an aerial view of ocean with residential house with outdoor space

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...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.

Property Details for 1400 Alabama Drive

Architectural Style
Contemporary, Other
Subdivision Name
J KRONENBERGER SUB
Township
21
Garage Spaces
4
View
Park/Greenbelt, Water
Waterfront
Yes
Water View
Lake - Chain of Lakes
LISTING UPDATED: 10/05/2025 01:14 PM

Property Details for 1400 Alabama Drive

StatusActive
MLS #O6285791
Days on Market244
Taxes$41,240 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1996
Lot Size0.70 AC / 30,423 SF
CountyOrange County

Location

Listing Courtesy of THE AGENCY ORLANDO, Rachel Peters, LLC
Add your commute

Building Information for 1400 Alabama Drive

Stories2Year Built1996Building Size-Lot Size0.70 AC / 30,423 SF

Payment Calculator

$32,566 per month

30 year fixed, 6.28% Interest

Principal and Interest

$29,129

Property Taxes

$3,437

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 1400 Alabama Drive

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 10175.0
  • Building Area Units: Square Feet
  • Direction Faces: Northwest
  • 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.
  • Elementary School: Lakemont Elem
  • Middle Or Junior School: Maitland Middle
  • High School: Winter Park High
  • Mls Major Change Type: Price Decrease
  • Listing Service: Full Service
  • Senior Community: No
  • Unit Number: No
  • Street Number: 1400
  • Street Name: ALABAMA
  • Street Suffix: DRIVE
  • State: FL
  • City: WINTER PARK
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
  • Parking Features: Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Faces Rear, Garage Faces Side
Taxes and HOA Information
  • Association: No
  • CDD: No
  • Tax Block: C
  • Tax Book Number: G-56
  • Tax Legal Description: J KRONENBERGER SUB G/56 LOTS 14 15 & 16BLK C & BOAT HOUSE LOTS 20-C & 21-C
  • Tax Lot: 14
  • Tax Year: 2024
Property
Lot Information
  • Additional Parcels: No
  • Parcel Number: 312130422003150
  • Total Acreage: 1/2 to less than 1
  • Water Access: Lake - Chain of Lakes
  • Water Access: Yes
  • Water Body Name: LAKE MAITLAND
  • Water Extras: Boathouse, Lift - Covered, Skiing Allowed
  • Water Extras: Yes
  • Water: Boathouse, Lift - Covered, Skiing Allowed
  • Zoning: R-1AA
  • Living Area: 7916
  • ILS Under Air SQFT: 500.0
Property and Assessments
  • Year Built Numeric: 1996
  • Flood Zone Code: X, AE
  • Homestead: Yes
  • New Construction: No
  • Public Survey Range: 30
  • Public Survey Section: 31
Utilities
  • Sewer: Public Sewer
  • Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Propane, Sewer Connected, Underground Utilities, Water Connected
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Builder Model: Custom
  • Builder Name: Charles Clayton
  • Construction Materials: Block, Stucco
  • Exterior Features: Awning(s), Balcony, Courtyard, French Doors, Irrigation System, Lighting, Outdoor Grill, Rain Gutters, Sidewalk
  • Fencing: Electric, Masonry, Other
  • Foundation Details: Slab
  • Levels: Two
  • Patio And Porch Features: Covered, Patio
  • Pool Dimensions: 15 x 26.4
  • Pool Features: Gunite, In Ground, Pool Sweep
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Tile
  • Security Features: Security System
  • Spa Features: Heated, In Ground
  • Spa: Yes
  • Vegetation: Mature Landscaping, Trees/Landscaped
  • Waterfront Features: Lake - Chain of Lakes
  • Waterfront Feet Total: 0
  • Number Of Stories: 2
Interior Features
  • Bedrooms Total: 5
  • Bathrooms Full: 5
  • Additional Rooms: Den/Library/Office, Inside Utility, Media Room
  • Appliances: Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Range, Range Hood, Refrigerator, Washer
  • Cooling: Central Air
  • Fireplace Features: Gas, Living Room, Other Room, Outside, Master Bedroom, Wood Burning
  • Fireplace: Yes
  • Flooring: Carpet, Marble, Travertine
  • Heating: Central
  • 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
  • Laundry Features: Electric Dryer Hookup, Inside, Laundry Room, Other, Washer Hookup
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 11.0
  • Water View: Yes
  • Window Features: Shades, Shutters, Window Treatments
  • Bathrooms Half: 4

Property History for 1400 Alabama Drive

DateEvent & SourcePriceAppreciation
Oct 5, 2025

Price Change

MFRMLS #O6285791

$5,895,000—
Sep 29, 2025

Listed (Active)

MFRMLS #O6285791

—
Sep 1, 2025

Temporarily Off Market

MFRMLS #O6285791

$6,200,000—
Apr 16, 2025

Price Change

MFRMLS #O6285791

$6,500,000—
Mar 23, 2025

Listed (Active)

MFRMLS #O6285791

—
Mar 5, 2025

Pending

MFRMLS #O6285791

—
Feb 28, 2025

Listed (Active)

MFRMLS #O6285791

$6,950,000—
Feb 27, 2025

Withdrawn

MFRMLS #O6212012

$6,950,000—
Jun 7, 2024

Listed (Active)

MFRMLS #O6212012

$7,999,999—
Jun 24, 2005

Sold

MFRMLS #O4601223

$3,599,482—
May 5, 2005

Pending

MFRMLS #O4601223

—
Mar 25, 2005

Listed (Active)

MFRMLS #O4601223

$4,150,000—
Dec 10, 2004

Sold

MFRMLS #O4582175

$3,575,000—
Nov 1, 2004

Pending

MFRMLS #O4582175

—
Sep 24, 2004

Listed (Active)

MFRMLS #O4582175

$3,689,000—
Aug 2, 2004

Withdrawn

MFRMLS #O4537374

$4,500,000—
Feb 20, 2004

Listed (Active)

MFRMLS #O4537374

$4,975,000—
DateEvent & SourcePrice
10/05/2025

Price Change

MFRMLS #O6285791

$5,895,000
09/29/2025

Listed (Active)

MFRMLS #O6285791

—
09/01/2025

Temporarily Off Market

MFRMLS #O6285791

$6,200,000
04/16/2025

Price Change

MFRMLS #O6285791

$6,500,000
03/23/2025

Listed (Active)

MFRMLS #O6285791

—
03/05/2025

Pending

MFRMLS #O6285791

—
02/28/2025

Listed (Active)

MFRMLS #O6285791

$6,950,000
02/27/2025

Withdrawn

MFRMLS #O6212012

$6,950,000
06/07/2024

Listed (Active)

MFRMLS #O6212012

$7,999,999
06/24/2005

Sold

MFRMLS #O4601223

$3,599,482
05/05/2005

Pending

MFRMLS #O4601223

—
03/25/2005

Listed (Active)

MFRMLS #O4601223

$4,150,000
12/10/2004

Sold

MFRMLS #O4582175

$3,575,000
11/01/2004

Pending

MFRMLS #O4582175

—
09/24/2004

Listed (Active)

MFRMLS #O4582175

$3,689,000
08/02/2004

Withdrawn

MFRMLS #O4537374

$4,500,000
02/20/2004

Listed (Active)

MFRMLS #O4537374

$4,975,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 1400 Alabama Drive

Taxable ValueLand-Additions-Total-
Tax Record2024$41,240 ($3,437 / month)
Home Facts
Beds4Total Finished SqFt7,916 SqFtAbove Grade Finished SqFt7,916 SqFtStories2Lot Size31,322 SqFtStyleSingle Family ResidenceYear Built1996ZoningPRCountyORANGEAPN31-21-30-4220-03-150Fireplace TypeHas Fireplace

Schools near 1400 Alabama Drive

This home is within Orange County Public Schools.
Rating
School
Type
Grades
Distance
Lakemont Elementary School
Public - PK to 5
Cornerstone Academy Charter
Charter - K to 8
Maitland Middle School
Public - 6 to 8
Cornerstone Charter Academy High School
Charter - 9 to 12
Rating
School
Distance
Lakemont Elementary School
PublicPK to 5

Cornerstone Academy Charter
CharterK to 8

Maitland Middle School
Public6 to 8

Cornerstone Charter Academy High School
Charter9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 1400 Alabama Drive, Winter Park, FL 32789

1400 Alabama Drive is a single family home for sale in Winter Park, FL 32789. This property was listed for sale on February 28, 2025 by THE AGENCY ORLANDO, it's currently listed at $5,895,000. It has been on the market for a total of 244 days and was last sold on June 24, 2005. This listing's school district is Orange County Public Schools. Nearby schools include Lakemont Elementary School, Cornerstone Academy Charter and Maitland Middle School. 1400 Alabama Drive is a 5-bed, 9-bath, 7,916 sqft single family home built in 1996.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of THE AGENCY ORLANDO, Rachel Peters, LLC

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 10/05/2025 01:14 PM