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.
Sold for $5,400,000
$5,400,000
1400 ALABAMA DRIVE, WINTER PARK, FL 32789
5beds
7,916sqft
Single Family Residence
Built in 1996
0.72 Acres Lot
$5,439,000 Zestimate®
$682/sqft
$7,781 Estimated rent
Home value
$5,439,000
$5.00M - $5.93M
$7,781/mo
Zestimate® history
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List your homeWhat's special
Private covered boat dockFresh neutral interiorsImpressive entertainment roomMultiple terracesOutdoor grillNewly replaced double ovenTrash compactor
Zillow last checked:
Listing updated:
Listed by:
Rachel Peters, LLC 407-625-3227,
THE AGENCY FL 407-335-4119
Bought with:
Mick Night, 525290
PREMIER SOTHEBY'S INTL. REALTY
Source: Stellar MLS,MLS#: O6285791
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 9
- Full bathrooms: 5
- 1/2 bathrooms: 4
Rooms
- Room types: Den/Library/Office, Utility Room, Media Room
Primary bedroom
- Features: Built-In Shelving, Built-in Features, En Suite Bathroom, Dual Closets
- Level: First
- Area: 504 Square Feet
- Dimensions: 18x28
Bedroom 2
- Features: Jack & Jill Bathroom, Walk-In Closet(s)
- Level: Second
- Area: 145.18 Square Feet
- Dimensions: 12.2x11.9
Bedroom 3
- Features: Jack & Jill Bathroom, Walk-In Closet(s)
- Level: Second
- Area: 207.6 Square Feet
- Dimensions: 12x17.3
Bedroom 4
- Features: En Suite Bathroom, Walk-In Closet(s)
- Level: Second
- Area: 259.17 Square Feet
- Dimensions: 15.9x16.3
Dinette
- Features: Built-In Shelving
- Level: First
- Area: 156 Square Feet
- Dimensions: 13x12
Dining room
- Level: First
- Area: 247 Square Feet
- Dimensions: 13x19
Kitchen
- Features: Stone Counters, Pantry
- Level: First
- Area: 312 Square Feet
- Dimensions: 13x24
Library
- Features: Bar
- Level: First
- Area: 357 Square Feet
- Dimensions: 17x21
Living room
- Level: First
- Area: 459 Square Feet
- Dimensions: 17x27
Loft
- Features: Built-In Shelving
- Level: Second
- Area: 272 Square Feet
- Dimensions: 17x16
Media room
- Level: First
- Area: 504 Square Feet
- Dimensions: 18x28
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Bar Fridge, Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Range, Range Hood, Refrigerator, Washer
- Laundry: Electric Dryer Hookup, Inside, Laundry Room, Other, Washer Hookup
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
- Flooring: Carpet, Marble, Travertine
- Doors: French Doors, Outdoor Grill
- Windows: Shades, Shutters, Window Treatments
- Has fireplace: Yes
- Fireplace features: Gas, Living Room, Other Room, Outside, Master Bedroom, Wood Burning
Interior area
- Total structure area: 10,175
- Total interior livable area: 7,916 sqft
Property
Parking
- Total spaces: 4
- Parking features: Circular Driveway, Driveway, Electric Vehicle Charging Station(s), Garage Faces Rear, Garage Faces Side
- Attached garage spaces: 4
- Has uncovered spaces: Yes
Features
- Levels: Two
- Stories: 2
- Patio & porch: Covered, Patio
- Exterior features: Awning(s), Balcony, Courtyard, Irrigation System, Lighting, Outdoor Grill, Rain Gutters, Sidewalk
- Has private pool: Yes
- Pool features: Gunite, In Ground, Pool Sweep
- Has spa: Yes
- Spa features: Heated, In Ground
- Fencing: Electric,Masonry,Other
- Has view: Yes
- View description: Park/Greenbelt, Water, Lake
- Has water view: Yes
- Water view: Water,Lake
- Waterfront features: Lake - Chain of Lakes, Lake Privileges, Lift - Covered, Skiing Allowed
- Body of water: LAKE MAITLAND
Lot
- Size: 0.72 Acres
- Residential vegetation: Mature Landscaping, Trees/Landscaped
Details
- Additional structures: Boat House
- Parcel number: 312130422003150
- Zoning: R-1AA
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Contemporary,Other
- Property subtype: Single Family Residence
Materials
- Block, Stucco
- Foundation: Slab
- Roof: Tile
Condition
- New construction: No
- Year built: 1996
Details
- Builder model: Custom
- Builder name: Charles Clayton
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: BB/HS Internet Available, Cable Connected, Electricity Connected, Propane, Sewer Connected, Underground Utilities, Water Connected
Community & HOA
Community
- Security: Security System
- Pet fee: $0 monthly
- Subdivision: J KRONENBERGER SUB
HOA
- Has HOA: No
Location
- Region: Winter Park
Financial & listing details
- Price per square foot: $682/sqft
- Tax assessed value: $4,411,727
- Annual tax amount: $42,460
- Date on market: 2/28/2025
- Cumulative days on market: 559 days
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Brick, Paved
Price history
| Date | Event | Price |
|---|---|---|
| 2/27/2026 | Sold | $5,400,000-8.4%$682/sqft |
Source:  Stellar MLS #O6285791 Report a problem | ||
| 2/4/2026 | Pending sale | $5,895,000$745/sqft |
Source: Stellar MLS #O6285791 Report a problem | ||
| 10/5/2025 | Price change | $5,895,000-4.9%$745/sqft |
Source: Stellar MLS #O6285791 Report a problem | ||
| 9/30/2025 | Listed for sale | $6,200,000$783/sqft |
Source: Stellar MLS #O6285791 Report a problem | ||
| 9/1/2025 | Listing removed | $6,200,000$783/sqft |
Source: Stellar MLS #O6285791 Report a problem | ||
| 7/20/2025 | Price change | $6,200,000-4.6%$783/sqft |
Source: Stellar MLS #O6285791 Report a problem | ||
| 4/16/2025 | Price change | $6,500,000-6.5%$821/sqft |
Source: Stellar MLS #O6285791 Report a problem | ||
| 3/23/2025 | Listed for sale | $6,950,000$878/sqft |
Source: Stellar MLS #O6285791 Report a problem | ||
| 3/6/2025 | Pending sale | $6,950,000$878/sqft |
Source: Stellar MLS #O6285791 Report a problem | ||
| 3/1/2025 | Listed for sale | $6,950,000$878/sqft |
Source: Stellar MLS #O6285791 Report a problem | ||
| 2/28/2025 | Listing removed | $6,950,000$878/sqft |
Source: Stellar MLS #O6212012 Report a problem | ||
| 10/22/2024 | Price change | $6,950,000-7.3%$878/sqft |
Source: Stellar MLS #O6212012 Report a problem | ||
| 7/5/2024 | Price change | $7,500,000-6.2%$947/sqft |
Source: Stellar MLS #O6212012 Report a problem | ||
| 6/7/2024 | Listed for sale | $7,999,999+122.3%$1,011/sqft |
Source: Stellar MLS #O6212012 Report a problem | ||
| 8/9/2005 | Sold | $3,599,500+0.7%$455/sqft |
Source: Public Record Report a problem | ||
| 12/10/2004 | Sold | $3,575,000+98.6%$452/sqft |
Source: Public Record Report a problem | ||
| 5/12/1998 | Sold | $1,800,000+2669.2%$227/sqft |
Source: Public Record Report a problem | ||
| 7/29/1997 | Sold | $65,000$8/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $41,240 +3.5% | $2,665,851 +3% |
| 2023 | $39,862 +4.5% | $2,588,205 +3.2% |
| 2022 | $38,140 +0.9% | $2,507,966 +3% |
| 2021 | $37,783 -0.3% | $2,434,918 +1.4% |
| 2020 | $37,890 +0.6% | $2,401,300 +2.3% |
| 2019 | $37,660 +0.4% | $2,347,312 +1.9% |
| 2018 | $37,495 | $2,303,545 -23.2% |
| 2017 | $37,495 +0.8% | $3,000,927 +1.6% |
| 2016 | $37,212 +2% | $2,952,275 +2.3% |
| 2015 | $36,475 -3.2% | $2,885,900 +20% |
| 2014 | $37,680 +2% | $2,405,755 +12% |
| 2013 | $36,925 +0.9% | $2,148,814 +1.9% |
| 2012 | $36,578 -1.8% | $2,108,960 -1.4% |
| 2011 | $37,232 +2% | $2,138,192 -1.2% |
| 2010 | $36,512 | $2,164,032 -14.1% |
| 2009 | -- | $2,518,290 -20% |
| 2008 | $50,929 -13.3% | $3,147,134 -12.8% |
| 2007 | $58,727 +1.2% | $3,607,585 +11.2% |
| 2006 | $58,026 +2.6% | $3,244,391 +6% |
| 2005 | $56,577 +96.4% | $3,062,016 +65.3% |
| 2004 | $28,813 -12.5% | $1,852,501 -0.7% |
| 2003 | $32,914 +11.5% | $1,865,015 +11.4% |
| 2002 | $29,516 +3.4% | $1,673,460 +4.8% |
| 2001 | $28,553 +9.7% | $1,597,438 +8.8% |
| 2000 | $26,021 | $1,468,287 |
Find assessor info on the county website
Neighborhood: 32789
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Nearby schools
GreatSchools rating
- 7/10Lakemont Elementary SchoolGrades: K-5Distance: 1 mi
- 6/10Maitland Middle SchoolGrades: 6-8Distance: 1.6 mi
- 7/10Winter Park High SchoolGrades: 9-12Distance: 2.2 mi
Schools provided by the listing agent
- Elementary: Lakemont Elem
- Middle: Maitland Middle
- High: Winter Park High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$5,439,000
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Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$5,439,000
- Florida
- Orange County
- Winter Park
- 32789
- 1400 ALABAMA DRIVE
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