1400 ALABAMA DRIVE, Winter Park, FL 32789

• 5 beds |
• 9 baths |
• 7,916 sqft

Property Description

Under contract-accepting backup offers. 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.

Listing Status:

Pending

Date Added:

February 28, 2025

Data Last Updated:

February 9, 2026 at 7:22AM

Listing Office:

THE AGENCY FL : 407-335-4119

Listing Agent:

Rachel Peters, LLC : 407-625-3227

MLS ID:

O6285791

Interior

• General: Built-in FeaturesCoffered Ceiling(s)Crown MoldingHigh CeilingsPrimary Bedroom Main FloorSolid Surface CountersSolid Wood CabinetsSplit BedroomStone CountersThermostatWalk-In Closet(s)Wet BarWindow Treatments
• Rooms: Den/Library/OfficeInside UtilityMedia Room
• Appliances: Bar FridgeBuilt-In OvenDishwasherDisposalDryerElectric Water HeaterRangeRange HoodRefrigeratorWasher
• Laundry: Electric Dryer HookupInsideLaundry RoomOtherWasher Hookup
• Flooring: CarpetMarbleTravertine
• A/C: Central Air
• Heating: Central
• Fireplace: GasLiving RoomOtherOutsidePrimary BedroomWood BurningFireplace

Exterior

• General: Awning(s)BalconyCourtyardFrench DoorsLightingOutdoor GrillRain GuttersSidewalkHeatedIn Ground
• Style: ContemporaryOther
• Other Structures: PatioCovered
• Pool: GuniteIn GroundPool Sweep
• Parking: Circular DrivewayDrivewayElectric Vehicle Charging Station(s)Garage Faces RearGarage Faces Side

Construction

• Roofing: Tile
• Windows: ShadesShuttersWindow Treatments
• General: BlockStuccoTwoSlab

Location

• Road/Access: BrickPaved
• Originating MLS: Stellar MLS
• County: Orange

Lot

• Zoning: R-1AAJ KRONENBERGER SUB G/56 LOTS 14 15 & 16BLK C & BOAT HOUSE LOTS 20-C & 21-C31-21-30-4220-03-150
• View: Park/GreenbeltWater
• Fencing: ElectricMasonryOther

Utilities

• Utilities: BB/HS Internet AvailableCable ConnectedElectricity ConnectedPropaneSewer ConnectedUnderground UtilitiesWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple