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1400 Alabama Drive

Winter Park, FL 32789
  • $5,895,000
  • STATUS: Active
  • ON SITE: 284 Days
  • MLS #: O6285791
UPDATED: 47 min ago
$5,895,000
  • 5
    BEDS
  • 0.7
    ACRES
  • 5
    BATHS
  • 4
    1/2 BATHS
  • 7,916
    SQFT
  • $745
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1996
County:
Area:

School Information

Elementary School:
Middle School:
High School:

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 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.

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© 2025 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2025-12-11T18:44:59.183.
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1400 Alabama Drive Winter Park, FL 32789

  • Price: $5,895,000
  • Status: Active
  • On Site: 284 Days
  • Updated: 47 min ago
  • MLS #: O6285791
5
Beds
5
Baths
4
½ Baths
0.7
Acres
7,916
SQFT
$745
$/SQFT
1996
Built
Neighborhood:
J Kronenberger Sub
County:
Orange
Area:
Winter Park
Elementary School:
Lakemont Elem
Middle School:
Maitland Middle
High School:
Winter Park High
Property 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 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.
Exterior Features

Architectural Style ContemporaryOther Attached Garage Yn Yes Carport Yn No Construction Materials BlockStucco Covered Spaces 4 Direction Faces Northwest Exterior Features Awning(s)BalconyCourtyardFrench DoorsIrrigation SystemLightingOutdoor GrillRain GuttersSidewalk Fencing ElectricMasonryOther Foundation Details Slab Open Parking YN Yes Parking Features Circular DrivewayDrivewayElectric Vehicle Charging Station(s)Garage Faces RearGarage Faces Side Patio And Porch Features CoveredPatio Pool Dimensions 15 x 26.4 Pool Features GuniteIn GroundPool Sweep Pool Private Yn Yes Road Surface Type BrickPaved Roof Tile Spa Features HeatedIn Ground Spa YN Yes View Park/GreenbeltWater Water Access Lake - Chain of Lakes Water Access Yn Yes Water Body Name LAKE MAITLAND Water Extras BoathouseLift - CoveredSkiing Allowed Water Extras Yn Yes Water View Lake - Chain of Lakes Water View Yn Yes Waterfront Features Lake - Chain of Lakes Waterfront Feet Total 0 Waterfront Yn Yes

Interior Features

Additional Rooms Den/Library/OfficeInside UtilityMedia Room Appliances Bar FridgeBuilt-In OvenDishwasherDisposalDryerElectric Water HeaterRangeRange HoodRefrigeratorWasher Building Area Total 10175 Cooling Central Air Cooling YN Yes Fireplace Features GasLiving RoomOther RoomOutsideMaster BedroomWood Burning Fireplace Yn Yes Flooring CarpetMarbleTravertine Heating Central Heating YN Yes Interior Features Built-in FeaturesCoffered Ceiling(s)Crown MoldingHigh CeilingsPrimary Bedroom Main FloorSolid Surface CountersSolid Wood CabinetsSplit BedroomStone CountersThermostatWalk-In Closet(s)Wet BarWindow Treatments Laundry Features Electric Dryer HookupInsideLaundry RoomOtherWasher Hookup Levels Two Rooms Primary Bedroom (Built-In ShelvingBuilt-in FeaturesEn Suite BathroomDual Closets) Living Room Library (Bar) Dinette (Built-In Shelving) Dining Room Bedroom 2 (Jack & Jill BathroomWalk-In Closet(s)) Loft (Built-In Shelving) Bedroom 3 (Jack & Jill BathroomWalk-In Closet(s)) Kitchen (Kitchen IslandStone CountersPantry) Media Room Bedroom 4 (En Suite BathroomWalk-In Closet(s)) Sewer Public Sewer Stories Total 2 Water Source Public Window Features ShadesShuttersWindow Treatments

Property Features

Association Yn No Builder Name Charles Clayton Cdd Yn No Down Payment Resource No Flood Zone Code XAE Garage Yn Yes Homestead Yn Yes Lease Considered YN Yes Lease Restrictions YN No Listing Terms CashConventional Minimum Lease 1 Week Month To Month Or Weekly Yn Yes New Construction Yn No Ownership Fee Simple Property Sub Type Single Family Residence Realtor Info As-IsFloor Plan AvailableSurvey Available Security Features Security System Senior Community Yn No Special Listing Conditions None Tax Annual Amount 41240.46 Total Annual Fees 0 Total Monthly Fees 0 Utilities BB/HS Internet AvailableCable ConnectedElectricity ConnectedPropaneSewer ConnectedUnderground UtilitiesWater Connected Zoning R-1AA


Listing information © 2025 My Florida Regional MLS DBA Stellar MLS..
Listing provided courtesy of THE AGENCY ORLANDO: 407-951-2472.



© 2025 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2025-12-11T18:44:59.183.
 
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400 N Mills Ave
Orlando FL, 38203