1400 Alabama Drive, Winter Park, FL 32789
Local realty services provided by:Gulf Shores Realty ERA Powered
1400 Alabama Drive,Winter Park, FL 32789
$5,895,000
- 5 Beds
- 9 Baths
- 7,916 sq. ft.
- Single family
- Active
Listed by: rachel peters, llc.
Office: the agency orlando
MLS#:O6285791
Source:MFRMLS
Price summary
- Price:$5,895,000
- Price per sq. ft.:$579.36
About this home
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.
Contact an agent
Home facts
- Year built:1996
- Listing ID #:O6285791
- Added:529 day(s) ago
- Updated:November 19, 2025 at 01:02 PM
Rooms and interior
- Bedrooms:5
- Total bathrooms:9
- Full bathrooms:5
- Half bathrooms:4
- Living area:7,916 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Central
Structure and exterior
- Roof:Tile
- Year built:1996
- Building area:7,916 sq. ft.
- Lot area:0.7 Acres
Schools
- High school:Winter Park High
- Middle school:Maitland Middle
- Elementary school:Lakemont Elem
Utilities
- Water:Public, Water Connected
- Sewer:Public Sewer, Sewer Connected
Finances and disclosures
- Price:$5,895,000
- Price per sq. ft.:$579.36
- Tax amount:$41,240 (2024)
New listings near 1400 Alabama Drive
- Open Sat, 12 to 2pmNew
$845,000Active3 beds 4 baths2,116 sq. ft.1251 Arlington Place, WINTER PARK, FL 32789
MLS# O6358201Listed by: FANNIE HILLMAN & ASSOCIATES - New
$425,000Active3 beds 2 baths1,050 sq. ft.1030 N Lakemont Ave., WINTER PARK, FL 32792
MLS# O6361518Listed by: PREMIER SOTHEBY'S INTL. REALTY - New
$2,289,000Active5 beds 5 baths3,334 sq. ft.2722 Eastern Parkway, WINTER PARK, FL 32789
MLS# O6360734Listed by: COMPASS FLORIDA LLC - New
$175,000Active1 beds 1 baths747 sq. ft.4892 Tangerine Avenue #4892, WINTER PARK, FL 32792
MLS# O6360622Listed by: EXP REALTY LLC - New
$409,999Active3 beds 2 baths1,436 sq. ft.5563 Garden Grove Circle, WINTER PARK, FL 32792
MLS# G5104577Listed by: COLDWELL BANKER HUBBARD HANSEN - New
$569,990Active4 beds 3 baths1,776 sq. ft.2189 Sussex Road, WINTER PARK, FL 32792
MLS# O6359226Listed by: LPT REALTY, LLC - New
$235,000Active2 beds 1 baths768 sq. ft.151 N Orlando Avenue #226, WINTER PARK, FL 32789
MLS# O6361027Listed by: LOKATION - New
$975,000Active3 beds 3 baths1,875 sq. ft.870 Carver Street, WINTER PARK, FL 32789
MLS# O6360210Listed by: PREMIER SOTHEBY'S INTL. REALTY - New
$375,000Active3 beds 2 baths1,200 sq. ft.3083 Crane Strand Drive, WINTER PARK, FL 32792
MLS# O6360511Listed by: REDFIN CORPORATION - New
$347,500Active3 beds 2 baths1,285 sq. ft.1605 Puritan Avenue, WINTER PARK, FL 32792
MLS# O6359457Listed by: REALTY LYNK INC