Skip to content
Property for sale at 1401 GREEN COVE ROAD, WINTER PARK, FL, 32789

1401 Green Cove RoadWinter Park, FL, 32789

3beds
7baths
5,483sqft
Single Family Residence
Built in 2009
$2,500,000
Sold
Price per sqft
$456
Sold on
Mar 31, 2026
MLS #O6358093Updated Apr 1, 2026

About this property

Set across Lake Maitland on a street where every home is an architectural gem, this Award-winning Villa Toscana blends Old-World craftsmanship with timeless architectural elegance in one of Winter Park’s most coveted enclaves. Built in 2009 and named “Best of Show” in the Parade of Homes, this 5,483 sq ft estate offers 3 bedrooms, 7 bathrooms, and 7 versatile bonus rooms, including a private guest casita and a fully finished basement. Total area including outdoor spaces: 6,821 sq ft.

The exterior showcases a stone façade, barrel-tile roof, wrought-iron detailing, and lush courtyards. A gated entry with outdoor fireplace leads to the guest casita with full bath, ideal for extended family, live-in support, or private office use.

Inside, arched walkways, travertine floors, and soaring ceilings define the main level. The formal dining room, executive office, and great room flow seamlessly to the resort-style pool and lanai. The chef’s kitchen features dual Sub-Zero refrigerators, separate freezer, hidden walk-in pantry, Dacor 6-burner gas range, double ovens, Sharp drawer microwave, and built-in Miele coffee station. A butler’s hallway, half bath, and custom laundry suite add function and refinement.

The primary suite on the main level features marble flooring, French doors to a private courtyard, a spa bath with soaking tub, dual-entry shower, and boutique-style custom closet.

Upstairs offers two bedrooms, each with en-suite bath and custom closets, plus two open seating areas/lofts and a half bath. One suite opens to arched French doors overlooking the courtyard, stone architecture, and partial Lake Maitland views.

The finished basement completes the 7 bonus rooms, providing flexible space for a home theater, gym, game room, or recreation lounge.

Outdoor living includes a heated pool and spa, summer kitchen (installed 2021) with gas grill, beer tap, coolers, hibachi station, and a full cabana bath with accent shower on astro turf. Roof 2024. Three SEER 22 high-efficiency HVAC units (2020).

Perfectly positioned on the Winter Park side of Lake Maitland within the renowned Chain of Lakes, Villa Toscana offers exceptional privacy and timeless appeal. This exclusive address places you just five minutes from Park Avenue’s fine dining, boutiques, and cultural attractions, while surrounded by some of Central Florida’s most distinguished waterfront estates. With access to the Winter Park Chain of Lakes, top-rated schools, and the charm of the city’s historic brick streets, Villa Toscana embodies the essence of refined Winter Park living.

Interested in this property?
Gaby, Property Specialist
Speak to GabyProperty Specialist, SerhantGaby can share what this home sold for, and find you comparable properties still on the market.
+1 (407) 490-0475
No pressure. Your details stay private.

Property details

Property type
Single Family Residence
Street address
1401 Green Cove Road
City
Winter Park
State
FL
ZIP code
32789
Year built
2009
New construction
No
Faces
Northeast
Rooms
12
Building stories
2
Living area
5,483 sqft
Total building area
6,821 sqft
Architectural style
Mediterranean
Levels
Two

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. 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; the 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.Stellar (MFR) data last updated at October 8, 2026 at 4:01 AM EDT

Price & sale history

EventPrice
SoldMLS #O6358093$2,500,000
Listed for saleMLS #O6358093$2,900,000
SoldMLS #O5749543$1,472,500
Price reducedMLS #O5749543$1,524,900Change: −9%−$150,100
History may be incomplete.
Explore nearby sales

Location

Recent sales nearby

Property for sale at 1401 GREEN COVE ROAD, WINTER PARK, FL, 32789
Learn more about this propertyGet in touch for more information
We will use your details to respond to this request and may share them with a suitable real estate professional when needed. Marketing is optional.