Gabriella Massaro

Gabriella Massaro Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990

$5,999,000.00
800 W 2ND AVENUE, WINDERMERE, FL - 34786
5 beds
4.5 baths
5,511 sqft
$5,999,000.00
800 W 2ND AVENUE, WINDERMERE, FL - 34786
Gabriella Massaro
$5,999,000.00
5 beds
4.5 baths
5,511 sqft
800 W 2ND AVENUE, WINDERMERE, FL - 34786
For Sale
Photo 1
  • Built in 1993
  • 3 garage spaces
  • $1,088.55/sqft
  • Lot size: 19,749 sqft
  • 3 days on market

Set beneath a canopy of majestic live oaks along the shores of the Butler Chain of Lakes, this timeless estate has been comprehensively reimagined to blend enduring architecture with modern luxury. Rebuilt with uncompromising attention to detail, every major component of the home has been replaced, including the roof, windows & doors, HVAC systems, water heaters, pool equipment, dock, and landscaping. The home is also complete with a professionally curated furnishing package by Wassers. A refined palette of natural materials and exceptional craftsmanship defines every space, including custom Italian cabinetry, a premium SKS appliance suite, Taj Mahal quartzite countertops and full-height backsplashes, imported Portuguese limestone extending seamlessly from the interior to the pool terrace, and wide-plank light oak flooring throughout the upper level. Arched impact-rated windows and doors frame picturesque lake views while filling the home with natural light. Privately positioned to maximize the home's spectacular waterfront setting, the primary suite serves as a luxurious retreat featuring its own fireplace, a spacious sitting area, and a private balcony overlooking the lake. The spa-inspired bath rivals those found in the world's finest resorts, showcasing a dramatic wet room with a hand-carved marble soaking tub, handcrafted marble vanity, exquisite limestone, and an extraordinary custom Italian wardrobe system. Designed for effortless indoor-outdoor living, the private courtyard is inspired by timeless Mediterranean estates and framed by graceful arcades, tapered stone columns, restored architectural lanterns, and custom lighting. A freeform pool and elevated spa create a tranquil focal point, while the fully equipped summer kitchen, multiple covered terraces, and expansive entertaining spaces provide an exceptional setting for lakeside gatherings. Beyond the courtyard, beautifully landscaped grounds lead to a restored private dock and covered boathouse with direct access to the renowned Butler Chain of Lakes. No detail was overlooked, with additional highlights including a private elevator, custom wine room, designer lighting, thoughtfully restored architectural details, and curated finishes that create a timeless residence balancing warmth, elegance, and seamless indoor-outdoor living. Situated on renowned 2nd Avenue just moments from downtown Windermere, this remarkable residence establishes an entirely new benchmark for luxury renovation. Meticulously executed, flawlessly designed, and unlike anything else available today, this is more than a home it is a legacy property destined to become one of Central Florida's most iconic waterfront estates.

  • Directions: Start on Conroy-Windermere Road, continue for about 2 miles into downtown Windermere, turn left onto Main Street, turn right onto W 2nd Avenue, home is on the left.
  • County: Orange
  • Geo subdivision: ALADAR ON LAKE BUTLER

Nearby Schools

Windermere Elem

Gotha Middle

Olympia High

Features

Financial

Let's get in touch!

Gabriella Massaro

Gabriella Massaro

Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990

See also

For Sale
12264 MONTALCINO CIRCLE, WINDERMERE, FL - 34786
$5,490,000.00
4 bds
5.5 ba
7,872 sqft
12264 MONTALCINO CIRCLE, WINDERMERE, FL - 34786
For Sale
9316 GLADYS GARDEN CT, WINDERMERE, FL - 34786
$6,500,000.00
5 bds
6.5 ba
5,471 sqft
9316 GLADYS GARDEN CT, WINDERMERE, FL - 34786
For Sale
6462 DEACON CIR, WINDERMERE, FL - 34786
$6,499,999.00
5 bds
5.0 ba
7,178 sqft
6462 DEACON CIR, WINDERMERE, FL - 34786
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6422976
Listing updated: July 25, 2026 at 7:05PM
Listing provided by: Julie Christensen, ONE LUXURY INTERNATIONAL LLC
Last checked 12 hours ago
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