Gabriella Massaro

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

$1,399,000.00
106 PALM STREET, WINDERMERE, FL - 34786
5 beds
4.5 baths
3,082 sqft
$1,399,000.00
106 PALM STREET, WINDERMERE, FL - 34786
Gabriella Massaro
$1,399,000.00
5 beds
4.5 baths
3,082 sqft
106 PALM STREET, WINDERMERE, FL - 34786
For Sale
Photo 1
  • Built in 1960
  • 2 garage spaces
  • $453.93/sqft
  • Lot size: 16,010 sqft
  • 7 days on market

Set on a large, tree-lined lot just moments from historic downtown Windermere, this fully reimagined residence blends modern luxury with timeless charm—delivering a level of craftsmanship and detail that truly stands out. Every inch of this home has been thoughtfully redesigned, including a newly configured floor plan, all new interior doors and trim, and beautiful wide-plank flooring throughout. Light pours into the home, creating a bright, inviting atmosphere from the moment you step inside. At the center of it all is a completely NEW kitchen—designed for both everyday living and elevated entertaining. Featuring an impressive 10-foot quartz island with seating, custom wood cabinetry, a double-door pantry, and a stunning suite of GE Café appliances including a four-panel refrigerator, double ovens, 6-burner gas cooktop, microwave drawer, dishwasher, and a custom hood. A dedicated coffee bar adds the perfect finishing touch. The family room is equally striking, with high ceilings and a custom dry bar complete with dual beverage refrigerators—creating a seamless space for gathering and hosting. The private primary suite has been elevated to feel like a true retreat, now featuring dual walk-in closets and a beautifully renovated spa-style bathroom with a quartz-topped double vanity and a luxurious walk-in shower with rain head. A newly created private office with glass French doors and a decorative fireplace offers a quiet, stylish workspace. The home also features a newly added fourth bathroom and additional bedroom / or flex space, enhancing both functionality and flexibility. Step outside to your own backyard escape, where a private pool is surrounded by mature trees, offering both shade and privacy. Beyond the stunning design, this home offers true peace of mind with major system upgrades including a 50-year architectural shingle roof, full home replumb (2024), new tankless water heater (2025), and a new well, pump, and irrigation system (2025). All of this just minutes from the charm of downtown Windermere and the shops and restaurants along Conroy-Windermere Road. This is more than a renovation—it’s a complete reimagination of what Windermere living can be.

  • Directions: From I-4, take the Conroy Windermere Road exit west, go through the intersection of South Apopka Vineland Road, take a right onto Main Street, left onto West 1st Avenue and the home is on the corner of West 1st Avenue and Palm Street.
  • County: Orange
  • Geo subdivision: WINDERMERE TOWN

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
12640 SALOMON COVE DRIVE, WINDERMERE, FL - 34786
$1,300,000.00
5 bds
3.5 ba
3,694 sqft
12640 SALOMON COVE DRIVE, WINDERMERE, FL - 34786
For Sale
11537 CLAYMONT CIR, WINDERMERE, FL - 34786
$1,400,000.00
5 bds
4.0 ba
3,164 sqft
11537 CLAYMONT CIR, WINDERMERE, FL - 34786
For Sale
11044 HAWKSHEAD COURT, WINDERMERE, FL - 34786
$1,359,999.00
5 bds
4.5 ba
4,257 sqft
11044 HAWKSHEAD COURT, WINDERMERE, FL - 34786
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6391350
Listing updated: April 1, 2026 at 7:58PM
Listing provided by: Jill Healey, KELLER WILLIAMS WINTER PARK
Last checked 17 hours ago
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