Gabriella Massaro

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

$5,300,000.00
9615 WINDY RIDGE ROAD, WINDERMERE, FL - 34786
6 beds
7.0 baths
9,669 sqft
$5,300,000.00
9615 WINDY RIDGE ROAD, WINDERMERE, FL - 34786
Gabriella Massaro
$5,300,000.00
6 beds
7.0 baths
9,669 sqft
9615 WINDY RIDGE ROAD, WINDERMERE, FL - 34786
For Sale
Photo 1
  • Built in 2007
  • 4 garage spaces
  • $548.14/sqft
  • Lot size: 2.49 acres
  • 7 days on market

A palm-framed pool and spa, a balcony-connected game room and a dedicated theater give this Mediterranean-inspired estate a distinctive rhythm of outdoor relaxation and evenings at home. Set on 2.5 fully fenced acres with a private gated entrance, the residence welcomes you along a fountain-centered circular drive to 12-foot iron cathedral-style doors. Inside, marble flooring with decorative inlays flows through most first-floor living areas, while soaring ceilings and a two-story mitered glass window frame views toward the pool and covered terrace. A grand two-story marble staircase rises from the formal living room to an iron-railed interior balcony, with an elevator providing additional access between floors. Beneath coffered ceilings, the kitchen’s curved breakfast bar creates a gathering spot connected to the family room, where an entertainment center and sliding glass wall doors lead to a covered poolside terrace with a fireplace. An elaborately decorated vaulted ceiling gives the formal dining room its own character, complemented by a wine cellar with capacity for 500 bottles. Six oversized bedroom suites include two primary suites and a 19' × 25' suite configured as an executive office with a full bathroom. Decorative ceilings continue through the bedroom spaces, while an elaborate bathroom pairs separate vanities with a tub and walk-in shower. A separate study and mirrored 20-foot fitness studio provide spaces for work and exercise, while a 29' × 29' theater with reclining lounge chairs and tiered seating platforms gives movie nights their own dedicated setting. Upstairs, the 41-foot billiards, game and media room combines a refreshment bar with space for game tables and a pool table, opening through sliding glass walls to a covered stone balcony overlooking the grounds. The 45-foot pool’s shallow beach-style landing, raised spa and expansive terrace invite afternoons outdoors, with broad lawns and a sand volleyball area extending the recreation. Four oversized garages and abundant storage add practical space, while the acreage offers potential to expand the residence or build a detached guesthouse, subject to applicable approvals. Approximately 15 minutes from restaurants, hotels, shopping, Universal Studios and Disney attractions, this estate brings distinctive architecture and varied recreation together for an inviting experience at home.

  • Directions: Heading north on S Apopka Vineland Rd, turn left onto Windy Ridge Rd. Home will be on the right.
  • County: Orange
  • Geo subdivision: WINDSOR HILL

Nearby Schools

Thornebrooke 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
800 W 2ND AVENUE, WINDERMERE, FL - 34786
$5,600,000.00
5 bds
4.5 ba
5,511 sqft
800 W 2ND AVENUE, WINDERMERE, FL - 34786
For Sale
5070 DOWN POINT LANE, WINDERMERE, FL - 34786
$4,945,000.00
6 bds
6.5 ba
7,349 sqft
5070 DOWN POINT LANE, WINDERMERE, FL - 34786
For Sale
1330 LAKE OLIVIA, WINDERMERE, FL - 34786
$5,500,000.00
6 bds
7.0 ba
6,442 sqft
1330 LAKE OLIVIA, WINDERMERE, FL - 34786
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6449197
Listing updated: October 22, 2026 at 7:05PM
Listing provided by: Traci Cleveland, KELLER WILLIAMS CLASSIC
Last checked 2 hours ago
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