Pablo Farias

Pablo Farias Consultor Imobiliário Licenciado 🇺🇸

$1,495,000.00
16614 HARBOR SAIL WAY, WINTER GARDEN, FL - 34787
6 beds
5.5 baths
4,882 sqft
$1,495,000.00
16614 HARBOR SAIL WAY, WINTER GARDEN, FL - 34787
Pablo Farias
$1,495,000.00
6 beds
5.5 baths
4,882 sqft
16614 HARBOR SAIL WAY, WINTER GARDEN, FL - 34787
For Sale
Photo 1
  • Built in 2016
  • 3 garage spaces
  • $306.23/sqft
  • Lot size: 14,997 sqft
  • 42 days on market

An Irreplaceable Gated Estate: Unmatched Scale, Double-Lot Privacy, & Private Oasis Behind the gates of the highly coveted Waterside community, 16614 Harbor Sail Way breaks the mold of standard luxury builds. This is not a high-density, cookie-cutter residence; it is an established, substantial family estate defined by an extraordinary sense of space, meticulous craftsmanship, and structural authority. Positioned beautifully on an expansive, premium lot that nearly doubles the community average, this rare property offers a refined lifestyle designed for those who value space to breathe, long-term permanence, and effortless entertaining. While typical Mansfield floor plans in the neighborhood occupy a standard lot, this home’s visionary owners secured the adjacent parcel, resulting in a commanding 14,973-square-foot footprint. This unique layout introduces a majestic private turning circle with dedicated parking for an additional six vehicles (bringing total driveway capacity to ten)—ideal for hosting executive gatherings or multi-generational families. Beyond the striking courtyard entry, the residence spans an impressive 4,882 square feet of meticulously maintained living space, delivering structural scale that effortlessly handles the demands of modern family life. The heart of the home centers on a dramatic great room bathed in natural light, seamlessly connecting to a gourmet kitchen equipped with premium finishes and gas cooking. Every corner of the main level emphasizes functional luxury, including a private home office, formal dining room, a secluded guest suite, and a magnificent primary sanctuary. Ascending to the second level reveals a sprawling, open flex room suspended over the main living area that opens to a fully enclosed, private balcony, creating an incredible architectural anchor. This level features four additional large bedrooms and media room, offering families the chance to spend time together, or unwind in complete peace. For ultimate daily convenience, a built-in central vacuum system services the ground floor of the home. While neighboring homes may provide "room for a future pool," this estate delivers the ultimate outdoor lifestyle immediately. The west-facing backyard is a private, sun-drenched sanctuary featuring a spectacular custom salt-water pool and integrated spa. Surrounded by extended paver decking and lush, manicured grassed areas made possible by the expanded double-lot footprint, this outdoor space offers complete privacy with no direct rear neighbors—perfect for enjoying vibrant Central Florida sunsets. Living in Waterside means enjoying a resort-style lifestyle with access to a premier clubhouse, fitness center and community pool. You are uniquely positioned just minutes from Horizon West’s top-rated schools (Hamlin Elementary/Middle), West Orange (High), the charm of downtown Winter Garden, major executive corridors (SR-429, Turnpike), and premier dining and shopping. This is more than a home; it is a strategic asset of scarcity, privacy, and generational quality. Schedule your private tour to experience it firsthand.

  • Directions: Exit SR 429 at Stoneybrook West Parkway (Exit 19). Head west on Stoneybrook West Parkway. Continue onto Marsh Road for approximately 1 mile. Turn right onto Broadwater Avenue (entrance to Waterside on Johns Lake). Follow Broadwater Avenue through the community. Continue until you reach Harbor Sail Way. Turn left onto Harbor Sail Way. Continue to 16614 Harbor Sail Way, Winter Garden, FL 34787.
  • County: Orange
  • Geo subdivision: WATERSIDE/JOHNS LAKE PH 1

Nearby Schools

Hamlin Elementary

Hamlin Middle

West Orange High

Features

Financial

Let's get in touch!

Pablo Farias

Pablo Farias

Consultor Imobiliário Licenciado 🇺🇸

See also

For Sale
13124 FILLY COURT, WINDERMERE, FL - 34786
$1,575,000.00
5 bds
3.0 ba
3,300 sqft
13124 FILLY COURT, WINDERMERE, FL - 34786
For Sale
1700 LAKE ROBERTS COURT, WINDERMERE, FL - 34786
$1,400,000.00
5 bds
4.0 ba
3,929 sqft
1700 LAKE ROBERTS COURT, WINDERMERE, FL - 34786
For Sale
217 W BAY STREET, WINTER GARDEN, FL - 34787
$1,349,000.00
5 bds
4.0 ba
2,800 sqft
217 W BAY STREET, WINTER GARDEN, FL - 34787
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6414639
Listing updated: July 14, 2026 at 8:18PM
Listing provided by: Garry Walmsley, GLOBAL FLORIDA REALTY
Last checked 2 days ago
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