16614 Harbor Sail Way, Winter Garden, FL 34787
Local realty services provided by:CENTURY 21 Affiliates
Listed by: garry walmsley
Office: global florida realty
MLS#:O6414639
Source:MFRMLS
Price summary
- Price:$1,495,000
- Price per sq. ft.:$231.82
- Monthly HOA dues:$168
About this home
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 entire 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, community pool, and exclusive Johns Lake access. 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....
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Home facts
- Year built:2016
- Listing ID #:O6414639
- Added:4 day(s) ago
- Updated:June 14, 2026 at 02:53 PM
Rooms and interior
- Bedrooms:6
- Total bathrooms:6
- Full bathrooms:5
- Half bathrooms:1
- Flooring:Carpet, Tile, Wood
- Dining Description:Eat In Kitchen, Formal Dining Room
- Kitchen Description:Built-In Oven, Cooktop, Dishwasher, Disposal, Eat-in Kitchen, Microwave, Range, Range Hood, Refrigerator, Solid Wood Cabinets, Stone Counters
- Bedroom Description:High Ceilings, Primary Bedroom Main Floor, Walk-In Closet(s)
- Living area:4,882 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Electric
- Central air:Yes
Structure and exterior
- Roof:Tile
- Year built:2016
- Building area:4,882 sq. ft.
- Lot area:0.34 Acres
- Architectural Style:Mediterranean
- Construction Materials:Block, Stone, Stucco
- Exterior Features:Balcony, Courtyard, Covered Porch/Patio, Garden, Lighting, Patio, Rain Gutters, Rear Porch, Screened, Sidewalk
- Foundation Description:Slab
- Levels:2 Story
Schools
- High school:West Orange High
- Middle school:Hamlin Middle
- Elementary school:Hamlin Elementary
Utilities
- Water:Public, Water Connected
- Sewer:Public Sewer, Sewer Connected
Finances and disclosures
- Price:$1,495,000
- Price per sq. ft.:$231.82
- Tax amount:$11,216 (2025)
Features and amenities
- Appliances:Built-in Oven, Cooktop, Dishwasher, Disposal, Dryer, Irrigation Equipment, Microwave, Range, Range Hood, Refrigerator
- Laundry features:Dryer, Gas Dryer Hookup, Inside, Washer Hookup
- Amenities:BB/HS Internet Available, Built-In Features, Cable Available, Cable Connected, Ceiling Fans(s), Central Vaccum, Clubhouse, Crown Molding, Eat-in Kitchen, Fitness Center, High Ceilings, In Wall Pest System, Irrigation Equipment, Open Floorplan, Phone Available, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Thermostat, Underground Utilities, Vaulted Ceiling(s), Walk-In Closet(s)
- Pool features:Automatic Cleaner, Gunite, Heated, In Ground, Private Pool, Salt Water, Screen Enclosure
Parking
- Parking description:Attached Garage, Circular Driveway, Driveway, Garage, Garage Door Opener, Garage Faces Side, Guest, Off Street, Workshop in Garage
- Garage:Yes
- Garage spaces:3
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