16614 HARBOR SAIL WAY, Winter Garden, FL 34787

• 6 beds |
• 6 baths |
• 4,882 sqft

Property Description

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.

Listing Status:

Active

Date Added:

June 10, 2026

Data Last Updated:

June 26, 2026 at 2:22AM

Listing Office:

GLOBAL FLORIDA REALTY : 407-380-3030

Listing Agent:

Garry Walmsley : 407-923-2134

MLS ID:

O6414639

Interior

• General: Built-in FeaturesCeiling Fans(s)Central VaccumCrown MoldingEat-in KitchenHigh CeilingsIn Wall Pest SystemOpen FloorplanPrimary Bedroom Main FloorSolid Wood CabinetsStone CountersThermostatVaulted Ceiling(s)Walk-In Closet(s)
• Rooms: AtticBonus RoomDen/Library/OfficeFamily RoomFormal Dining Room SeparateInside UtilityLoftMedia Room
• Appliances: Built-In OvenCooktopDishwasherDisposalDryerMicrowaveRangeRange HoodRefrigerator
• Laundry: Gas Dryer HookupInsideWasher Hookup
• Flooring: CarpetTileWood
• A/C: Central Air
• Heating: Electric
• Fireplace: DecorativeElectricLiving RoomFireplace

Exterior

• General: BalconyCourtyardGardenLightingRain GuttersSidewalkHeatedIn Ground
• Style: Mediterranean
• Other Structures: Rear PorchScreenedPatioCovered
• Pool: Auto CleanerGuniteHeatedIn GroundSalt WaterScreen Enclosure
• Parking: Circular DrivewayDrivewayGarage Door OpenerGarage Faces SideGuestOff StreetGarageWorkshop in Garage

Construction

• Roofing: Tile
• Windows: BlindsDrapesShadesWindow Treatments
• General: BlockStoneStuccoTwoSlab

Location

• Road/Access: Paved
• HOA Amenities: ClubhouseFitness Center168.0Monthly
• Originating MLS: Stellar MLS
• County: Orange

Lot

• Zoning: UVPUDWATERSIDE ON JOHNS LAKE - PHASE 1 82/74LOT 12905-23-27-8900-01-290

Utilities

• Utilities: BB/HS Internet AvailableCable AvailableCable ConnectedElectricity ConnectedPhone AvailableSewer ConnectedUnderground UtilitiesWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple