16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787

Description of 16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787

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.

Property Details for 16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787

Bathrooms Full

5

Bathrooms Half

1

Interior Features

Built-in Features, Ceiling Fan(s), Central Vacuum, Crown Molding, Eating Space In Kitchen, High Ceilings, In Wall Pest System, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)

Appliances

Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Range, Range Hood, Refrigerator

Flooring

Carpet, Tile, Hardwood

Heating

Electric

Cooling

Central Air

Furnished

Negotiable

Architectural Style

Mediterranean

Garage Spaces

3

Attached Garage

Yes

Parking Features

Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Guest, Off Street, Split Garage, Workshop in Garage

Pool Features

Auto Cleaner, Gunite, Heated, In Ground, Salt Water, Screen Enclosure

Pool Private

Yes

Direction Faces

East

Building Information for 16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787

Building Area Total

6449

Building Area Units

Square Feet

Stories Total

2

Association

Yes

Association Fee

$168

Association Fee Frequency

Monthly

Association Amenities

Clubhouse, Fitness Center

Pets Allowed

Yes

Security Features

Gated Community, Security Lights, Security System, Smoke Detector(s)

Property Information for 16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787

Lot Size Square Feet

14,997

Waterfront

No

View

No

Construction Materials

Block, Stone, Stucco

Roof

Tile

Exterior Features

Balcony, Courtyard, Garden, Irrigation System, Lighting, Rain Gutters, Sidewalk

Sewer

Public Sewer

Water Source

Public

New Construction

No

Public Records for 16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787

Parcel Number

052327890001290

Tax Annual Amount

$11,216

Tax Year

2025

Tax Legal Description

WATERSIDE ON JOHNS LAKE - PHASE 1 82/74LOT 129

Zoning

UVPUD

County Or Parish

Orange

Schools Near 16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787

Elementary School

Hamlin Elementary

Middle School

Hamlin Middle

High School

West Orange High

School assignments are provided by the listing and should be independently verified.

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