16614 Harbor Sail Way, Winter Garden, FL 34787

$1,495,000
6
BD
6
BA
4,882
SqFt

Show Photos

Verify your account to unlock exclusive photos, mortgage tools, and more.

List Price
$1,495,000
Status
PENDING
Days on Market
19
MLS#
O6414639
Subtype
Residential
Style
Two Story
Architectural Style
Mediterranean
Year Built
2016
Bedrooms
6
Bathrooms
6
Full Baths
5
Half Baths
1
Living Area
4,882
Lot Size
14,997
Acres
0.34
Subdivision
Waterside/Johns Lake Ph 1
MLS Area Major
Winter Garden/Oakland

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 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.

Additional Information

Amenities
Clubhouse, Fitness Center
Interior Features
Built-in Features, Ceiling Fans(s), Central Vaccum, Crown Molding, Eat-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)
Exterior Features
Balcony, Courtyard, Garden, Lighting, Rain Gutters, Sidewalk
HOA Fee
$168
HOA Freqency
Monthly
Financing
Cash, Conventional
Community Features
Clubhouse, Fitness Center, Gated Community - No Guard, Playground, Sidewalks, Street Lights, No Deed Restriction
Property Description
Two Story
Zoning
UVPUD
Appliances
Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Range, Range Hood, Refrigerator
Heating
Electric
Air Conditioning
Central Air
Exterior Construction
Block, Stone, Stucco
Exterior Features
Balcony, Courtyard, Garden, Lighting, Rain Gutters, Sidewalk
Stories
2
Levels
Two
Roof
Tile
Foundation
Slab
Pool
Yes
Pool Type
Auto Cleaner, Gunite, Heated, In Ground, Salt Water, Screen Enclosure
Parking
Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Guest, Off Street, Garage, Workshop in Garage
Parking Features
Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Guest, Off Street, Garage, Workshop in Garage
Garage
3 Car Garage
Garage Spaces
3
Garage Features
Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Guest, Off Street, Garage, Workshop in Garage
Elementary School
Hamlin Elementary
Middle School
Hamlin Middle
High School
West Orange High

Courtesy of GLOBAL FLORIDA REALTY

StellarMLS is the source of this information via Internet Data Exchange Program. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale. Availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase. All other use is strictly prohibited and may violate relevant federal and state law. Data last updated on

Mortgage Calculator

Amount of Loan
Annual Interest Rate
%
Term of Loan
Years

Does not include any taxes or fees.
Please consult a financial professional.
Calculator source: Real Geeks