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Listed by Garry Walmsley · Courtesy of GLOBAL FLORIDA REALTY· Agent MLS ID# MFR272502237 · Deemed reliable but not guaranteed. · Data last updated: Sep 8, 2026 · 3:27 PM

16614 HARBOR SAIL WAY

Winter Garden, Orange, FL, 34787

Active

$1,399,000

$287/sqft

6Beds
6Baths
4,882Sq Ft
2016Built
62Days on Market

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 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.

Facts & Features

MFRO6414639
$1,399,000
Active
6
6
5
1
4,882 sqft
0.3400
2016
Residential
Single Family Residence
Mediterranean

Community Information

16614 HARBOR SAIL WAY
Waterside/Johns Lake Ph 1
Winter Garden
Orange
FL
34787
No

Amenities

Clubhouse, Fitness Center
N/A
No
No
Yes

Interior

Ceiling Fans(s), High Ceilings, Open Floorplan, Vaulted Ceiling(s), Walk-In Closet(s), Eat-in Kitchen, Solid Wood Cabinets, Stone Counters, Thermostat, Crown Molding, Built-in Features, Primary Bedroom Main Floor, In Wall Pest System, Central Vaccum
Electric
Central Air
Tile, Carpet, Wood
Living Room, Decorative, Electric
2
Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Range, Range Hood

Exterior

Rain Gutters, Lighting, Garden, Sidewalk, Balcony, Courtyard
Block, Stucco, Stone
Slab
Tile
N/A
N/A

School Information

Hamlin Elementary
Hamlin Middle
West Orange High

Additional Information

June 10, 2026
62
UVPUD
East
No

Mortgage Calculator

This calculator provides estimates for informational purposes only and is not a loan offer, pre-approval, or commitment to lend. Actual rates, payments, and loan terms vary by lender and are subject to credit approval, income/asset verification, and market conditions. Property tax and homeowners insurance shown are estimates and may differ. PMI applies when the down payment is under 20%. For an official Loan Estimate, contact a licensed mortgage lender. GLOBAL FLORIDA REALTY is a licensed real estate brokerage, not a mortgage lender. Equal Housing Opportunity.

62 days on market

Listing updated: Sep 8, 2026 · 3:27 PM

Listed by: Garry Walmsley · 407-923-2134GLOBAL FLORIDA REALTY · 407-380-3030

Updated from Real Estate Market Data

Location

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