16614 Harbor Sail WayWinter Garden, FL 34787Price: $1,495,000

  • Price: $1,495,000
  • Est. Mortgage of $/month
  • 4 Days on Market
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Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
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16614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 3478716614 Harbor Sail Way Winter Garden FL 34787
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  • 6Bedrooms
  • 0.34Acreage
  • 6Bathrooms
  • 2016Year Built
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 Courtesy of GLOBAL FLORIDA REALTY

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More Info

Location Information

  • Road Frontage DescriptionPaved

School Information

  • Elementary SchoolHamlin Elementary
  • High SchoolWest Orange High
  • Junior HighHamlin Middle

Parking

  • Parking Features
    • Circular Driveway
    • Driveway
    • Garage
    • Garage Door Opener
    • Garage Faces Side
    • Guest
    • Off Street
    • Workshop in Garage

Location

  • Address16614 Harbor Sail Way
  • AreaWinter Garden/Oakland
  • CountyOrange
  • Exterior Features
    • Balcony
    • Courtyard
    • Garden
    • Lighting
    • Rain Gutters
    • Sidewalk
  • StateFL
  • SubdivisionWaterside/johns Lake Ph 1
  • TownWinter Garden
  • Township 23
  • Zip34787

Property Information

  • Acreage0.34
  • Attached Garage YN Yes
  • Building Area Total 6,449
  • BuildingAreaUnitsSquare Feet
  • LivingAreaUnitsSquare Feet
  • Lot Size Square Feet 14,997
  • MFR Living Area Meters 453
  • MFR Lot Size Square Meters 1393
  • MFR Total Acreage 1/4 to less than 1/2
  • Square Feet4,882

Basic Information

  • List Price$1,495,000
  • ListingContractDate2026-06-08
  • MLS NumberO6414639
  • Mls Status Active
  • OriginalListPrice1495000
  • PostalCodePlus416
  • PublicSurveyRange27
  • StatusACT

Rooms

  • Bedrooms6
  • Full Bath5
  • Half Baths1
  • MFR Additional Rooms Attic, Bonus Room, Den/Library/Office, Family Room, Formal Dining Room Separate, Inside Utility, Loft, Media Room

Building

  • Bathroom6
  • Builder Model MANSFIELD
  • Construction Materials Block, Stone, Stucco
  • FireplaceDecorative, Electric, Living Room
  • Fireplace YN Yes
  • Foundation Details Slab
  • GarageYes
  • Garage Spaces3
  • Levels Two
  • Patio And Porch Features Covered, Patio, Rear Porch, Screened
  • Property StyleMediterranean
  • RoofTile
  • Rooms15
  • Stories2
  • Window Features Blinds, Drapes, Shades, Window Treatments
  • Year Built2016

Water Body

  • MFR Water Access YN No
  • Pool Private YN Yes
  • Water ViewNo

Other

  • Building Area Source Public Records
  • Date Listed06/10/2026
  • MFR Additional Lease Restrictions Long-Term Rental Accepted with Minimum 7 Month Lease Term
  • MFR Exist Lse Tenant YN No
  • MFR Flood Zone Code X
  • MFR Flood Zone Date 2021-09-24
  • MFR Minimum Lease 7 Months
  • Status Change Timestamp2026-06-10T15:50:22
  • Usm Previous StatusComing Soon
  • Vegetation Fruit Trees, Mature Landscaping, Trees/Landscaped
  • View Count1

Tax Information

  • Association Fee $168
  • Association Fee Frequency Monthly
  • Fees$4,596
  • MFR Association Fee Requirement Required
  • Monthly HOA Amount $168
  • Tax Year 2025
  • Taxes$11,216
  • Total Monthly Fees $383

Basic Information

  • Property SubTypeSingle Family Residence
  • Property TypeResidential
  • Virtual TourView Tour

Property

  • Builder Name STANDARD PACIFIC
  • ZoningUVPUD

Interior

  • Flooring Carpet, Tile, Wood
  • Furnished Negotiable

Utilities

  • Cooling Central Air
  • Heating Electric
  • Laundry Features Gas Dryer Hookup, Inside, Washer Hookup
  • Sewer Public Sewer
  • Utilities
    • BB/HS Internet Available
    • Cable Available
    • Cable Connected
    • Electricity Connected
    • Phone Available
    • Sewer Connected
    • Underground Utilities
    • Water Connected
  • Water Source Public

Amenities

  • Appliances IncludedBuilt-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Range, Range Hood, Refrigerator
  • Association Amenities Clubhouse, Fitness Center
  • Association YN Yes
  • Community Features
    • Clubhouse
    • Fitness Center
    • Gated Community - No Guard
    • Playground
    • Sidewalks
    • Street Lights
  • Other AmenitiesFireplace, Garden, Pool, Lake Access
  • Other Equipment Irrigation Equipment
  • PetsYes
  • Pool Features
    • Auto Cleaner
    • Gunite
    • Heated
    • In Ground
    • Salt Water
    • Screen Enclosure
  • Security Features Gated Community, Security Lights, Security System, Smoke Detector(s)
  • Spa Features Heated, In Ground
Fusilier Realty Group
Fusilier Realty Group
Office: 407-281-8455
10016 Wellness Way
Orlando, FL 32832

Listings courtesy of StellarMLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of June 13, 2026 9:05 AM UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end user license agreement.

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