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Pending
    • $1,495,000

    16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787

    6beds
    4,882sqft
    : 
    $9,996/mo
    Get pre-qualified
    Single Family Residence
    Built in 2016
    0.34 Acres Lot
    $1,420,600 Zestimate®
    $306/sqft
    $383/mo HOA

    What's special

    Private oasisPrivate sun-drenched sanctuaryStriking courtyard entryFour additional large bedroomsPrivate home officeWest-facing backyardMedia room
    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.
    49 days
    |
    184
    |
    1
    |

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Garry Walmsley 407-923-2134,

    GLOBAL FLORIDA REALTY 407-380-3030

    Source: Stellar MLS,MLS#: O6414639MLS LogoOriginating MLS: Orlando Regional

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 6
      • Bathrooms: 6
      • Full bathrooms: 5
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Attic, Bonus Room, Den/Library/Office, Family Room, Dining Room, Utility Room, Loft, Media Room
      Primary bedroom
      • Features: No Closet
      • Level: First
      • Area: 378.1 Square Feet
      • Dimensions: 19x19.9
      Bedroom 1
      • Features: Ceiling Fan(s), Built-in Closet
      • Level: First
      • Area: 270.4 Square Feet
      • Dimensions: 16x16.9
      Bedroom 3
      • Features: Ceiling Fan(s), Built-in Closet
      • Level: Second
      • Area: 150.04 Square Feet
      • Dimensions: 12.1x12.4
      Bedroom 4
      • Features: Ceiling Fan(s), Built-in Closet
      • Level: Second
      • Area: 205.62 Square Feet
      • Dimensions: 14.9x13.8
      Bedroom 5
      • Features: Built-in Closet
      • Level: Second
      • Area: 172.86 Square Feet
      • Dimensions: 13.4x12.9
      Primary bathroom
      • Features: En Suite Bathroom, Split Vanities, Stone Counters, Tub with Separate Shower Stall, Water Closet/Priv Toilet, Walk-In Closet(s)
      • Level: First
      • Area: 250.74 Square Feet
      • Dimensions: 12.6x19.9
      Bathroom 1
      • Features: En Suite Bathroom, Shower No Tub, Single Vanity, Urinal, No Closet
      • Level: First
      • Area: 45.5 Square Feet
      • Dimensions: 5x9.1
      Bathroom 3
      • Features: Exhaust Fan, Granite Counters, Jack & Jill Bathroom, No Closet
      • Level: Second
      • Area: 103.85 Square Feet
      • Dimensions: 6.7x15.5
      Bathroom 4
      • Features: Dual Sinks, Granite Counters, Shower No Tub, Stone Counters, No Closet
      • Level: Second
      • Area: 75.06 Square Feet
      • Dimensions: 5.4x13.9
      Dining room
      • Features: No Closet
      • Level: First
      • Area: 187.68 Square Feet
      • Dimensions: 13.6x13.8
      Kitchen
      • Features: Breakfast Bar, Built-In Shelving, Central Vacuum, Exhaust Fan, Kitchen Island, Stone Counters, Pantry, No Closet
      • Level: First
      • Area: 332.64 Square Feet
      • Dimensions: 17.6x18.9
      Living room
      • Features: Central Vacuum, No Closet
      • Level: First
      • Area: 369.07 Square Feet
      • Dimensions: 22.1x16.7
      Loft
      • Features: No Closet
      • Level: Second
      • Area: 405.12 Square Feet
      • Dimensions: 21.1x19.2
      Media room
      • Features: No Closet
      • Level: Second
      • Area: 423.12 Square Feet
      • Dimensions: 24.6x17.2
      Office
      • Features: Storage Closet
      • Level: First
      • Area: 127.68 Square Feet
      • Dimensions: 11.4x11.2
      Heating
      • Electric
      Cooling
      • Central Air
      Appliances
      • Included: Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Range, Range Hood, Refrigerator
      • Laundry: Gas Dryer Hookup, Inside, Washer Hookup
      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)
      • Flooring: Carpet, Tile, Hardwood
      • Has fireplace: Yes
      • Fireplace features: Decorative, Electric, Living Room
      Interior area
      • Total structure area: 6,449
      • Total interior livable area: 4,882 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 3
      • Parking features: Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Guest, Off Street, Split Garage, Workshop in Garage
      • Attached garage spaces: 3
      • Has uncovered spaces: Yes
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Covered, Patio, Rear Porch, Screened
      • Exterior features: Balcony, Courtyard, Garden, Irrigation System, Lighting, Rain Gutters, Sidewalk
      • Has private pool: Yes
      • Pool features: Auto Cleaner, Gunite, Heated, In Ground, Salt Water, Screen Enclosure
      • Has spa: Yes
      • Spa features: Heated, In Ground
      Lot
      • Size: 0.34 Acres
      • Residential vegetation: Fruit Trees, Mature Landscaping, Trees/Landscaped
      Details
      • Parcel number: 052327890001290
      • Zoning: UVPUD
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Mediterranean
      • Property subtype: Single Family Residence
      Materials
      • Block, Stone, Stucco
      • Foundation: Slab
      • Roof: Tile
      Condition
      • New construction: No
      • Year built: 2016
      Details
      • Builder model: MANSFIELD
      • Builder name: STANDARD PACIFIC

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: BB/HS Internet Available, Cable Available, Cable Connected, Electricity Connected, Phone Available, Sewer Connected, Street Lights, Underground Utilities, Water Connected

      Community & HOA

      Community
      • Features: Clubhouse, Fitness Center, Gated Community - No Guard, Playground, Sidewalks
      • Security: Gated Community, Security Lights, Security System, Smoke Detector(s)
      • Pet fee: $0 monthly
      • Subdivision: WATERSIDE/JOHNS LAKE PH 1
      HOA
      • Has HOA: Yes
      • Amenities included: Clubhouse, Fitness Center
      • HOA fee: $383 monthly
      • HOA name: ARTEMIS LIFESTYLES
      • HOA phone: 407-395-8445
      • Second HOA name: WATERSIDE / JOHNS LK-PH1
      • Second HOA phone: 407-395-8445
      Location
      • Region: Winter Garden

      Financial & listing details

      • Price per square foot: $306/sqft
      • Tax assessed value: $1,022,913
      • Annual tax amount: $11,216
      • Date on market: 6/10/2026
      • Cumulative days on market: 32 days
      • Listing terms: Cash,Conventional
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Paved

        Estimated market value

        $1,420,600

        $1.35M - $1.49M

        $6,679/mo

        Price history

        DateEventPrice
        6/29/2026Pending sale$1,495,000$306/sqft
        Source: Stellar MLS #O6414639 Report a problem
        6/10/2026Listed for sale$1,495,000+106.8%$306/sqft
        Source: Stellar MLS #O6414639 Report a problem
        11/18/2016Sold$722,825$148/sqft
        Source: Public Record Report a problem
        11/15/2016Pending sale$722,825$148/sqft
        Source: BHHS FLORIDA REALTY #O5476430 Report a problem
        11/15/2016Listed for sale$722,825$148/sqft
        Source: BHHS FLORIDA REALTY #O5476430 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$10,664 +3.5%$708,366 +3%
        2023$10,307 +2.8%$687,734 +3%
        2022$10,026 +1.3%$667,703 +3%
        2021$9,899 -1.1%$648,255 -0.3%
        2020$10,009 -0.1%$650,050 +1.5%
        2019$10,016 -7.7%$640,520 +3.6%
        2018$10,850 $618,146 +16.3%
        2017$10,850 +21.5%$531,496 +525.3%
        2016$8,930 +626.3%$85,000 +54.5%
        2015$1,230 +130.4%$55,000 +83.9%
        2014$534 $29,900
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 34787

        Getting around

        6 / 100
        Car-Dependent
        27 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Hamlin Elementary
        • Middle: Hamlin Middle
        • High: West Orange High

        Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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