16614 HARBOR SAIL WAY
Winter Garden, FL 34787
$1,340,000
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 ...
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Listing Courtesy of: GLOBAL FLORIDA REALTY
407-387-3030
Buyer Represented by: FL PRO BROKERS LLC
| Listing Id: | O6414639 |
|---|---|
| List Price: | $1,399,000 |
| Close Price: | $1,340,000 |
| Close Date: | 2026-10-29 |
| Property Type: | Residential |
| Property Sub Type: | Single Family Residence |
| Status: | Closed |
| Bedrooms Total: | 6 |
| Bathrooms Full: | 5 |
| Bathrooms Half: | 1 |
| Living Area: | 4,882 |
| Condo Fees: | 215.0 |
| Tax Annual Amount: | $11,216 |
| Lot Size Square Feet: | 14,997 |
| Lot Size Acres: | 0.34 |
| Architectural Style: | Mediterranean |
| Waterfront?: | No |
| City: | Winter Garden |
| County Or Parish: | Orange |
| Subdivision Name: | Waterside/Johns Lake Ph 1 |
| Postal Code: | 34787 |
| Year Built: | 2016 |
| Additional Parcels?: | No |
| Association Fee2: | $215 |
| Appliances: | Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Range, Range Hood, Refrigerator |
| Association Amenities: | Clubhouse, Fitness Center |
| Builder Name: | STANDARD PACIFIC |
| Association Fee: | $168 |
| Association Fee Frequency: | Monthly |
| Attached Garage?: | Yes |
| Bathrooms Total Integer: | 6 |
| Building Area Source: | Public Records |
| Building Area Total: | 6449 |
| Building Area Units: | Square Feet |
| Carport?: | No |
| Direction Faces: | East |
| Foundation Details: | Slab |
| Construction Materials: | Block, Stone, Stucco |
| Cooling: | Central Air |
| Fireplace Features: | Decorative, Electric, Living Room |
| Directions: | Exit SR 429 at Stoneybrook West Parkway (Exit 19). Head west on Stoneybrook West Parkway. Continue onto Marsh Road for approximately 1 mile. Turn right onto Broadwater Avenue (entrance to Waterside on Johns Lake). Follow Broadwater Avenue through the community. Continue until you reach Harbor Sail Way. Turn left onto Harbor Sail Way. Continue to 16614 Harbor Sail Way, Winter Garden, FL 34787. |
| Elementary School: | Hamlin Elementary |
| Exterior Features: | Balcony, Courtyard, Garden, Lighting, Rain Gutters, Sidewalk |
| Flooring: | Carpet, Tile, Wood |
| Furnished: | Negotiable |
| Garage Spaces: | 3 |
| Garage?: | Yes |
| Community Features: | Clubhouse, Fitness Center, Gated Community - No Guard, Playground, Sidewalks, Street Lights |
| Heating: | Electric |
| High School: | West Orange High |
| 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) |
| Laundry Features: | Gas Dryer Hookup, Inside, Washer Hookup |
| Levels: | Two |
| Ownership: | Fee Simple |
| Living Area Source: | Public Records |
| Living Area Units: | Square Feet |
| Lot Size Acres: | 0.34 |
| Postal Code Plus4: | 0016 |
| Middle Or Junior School: | Hamlin Middle |
| MLS Area Major: | 34787 - Winter Garden/Oakland |
| MLS Area Major: | 34787 - Winter Garden/Oakland |
| Original List Price: | $1,495,000 |
| Other Equipment: | Irrigation Equipment |
| Parcel Number: | 05-23-27-8900-01-290 |
| Parking Features: | Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Guest, Off Street, Garage, Workshop in Garage |
| Patio And Porch Features: | Covered, Patio, Rear Porch, Screened |
| Pets Allowed: | Yes |
| Pool Features: | Auto Cleaner, Gunite, Heated, In Ground, Salt Water, Screen Enclosure |
| Stories Total: | 2 |
| Township: | 23 |
| Road Surface Type: | Paved |
| Roof: | Tile |
| Listing Terms: | Cash, Conventional |
| Tax Year: | 2025 |
| Security Features: | Gated Community, Security Lights, Security System, Smoke Detector(s) |
| Senior Community?: | No |
| Sewer: | Public Sewer |
| Special Listing Conditions: | None |
| State Or Province: | FL |
| Association?: | Yes |
| Builder Model: | MANSFIELD |
| Utilities: | BB/HS Internet Available, Cable Available, Cable Connected, Electricity Connected, Phone Available, Sewer Connected, Underground Utilities, Water Connected |
| Lease Amount Frequency: | Monthly |
| Water Source: | Public |
| Public Survey Range: | 27 |
| Public Survey Section: | 05 |
| Zoning: | UVPUD |
| Spa Features: | Heated, In Ground |
| Spa?: | Yes |
| Vegetation: | Fruit Trees, Mature Landscaping, Trees/Landscaped |
| Window Features: | Blinds, Drapes, Shades, Window Treatments |
| Additional Lease Restrictions: | Long-Term Rental Accepted with Minimum 7 Month Lease Term |
| Additional Rooms: | Attic, Bonus Room, Den/Library/Office, Family Room, Formal Dining Room Separate, Inside Utility, Loft, Media Room |
| Alternate Key Folio Num: | 272305890001290 |
| Association Approval Required Yn: | No |
| Association Email: | waterside@artemislifestyles.com |
| Association Fee Requirement: | Required |
| Association Url: | https://wastersidejohnslake.com/ |
| Available For Lease Yn: | Yes |
| Backups Requested Yn: | Yes |
| Building Area Total Srch Sq M: | 599.13 |
| Calculated List Price By Calcula: | 286.56 |
| Cddyn: | No |
| Dprurl: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6414639?w=Agent&skip_sso=true |
| Dprurl 2: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6414639?w=Customer |
| Dpryn: | No |
| Exist Lse Tenant Yn: | No |
| Flood Zone Code: | X |
| Flood Zone Date: | 2021-09-24 |
| Flood Zone Panel: | 12095C0200H |
| Green Verification Count: | 0 |
| Homestead Yn: | Yes |
| Lease Restrictions Yn: | Yes |
| Listing Exclusion Yn: | No |
| Living Area Meters: | 453.55 |
| Lot Size Square Meters: | 1393 |
| Minimum Lease: | 7 Months |
| Monthly Hoa Amount: | $168 |
| Pool Dimensions: | 17.11 30.1 |
| Room Count: | 15 |
| Sdeo yn: | No |
| Total Acreage: | 1/4 to less than 1/2 |
| Total Annual Fees: | $4,596 |
| Total Monthly Fees: | $383 |
| Unit Number Yn: | No |
| Water Access Yn: | No |
| Water Extras Yn: | No |
| Water View: | No |
| Yrs Of Owner Prior To Leasing Re: | 0 |
| Association Name: | ARTEMIS LIFESTYLES |
| Association Name 2: | WATERSIDE / JOHNS LK-PH1 |
| Association Phone: | (407) 395 8445 |
| Association Phone 2: | (407) 395 8445 |
| Association 2 Yn: | 1 |
| Attribution Contact: | 407-387-3030 |
| Originating System Name : | Stellar MLS |
| Dock Yn: | No |
| In Law Suite Yn: | No |
| Green Energy Generation Yn: | No |
| Listing Contract Date: | 2026-06-08 |
| Fireplace?: | Yes |
| Pool Private?: | Yes |
| New Construction?: | No |
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Property Last Updated: October 31, 2026 04:24 AM - ET
