$1,495,000
16614 Harbor Sail Way Winter Garden, FL 34787
For Sale MLS# O6414639
6 beds 6 baths 4,882 sq ft Single Family
Details for 16614 Harbor Sail Way
MLS# O6414639
Description for 16614 Harbor Sail Way, Winter Garden, FL, 34787
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 Information
Property Type: Residential, Single Family Residence
Status: Active
Bedrooms: 6
Bathrooms: 6
Lot Size: 0.34 Acres
Square Feet: 4,882 sq ft
Year Built: 2016
Garage: Yes
Stories: 2 Story
Construction: Block,Stone,Stucco
Subdivision: Waterside/Johns Lake Ph 1
Builder: STANDARD PACIFIC
Foundation: Slab
County: Orange
School Information
Elementary: Hamlin Elementary
Middle: Hamlin Middle
High: West Orange High
Room Information
Main Floor
Dining Room: 13.8x13.6
Bedroom 1: 16.9x16
Primary Bathroom: 19.9x12.6
Office: 11.2x11.4
Primary Bedroom: 19.9x19
Kitchen: 18.9x17.6
Living Room: 16.7x22.1
Dining Room: 13.8x13.6
Bathroom 1: 9.1x5
Upper Floor
Bathroom 4: 13.9x5.4
Bedroom 5: 12.9x13.4
Bathroom 3: 15.5x6.7
Bedroom 4: 13.8x14.9
Bedroom 3: 12.4x12.1
Media Room: 17.2x24.6
Loft: 19.2x21.1
Bathrooms
Full Baths: 5
1/2 Baths: 1
Additonal Room Information
Laundry: Inside, Washer Hookup, Gas Dryer Hookup
Interior Features
Appliances: Built-In Oven, Cooktop, Microwave, Range, Refrigerator, Dishwasher, Disposal, Dryer, Range Hood
Flooring: Carpet,Tile,Wood
Doors/Windows: Blinds, Window Treatments, Drapes
Fireplaces: Living Room, Electric, Decorative
Additional Interior Features: Eat-In Kitchen, Vaulted Ceiling(s), Ceiling Fan(s), Central Vacuum, High Ceilings, Loft, Walk-In Closet(s), Attic, Built-in Features, Open Floorplan, Stone Counters, Wood Cabinets, Main Level Primary, Crown Molding, Separate/Formal Dining Room
Utilities
Water: Public
Sewer: Public Sewer
Other Utilities: Cable Available,Cable Connected,Electricity Connected,High Speed Internet Available,Phone Available,Sewer Connected,Underground Utilities,Water Connected
Cooling: Ceiling Fan(s), Central Air
Heating: Electric
Exterior / Lot Features
Attached Garage: Attached Garage
Garage Spaces: 3
Parking Description: Workshop in Garage, Garage, Garage Door Opener, Off Street, Garage Faces Side, driveway, Guest, Circular Driveway
Roof: Tile
Pool: Gunite, Pool Sweep, Salt Water, Screen Enclosure, In Ground, Heated
Additional Exterior/Lot Features: Sprinkler/Irrigation, Rain Gutters, In-Wall Pest Control System, Courtyard, Balcony, Garden, Lighting, Balcony, Patio, Covered, Screened, Rear Porch, Landscaped
Community Features
Community Features: Sidewalks, Playground, Clubhouse, Street Lights, Gated, Fitness
Security Features: Security System, Gated Community, Security Lights, Smoke Detector(s)
Association Amenities: Fitness Center, Clubhouse
Homeowners Association: Yes
HOA Dues: $168 / Monthly
Driving 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.
Financial Considerations
Terms: Cash,Conventional
Tax/Property ID: 05-23-27-8900-01-290
Tax Amount: 11216.47
Tax Year: 2025
A broker reciprocity listing courtesy: GLOBAL FLORIDA REALTY
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Sales History & Tax Summary for 16614 Harbor Sail Way
Sales History
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Tax Summary
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Schools
Schools nearby 16614 Harbor Sail Way
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The schools shown represent both the assigned schools and schools by distance based on local school and district attendance boundaries. Attendance boundaries change based on various factors and proximity does not guarantee enrollment eligibility. Please consult your real estate agent and/or the school district to confirm the schools this property is zoned to attend. Information is deemed reliable but not guaranteed.
SchoolDigger ® Rating
The SchoolDigger rating system is a 1-5 scale with 5 as the highest rating. SchoolDigger ranks schools based on test scores supplied by each state's Department of Education. They calculate an average standard score by normalizing and averaging each school's test scores across all tests and grades.
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