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$1,495,000
Active
16614 HARBOR SAIL WAY
WINTER GARDEN, FL 34787 — WATERSIDE/JOHNS LAKE PH 1
6 Beds
6 Baths
4,882 sqft
0.34 acres
Built 2016
3-Car Garage
About This Property
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.
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.
Property Details
Basics
- Property Type
- Residential
- Property Subtype
- Single Family Residence
- MLS Number
- O6414639
- Year Built
- 2016
- Levels
- Two
- Architectural Style
- Mediterranean
- Additional Rooms
- Attic,Bonus Room,Den/Library/Office,Family Room,Formal Dining Room Separate,Inside Utility,Loft,Media Room
- Direction Faces
- East
- Occupant Type
- Owner
Size & Structure
- Living Area
- 4,882 sqft
- Total Area
- 6,449 sqft
- Lot Size
- 0.34 acres
- Lot Sq Ft
- 14,997 sqft
- Bedrooms
- 6
- Full Baths
- 5
- Half Baths
- 1
- Garage Spaces
- 3
- Stories
- 2
Interior
- Flooring
- Carpet, Tile, Wood
- Appliances
- Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Range, Range Hood, Refrigerator
- 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
- Gas Dryer Hookup, Inside, Washer Hookup
- Windows
- Blinds, Drapes, Shades, Window Treatments
- Fireplace
- Yes — Decorative, Electric, Living Room
- Furnished
- Negotiable
- A/C
- Central Air
- Heating
- Electric
Exterior & Lot
- Exterior Features
- Balcony, Courtyard, Garden, Lighting, Rain Gutters, Sidewalk
- Construction
- Block, Stone, Stucco
- Roof
- Tile
- Foundation
- Slab
- Patio/Porch
- Covered, Patio, Rear Porch, Screened
Water & Pool
- Pool
- Yes — Auto Cleaner, Gunite, Heated, In Ground, Salt Water, Screen Enclosure
- Spa
- Yes — Heated, In Ground
Community & HOA
- HOA
- Yes
- HOA Fee
- $168/Monthly
- HOA Amenities
- Clubhouse, Fitness Center
- Community Features
- Clubhouse, Fitness Center, Gated Community - No Guard, Playground, Sidewalks, Street Lights
- Pets Allowed
- Yes
- Homestead
- Yes
- Security
- Gated Community, Security Lights, Security System, Smoke Detector(s)
Utilities & Systems
- Water
- Public
- Sewer
- Public Sewer
- Utilities
- BB/HS Internet Available, Cable Available, Cable Connected, Electricity Connected, Phone Available, Sewer Connected, Underground Utilities, Water Connected
- Cooling
- Central Air
- Heating
- Electric
- Flood Zone
- X
- Parking
- Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Guest, Off Street, Garage, Workshop in Garage
Financial
- List Price
- $1,495,000
- Annual Taxes
- $11,216
- Tax Year
- 2025
- Listing Terms
- Cash, Conventional
- Special Conditions
- None
Schools
- Elementary
- Hamlin Elementary
- Middle School
- Hamlin Middle
- High School
- West Orange High