To schedule a showing of 16614 Harbor Sail Way, Winter Garden, Florida, Call David Shippey at 863-521-4517 TODAY!
$1,495,000 | 6 beds | 5 full baths | 1 half baths | 4,882 sqft
Winter Garden, FL 34787
- 6Beds
- 6.00Total Baths
- 5 Full, 1 HalfBaths
- 4,882SqFt
- 2016Year Built
- 0.34Acres
- MLS# O6414639
- Residential
- SingleFamilyResidence
- Active
- Approx Time on Market8 days
- Area34787 - Winter Garden/oakland
- CountyOrange
- Subdivision Waterside/johns Lake Ph 1
Overview
An Irreplaceable Gated Estate: Unmatched Scale, Double-Lot Privacy, & Private OasisBehind 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 homes 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 neighborsperfect 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 Wests 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.
Agriculture / Farm
Association Fees / Info
Community Features: Clubhouse, Fitness, Playground, Gated, StreetLights, Sidewalks
Pets Allowed: Yes
Hoa Frequency Rate: 168
Association: Yes
Association Amenities: Clubhouse, FitnessCenter
Hoa Fees Frequency: Monthly
Bathroom Info
Total Baths: 6.00
Fullbaths: 5
Building Info
Window Features: Blinds, Drapes, WindowTreatments
Roof: Tile
Builder: STANDARD PACIFIC
Building Area Source: PublicRecords
Buyer Compensation
Exterior Features
Style: SpanishMediterranean
Pool Features: Gunite, Heated, InGround, PoolSweep, ScreenEnclosure, SaltWater
Patio: RearPorch, Covered, Patio, Screened, Balcony
Pool Private: Yes
Exterior Features: Balcony, Courtyard, Garden, SprinklerIrrigation, Lighting, RainGutters, InWallPestControlSystem
Fees / Restrictions
Association Fee: 215
Association Fee Frequency: Monthly
Financial
Original Price: $1,495,000
Garage / Parking
Parking Features: CircularDriveway, Driveway, Garage, GarageDoorOpener, Guest, OffStreet, GarageFacesSide, WorkshopInGarage
Attached Garage: Yes
Garage: Yes
Green / Env Info
Interior Features
Fireplace Desc: Decorative, Electric, LivingRoom
Fireplace: Yes
Floors: Carpet, Tile, Wood
Levels: Two
Spa: Yes
Laundry Features: WasherHookup, GasDryerHookup, Inside
Interior Features: BuiltInFeatures, CeilingFans, CrownMolding, CentralVacuum, EatInKitchen, HighCeilings, MainLevelPrimary, OpenFloorplan, StoneCounters, VaultedCeilings, WalkInClosets, WoodCabinets, Attic, SeparateFormalDiningRoom, Loft
Appliances: BuiltInOven, Cooktop, Dryer, Dishwasher, Disposal, Microwave, Range, Refrigerator, RangeHood
Spa Features: Heated, InGround
Lot Info
Direction Remarks: 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.
Lot Size Units: Acres
Lot Size Acres: 0.34
Lot Sqft: 14,997
Vegetation: FruitTrees, PartiallyWooded
Lot Desc: Landscaped
Misc
Builder Model: MANSFIELD
Other
Special Conditions: None
Security Features: SecuritySystem, SmokeDetectors, SecurityLights, GatedCommunity
Other Rooms Info
Property Info
Section: 05
Class Type: SingleFamilyResidence
Property Sub Type: SingleFamilyResidence
Construction Materials: Block, Stone, Stucco
Stories: 2
Total Stories: 2
Foundation: Slab
Human Modified: Yes
Room Info
Total Rooms: 15
Sqft Info
Sqft: 4,882
Bulding Area Sqft: 6,449
Living Area Units: SquareFeet
Living Area Source: PublicRecords
Tax Info
Tax Year: 2,025
Tax Lot: 129
Tax Legal Description: WATERSIDE ON JOHNS LAKE - PHASE 1 82/74LOT 129
Tax Block: 00
Tax Annual Amount: 11216.47
Tax Book Number: 82/80
Unit Info
Utilities / Hvac
Heating: Electric
Water Source: Public
Sewer: PublicSewer
Cool System: CentralAir, CeilingFans
Cooling: Yes
Heating: Yes
Utilities: CableAvailable, CableConnected, ElectricityConnected, HighSpeedInternetAvailable, PhoneAvailable, SewerConnected, UndergroundUtilities, WaterConnected
Waterfront / Water
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.This listing courtesy of Global Florida Realty
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MLS IDX data last updated on 06-16-2026 1:55 PM EST.
If you have any questions on 16614 Harbor Sail Way, Winter Garden, Florida, please call David Shippey at 863-521-4517.
MLS# O6414639 located at 16614 Harbor Sail Way, Winter Garden, Florida is brought to you by David Shippey REALTOR®
16614 Harbor Sail Way, Winter Garden, Florida has 6 Beds, 5 Full Bath, and 1 Half Bath.
The MLS Number for 16614 Harbor Sail Way, Winter Garden, Florida is O6414639.
The price for 16614 Harbor Sail Way, Winter Garden, Florida is $1,495,000.
The status of 16614 Harbor Sail Way, Winter Garden, Florida is Active.
The subdivision of 16614 Harbor Sail Way, Winter Garden, Florida is Waterside/johns Lake Ph 1.
The home located at 16614 Harbor Sail Way, Winter Garden, Florida was built in 2026.