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$1,399,000

Under contract-accepting backup offers. 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.

6 Beds ⋅ 6 Baths ⋅ Waterside/Johns Lake Ph 1 SubDv. ⋅ 34787 Zip Code

16614 Harbor Sail Way, Winter Garden

$1,159,000

Under contract-accepting backup offers. Exquisite Sanctuary with Private Pool in Gated Waterside! Welcome home to this meticulously maintained, one-story masterpiece situated in the heart of Waterside, Winter Garden's established, sought-after gated community. Offering an unparalleled blend of luxury and privacy, this spectacular residence invites you to enjoy calming lakefront views the moment you enter the neighborhood. From the moment you step through the charming front courtyard, the home showcases exceptional quality and elegant upgrades. The gourmet kitchen serves as the heart of this open-concept layout, featuring custom cabinetry and a sun-drenched breakfast room that overlooks your private pool and a serene conservation lot. Retreat to the thoughtfully designed primary suite—a true oasis featuring a spacious walk-in closet with custom built-ins, French door opening to the covered patio, and a spa-like ensuite bath complete with dual vanities, a private commode room, garden tub, and a separate walk-in shower. Custom craftsmanship highlights every detail of this home, from the elegant coffered ceilings in the dining room to custom cabinetry and built-in closets. Off the sunlit breakfast room, a dedicated office area with custom built-in counters provides a functional workspace. Outside, enjoy a freshly painted exterior (2024) and an inviting covered screened lanai featuring a built-in outdoor grill with a sleek bar—perfect for year-round entertaining. Designed for comfortable living and entertaining, the home features a 3-way split bedroom layout, a custom-built entertainment center in the family room, and a Sonos sound system with five separate zones throughout. Embrace the ultimate Florida lifestyle in your private backyard paradise. Designed for inviting entertaining, the space includes a custom pool, spa, and a built-in outdoor grill, all set against a tranquil green space with the privacy of no rear neighbors. Watch the sunset over the lake and unwind in your own personal oasis. Residents of Waterside enjoy an exclusive atmosphere with premier amenities, including a community pool, fitness center, clubhouse, and a playground. Ideally positioned just minutes from top-rated schools, shopping, Disney, downtown Winter Garden, and major roadways, including the 429, 408, and the Florida Turnpike.

4 Beds ⋅ 4 Baths ⋅ Waterside/Johns Lake Ph 1 SubDv. ⋅ 34787 Zip Code

16753 Turtle Hatch Drive, Winter Garden