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Experience lakefront living in the heart of Winter Park. One of only two residences in The Cloisters with soaring 9-foot ceilings, this first-floor, three-bedroom, two-bath home offers a rare blend of privacy, scale and panoramic Lake Osceola views. Just two blocks from Park Avenue and adjacent to the Alfond Inn, this condominium lives like a private residence with unmatched access to boutique shopping, fine dining and cultural landmarks. Designed for elegant everyday living and entertaining, the open floor plan showcases a chef's kitchen with granite countertops, solid wood cabinetry, and an island for prep and serving. The spacious dining and living areas are enhanced by hardwood flooring, crown molding and a marble-trimmed wood-burning fireplace. More than 20 feet of sliding glass doors open to an expansive, L-shaped terrace that brings in natural light and offers breathtaking lake vistas. The oversized primary suite offers serene lake views and includes an en-suite bath with dual vanities, built-in closets and a walk-in shower. Additional features include a rare laundry and utility room with a full-size washer, dryer and sink, updated electrical and plumbing, and upgraded water heater and HVAC system. Just two blocks from Park Avenue, this residence places you in the heart of downtown Winter Park's sought-after lifestyle. Enjoy effortless access to fine dining, boutique shopping, world-class museums, Rollins College and year-round cultural events, all in an accessible, lakefront setting. Whether going to the Saturday farmers market, dining alfresco along the avenue or taking in the scenic views of Lake Osceola from your private residence, this property offers a seamless blend of luxury and urban elegance.
…By Premier Sotheby's International Realty
Welcome to Chiltern Garden Drive, a beautifully rebuilt home offering over 3,400sf of thoughtfully designed living space with 4 bedrooms & 4.5 baths. Completely expanded & reimagined, this exceptional residence blends elevated modern design, quality craftsmanship, & comfortable living in a way that feels sophisticated & inviting. Originally rebuilt as the personal residence of a nationally recognized contractor & structural engineer, this home was reconstructed with an extraordinary level of care, engineering, & attention to detail. The property underwent a total rebuild, with only three perimeter walls & the garage floors remaining from the original structure. The extensive reconstruction included all new framing, electrical, plumbing, & mechanical systems, including the addition of a roof dehumidifier system for enhanced climate control & efficiency. Additional improvements include a new roof, windows, doors, & garage doors, professionally installed stucco system, waterproofing of all interior masonry walls, interior foam insulation, & upgraded 3/4-inch drywall throughout for enhanced durability & sound control. Inside, warm white oak flooring flows throughout the home, complemented by custom-built millwork, designer wallpaper, & beautiful lighting selections that add warmth & character to each space. Statement chandeliers in the foyer & dining room create elegant focal points, while natural light fills the interiors & highlights the thoughtfully curated finishes. Level 5 wall finishes further elevate the clean & sophisticated aesthetic. Designed for both entertaining & everyday living, the open-concept layout seamlessly connects the kitchen, dining area, & family room. The completely reconfigured gourmet kitchen is both stunning & functional, featuring custom two-tone cabinetry, new top-of-the-line appliances, dramatic quartzite countertops, & a large center island that naturally becomes the heart of the home. Beautiful stone selections continue throughout, creating a cohesive & timeless feel. The family room offers a warm & inviting atmosphere centered around a sleek contemporary firebar that adds both ambiance & modern elegance to the space. Each bathroom was thoughtfully designed with custom vanities, imported tile, exotic stone selections, & statement lighting, creating spa-inspired spaces that feel elevated yet comfortable. The outdoor living space feels like a private retreat & serves as a seamless extension of the home. The covered lanai features motorized screens, tongue-and-groove ceilings, a dramatic accent wall, & a modern electric firebar, creating the perfect setting for year-round entertaining & relaxation. Beyond the lanai, the extended patio, pergola, & stainless steel spa tub provide additional spaces to enjoy the beautifully designed outdoor setting. Colored concrete driveways, curbs, & patio areas further enhance the home’s curb appeal & outdoor areas. Additional features include a whole-home generator, security system, security cameras, Sonos system, & professionally designed router locations for optimized connectivity. Thoughtfully rebuilt with exceptional craftsmanship, engineering, & intentionally selected finishes throughout, this extraordinary home offers a rare opportunity to own a truly turnkey residence with the feel & quality of custom new construction. Year built of 2025 per builder/owner is different than the property tax record of 1990 (house knocked down except garage slab & 3 exterior walls).
…By Annonceur International
LUXURY LAKEFRONT ESTATE – Minutes from Historic Downtown Winter Garden! Experience elevated waterfront living in this beautiful 4-bedroom, 4.5-bath lakefront pool residence on just under 1 acre, ideally located just minutes from the heart of Winter Garden and the charm of Plant Street. Built in 2020 and situated within the coveted GOLF CART DISTRICT near Historic Downtown, this property offers the rare combination of private lakefront serenity and walkable convenience. RECENT CUSTOM UPGRADES with designer millworker throughout, new wide plank oak wood floors, entire property custom fenced and designer hardscape and landscape with lakefront hot tub and lakefront sauna house! Inside, gorgeous hardwood floors flow throughout the thoughtfully designed single-story layout. The open-concept living spaces are warm yet modern, highlighted by a cozy electric fireplace and seamless indoor-outdoor connection. A distinctive wine and bourbon room adds a refined touch—perfect for entertaining or curating your private collection. The primary suite is positioned to capture sweeping lake views and features a spa-inspired bath and generous walk-in closet. Each additional bedroom includes ensuite bath access, while a private guest cottage provides flexible space for visitors, extended family, or a studio retreat. Step outdoors to your personal resort-style setting. Enjoy the screened salt water heated pool and spa, summer kitchen, and private dock for boating and sunset cruises. A detached private sauna house offers a true at-home wellness experience, while the outdoor fire pit overlooking the lake creates an unforgettable gathering space framed by panoramic water views. OWNED and FULLY PAID SOLAR PANELS with extremely low utilities cost. With upscale finishes, distinctive amenities, and an unbeatable lakefront location just moments from dining, shopping, and the vibrant downtown district, this exceptional property delivers the ultimate Florida lifestyle—where luxury meets laid-back lakeside living.Schedule your private showing and discover one of Winter Garden’s most compelling lakefront opportunities.
…By Annonceur International
Positioned along the golf frontage within the gated enclave of Palma Vista, this Mediterranean-inspired estate presents a refined expression of timeless architecture and elevated living, showcasing a 2018 renovation with over $1.2 million in transformative luxury upgrades. Designed as a private courtyard residence, the home unfolds with intention, where a resort-style saltwater pool and spa with tranquil fountains create a striking focal point for everyday living and elegant entertaining. The interiors feel warm, polished and cohesive, enhanced by a fresh coat of paint that brings a renewed sense of light throughout. Marble-inlaid flooring, coffered wood ceilings and curated finishes are carried from space to space with a natural sense of flow. A double-sided stone fireplace adds depth and character, while expansive golf course views create a serene backdrop. The kitchen is sophisticated and inviting, centered around a statement marble island and complemented by professional-grade appliances and custom cabinetry. It opens seamlessly to the family room, where custom built-ins and tailored media elements offer a comfortable, yet elevated, setting for gathering. The primary suite is a true retreat, offering a spacious and well-proportioned layout, a private sitting area, a fireplace and a spa-inspired bath designed for relaxation. Upstairs, a flexible lounge or fifth bedroom with balcony access provides additional space for guests, while a dedicated office with custom built-ins offers a quiet and refined workspace. A separate guest suite adds versatility, well suited for private accommodations, a fitness studio or extended stays. Beyond the courtyard, a terrace and lush verandah overlook the golf course, creating a peaceful setting for both morning and evening moments. The home's elevated positioning captures sweeping views while maintaining a sense of privacy. Ideally located near downtown Orlando, renowned attractions, and major thoroughfares, this residence offers a lifestyle defined by elegance, comfort and thoughtful design. Offered for those who value quality, privacy and an elevated living experience.
…By Premier Sotheby's International Realty
Under contract-accepting backup offers. Discover luxury living in this stunning custom-built, lakefront estate nestled on a private gated lot along the tranquil shores of Lake Hill. Spanning over 6,700 sq ft of heated living space and nearly 9,640 sq ft total, this three-story single-family home offers refined comfort, timeless craftsmanship, and breathtaking panoramic water views.The main level features a grand foyer leading to formal dining and a private office—both showcasing crown molding, built-in cabinetry, and elegant architectural touches like the stained glass interior window in the office. The living room boasts a cozy fireplace, lake-view balcony access, and stairs descending to the expansive lower level. The chef’s kitchen is fully equipped with a center island, pot filler, stainless steel appliances, ample counter space, and a charming breakfast nook.The primary suite is a true retreat with crown molding, walk-in closet, and a luxurious en-suite bath complete with a dressing room, dual vanities, soaking tub, walk-in shower, bidet, and built-in storage. Additional main-level highlights include a spacious laundry room with a sink, walk-in wash tub, and plenty of cabinetry.On the lower level, enjoy a large den with fireplace, wet bar, built-in entertainment center, and flexible space for recreation or entertaining. Two generously sized bedrooms on this floor feature en-suite baths, crown molding, and direct access to the rear patio.The upper level attic presents a versatile bonus room—perfect for a home gym, media room, or additional bedroom.Outside, the estate features meticulous landscaping, a circular drive, a 4-car oversized garage, and multiple outdoor living spaces to take in the serene lake views. This home is truly a private oasis—ideal for those seeking space, luxury, and lakeside serenity just minutes from Orlando conveniences.
…By Annonceur International
Welcome to 747 N Lake Sybelia Drive, an extraordinary lakefront estate gracefully positioned along the desired northern shoreline of beautiful Lake Sybelia. Completed in late 2023, this breathtaking California Coastal-inspired residence spans 4,755 square feet on an expansive 0.76-acre homesite, blending timeless architecture with refined finishes to create a lifestyle defined by elegance, comfort and effortless lakefront living. Ideally situated on a gently sloping lot, the home captures stunning elevated views of the water, offering a rare sense of privacy, tranquility and perspective. Thoughtfully designed interiors are filled with natural light and crafted for everyday living and exceptional entertaining. The main level showcases a beautifully appointed chef's kitchen anchored by an oversized island and complemented by a spacious walk-in butler's pantry. Open-concept dining and living spaces are framed by picturesque lake views, while the expansive great room seamlessly connects indoor and outdoor living. A private office, guest suite and dedicated pool bath complete the first floor. Upstairs, a versatile loft and homework nook provide flexible living space, while two en-suite bedrooms and a serene primary retreat offer exceptional comfort and privacy. The luxurious primary suite and one secondary bedroom open to a spacious lakeside balcony, an idyllic place to enjoy morning coffee, evening sunsets and sweeping water views. Exceptional outdoor living spaces surround the home. A welcoming covered front porch offers the perfect vantage point to enjoy lake views and watch boating activity, while the expansive rear covered lanai is designed for year-round entertaining with a summer kitchen and generous space for lounging and dining. Overlooking the beautifully landscaped backyard, complete with bamboo-lined fencing for privacy, is a sparkling saltwater pool and spa by Titan Pools, thoughtfully designed for resort-style enjoyment and capable of both gas and electric heating. Uniquely embraced by water and recreation, the home enjoys tranquil lake vistas to the south and the stunning pool retreat to the north. The waterfront experience is elevated by a newly constructed composite dock with a heavy-duty dual-motor lift, while a thoughtfully designed shell-base boat ramp provides seamless, eco-conscious access for launching watercraft directly from your property. Adding even more versatility, a 500+ square-foot unfinished bonus room above the garage offers incredible potential for customization, ideal for a media room, guest retreat, fitness studio or creative space. Plumbing has been extended for a future bath or bar, and the space is currently enjoyed as a golf simulator. Car enthusiasts will appreciate the impressive four-car tandem garage featuring soaring 15-foot ceilings designed to accommodate vehicle lifts, premium wall-mounted jackshaft openers for maximum overhead clearance and a separate side-access bay ideal for golf cart storage. Engineered for longevity as much as luxury, the home features an extensive stormwater drainage system with hard-piped gutters designed to protect the land and prevent erosion. Ideally located, enjoy a short visit or golf cart ride to Maitland City Centre and Homer Hough Park at Sybelia Point, while the shopping and dining of Park Avenue are just minutes away. Convenient access to Interstate 4 and express lanes ensures effortless travel throughout the greater Orlando area.
…By Premier Sotheby's International Realty
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