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4906 Aviva Garden Court, Windermere
$3,725,000
4 Beds ⋅ 6 Baths ⋅ O6446042 MLS
Welcome to an exceptional estate built in 2016 by Wyatt, nestled within the prestigious guarded gates of Isleworth. Ideally situated in the intimate Gardens of Isleworth, this beautifully appointed two-story residence offers approximately 6,600 square feet of refined living space, complemented by serene water views, lush landscaping, and a private walking trail. Elegant interiors showcase inlaid wood and travertine flooring, custom ceiling details, a beautiful fireplace, and expansive sliding glass pocket doors that effortlessly connect the interior living spaces to the spectacular outdoor retreat. The chef’s kitchen is designed for both everyday living and sophisticated entertaining, featuring Viking appliances, a striking copper hood, oversized center island, wet bar, butler’s pantry, breakfast nook, and hidden walk-in pantry. The luxurious primary suite offers a private lounge, dual-sided fireplace, cozy sitting area, dual walk-in closets, dressing area, and spa-inspired bath with dual vanities, soaking tub, and an impressive indoor-outdoor shower. Additional highlights include a private theater, balcony, bonus space, elevator, whole-house generator, and a smart-home system. Outdoor living is exceptional, featuring a sparkling pool and spa, fire pit, summer kitchen, outdoor shower, and expansive covered lanai with retractable screens, creating a comfortable year-round setting for relaxing and entertaining while overlooking the tranquil water. An extraordinary six-car garage setup includes four individual single-car garages, with two equipped with vehicle lifts. This exceptional residence seamlessly combines sophisticated design, modern technology, resort-style outdoor living, and privacy within one of Windermere’s most coveted guard-gated communities. Grounds maintenance is included through the HOA. Be sure to explore the virtual tour links for an immersive look at this remarkable Isleworth estate.

4906 Aviva Garden Court, Windermere
5379 Isleworth Country Club Drive, Windermere
$2,750,000
4 Beds ⋅ 4 Baths ⋅ O6438449 MLS
This luxury estate in Isleworth offers a rare opportunity to remodel or create a custom estate in the highly coveted Isleworth community. Situated directly on the 17th hole of the Isleworth Country Club golf course, this property offers a unique combination of golf-course frontage and beautiful lake views. Designed for ultimate privacy, this spacious layout offers four bedroom suites each complete with a dedicated ensuite. Schedule your private tour today!!!

5379 Isleworth Country Club Drive, Windermere
9648 Mccormick Place, Windermere
$3,337,000
3 Beds ⋅ 4 Baths ⋅ O6346918 MLS
Stunning golf and lake views and beautifully updated grounds are hallmarks of this elegant Isleworth estate. Nestled along the front nine overlooking Isleworth’s 2nd fairway and beautiful Lake Chase, this two-story home spans more than 4,800 square feet and features modern finishes throughout. Beautiful porcelain tile travels throughout the main level from the spacious living room with an oversized modern built-in featuring slate stonework and lit shelves. The spacious master suite features a large sitting area and an en-suite bathroom with dual vanities, a walk-in closet, modern soaking tub and separate walk-in shower. Completing the main level are the home office, formal dining room, elegant powder bath and center-island kitchen with casual dining area. Two additional bedrooms with balcony access are on the upper level. Step outside and discover a newly reimagined outdoor living experience. The expansive pool deck has been fully updated with sleek new pavers, while fresh turf and lush landscaping create a vibrant backdrop for relaxation and entertaining. A striking glass wall encases the pool area, maximizing panoramic views of both the golf course and the lake. The outdoor kitchen has been thoughtfully upgraded with new granite, a built-in grill, pizza oven, sink, and designer lighting—seamlessly blending function with style. Enjoy evenings around the modern fire pit, take a dip in the resurfaced pool with its brand-new heater, or unwind in the extended backyard, which offers an additional 15 feet added to one side of the property. Every detail of this outdoor transformation has been designed to enhance both beauty and livability, making this property the perfect retreat for year-round enjoyment.

9648 Mccormick Place, Windermere
4806 Alexandra Garden Ct, Windermere
$3,900,000
5 Beds ⋅ 7 Baths ⋅ O6408804 MLS
Located within the Gardens Villas enclave of Isleworth Golf & Country Club, this updated and spacious estate epitomizes luxury living. Offering an impressive 5,695 square feet of meticulously designed living space, this villa presents an exquisite blend of elegance, comfort, and modern convenience, complemented by an array of exceptional features and amenities.The property encompasses five generously appointed ensuite bedrooms, ensuring residents and guests enjoy the utmost privacy and convenience, along with a dedicated office space ideally suited for professionals working from home. The spacious chef’s kitchen is outfitted with high-end Viking, Wolf, and TRUE appliances, abundant storage, a butler’s pantry, and an adjacent entertaining bar designed for effortless hosting. Enhancing both peace of mind and functionality, the residence is equipped with a Moen whole-home water management system, along with a sophisticated home automation and security system that controls many of the home’s key functions. Designed to embrace the Florida lifestyle, the outdoor living spaces are equally exceptional. A private pool and spa, expansive lanai, and fully appointed summer kitchen create the perfect setting for relaxing or entertaining while enjoying the picturesque surroundings. In every detail, this Garden Villa exemplifies the pinnacle of luxury living by seamlessly combining spacious design, refined finishes, advanced smart-home technology, and thoughtfully curated custom features. Whether enjoying the tranquility of the Gardens, entertaining poolside, or working from the comfort of your private office, this residence offers an unparalleled lifestyle of distinction.

4806 Alexandra Garden Ct, Windermere
5036 Latrobe Drive, Windermere
$4,350,000
5 Beds ⋅ 5 Baths ⋅ O6346003 MLS
Within the gates of the renowned Isleworth Golf & Country Club, this beautiful lakefront estate captures the essence of timeless luxury and gracious living. Poised on the shores of Lake Bessie, the 5,548 square-foot residence unfolds across two levels, designed to frame sweeping water views and create effortless spaces for both grand entertaining and quiet retreat. The upper level greets guests with custom French entry doors that flow into the open formal living and dining rooms, perfectly designed for gatherings. The kitchen is spacious and inviting, offering casual dining and seamless access to the main living areas. A richly appointed library adds warmth and refinement, while two en-suite bedrooms complete this floor, including the primary suite. With its oversized windows capturing endless lake vistas, a large sitting area, exterior balcony, and an en-suite bath featuring dual vanities, a soaking tub, and walk-in shower, the primary suite is a sanctuary of light and serenity. On the lower level, the estate offers two expansive bonus areas joined by a well-equipped kitchenette. Ideal for gaming, entertaining, or working from home, both spaces connect effortlessly to the sun-drenched pool terrace—seamlessly integrating indoor luxury and outdoor living. A stunning mature oak tree anchors the property's beautiful lakefront grounds, stretching gracefully toward the water’s edge—a signature of the property’s natural beauty. Beyond the oak tree, Lake Bessie shimmers in full view, offering a breathtaking backdrop to the estate. A rare combination of elegance, versatility, and iconic setting, this residence presents a lifestyle within one of Central Florida's finest communities.

5036 Latrobe Drive, Windermere
6113 Payne Stewart Drive, Windermere
$4,287,500
3 Beds ⋅ 4 Baths ⋅ O6386548 MLS
Timeless Waterfront Elegance in Isleworth’s Golf Villas Perfectly positioned along the tranquil shoreline of Lake Chase — part of the coveted Butler Chain of Lakes — this exquisitely renovated residence offers breathtaking sunrise views and a level of craftsmanship rarely seen. Located just steps from the Isleworth clubhouse, with its multiple dining venues, world-class fitness center, and premier amenities, this home sits within the highly sought-after Golf Villas enclave — an area known for its charm, walkability, and refined lifestyle. Encompassing approximately 3,000 square feet with three bedrooms and three bathrooms, the home has been completely reimagined by Akers Custom Homes thoughtfully perfecting every detail. The result is a residence that feels both timeless and impeccably curated. The exterior showcases a striking tabby façade, setting the tone for the craftsmanship within. Inside, 24” x 24” imported Italian tile flows seamlessly throughout the home, creating continuity and understated sophistication. Pecky cypress beams add warmth and architectural character, while a gas fireplace anchors the main living area with inviting elegance. The gourmet kitchen is a true centerpiece, appointed with Taj Mahal quartzite countertops, a dramatic onyx backsplash, and premium KitchenAid gas appliances. Designed for both beauty and function, it opens effortlessly to the living and dining spaces — ideal for everyday living and entertaining alike. The primary suite offers a private retreat with spa-inspired luxuries including a jacuzzi tub, and an expansive custom closet. Every space reflects thoughtful design — even the laundry room includes a dedicated dog shower, blending practicality with refined living. Outdoor living is equally exceptional. A heated pool overlooks the serene waterfront, while a motorized retractable screen enclosure allows the covered lanai to transition seamlessly between open-air and screened comfort. The expansive outdoor area features a full summer kitchen, dining space, and lounging area — creating a true extension of the home designed for year-round enjoyment. Completing the residence are two separate two-car garages, each equipped with retractable overhead storage for maximum organization and convenience. With its architectural integrity, superior materials, and unmatched location just moments from Isleworth’s clubhouse, this Lake Chase waterfront villa represents a rare opportunity to enjoy refined lakefront living within one of Central Florida’s most esteemed communities.

6113 Payne Stewart Drive, Windermere
5525 Isleworth Country Club Dr, Windermere
$11,500,000
5 Beds ⋅ 6 Baths ⋅ O6304800 MLS
One or more photo(s) has been virtually staged. Exceptional in both style and scale, this extraordinary Isleworth estate represents the pinnacle of luxury living in one of the finest golf club communities in the world. Designed by architect Terry Irwin and built by Ballard Construction, with interior designs by Faith Fournet, the property has been fully transformed and thoughtfully curated over the last three years to deliver exceptional comfort, sophistication and panache at every turn. The two-story estate is set on a pristine 1.02-acre golf-front home site along Isleworth's famed championship golf course and from the moment you enter, you'll be captivated by the artistry in design and modern innovation. The interiors span more than 9,500 square feet living and 13,000 under roof, blending 5 bedrooms, 5.5 baths and an array of indoor and outdoor living areas with uncompromisingly luxurious finishes designed for effortless entertaining and quiet moments alike. At the heart of the home, the showstopping glass-enclosed wine room—temperature-controlled and with more than 2,200-bottle capacity—is a collector's dream and the ultimate conversation piece. The primary suite is a sanctuary unto itself, featuring a magnificent two-story closet and dedicated dressing room with a bar. Indulge in true tranquility within the home’s private wellness suite, complete with exercise room, a rejuvenating steam room, dry sauna and invigorating cold plunge tub. Additional interior highlights include the grand kitchen with Cristallo quartzite lighted countertops; a fully custom lounge with full bar; an upper-level game room with bar; an oversized, air-conditioned garage accommodating up to 8 vehicles; two laundry rooms; and more. Outdoor spaces are equally impressive, with an expansive lanai and balcony, a custom swimming pool with fire pits, meticulously landscaped yard adorned with integrated lighting, sound and lush, native greenery and putting green —all overlooking panoramic views of Isleworth’s championship golf course. Whether hosting guests or enjoying a peaceful evening at home, this estate offers a rare opportunity to live a life of unmatched beauty, comfort, and distinction in one of Central Florida's most desirable enclaves.

5525 Isleworth Country Club Dr, Windermere
6474 Deacon Circle, Windermere
$4,475,000
6 Beds ⋅ 6 Baths ⋅ J999200 MLS
Within the gates of Isleworth, on beautiful Lake Chase among the Butler Chain of Lakes, sits this exquisite estate offering the best of Florida waterfront living. The six-bedroom, five and a half bath home is located adjacent to the driving range and tennis center, and is in close proximity to the renowned Isleworth Golf & Country Club house. Boasting an updated interior spanning more than 5,800 square feet, the estate offers spacious, light-filled rooms showcasing a phenomenal mix of fine finishes which create a home that is chic, stylish and relaxing. From the formal foyer featuring breathtaking views, to the dining room, open kitchen, breakfast nook and large family room, the sprawling floor plan captures exquisite vistas at every turn. The second-floor primary suite overlooks an outdoor oasis with views of Lake Chase, and the primary bath holds an oversized walk-in shower as well as an additional laundry room. Two home offices has separate workspace options. A private guest suite opening to a kitchenette and loft area conveniently rounds out the additional spaces in the home. Enjoy numerous outdoor dining and lounging areas and summer kitchen, along with the grounds featuring an open-air swimming pool, heated spa and boat dock.

6474 Deacon Circle, Windermere
6186 Louise Cove Drive, Windermere
$2,900,000
4 Beds ⋅ 6 Baths ⋅ O6392133 MLS
A Masterpiece of Design in the Heart of Isleworth – 6186 Louise Cove Drive. Stunning, design magazine-worthy residence nestled behind the exclusive 24-hour guard-gated community of Isleworth, one of Central Florida’s most prestigious neighborhoods. This exquisite estate sits on a spacious 0.75-acre corner lot, surrounded by mature landscaping and a stately circular driveway that sets the tone for the luxury that awaits inside. No expense was spared in the recent $1 million designer remodel, which brought in California-based interior designers to source the finest materials from around the globe. Step through grand arched solid wood double doors into a soaring foyer where 16-foot ceilings and imported white French oak floors flow throughout the home. Walls were meticulously finished to level 5 smoothness a testament to the craftsmanship and attention to detail throughout. Designed for both entertaining and everyday living, the open-concept family room centers around a venetian plaster fireplace and effortlessly flows into a show-stopping double island kitchen. Imported German cabinetry is complemented by one piece quartzite slabs and backsplash, while high-end appliances include a 6-burner Wolf range with double ovens, a paneled Thermador refrigerator & freezer, venetian plastered hood, beverage fridge, and under counter microwave are all seamlessly integrated for a refined look. Retreat to the expansive primary suite, where comfort meets luxury. Enjoy access to a private study, Florida room, and a spa-inspired bathroom featuring a stand-alone soaking tub, oversized glass shower with handmade 4x4 Moroccan tile, French brass fixtures, and custom lighting. Primary suite also features a spacious walk-in closet offering custom built-ins, providing both elegance and functionality. The home’s Santorini-inspired full pool bath is a work of art in itself, with artisan stucco finishes adorning every surface. Each secondary bedroom is an en-suite, with marble or handcrafted tile finishes and ample closet space. Outdoors, your private fenced backyard oasis features a heated pool & spa, covered summer kitchen, and expansive lanai, perfect for enjoying Florida’s year-round sunshine. Additional highlights include a whole-house generator, tankless water heaters, four AC units, and a designer laundry room with imported German cabinetry. Live minutes from world-class attractions, dining, and elite schools, yet enjoy the serenity and security of one of the region’s most sought-after enclaves.

6186 Louise Cove Drive, Windermere
4711 Joanna Garden Ct, Windermere
$2,950,000
3 Beds ⋅ 4 Baths ⋅ O6359789 MLS
Nestled within the exclusive Gardens of Isleworth enclave within Isleworth Golf & Country Club, this exquisite residence exemplifies refined Florida living. Crafted by Pellegrini Homes with professionally designed interiors, the single-story home seamlessly blends architectural sophistication with inviting comfort. A brick paver motor court introduces the residence, where a gracious custom arched French entry door sets the tone for the elegance within. The formal foyer makes a lasting impression with its soaring octagonal ceiling accented in tongue-and-groove woodwork. Inside, the formal living room—currently styled as a music salon—showcases a faux-painted garden ceiling and a custom brick wine nook, adding artistic charm and warmth. Throughout the home, travertine floors and curated details complement a spacious open plan, lending to the home's exceptional design and craftsmanship. Framed by reclaimed rustic wood beams and sliding glass doors, the family room flows naturally to the courtyard pool, creating effortless indoor-outdoor living. The center-island kitchen serves as a culinary showcase with custom cabinetry and premium appliances by Viking, Sub-Zero, and GE Monogram, while the adjoining casual dining area offers views of the pool and lush surroundings. The thoughtfully designed layout includes three bedrooms, one of which is a private cabana suite opening directly to the pool—ideal for guests or quiet retreat. The primary suite features a large bedroom, dual closets and a beautifully finished bath. Beyond the courtyard, a patio with pergola overlooks serene pond views, providing yet another setting for relaxation and entertaining. Centered around its picturesque courtyard pool with fireplace, summer kitchen, and hot tub, this remarkable residence offers both privacy and elegance in perfect balance—an exceptional opportunity to live beautifully within one of Isleworth's most coveted enclaves.

4711 Joanna Garden Ct, Windermere
5157 Latrobe Drive, Windermere
$4,400,000
6 Beds ⋅ 9 Baths ⋅ O6370038 MLS
Fully rebuilt and expanded in 2019, this rare single-story golf-front estate offers sun-filled living and panoramic views of Hole 4. Designed for refined luxury and effortless entertaining, the residence spans 5,721 square feet of interior living space (approximately 7,330 square feet total) on a professionally landscaped 0.51-acre lot. The open, light-filled floor plan includes six bedrooms, eight and a half baths, a private executive office, and a dedicated gym. Highlights include a chef’s kitchen with Sub-Zero and Wolf appliances, updated plumbing and electrical systems, smart-home prewiring, heated resort-style pool, epoxy-finished three-car garage, and numerous modern upgrades throughout. Set within one of Florida’s most exclusive private golf communities, residents enjoy championship golf, access to the Butler Chain of Lakes, luxury fitness and dining, curated social events, and 24-hour guarded security. Move-in ready and thoughtfully reimagined, this estate offers a rare combination of single-story living, golf-front views, and elevated lifestyle appeal for the most discerning buyer.

5157 Latrobe Drive, Windermere
9310 Isleworth Gardens Drive, Windermere
$3,550,000
3 Beds ⋅ 5 Baths ⋅ O6349960 MLS
Experience the art of fine living in this exquisite one-story Modern Mediterranean garden villa, offered fully furnished with a curated designer furniture package. Every detail has been thoughtfully crafted, blending timeless architecture with refined finishes and effortless comfort. Inside, travertine floors, wood-beamed ceilings, and solid wood doors set a warm, sophisticated tone. Custom cabinetry, designer window treatments, and rich textures throughout create a sense of understated luxury. The double island kitchen is a culinary masterpiece, featuring Quartzite countertops, a marble mosaic backsplash, gourmet appliances, a gas stove, wet bar, and butler’s pantry—perfect for both intimate dining and grand entertaining. A cast stone fireplace anchors the elegant living room, while the expansive family room opens through panoramic sliding doors to a covered lanai, creating a seamless indoor-outdoor experience. The primary suite is a sanctuary of indulgence, complete with a morning bar, private sitting area, spa-inspired bath, and generous walk-in closet. A wood-floored study with custom built-ins provides a refined space for work or reflection. Outdoors, the resort-style setting is framed by lush tropical landscaping and tranquil pond views. The spacious lanai features a summer kitchen and pool bath overlooking a heated saltwater pool and spa—your private oasis for relaxation and entertaining. A three-car garage completes this extraordinary residence, where every element has been designed for the most discerning homeowner. Isleworth is surrounded by the Butler Chain of Lakes and known for its manicured gardens, timeless architecture, and unparalleled privacy. This exclusive guard-gated community offers 24-hour security and the opportunity to join the Isleworth Golf & Country Club featuring world-class golf, tennis, resort-style pool, fitness, dining, and social events. Garden Villas include exterior grounds maintenance for effortless living.

9310 Isleworth Gardens Drive, Windermere
9915 Giffin Court, Windermere
$3,800,000
5 Beds ⋅ 4 Baths ⋅ J995374 MLS
Set along the shores of Lake Butler, the property showcases gorgeous lake views and offers direct access to the famed Butler Chain of Lakes. ,69 acres within the gates of Isleworth Country Club.

9915 Giffin Court, Windermere

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