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5525 Isleworth Country Club Dr, Windermere

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.

5 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

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

$4,350,000

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.

5 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

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

$4,287,500

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.

3 Beds ⋅ 4 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

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

$3,900,000

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.

5 Beds ⋅ 7 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

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

$3,725,000

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.

4 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

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

$3,337,000

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.

3 Beds ⋅ 4 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

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

5379 Isleworth Country Club Drive, Windermere

$2,750,000

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!!!

4 Beds ⋅ 4 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

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