Isleworth Homes with Lake Front Water Frontage

Isleworth Homes with Lake Front Water Frontage

Welcome to Isleworth, a stunning subdivision nestled in the picturesque city of Windermere, Florida, within the enchanting Orange County. This exclusive community is renowned for its captivating lakefront properties, offering residents a unique blend of luxury living and serene natural beauty.

Isleworth is not just a neighborhood; it’s a lifestyle. With its meticulously designed homes, many of which boast breathtaking lakefront views, residents enjoy a tranquil oasis right in their backyards. Imagine waking up to the gentle lapping of water and stunning sunrises over the shimmering surface of the lake. The waterfront homes here feature expansive outdoor spaces, perfect for entertaining or simply soaking in the tranquility of the surroundings.

The community also provides an array of upscale amenities, including a world-class golf course, a luxurious clubhouse, and a state-of-the-art fitness center, ensuring that every resident can indulge in a lifestyle of comfort and leisure. With lush landscaping and scenic walking trails, Isleworth is ideal for outdoor enthusiasts and those seeking a peaceful retreat.

Located just minutes from downtown Windermere, residents enjoy easy access to boutique shopping, gourmet dining, and vibrant community events. The area's top-rated schools and family-friendly atmosphere make Isleworth an ideal choice for families looking to settle down in a nurturing environment.

Whether you’re seeking a permanent residence or a vacation retreat, Isleworth offers an unparalleled living experience, where luxury meets nature in perfect harmony. Come discover your dream home in this idyllic lakeside community today!

Newest Isleworth Homes with Lake Front Water Frontage

5092 Isleworth Country Club Drive, Windermere
$8,500,000
4 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Set along the front nine of Isleworth championship golf course with breathtaking views of Hole 6, this grand estate occupies an oversized lot along Isleworth’s main drive and has been beautifully reimagined with an extensive transformation over the last two years. The result is a sophisticated, move-in-ready home where timeless architectural character blends seamlessly with thoroughly modern style. Originally built by Pellegrini Homes and expanded to 7,100 square feet, the residence retains its signature architectural details, including custom ceilings, travertine floors with intricate tile inlays, and carefully crafted shell stone columns. The grandeur of the formal living room is accentuated by its soaring 20-foot ceiling, magnificent chandelier, and stately stone fireplace. A former bonus room has been thoughtfully transformed into the home's impressive new chef's kitchen, featuring custom cabinetry, an Italian-made 48-inch ILVE range, a luxury appliance collection, and elegant finishes. The original kitchen has been reimagined as a sophisticated entertaining bar with custom cabinetry, a built-in espresso cabinet, wine storage, and dedicated space for morning coffee and smoothies. Both spaces connect effortlessly to the casual dining area and formal dining room, creating an exceptional flow for everyday living and entertaining. The family room offers an open, airy setting with a built-in media display and effortless connection to the lanai. The main-level owner's suite provides a private retreat with a cozy fireplace, dual closets, and a lavish bath featuring dual vanities, a walk-in shower, and a luxurious soaking tub framed by elegant stone columns. A new main-level bedroom with private en-suite bath and an enlarged loft suite add flexibility for family and guests. Throughout the residence, new flooring, custom cabinetry and built-ins, designer lighting including bespoke Italian Murano glass fixtures, custom drapery, automated shades, and beautifully appointed furnishings create a cohesive, elevated aesthetic. Custom London-made closet lighting adds another layer of thoughtful detail, while modernized infrastructure, integrated technology, whole-home Wi-Fi, security, and smart-home features provide a seamless foundation for today's lifestyle. Outside, the residence has been transformed into an exceptional setting for both relaxation and entertaining. The pool has been resurfaced, outdoor living areas expanded, and a new outdoor kitchen and grilling area added, while a completely redesigned landscape, lighting, fencing, and fountain features enhance the grounds. Upstairs, the bedroom suites and expansive balcony capture panoramic views of the golf course and sparkling waters of Lake Bessie. The European-style lanai, with its graceful balustrade, creates an inviting setting for al fresco gatherings and captivating sunsets. This exceptional estate offers a rare combination of timeless architectural character, comprehensive modern improvements, sophisticated design, and an enviable golf-front setting within Isleworth.

5092 Isleworth Country Club Drive, Windermere
9310 Isleworth Gardens Drive, Windermere
$3,595,000
3 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Set within the Gardens of Isleworth, an intimate enclave of custom homes surrounded by lush gardens, water features, bridges and walking paths, this elegant single-story garden villa offers elevated garden views. The residence pairs timeless Mediterranean architecture with sophisticated finishes and a seamless indoor-outdoor design. Beautiful finishes throughout the interior include travertine flooring, wood-beamed ceilings and solid wood doors, creating a warm and gracious aesthetic. The expansive kitchen is designed for both everyday living and entertaining, with double islands, Quartzite countertops, a marble mosaic backsplash, Wolf appliances, a gas range, wet bar and butler’s pantry. A stone fireplace provides a focal point in the living room, while the spacious family room opens through panoramic sliding doors to a covered lanai, extending the living spaces naturally outdoors.The primary suite offers a private retreat with a morning bar, sitting area, spa-inspired bath and generous walk-in closet. A wood-floored study with custom built-ins provides an elegant setting for work, while additional bedrooms offer comfort and privacy for family and guests. Additional interior highlights include the laundry room, powder bath, and a three-car garage.Beyond the interiors, the home embraces its lush garden setting with tranquil pond views and an expansive outdoor living area. The covered lanai features a summer kitchen and pool bath overlooking a heated saltwater pool and spa, creating a private setting for relaxed afternoons and beautiful entertaining. The Gardens of Isleworth offer convenient living in a beautiful setting within Central Florida’s most iconic golf course community.

9310 Isleworth Gardens Drive, Windermere
6126 Payne Stewart Drive, Windermere
$3,250,000
3 Beds ⋅ 4 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Welcome to 6126 Payne Stewart Drive, a beautifully renovated golf villa in Isleworth, just steps from the club house. This 2,848-square-foot home offers three bedrooms, each with its own full bathroom, plus a powder room for guests. Soaring ceilings and an open floor plan bring a sense of space to the main living areas, where travertine floors and new doors complement the recent renovations. The gourmet kitchen features a 10-ft center island and top of the line appliances. The primary suite includes a recently renovated bathroom with a generously sized shower and soaking tub. Outside, a fully fenced garden setting surrounds the pool and spa. A summer kitchen and fireplace make the space inviting for outdoor dining and relaxing in the Florida Sunshine.

6126 Payne Stewart Drive, Windermere
5186 Vardon Drive, Windermere
$4,395,000
6 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Set along the front nine of Isleworth’s championship golf course, the 4,739-square-foot residence has been beautifully reimagined, pairing a grand architectural presence with contemporary interiors and expansive views across the course. Beyond the private entry gate to the property, a long, dramatic drive leads to the circular motor court anchored by a distinctive tiered fountain, creating an impressive arrival to this beautifully reimagined Isleworth estate. Inside, soaring ceilings and a dramatic two-story foyer introduce beautifully updated living spaces, where new flooring, refined architectural details and distinctive backlit feature walls create a fresh, elevated aesthetic. Primary living spaces include formal living and dining rooms, a kitchen with casual dining, and a home office. The six-bedroom residence offers two bedrooms on the main level, one on the lower level and three on the upper level. The expansive primary suite is includes a large bath finished with oversized floor-to-ceiling stone tile, a freestanding soaking tub, walk-in shower and dual-sink vanity. Designed for year-round enjoyment, the outdoor living experience begins in the enclosed Florida room and unfolds onto a sprawling pool deck overlooking the golf course. A large pool is complemented by an intimate oasis dining area surrounded by a pool moat, a separate sundeck and a covered outdoor grilling area, creating multiple spaces for entertaining, dining and relaxing. With its exceptional arrival, thoughtfully renovated interiors and expansive indoor-outdoor living, this distinctive estate offers a refined setting within one of Isleworth’s most sought-after golf-course locations.

5186 Vardon Drive, Windermere
5373 Isleworth Country Club Drive, Windermere
$7,200,000
5 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Impressively elegant NEW CONSTRUCTION Isleworth estate, prominently positioned on the 17th fairway of the championship golf course, with sweeping Lake Louise vistas beyond. This home was completely gutted and rebuilt with everything masterfully crafted to create a shimmering grand statement of luxury living on one of the most premier lots in the community. The spectacular 10-foot tall, 6-foot wide swinging front door sets the stage for a residence of distinction. A grand, light filled entry welcomes with soaring ceilings, polished marble floors, and a dramatic glass railed staircase that create an immediate sense of scale and sophistication. The open layout flows seamlessly through the dramatic great room toward a wall of floor to ceiling windows and accordion folding glass doors, inviting natural light and showcasing picturesque views of the just-completed saltwater pool and hot tub, golf course, and lake beyond. An elegant chandelier anchors the space, while the upper level glass balcony adds architectural interest and a modern, gallery style feel. Two bedroom suites on the first floor include an extraordinary primary retreat with double closets - one with a stackable washer and dryer - sitting room, and spa-like bath with glassed wet room with enclosed shower and tub. The stunning chef’s kitchen blends modern elegance with exceptional functionality, showcasing a stunning waterfall edge island wrapped in premium marble. Sleek, custom white cabinetry pairs with professional stainless steel appliances – which include WOLF 6-burner plus griddle cooktop, dishwasher, ice maker, and double ovens - create a clean, architectural aesthetic, while the rich wood flooring adds warmth and contrast. Designer pendant lighting highlights the generous prep and gathering areas, making the kitchen equally suited for intimate mornings or elevated entertaining. The open layout flows seamlessly into the surrounding living spaces, including a formal dining room with butler’s pantry, family dining room and secondary gathering space, enhancing the home’s sense of scale and sophistication. Every detail—from the integrated hood to the refined hardware—reflects a commitment to luxury craftsmanship and timeless style. Upstairs are three additional bedroom suites including one that could be a second master. Outdoor entertaining is inviting and refined with a sparkling pool and spa, expansive pool deck, and just-built cabana with summer kitchen. Full-house generator. The 600-acre Isleworth community is surrounded by the pristine Butler Chain of Lakes and is an exclusive residential enclave that sets the standard of excellence for Central Florida living, with 24-hour manned gates, a full security force, and available on-site home services for carefree living. Isleworth Golf & Country Club is located within the community offering optional golf and social membership opportunities.

5373 Isleworth Country Club Drive, Windermere
5237 Isleworth Country Club Drive, Windermere
$3,600,000
5 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Located along the 2nd tee of Isleworth's renowned championship golf course, this beautiful golf-front estate offers an exceptional location within the gates. The five-bedroom home features offers a spacious and open floor plan of more than 5,900 square feet overlooking the serene golf and water vistas. .

5237 Isleworth Country Club Drive, Windermere
9316 Gladys Garden Ct, Windermere
$6,500,000
5 Beds ⋅ 7 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Virtually Staged. An exceptional new construction offering within The Gardens of Isleworth, this newly completed residence by premier custom homebuilder Goehring & Morgan presents a rare opportunity to enjoy the ease of modern luxury within one of the world's most distinguished golf club communities. Thoughtfully designed and never lived in, the home combines timeless architecture with professionally curated interiors by Design Specifications, creating a refined retreat where every detail has been carefully considered. Spanning more than 5,400 square feet, the five-bedroom residence unfolds through a series of light-filled living spaces distinguished by bespoke millwork, tailored cabinetry, and a sophisticated palette of designer-selected finishes. Clean architectural lines and expansive gathering areas create an atmosphere that feels both grand and inviting, while thoughtfully integrated design elements elevate everyday living. Throughout the home, custom cabinetry conceals a fully integrated Sub-Zero, Wolf, and Cove appliance suite, allowing the chef's kitchen to maintain its beautiful aesthetic while delivering professional-grade performance. Well-appointed entertaining spaces nearby transition effortlessly from intimate family gatherings to larger celebrations.Private bedroom retreats offer comfort and tranquility, while spa-inspired baths showcase carefully selected finishes, fixtures and materials that evoke exceptional craftsmanship. The primary suite serves as a sanctuary unto itself, complete with a private beverage bar and thoughtfully designed spaces that encourage both relaxation and retreat.Beyond the interiors, walls of glass open to an inviting outdoor environment designed for year-round enjoyment. A fully equipped summer kitchen anchors the outdoor living experience, creating a natural extension of the home's entertaining spaces and providing the perfect backdrop for gatherings beneath Florida's sunshine and tropical climate.Surrounded by lush landscaping, sparkling water features, and the natural beauty that defines The Gardens of Isleworth, the residence enjoys a setting that feels both private and refined. Residents of Isleworth enjoy access to a lifestyle renowned for championship golf, world-class amenities, exceptional service, and a level of privacy rarely found. Combining the freshness of brand-new construction with the prestige of an established luxury community, this is more than a home, it is an opportunity to experience Isleworth at its finest.

9316 Gladys Garden Ct, Windermere
5073 Latrobe Dr, Windermere
$2,800,000
4 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Set on an elevated corner homesite within Isleworth, this four-bedroom residence presents a unique opportunity to secure a coveted address in one of Central Florida's most distinguished private golf communities. Encompassing more than 4,700 square feet, the property offers exceptional potential for renovation, customization, or the creation of a new vision tailored to today's luxury lifestyle.Positioned overlooking the 6th tee of Isleworth's renowned championship golf course and across from a scenic pond with water features, the homesite enjoys a picturesque setting with golf and water views and mature landscaping. Existing amenities include a pool, summer kitchen, circular driveway, and a three-car garage.For buyers seeking an opportunity to personalize a home within Isleworth or establish a long-term presence in this exceptional community, few properties offer such a compelling combination of location, scale, and potential. Surrounded by the Butler Chain of Lakes and secured by four staffed guard gates, Isleworth is renowned for its championship golf, exceptional amenities, and unparalleled lifestyle, with club membership available separately.

5073 Latrobe Dr, Windermere
5199 Latrobe Dr, Windermere
$5,300,000
6 Beds ⋅ 7 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Virtually Staged. Set within the gates of renowned Isleworth, this beautifully reimagined golf-front estate presents an exceptional opportunity to experience refined Central Florida living at its finest. Perfectly positioned along Isleworth’s celebrated championship golf course, the residence captures sweeping views of the fourth fairway while offering the privacy, comfort, and sophistication synonymous with the community’s distinguished lifestyle.Thoughtfully renovated and impeccably maintained, the home encompasses more than 6,600 square feet of combined indoor living and covered outdoor space, where contemporary finishes, designer lighting, and warm architectural details create an atmosphere that is both elegant and inviting. Every space has been intentionally curated—from the centrally located gourmet kitchen to the well-appointed utility spaces, resulting in a residence designed for effortless everyday living and elevated entertaining alike.The flexible floor plan offers exceptional versatility to suit a variety of lifestyles, accommodating configurations of up to six bedrooms, or alternatively a combination of bedrooms, office space, fitness room, or additional gathering areas. Six full baths and one half bath are finished with timeless materials and meticulous attention to detail throughout.At the heart of the home, the designer kitchen features sleek white cabinetry, quartz countertops, stainless steel appliances, and seamless connectivity to the expansive family room and casual dining area. Large glass openings invite natural light indoors while providing direct access to the screened lanai and resort-style pool environment beyond.The private primary suite serves as a luxurious retreat, highlighted by porcelain plank flooring, a spa-inspired bath with freestanding soaking tub and walk-in shower, and an oversized custom walk-in closet. Additional guest suites provide comfort and flexibility for family and visitors, while the home’s four-car garage and expansive motor court offer abundant space for automobile enthusiasts and guests alike.Outdoors, the estate transforms into a true private sanctuary. A newly redesigned saltwater pool and spa are enclosed within a custom lanai structure and complemented by an expansive new pool deck, creating a year-round setting for relaxation and entertaining. Lush landscaping, a fenced rear lawn, and panoramic golf course vistas further enhance the sense of serenity and exclusivity.Blending timeless elegance with modern livability, this exceptional Isleworth residence offers a rare combination of spacious design, privacy, and premier golf-front surroundings within one of the finest golf club communities in the world.

5199 Latrobe Dr, Windermere
6462 Deacon Cir, Windermere
$6,595,000
5 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Within the gates of Isleworth Golf & Country Club, along the shores of Lake Chase, this exceptional lakefront offers a refined and contemporary waterfront lifestyle. Ideally positioned near the driving range and just moments from Isleworth’s racquet center, clubhouse, fitness facilities, dining, and pool, the residence combines privacy with convenience.Designed by renowned architect Mark Nasrallah, the home spans more than 7,100 square feet and showcases sophisticated detailing and elevated finishes throughout. A grand foyer introduces the residence with a sweeping floating staircase and dramatic tiered crystal chandelier, leading into the formal living room where soaring ceilings, dual chandeliers, a fireplace, and expansive lake views create an impressive yet inviting setting.Marble flooring transitions seamlessly into the home’s primary living spaces, where rich hardwood floors enhance the warmth of the open-concept kitchen, casual dining area, and family room. The kitchen is both functional and elegant, featuring an oversized island, custom cabinetry, quarried quartz countertops, and professional-grade appliances by Wolf, Sub-Zero, and Bosch. A contemporary, temperature-controlled wine room accommodating over 100 bottles adds a distinctive touch. Architectural millwork in a diamond pattern defines the dining space, while custom media built-ins in the family room enhance the home’s cohesive design. Both areas open effortlessly to the lanai and pool deck.The primary suite serves as a private retreat, complete with a sitting area, designer lighting, and a spa-inspired bath featuring a soaking tub, expansive dual vanities, and a large walk-in shower. Additional interior highlights include a modern office with custom built-ins and private pool access, as well as a spacious game room with a full bar and captivating water views. Outdoors, the covered lanai extends to a resort-style pool and spa, surrounded by generous lounging areas and complemented by the private boat dock - creating an unparalleled setting for boating, entertaining, and year-round enjoyment in Florida's tropical climate.

6462 Deacon Cir, Windermere
5138 Fairway Oaks Dr, Windermere
$4,999,500
4 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Set along Isleworth’s signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Club—recognized among the finest private club communities in the world. Encompassing more than 4,300 square feet, the single-story residence has been completely transformed inside and out. Thoughtfully redesigned interiors showcase all-new flooring throughout, beautifully renovated bedrooms and baths, and a striking glass-enclosed wine tower serving as a true centerpiece that is both functional and an unforgettable conversation element anchoring the main living spaces. Every detail throughout the home has been elevated, from designer lighting installations that bring character and sophistication to each room, to the seamless flow of living and entertaining spaces. The kitchen is a true showpiece, featuring all-new appliances—including a striking black range with matching hood, refrigerator, and microwave—all accented with elegant gold detailing for a bold, designer-forward statement. Custom cabinetry is paired with exquisite countertops, highlighted by a dramatic waterfall-edge island that anchors the space and seamlessly blends everyday functionality with elevated, modern style.The outdoor living area features a reimagined pool and all-new pool deck creating a resort-style setting, perfectly positioned to take in breathtaking sunsets over the golf course and water. The half-acre homesite has been thoughtfully cleared and fenced to maximize both privacy and panoramic views, offering an exceptional backdrop for everyday living and entertaining alike. Framed by the fairways, the residence captures views of Lake Brenda - also known as Hourglass Pond - a small, privately maintained 10-acre water body that serves as a peaceful and picturesque part of the community setting. Additional features include a home office, in-home laundry room, and a three-car garage. Residents of Isleworth enjoy an unparalleled lifestyle surrounded by the Butler Chain of Lakes, with access to world-class golf, dining, and amenities, all just moments from Central Florida’s premier shopping, dining, and entertainment destinations.

5138 Fairway Oaks Dr, Windermere
5151 Latrobe Dr, Windermere
$3,800,000
4 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Positioned along the stunning 4th fairway of the renowned Isleworth Golf & Country Club, this exceptional single-story estate offers four bedrooms and more than 5,300 square feet of meticulously crafted living space. Every detail of this residence reflects the owner’s exceptional craftsmanship, with bespoke woodwork woven throughout the home, culminating in the crown jewel: the primary suite’s expansive wardrobe, featuring a central island, tiger wood floors, and cherry birch built-in displays—a true collector’s dream. The elegant foyer sets the tone, leading to formal living and dining spaces, and flowing effortlessly past a private office into the heart of the home: an open-concept kitchen, casual dining area, and family room designed for both entertaining and daily living. The gourmet kitchen is appointed with anigre wood cabinetry, a center island, dual sinks, a walk-in pantry, and professional appliances by Sub-Zero, Dacor, and Kitchenaid, marrying style and functionality in perfect harmony. A spacious game room with a wet bar provides an ideal space for recreation or hosting, while four luxurious bedrooms and 4.5 spa-inspired baths ensure comfort and privacy for family and guests alike. Seamlessly blending indoor and outdoor living, the estate features a sparkling open-air pool set against serene golf course vistas—an idyllic setting for year-round leisure and entertaining. Additional highlights include a circular driveway and motor court, a three-car garage, and a separate workshop. This is a rare opportunity to acquire a residence where world-class craftsmanship, refined design, and premier golf-front location converge, offering an unparalleled lifestyle in one of Central Florida’s most coveted enclaves.

5151 Latrobe Dr, Windermere
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