Isleworth Real Estate

Isleworth Real Estate

Welcome to Isleworth, a prestigious and picturesque subdivision nestled in the heart of Windermere, Florida. Known for its luxurious homes and stunning landscapes, Isleworth is a true gem in Orange County, offering an unparalleled lifestyle for those who seek both elegance and tranquility.

Isleworth is renowned for its striking Mediterranean-style architecture, with sprawling estates that boast exquisite designs and meticulously landscaped grounds. Residents enjoy the privacy and security of this exclusive community, which features 24-hour gated access and a warm, welcoming atmosphere. With a variety of home styles and sizes, Isleworth caters to a diverse range of tastes and preferences, ensuring that everyone can find their perfect sanctuary.

One of the crown jewels of Isleworth is its world-class amenities. The community is home to the Isleworth Golf & Country Club, a premier golfing destination that features an 18-hole championship course designed by the legendary Arnold Palmer. Residents can also take advantage of the state-of-the-art fitness center, tennis courts, and a luxurious clubhouse, making it easy to stay active and social within this vibrant community.

Nature lovers will appreciate the stunning views and serene surroundings, with the nearby Lake Butler providing opportunities for boating, fishing, and leisurely strolls along the water's edge. The area is also conveniently located near top-rated schools, fine dining, and shopping, making it an ideal place to settle down.

Experience the charm and sophistication of Isleworth, where luxury living meets the beauty of nature, and discover why this community is one of Florida’s most sought-after addresses. Your dream home awaits!

Newest Listings in Isleworth

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
4906 Aviva Garden Court, Windermere
$3,850,000
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
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
5036 Latrobe Drive, Windermere
$18,750,000
6 Beds ⋅ 9 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Virtually Staged. Pre-Construction. To be built. Poised on a remarkable .69-acre homesite along the shores of Lake Bessie, this exceptional new residence offers a rare opportunity to create a substantial private estate in one of Isleworth’s most coveted lakefront settings. Designed and to be built by Supreme International Construction, the residence will encompass approximately 15,337 square feet of living space across three levels, with six bedrooms, including two private primary suites, an elevator and a four-car garage accommodating up to eight vehicles with lifts. Created for both grand entertaining and effortless everyday living, the main level will feature a dramatic great hall, formal dining room, family room, expansive kitchen, private study and serene primary retreat. Soaring architectural spaces and multiple covered balconies create a natural connection to the lakefront setting. The lower level is envisioned as a private destination for leisure, with a beautifully appointed theater delivering an immersive viewing experience, complemented by a separate popcorn and snack room for added convenience and fun. A generous entertainment area, bar, summer kitchen, gym, yoga/Pilates studio, sauna and spa complete the level. The upper floor offers a second primary suite, additional bedroom suites, viewing lounge and PJ lounge. The outdoor living space is designed to maximize the breathtaking lakefront setting. Landlocked and private, Lake Bessie offers an intimate waterfront experience for boating, water sports and fishing, with no public access to the lake. This rare pre-construction opportunity offers the privilege of securing an extraordinary lakefront residence while personalizing select finishes as the residence takes shape. Within Isleworth’s 600-acre residential community, Isleworth Golf & Country Club, consistently recognized among the world’s finest private clubs, offers an exceptional lifestyle, with Membership offered separately and subject to application and approval.

5036 Latrobe 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
5050 Isleworth Country Club Drive, Windermere
$3,189,000
4 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Positioned along the 6th fairway of Isleworth Golf & Country Club, this thoughtfully updated single-story residence offers a rare combination of privacy, golf-course views and effortless everyday living. A welcoming circular drive and mature oaks set the stage, while inside, nearly 3,400 square feet unfolds in a light-filled collection of spaces designed to feel equally comfortable for quiet evenings at home or a house full of guests. Natural light pours through the glass entry into a dramatic foyer with a groin-vaulted ceiling, introducing the architectural character found throughout the home. Arched openings lead into the formal living room, where a striking stone fireplace creates a natural gathering place and walls of glass frame views of the garden and fairway beyond. The formal dining space provides an elegant backdrop for entertaining while remaining connected to the heart of the home. The renovated kitchen is both inviting and exceptionally functional, featuring a professional-style gas range, integrated appliances and a 40-bottle wine refrigerator. Custom cabinetry, marble countertops and a distinctive tile range hood complete the space, while additional cabinetry flows seamlessly into the family room to create a built-in entertainment center. Natural light reflects beautifully across the large-format tile floors, creating a bright, cohesive feel from room to room. The primary suite is privately positioned on the northeast wing, welcoming golden morning light into the space. The retreat features a distinctive dual-bath arrangement—one with a walk-in shower and the other with a freestanding soaking tub—along with a cedar-lined walk-in closet with custom built-ins. Three additional bedrooms provide comfortable accommodations for family and guests, including one with an ensuite bath, while the updated hall bath offers dual sinks and convenient pool access. A separate flex room easily adapts as an office, library, fitness room or additional retreat. Outside, a covered patio with fireplace extends the living space year-round, overlooking the open-air pool and spa with the manicured fairway beyond. A rear motor court, two-car garage and dedicated golf-cart parking complete the property. Recent improvements, including a 2020 slate roof, refreshed exterior paint, renovated kitchen and baths, complement the home’s established character. With its single-story footprint, private setting and half-acre golf-course homesite, the opportunity is as compelling as the lifestyle within the gates.

5050 Isleworth Country Club Drive, Windermere
5524 Worsham Court, Windermere
$3,500,000
4 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Welcome to the exclusive gates of Isleworth, golf front estate offers over 7,600 square feet of refined luxury living overlooking the fairway of the renowned Isleworth Golf & Country Club, one of the worlds most prestigious golf club communities, this championship course was designed by Arnold Palmer and set along the Butler Chain of Lakes. The neighborhood is defined by beautifully landscaped scenery, sweeping water views, and exceptional 24 hour guard gated privacy. This estate offers exceptional potential supporting four beds, six baths, a private office, inside gym, approached by a private driveway with ample guest parking and a 4 car garage. The two story residence opens with a regal marble foyer and fountain feature. Inside, vaulted ceilings, skylights, and wall to wall sliding glass doors fill the main living areas with natural light while framing views of the pool, sauna, golf views and rolling fairways beyond. A grand fireplace and wet bar create an inviting space for entertaining. The chef’s kitchen centers on a dramatic island and is highlighted by a striking copper range hood, warm cabinetry, and an open eat in layout designed for both everyday living and hosting. Above the garage, a private accessory dwelling unit provides flexible secondary living space or maids living. Each of the spacious bedrooms offers its own view and is finished with marble baths. A dedicated home gym adds further convenience. Exceptional amenities and sophisticated living in the world renowned community of Isleworth.

5524 Worsham Court, Windermere
9921 Lake Louise Drive, Windermere
$6,650,000
5 Beds ⋅ 7 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Positioned along the back nine of Isleworth’s renowned championship golf course, this exceptional estate spans nearly 7,000 square feet and has been thoughtfully reimagined through an extensive three-year renovation. Showcasing timeless architecture with a fresh, sophisticated aesthetic, the residence blends elegant European influences with light-filled interiors, superior craftsmanship and refined contemporary finishes. Custom French doors open to a breathtaking foyer, where soaring double-height ceilings introduce beautifully redesigned living spaces. Beautiful new flooring, designer lighting and a striking stone fireplace create an elegant backdrop, while expansive windows frame views of the sparkling pool, spa and outdoor living areas. Designed for both everyday living and effortless entertaining, the home's central gathering spaces include a warm and inviting family room with a fully modernized media display featuring handmade wooden slats and a custom fireplace, seamlessly connected to the spectacular new kitchen. Anchored by an oversized island, the kitchen features custom cabinetry, premium Wolf and Sub-Zero appliances and generous seating, creating a welcoming space for family and guests alike. The primary suite serves as a tranquil retreat, offering direct access to its own lanai along with a beautifully renovated spa-inspired bath featuring a walk-in shower, soaking tub and dual vanities. Four spacious en-suite guest bedrooms provide exceptional comfort and privacy, while the home office offers an ideal work-from-home setting. Upstairs, the original 19th Hole-inspired game room showcases a custom bar and opens to a private balcony overlooking the 16th green. Outside, meticulously manicured grounds provide a private resort-style setting. Offering an impressive sense of scale, the expansive covered lanai features soaring volume ceilings and beautiful new oversized stone tile flooring that elevate the space's timeless architecture. A fully equipped summer kitchen overlooks the custom swimming pool and spa, while generous areas for lounging and dining create an inviting extension of the home's beautifully reimagined interiors. Together, they create the perfect environment for year-round outdoor entertaining and relaxation in one of Central Florida's most prestigious golf communities.

9921 Lake Louise 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
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