5 Bathroom Homes for Sale in Windermere, FL

5 Beds ⋅ 5 Baths ⋅ Aladar On Lake Butler SubDv. ⋅ 34786 Zip Code

Set beneath a canopy of majestic live oaks along the shores of the Butler Chain of Lakes, this timeless estate has been comprehensively reimagined to blend enduring architecture with modern luxury. Rebuilt with uncompromising attention to detail, every major component of the home has been replaced, including the roof, windows & doors, HVAC systems, water heaters, pool equipment, dock, and landscaping. The home is also complete with a professionally curated furnishing package by Wassers. A refined palette of natural materials and exceptional craftsmanship defines every space, including custom Italian cabinetry, a premium SKS appliance suite, Taj Mahal quartzite countertops and full-height backsplashes, imported Portuguese limestone extending seamlessly from the interior to the pool terrace, and wide-plank light oak flooring throughout the upper level. Arched impact-rated windows and doors frame picturesque lake views while filling the home with natural light. Privately positioned to maximize the home's spectacular waterfront setting, the primary suite serves as a luxurious retreat featuring its own fireplace, a spacious sitting area, and a private balcony overlooking the lake. The spa-inspired bath rivals those found in the world's finest resorts, showcasing a dramatic wet room with a hand-carved marble soaking tub, handcrafted marble vanity, exquisite limestone, and an extraordinary custom Italian wardrobe system. Designed for effortless indoor-outdoor living, the private courtyard is inspired by timeless Mediterranean estates and framed by graceful arcades, tapered stone columns, restored architectural lanterns, and custom lighting. A freeform pool and elevated spa create a tranquil focal point, while the fully equipped summer kitchen, multiple covered terraces, and expansive entertaining spaces provide an exceptional setting for lakeside gatherings. Beyond the courtyard, beautifully landscaped grounds lead to a restored private dock and covered boathouse with direct access to the renowned Butler Chain of Lakes. No detail was overlooked, with additional highlights including a private elevator, custom wine room, designer lighting, thoughtfully restored architectural details, and curated finishes that create a timeless residence balancing warmth, elegance, and seamless indoor-outdoor living. Situated on renowned 2nd Avenue just moments from downtown Windermere, this remarkable residence establishes an entirely new benchmark for luxury renovation. Meticulously executed, flawlessly designed, and unlike anything else available today, this is more than a home it is a legacy property destined to become one of Central Florida's most iconic waterfront estates.

800 W 2nd Avenue, Windermere

$5,500,000

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

$4,300,000

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

Experience refined luxury living in this extraordinary 5,004-square-foot garden villa estate nestled within Isleworth Golf & Country Club. This impeccably designed residence offers three expansive bedrooms, each with its own beautifully appointed en-suite bathroom, along with two elegant half baths to accommodate guests with ease. From the moment you arrive, the home’s striking Mediterranean-inspired architecture, circular tower entry, and meticulously landscaped grounds set the tone for the sophistication that awaits inside. Step through the grand entrance into interiors defined by soaring ceilings, abundant natural light, and exquisite craftsmanship at every turn. The gourmet kitchen serves as the heart of the home, showcasing custom cabinetry, premium Sub-Zero appliances, an oversized center island, and designer finishes that seamlessly blend form and function—perfect for both intimate family moments and upscale entertaining. Flowing effortlessly into the main living areas, the open-concept layout creates a warm yet refined atmosphere, enhanced by elegant lighting, stone flooring, and thoughtful architectural details throughout. Retreat to the luxurious primary suite, a private sanctuary featuring a spa-inspired bathroom with soaking tub, walk-in shower, dual vanities, and custom finishes that evoke a five-star resort experience. Each additional bedroom offers generous proportions, privacy, ensuring comfort and convenience for family members and guests alike. The inclusion of two half bathrooms further elevates the home’s functionality for entertaining. The outdoor living spaces are equally impressive, offering the perfect backdrop for enjoying Florida’s year-round sunshine. Whether hosting gatherings or savoring quiet evenings, the seamless indoor-outdoor connection enhances the overall living experience. Located within the exclusive Isleworth community—renowned for its world-class golf, privacy, and unparalleled lifestyle, this residence presents a rare opportunity to own a home that embodies elegance, comfort, and timeless design in one of Central Florida’s most sought-after communities while being close to shopping, world class dining and attractions.

9144 Isleworth Gardens Drive, Windermere

$4,190,000

3 Beds ⋅ 5 Baths ⋅ Gardens/Isleworth Un #2 SubDv. ⋅ 34786 Zip Code

Welcome to an exceptional opportunity within the gates of Isleworth, one of Central Florida’s most Acclaimed private golf communities. Perfectly positioned along a tranquil pond and scenic walking trail, this move-in ready residence offers a rare blend of privacy, natural beauty, and refined living in the heart of Windermere. Thoughtfully designed for both everyday comfort and elevated entertaining, the home features a versatile layout including a spacious primary suite, multiple guest bedrooms, an oversized office/playroom, and a dedicated theater room. Expansive living areas flow seamlessly, creating a warm yet Elegant atmosphere throughout—all easily accessible via a private elevator connecting the home’s levels. The home delivers a true turnkey experience with modern finishes and enhancements, including a fully upgraded Crestron smart home system providing whole-home audio and video distribution for effortless control and convenience. A standout feature is the exceptional garage capacity, offering four individual single-car garages two of which are equipped with vehicle lifts. The outdoor living experience is a true highlight, featuring a resort-style pool, generous covered entertaining spaces, and serene water views that create a peaceful and private backdrop. Whether enjoying quiet mornings by the water or hosting guests in the evening, the setting is both inviting and unforgettable. Located within Isleworth—renowned for its championship golf course, world-class amenities, and guard-gated privacy—residents enjoy an unparalleled lifestyle surrounded by the Butler Chain of Lakes and beautifully manicured grounds. This is a rare opportunity to own a fully updated, move-in ready home that seamlessly combines luxury, technology, and exceptional outdoor living in one of Orlando’s most sought-after communities.

4906 Aviva Garden Court, Windermere

$3,900,000

5 Beds ⋅ 5 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code

Pre-Construction. To be built. Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an exceptional opportunity to live in the Town of Windermere. Boasting approximately 85 feet of private frontage, The property captures sweeping views across Wauseon Bay. Permits have been approved including a 900 sf covered boat dock with lift. There are 2 primary suites, one on the 1st floor and one on the 2nd that open to a private balcony and patio respectively overlooking the water creating a serene retreat. All secondary bedrooms have lake views and balconies. Open floor plan with 2 story great room and massive windows throughout. Just moments from Windermere’s parks, tennis courts, farmers market, and private boat ramp, this home embodies the charm and lifestyle of lakefront living in one of Central Florida’s most desirable communities. ** Also listed as vacant land MLS S5147532 for $1,650,000

212 W 1st Avenue, Windermere

$3,900,000

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

$3,800,000

5 Beds ⋅ 5 Baths ⋅ Lake Butler Estates SubDv. ⋅ 34786 Zip Code

Welcome to this spectacular 5-bedroom, 5-bathroom custom home offering over 8,000 square feet of thoughtfully designed luxury living—spared no expense and crafted to perfection. Nestled on a sprawling acre-plus level lot, this residence redefines your Florida lifestyle with elegance and comfort. Step inside to discover more than 5,000 heated square feet filled with spacious rooms adorned with wide plank wood flooring, tongue & groove ceilings, and exposed timber beams that create a warm, inviting atmosphere. The impressive 1st floor primary suite features a huge closet offering ultimate storage and style. Guests will enjoy complete privacy in the generously sized 1st floor guest suite. The gourmet kitchen is a chef’s dream, having Natural Gas & equipped with high-end Thermador appliances and crowned by stunning quartz countertops—perfect for preparing meals or entertaining. Step outside to the fully appointed summer kitchen and enjoy the screen-enclosed swimming pool on your expansive wrap-around porch, enhanced by elegant stacked stone columns. Car enthusiasts and hobbyists will appreciate the oversized 42 x 30 - 4 car garage with 10-foot tall doors, providing ample space for all your toys and vehicles. Additional modern comforts include natural gas for efficiency and convenience throughout the home. Laundry Rooms on each Floor - Located on the most sought-after street in Windermere, this masterpiece offers privacy, style, and unparalleled craftsmanship. Truly, this is everyone’s dream home—ready for you to create lasting memories.

11539 Lake Butler Boulevard, Windermere

$3,699,000

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

Luxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf & Country Club. This exceptional Southpoint built residence boasts a captivating courtyard floor plan that provides breathtaking views from every corner of the home. The rear of the residence presents serene views of a picturesque pond and the tranquil Isleworth Gardens, while interior windows reveal a private courtyard featuring a glistening pool adorned with a cascading waterfall from the pergola. An expansive covered patio houses a summer kitchen, pool bath, and attached third bedroom accessed only from the courtyard. The heart of this home is a chef's dream, with a gourmet kitchen featuring top-of-the-line Wolf appliances, striking custom cabinetry, and an open design that seamlessly connects to the family room and dining areas. The grand primary suite offers a private sitting area overlooking the peaceful pond, double walk-in closets, and a spa-like bath complete with a Jacuzzi tub and an expansive walk-in shower. The third garage was converted into a gym with air conditioning and can be converted back to additional garage space. Garden villas offer carefree living with exterior grounds maintenance included in the separate monthly fees. The 600-acre Isleworth community, surrounding the Butler Chain of Lakes, is a residential enclave that sets the standard of excellence for Central Florida living. Isleworth Golf & Country Club, which is located within the community, is recognized as one of the Top 100 Platinum Clubs of the World offering separate membership opportunities that provide access to golf, tennis, fitness, Clubhouse dining and social events, swimming in the resort-style pool and sundeck, dock, and an abundance of activities. Enjoy a lifestyle defined by casual elegance in a setting that sets the standard for luxury living.

4812 Alexandra Garden Court, Windermere

$3,299,999

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

One or more photo(s) has been virtually staged. Traditional five-bedroom four and a half bath pool home with an open layout in Isleworth Golf & Country Club. Perfectly positioned on a quiet cul-de-sac along the 6th fairway with serene views of Lake Bessie. Offering 4,417 square feet of refined living space, this elegant two-story residence features two primary suites downstairs with private en-suites and large walk-in closets, and three bedrooms upstairs, with one of the upstairs bedrooms having a private ensuite. This home underwent a $400,000 update in 2019. Looking for an open layout with the kitchen overlooking the family room? Look no further! Updated ivory cabinetry, a Viking gas range with a French hood, double islands, and three ovens are ideal for daily meal prep and for hosting get-togethers with friends and family. There is ample seating, perfect for accommodating family and guests, with a formal dining room that flows into a family room with panoramic views overlooking the 6th tee. The family room shares a double-sided fireplace with the living room, which is open to the kitchen and has French doors to the covered, screened-in patio. Enjoy the Florida lifestyle with a large covered travertine patio, summer kitchen, heated pool, and an open-air travertine courtyard overlooking Lake Bessie at sunset. A three-car garage and expansive paver driveway provide ample parking. This is an ideal first home in Isleworth or as a vacation home. This is the perfect size and layout for real, everyday livable luxury in Isleworth. All offers will be considered. Schedule your private showing today.

5001 Latrobe Drive, Windermere

$3,250,000

4 Beds ⋅ 5 Baths ⋅ Bellaria SubDv. ⋅ 34786 Zip Code

BREATHTAKING WINDERMERE ESTATE!!! Situated on nearly 1.5 acres in the gated/guarded community of Bellaria, this custom built 4BR/4.5BA pool residence is the pinnacle of detail and design. Follow the long drive winding amongst the towering Italian Cypress to your expansive motor court and magnificent entry. Upon opening the massive custom double doors, you will see elegance, functionality, and breathtaking detail in every corner. Features include: over 5500SqFt of living area, soaring ceiling heights, top-notch molding and finish work, travertine floors, NEW carpet, NEW interior paint, massive kitchen with bar seating and island, walk-in pantry, game room with full bar and refrigeration, over 3000SqFt of rear pool and patio space with hot tub, outdoor bar/kitchen with vent fan and refrigeration, patio shower, multiple gas fireplaces, corner sliding pocket doors opening onto patio, NO REAR NEIGHBORS, gigantic privacy hedge, spacious primary suite with seating area and pool access, dual walk-in closets, exquisite primary bath with enormous soaking tub, spacious guest bedrooms and beautifully appointed guest bathrooms, sauna, three car garage with a hydraulic lift for a fourth vehicle, generous utility room, 22kw natural gas generator installed in 2021, office with built-ins and fireplace, fully equipped theatre with elevated seating, A BRAND NEW TILE ROOF, ample storage opportunities, and the list goes on!!! This is all just minutes from Winter Garden Village with easy access to SR429, downtown, and all the attractions!!! Schedule your showing and prepare to be amazed, this property is special. Call today!!!

13431 Bellaria Circle, Windermere

$3,200,000

5 Beds ⋅ 5 Baths ⋅ Lake Roper Pointe SubDv. ⋅ 34786 Zip Code

Extraordinary lake front opportunity in Windermere on 1.75 acres! PRIVATE GATES! NO HOA! SPECTACULAR LAKE VIEWS, PRIVACY, SPORTS COURT, AND GAZEBO ON LAKE ROPER - A WATER SKI FRIENDLY LAKE! A grand entryway leads you to magnificent two story ceilings and welcomes you into a separate living and family room. Beautiful 5-bedroom, 3/2-bathroom Mediterranean-style home with inlaid marble medallion foyer floor design, coffered ceilings, crown molding, and European-style ironwork boasts spectacular views of Lake Roper. The upstairs master bedroom has a beautiful view of Lake Roper. Master bath features an oversized tub and walk-in closet. This Grand Retreat has plenty of outdoor amenities including a basketball court, boat dock and boat lift. Heated family pool and spa. For all your family entertainment, a large open backyard leads to the dock with plenty of land. Stunning cedar and cypress trees surrender the property reminding you of FLORIDA living at its best. The ideal setting for privacy and serenity! Entertainment and fine shopping just minutes away. Close to major highways such as 429, 408 & the Turnpike. Easy access to the airport and Downtown Orlando yet secluded enough to give you a unique home in the heart of Windermere! Close to Windermere Prep school. Convenient to major highways, shops, restaurants, historic sites, major hospitals, and theme parks! Privacy awaits you! Schedule showing!

13161 Lake Butler Boulevard, Windermere

$3,200,000

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

Discover the effortless blend of luxury, privacy, and modern design in this lovely Gardens of Isleworth villa. Featuring timeless elegance, this beautiful four-bedroom, four-bathroom custom villa, where every detail has been thoughtfully curated to create a refined sanctuary for everyday living and entertaining. Beyond the stately arched main entry door lies a secluded courtyard oasis—a private retreat centered around a sparkling pool, serene waterfall feature, and generous lounging areas. Whether basking in the sun or relaxing beneath the stars, this outdoor haven sets the tone for the extraordinary spaces within. Designed to embrace indoor-outdoor living, the oversized courtyard welcomes you with a seamless open-plan layout connecting the pool, summer kitchen, and a charming guest cabana. Perfect for hosting or escaping, the cabana offers a private retreat for guests or a peaceful haven for the homeowner. Inside the main residence, a sense of contemporary sophistication flows through the light-filled kitchen, elegant dining room—highlighted by a statement chandelier—and the spacious grand room. French doors throughout invite the outdoors in, offering lush views from nearly every space and extending the living area to multiple porches and verandas. The living room, centered around a calming fireplace, is the perfect spot to unwind after a long day, while the spa and cascading waterfall nearby add to the sensory appeal. Retreat to the expansive master suite, where a private porch overlooks vibrant greenery, offering a peaceful start and end to each day. Additional property highlights include a cozy morning room, a dedicated office with custom Burl wood built-ins, and a series of intimate outdoor and indoor spaces designed to inspire comfort and connection.

4819 Alexandra Garden Court, Windermere

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