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$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
$3,200,000
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
$5,000,000
6 Beds ⋅ 9 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Welcome to 9721 Carillon Park Dr, Windermere, FL 34786, a stunning estate inside the guard-gated community of Keene’s Pointe. This extraordinary residence offers 8,305 square feet of luxury living space with refined architectural details, elegant wood beams, and designer finishes throughout. MAIN FEATURES: • Five bedrooms plus DETACHED GUEST HOUSE and OFFICE— providing exceptional space and privacy. • Expansive master suite with private sitting room, balcony overlooking the pond, dual closets, fireplace, and breakfast area. • Chef’s kitchen with a large island, seating area, top-of-the-line appliances, and a hidden walk-in pantry. • Bar and game room featuring real wood finishes and picturesque pond views. • Private GYM with SAUNA for health and relaxation. • Nine-seat HOME THEATER with plush carpet flooring for an immersive movie experience. • Four-car split garage (2/2), ELEVATOR, and downstairs laundry room. * Additional laundry closet inside the upstairs primary bedroom closet. OUTDOOR & LIFESTYLE: Seamlessly blending indoor and outdoor living, the open floor plan connects to a heated pool and spa area, surrounded by tranquil pond views and lush landscaping. The fully retractable sliding doors make it ideal for entertaining year-round. RECENT UPGRADES INCLUDE: • Five new AC units (2023) • Hurricane-impact windows and ADT smart security system • New pool equipment (2022) • Exterior repaint (2023) • Full surround-sound system throughout the home COMMUNITY & LOCATION: Located within the prestigious Keene’s Pointe community, residents can enjoy The Golden Bear Club, featuring a Jack Nicklaus Signature golf course, clubhouse, fitness center, and dining. Windermere is renowned for its lakes, top-rated schools, and luxury lifestyle just minutes from downtown Orlando and Disney attractions. This home represents the pinnacle of luxury living in Windermere, offering elegance, privacy, and resort-style amenities. Schedule your private tour today and experience the sophistication of this remarkable estate.

9721 Carillon Park Drive, Windermere
$3,400,000
4 Beds ⋅ 4 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below. Travertine floors flow seamlessly into the gourmet kitchen appointed with stainless steel appliances, a sunlit casual dining space, and direct access to both the intimate family room and an outdoor balcony for effortless indoor-outdoor living. Also on the primary level, the serene master suite offers a separate access to the terrace along with a luxuriously updated bath, and dual closets. Completing the primary level is a richly detailed wood-paneled office and a well-appointed laundry room, adding both warmth and function. The home’s thoughtful layout places the secondary bedrooms on the lower level, ensuring privacy and comfort for family or guests. Here, glass doors open to the multi-level terrace that gracefully surrounds the sparkling pool and spa, featuring generous deck space for year-round lounging and entertaining under the Florida sun. Offering an exceptional combination of timeless design, resort-inspired grounds, and a premier location within the gates, this remarkable residence is truly a sanctuary to call home.

9731 Chestnut Ridge Drive, 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
$975,000
4 Beds ⋅ 4 Baths ⋅ Lake Buynak Estates SubDv. ⋅ 34786 Zip Code
Now offered at an exceptional value, this 1.3-acre property in Lake Buynak Estates presents a rare opportunity to enjoy acreage, privacy and flexibility in one of Central Florida's most desirable locations. Located within the highly sought-after Windermere ZIP code, this 4-bedroom, 3.5-bath residence offers more than 2,600 square feet of living space with a thoughtfully designed split floor plan, two ensuite bedrooms, multiple screened porches and a charming wood-burning fireplace. Whether you're seeking a primary residence, multigenerational living arrangement, investment opportunity or future custom estate, this property provides a versatile foundation for a wide range of possibilities. Some improvements include: energy-efficient double-pane windows and a dual septic system with an expanded drain field which add long-term functionality and value. The expansive 1.3-acre homesite offers abundant room to expand, create outdoor living spaces, accommodate recreational vehicles, add a guest house or accessory dwelling (subject to county approval) or reimagine the property entirely. One of the property's most compelling advantages is its location. Enjoy the prestige and convenience of a Windermere-area address while benefiting from county jurisdiction, providing a level of flexibility that is increasingly difficult to find. Optional HOA membership offers added choice without mandatory fees or oversight. Surrounded by luxury homes near Lake Butler and just minutes from Disney, Universal, premier shopping, dining and major roadways, this property combines convenience with the space and freedom that acreage buyers desire. With large homesites becoming increasingly scarce in the Windermere area, this unique offering presents an exceptional opportunity to create something truly special. Experience the space, flexibility and potential for yourself—call to schedule your private tour today.

3629 Lake Buynak Road, Windermere
$809,000
4 Beds ⋅ 4 Baths ⋅ Glenmuir SubDv. ⋅ 34786 Zip Code
Welcome to 6631 Crestmont Glen Lane, a beautifully maintained executive home in the gated community of Glenmuir. Set on a large and spacious, landscaped lot, this 4-bedroom, 3.5-bath residence offers an ideal blend of space, comfort, and everyday functionality. Step inside to soaring ceilings, abundant natural light, and an open-concept layout designed for both entertaining and relaxed living. The gourmet kitchen features granite countertops, ample cabinetry, and a breakfast nook that flows seamlessly into the inviting family room. Enjoy year-round Florida living in your private screened lanai—perfect for quiet mornings or hosting guests. The primary suite offers a true retreat with a spa-like bath, walk-in closets, and direct access to the outdoor living space. Residents of Glenmuir enjoy a peaceful, tree-lined setting with a private park, playground, and walking paths—just minutes from top-rated schools, golf, dining, shopping, and world-renowned attractions including Walt Disney World.

6631 Crestmont Glen Lane, Windermere
$900,000
Reserve At Windermere SubDv. ⋅ 34786 Zip Code
Final Opportunity – Last Lot Available in The Reserve at Windermere! Build your dream home in the exclusive community of The Reserve at Windermere with acclaimed custom builder Element Home Builders. This final remaining homesite of 8 offers a rare opportunity to craft a one-of-a-kind luxury residence in one of Central Florida’s most prestigious neighborhoods. Surrounded by the natural beauty of the Butler Chain of Lakes and the charm of Windermere’s quaint, Southern-style downtown, this premium lot provides the ideal setting for elegant, personalized living. Element Home Builders is renowned for creating custom homes where beauty, innovation, and functionality come together seamlessly. Each residence is thoughtfully tailored to reflect the unique lifestyle, dreams, and needs of its owners. From lush landscaping to distinctive architectural design, every detail showcases quality craftsmanship, comfort, and timeless value. Residents enjoy convenient access to top-rated schools, championship golf courses, boutique shopping, and lakeside recreation—all within a peaceful, private setting. Don’t miss your chance to be part of this exceptional community. This is the last lot available—a truly rare offering to design and build your custom home with one of the area’s most respected builders. Contact us today for more information and to begin planning your dream home in The Reserve at Windermere.

2504 Windermere Reserve Court, Windermere
$1,630,000
3 Beds ⋅ 2 Baths ⋅ Lake Butler Estates SubDv. ⋅ 34786 Zip Code
Nestled on one of Windermere’s most desirable streets, this charming home offers a rare opportunity to enjoy small-town living on a beautifully wooded one-acre lot. The property features a welcoming covered entry with double doors that open into a light-filled foyer and spacious family room with soaring vaulted ceilings and a cozy wood-burning fireplace. The open-concept kitchen includes a large center island and ample space to prepare gourmet meals. Enjoy the Florida lifestyle year-round from the screened-in lanai overlooking the serene, tree-lined backyard. Additional highlights include a side-entry 2-car garage and a detached private workshop or storage building with electricity—perfect for hobbies, home projects, or extra storage. As a resident of the Town of Windermere, you'll enjoy exclusive access to two private boat ramps on the Butler Chain of Lakes, six lighted tennis courts, multiple parks and playgrounds, frisbee golf, and scenic lakefront beaches. The town also hosts vibrant community events including weekly farmers markets, monthly food truck nights, and seasonal festivals. Zoned for top-rated schools and just minutes from world-class golf, premier shopping and dining, hospitals, and Central Florida’s renowned theme parks, this home offers the best of both serenity and convenience. Schedule your private showing today and discover the charm and lifestyle that only Windermere can offer!

11923 Lake Butler Boulevard, Windermere
$1,575,000
5 Beds ⋅ 3 Baths ⋅ Farms SubDv. ⋅ 34786 Zip Code
Welcome to a rare opportunity in one of Windermere’s most exquisite communities where luxury living meets farmland feel. The Farms community consists of 12 properties of one or more acres each. The community also has a horse stable that homeowners can keep horses. Nestled at the end of a cul-de-sac, this gorgeous estate offers sophistication, premium finishes and a quaint feeling throughout.As you step up to the front entrance, you are greeted by beautiful water fountain. Once inside your living room with a wood burning fireplace welcomes you to your living room on the right. Continuing your way into the house, your inviting family room awaits with an eat in kitchen island completing the scene. The gourmet kitchen is a chef’s dream, outfitted with top-of-the-line appliances and plentiful cabinetry. Retreat to the oversized owner’s suite with double walk-in closets, a luxurious master bathroom and a private sitting area overlooking the pool area. Enjoy an enclosed pool area and expansive backyard. There is also a second master suite with private bathroom and walk-in closet. At the opposite end of the family room there is a hallway leading to another full bathroom and three additional bedrooms. Located just minutes from championship golf courses, downtown Windermere, Winter Garden Village, and top-rated schools, this home offers the perfect blend of tranquility and convenience. Don’t wait, schedule your showing today!

13124 Filly Court, Windermere
$385,000
3 Beds ⋅ 3 Baths ⋅ Lake Sawyer South Ph 3 SubDv. ⋅ 34786 Zip Code
Welcome to this beautifully renovated 3-bedroom, 2.5-bathroom townhouse in Berkshire Park, a highly desirable community in the heart of Windermere, Florida. With 1,644 sq ft of meticulously maintained living space, this move-in ready home is perfect for anyone seeking comfort, style, and convenience—just minutes from Walt Disney World, top-rated schools, and all that Central Florida has to offer. Step inside and feel the care of the original owners, with brand-new carpet, fresh interior paint, new blinds, and professionally cleaned tile and grout throughout. The kitchen features modern appliances—including a refrigerator, dishwasher, and microwave—all less than two years old—plus a new faucet, garbage disposal, and updated fixtures for added convenience. The downstairs bathroom has been completely refreshed with a new vanity, toilet, and faucet, while the upstairs bathrooms feature new fixtures and faucets, and the primary bathroom includes newly upgraded exhaust fans for added comfort. The laundry room is upgraded for efficiency, with a high-performance exhaust fan, updated faucets, LED lighting, and thoughtful details that simplify daily routines. The garage is a standout feature, offering a new subpanel and GFCI-protected breakers, additional outlets, LED lighting, ceiling fan, and its very own AC unit—perfect for a home gym, workshop, or extra storage. Smart home touches include a Ring doorbell, Govee under-cabinet LED lighting, and an Aladdin smart garage door opener with keypad. Downstairs features sleek LED wafer lighting and dual ceiling fans in the living room for a stylish and energy-efficient vibe. Enjoy quiet evenings in your rear-facing backyard with peaceful conservation views, and hear the nightly Disney fireworks, and the nostalgic sounds of the Disney World Railroad —all from the comfort of home. Berkshire Park is part of an “A”-rated school district and known for its scenic walking trails, community pool, and proximity to everything—theme parks, shopping, dining, and major highways. This home is a rare find in one of Central Florida’s most coveted neighborhoods.

12930 Vennetta Way, Windermere
$3,999,999
5 Beds ⋅ 8 Baths ⋅ Metcalf Park Rep SubDv. ⋅ 34786 Zip Code
Price Adjustment! Lakefront Living in the Heart of Windermere – A Rare Opportunity for Multigenerational Luxury Situated along the tranquil, open waters of Wauseon Bay—part of the world-renowned Butler Chain of Lakes—this expansive estate on prestigious Lake Butler Boulevard is more than just a home: it’s a lifestyle destination, purposefully designed to inspire connection, relaxation, and recreation. With its flexible layout, multiple living spaces, and resort-style amenities, it offers the perfect setup for multigenerational living without compromise. From the moment you arrive, you’ll sense the pride and care that has gone into crafting this one-of-a-kind residence. Meticulously expanded and improved over decades, the home features five generously sized bedroom suites, including a luxurious owner’s retreat with fine finishes and boutique-style custom closets. Whether accommodating extended family, live-in help, or guests, everyone enjoys their own private space. For culinary enthusiasts and entertainers alike, two full gourmet kitchens—one upstairs and one downstairs—provide unmatched convenience and versatility. Host formal holiday gatherings, casual poolside brunches, or multiple family dinners with ease. Both kitchens are thoughtfully appointed with high-end appliances and stylish finishes that reflect the home’s refined character. The garage is a masterpiece in itself, built to accommodate your most ambitious lifestyle. Store your 45-foot Prevost RV with full hookups—sewer, water, cable, and power—or tuck away your 50-foot center console, classic cars, or workshop equipment in the four additional bays. Whether you’re an adventurer, collector, or weekend explorer, this space is a rare find in residential real estate. Outdoor living takes center stage. A private beach invites sunbathing and quiet reflection by day, while the oversized gas fire pit becomes a natural gathering point at night for family, friends, and unforgettable moments. The resort-style pool area includes a gas fireplace and summer kitchen, perfect for year-round entertaining. Speakers are integrated throughout both indoor and outdoor spaces, creating a seamless atmosphere of leisure and luxury. Inside, modern comforts abound: three zoned A/C units with Nest thermostats, two tankless gas water heaters, and a finished storage area above the garage offer functionality and peace of mind. Located in the highly coveted Town of Windermere, residents here enjoy more than just natural beauty—they cherish a community rooted in tradition, charm, and quality of life. Walk to the Farmer’s Market, explore local parks, or attend beloved events like food truck nights, craft festivals, and holiday parades. The town library, family-owned shops, and quaint cafes further enhance the walkable lifestyle. Minutes away, you’ll find world-class golf, upscale shopping, fine dining, and easy access to highways leading to Orlando’s top attractions, excellent schools, and international airport. As an added value, completed architectural plans by Dirk Arace of Arace Designs are available, offering an exciting opportunity to customize or expand the estate with one of Central Florida’s most respected designers. Whether you’re seeking a private lakeside sanctuary, a home for generations, or a place to live your dream by the water, this Windermere gem is truly extraordinary. Listing agent is owner of the property.

11002 Lake Butler Boulevard, Windermere
$17,250,000
7 Beds ⋅ 9 Baths ⋅ Metcalf Park Rep SubDv. ⋅ 34786 Zip Code
Presenting Sunset Isle: an iconic waterfront estate compound capturing timeless elegance on Windermere’s largest and most prestigious Lake Butler, offering captivating unobstructed views from its 700 feet of lake frontage, a private island with moat and drawbridge, sandy beaches, two story double residence guest house, and a majestic and stunning grand mansion with additional guest retreat, all spanning more than 14,444 square feet of living space and 11 bedrooms across both residences. Welcome to this one-of-a-kind haven of privacy and prominence showcasing the best of Central Florida living. Set on a rare 3.75 acres commanding enviable views on the northern shore of Lake Butler, every detail has been thoughtfully designed to celebrate both refinement and tranquility. The impressive palatial main residence boasts 10,649 square feet of living space with 6 bedrooms plus a one-bedroom guest retreat and an array of curated spaces. The Spanish Eclectic interior fuses classic craftsmanship with modern sophistication, creating an inviting and awe-inspiring escape from the ordinary. On entrance be greeted by sweeping floor to ceiling windows to allow breathtaking water vistas, double-sided gas fireplace, a grand colonnade hallway, and architectural details throughout. The gourmet chef’s kitchen features top of the line appliances, gas range with multiple burners, ovens, island with second sink, and walk-in pantry. A sports bar games room and showstopping home theater provide an abundance of entertaining options. Other notable amenities include a Castilian wine cellar, bay windows, two wet bars, private salon, elevator, gym, steam room and sauna. Outdoors, a generous summer kitchen with automatic roller screens provide an outdoor oasis for al fresco dining, cooking, or relaxing. The zero-entry infinity pool and vast resort decking provide a breathtaking vantage point for panoramic views of Lake Butler’s radiant sunsets, while the shaded Zen garden and white sandy beach offer a tranquil retreat for quiet reflection. With many distinct outdoor venues, serenity is never far away. The estate’s private island, accessed by an electric drawbridge, and a boat ramp provide unmatched exclusivity to Lake Butler and the world-famous Butler Chain of Lakes. The two-story detached guest house offers 3,795 sq feet of living space across two, 2-bedroom apartment homes, each with kitchens, laundry rooms, an elevator, and attached two-car garage. Built for a large multi-generational family, guest quarters, or on-site caretakers, the possibilities are endless. Truly a picture-perfect unmistakable showplace offering the very best for the most discriminating buyer.

11900 Lake Butler Boulevard, Windermere
$749,000
6 Beds ⋅ 6 Baths ⋅ Belmere Village G2 48 65 SubDv. ⋅ 34786 Zip Code
This stunning 6-bedroom Park Square home in Windermere combines elegance and functionality. The first floor features formal living and dining areas, a gourmet kitchen with stainless steel appliances and a gas stove, and a custom-designed patio garden with a water fountain and remote-controlled fans. Upstairs, enjoy luxury vinyl flooring, an oversized master suite with a walk-in closet, and spacious additional bedrooms. Located in the gated Belmere Village, residents benefit from low HOA fees and exceptional amenities, including a clubhouse, fitness center, resort-style pool, playground, basketball, volleyball courts and newly added pickleball courts. Conveniently near major highways and Orlando's theme parks, this home offers the perfect blend of luxury and location. Don't miss this opportunity—schedule a showing today!

11410 Rapallo Lane, Windermere
$7,795,000
7 Beds ⋅ 10 Baths ⋅ Keenes Pointe Unit 03 46/104 SubDv. ⋅ 34786 Zip Code
PRICE Improvenent!! Perfectly sited on pristine Lake Tibet in Keene's Pointe Country Club, this stunning lakefront Stonebridge custom home has been completely updated. The modern exterior color brightens the façade and creates a unique transitional style. The wrought Brand New oversized GLASS DOOR add a refined entry. Opening to the two-story formal areas featuring timeless elements of newly installed WOOD FLOORING, elegant ceiling details, clerestory windows, and expansive lake views set a modern tone. At the center of the home, the kitchen is a chef's dream; wood flooring and a massive working island, state-of-the-art appliances combine function and beauty with double ovens, exotic quartz, stunning glazed custom cabinetry, and a huge walk-in pantry. The gourmet kitchen opens naturally to the family gathering areas, complete with sparkling lake views.Just off the family area, the game room is finished with a beautiful area. The state-of-the-art home theatre is located just off the game room. Entertain outdoors in true Florida style; the outdoor gourmet area was added in 2019, including a large bbq grill area, massive dining/working island, wine cooler, XL Fridge as well as a pizza oven. The free-form pool, heated spa, and boat dock with lift. The master suite is private with huge master closet and beautifully finished master bath. All secondary bedrooms are ensuite. All baths have been updated. The entire home has been freshly painted and all carpet has been replaced. The detached guest house is great for extended family.

9343 Tibet Pointe Circle, Windermere
$2,950,000
34786 Zip Code
Back On The Market! Huge Price Improvement! Approx 20 Acres in a very sought after area of Horizon West by many builders. This land is undeveloped and ready for you to put your stamp on it. Just minutes from Disney. Location, Location, Location!!!

7545 Ficquette Road, Windermere