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$3,599,000
5 Beds ⋅ 7 Baths ⋅ Casabella Ph 2 SubDv. ⋅ 34786 Zip Code
EXCEPTIONAL LAKEFRONT LUXURY ESTATE IN CASABELLA AT WINDERMERE Discover an extraordinary luxury residence in the prestigious gated community of Casabella at Windermere, where elegant architecture, exceptional outdoor living, and one of the community’s most desirable lots come together. The true highlight of this property is its exceptional waterfront setting. The lake beautifully surrounds the rear of the home, pool, and outdoor living areas, creating a rare sense of privacy and tranquility. From the expansive covered lanai and upper-level balcony, enjoy breathtaking water views and a peaceful backdrop that makes this property truly special. Featuring two spacious levels and soaring ceilings, this magnificent home offers approximately 5,073 square feet of luxurious living space with 5 bedrooms, all featuring private en-suite bathrooms and walk-in closets. The primary suite is conveniently located on the first floor and offers a spa-inspired bathroom, large windows, and a serene connection to the outdoor surroundings. The gourmet kitchen combines functionality and elegance with modern wood cabinetry, stainless steel appliances, and generous counter space, creating an inviting space for both everyday living and entertaining. The open living areas feature impressive proportions and abundant natural light, perfectly complementing the home's sophisticated Mediterranean-inspired architecture. Step outside to your private resort-style retreat. The expansive outdoor living area features a private pool, heated spa, and spacious gourmet summer kitchen, creating the perfect setting for entertaining guests or enjoying relaxing evenings overlooking the lake. From the elegant façade and impressive two-story design to the spectacular waterfront setting and exceptional outdoor living spaces, this residence offers a rare combination of luxury, privacy, and breathtaking views. Located in Casabella at Windermere, a prestigious gated community known for its spacious homesites and elegant residences, the property is conveniently located near premier shopping, dining, top-rated schools, major roadways, and Orlando’s world-famous attractions. A truly remarkable opportunity to own a one-of-a-kind luxury estate in one of Windermere’s most desirable communities.

3986 Isabella Circle, Windermere
$899,999
3 Beds ⋅ 2 Baths ⋅ Manors At Butler Bay Ph 01 SubDv. ⋅ 34786 Zip Code
Incredible Opportunity to own a pool home with a huge lot in a fantastic neighborhood * Good Floorplan * Close to Everything * Home has 7 Rooms * Separate Office * Formal Living Room * 3 Bedrooms * Breakfast Nook with Open Kitchen * Formal Dining Room * Family or Great Room * Pool Bath * Vaulted Ceilings * Inside Laundry * Screened & Covered Pool with Large Deck * Formal Dining Room * Large Family Room with Fireplace * Must see to fully appreciate the home

2630 Stanton Hall Court, Windermere
$584,900
4 Beds ⋅ 2 Baths ⋅ Silver Woods Ph 05 SubDv. ⋅ 34786 Zip Code
Windermere Gem: Updated & Move-In Ready! Discover the perfect blend of modern luxury and prime location in the highly sought-after Windermere area. This beautifully updated home offers an incredible opportunity for homeowners and investors alike, situated just minutes from top-rated schools, premier shopping centers, and fitness facilities. This property has been meticulously maintained, featuring an extensive list of recent high-value upgrades: Recent Upgrades & Features: Brand New Kitchen (March 2026): Fully updated with modern flooring, custom cabinetry, and premium appliances. Comprehensive Pool Refresh (2026): Newly resurfaced pool and deck (Feb 2026), plus a brand-new pool pump and filter (March 2026). New Roof: Installed August 2024. Septic System: Installed January 2018. AC System: Installed 2017. Full House Re-pipe: Completed August 2016. Additional Features: Pool rescreened (2019) and nearby access to community tennis courts. Whether you're looking for a stylish family residence or a high-performing investment property, this home is truly move-in ready.

9011 Chapman Oak Court, Windermere
$1,500,000
4 Beds ⋅ 5 Baths ⋅ Waterstone SubDv. ⋅ 34786 Zip Code
WWaterstone is guard-gated, well-established, and home to something most neighborhoods can't match: a private pedestrian gate with direct access to Windermere Preparatory School, ranked the #1 private K–12 in Orange County. For families, that detail alone tends to end the search. The home itself is a custom Silliman Homes courtyard design, single-story, built with the kind of attention to detail that holds up over time. Wrought-iron courtyard gates and a solid wood entry door set the tone before you ever step inside. Beamed ceilings, hardwood floors throughout the main living areas, custom built-ins, and a gas fireplace. The separate dining room has detailed ceiling work that elevates it beyond most you'll see at this price point. The kitchen delivers at this level. Five-burner gas cooktop, built-in oven, a proper working island, exotic granite countertops, custom cabinetry, and a walk-in pantry that actually fits a household. It opens to the family room with stone accents and a wall of windows looking out to the pool. Good flow, good light. The primary suite is privately tucked away with an oversized walk-in closet and a bath with dual granite vanities, garden tub, and walk-in shower. Four bedrooms, four and a half baths in total, every bedroom with its own private full bath. Secondary bedrooms are generously sized and thoughtfully positioned relative to the rest of the home. Outside: a heat pump heated pool and spa, a full summer kitchen with built-in grill and refrigerator, and a gazebo with its own gas fireplace. Two gas fireplaces, one in the living room and one in the gazebo, mean the ambiance follows you inside or out. The kind of setup that actually gets used. Two whole-house gas water heaters and smart home features keep everything running effortlessly year-round. 24-hour guard-gated security, five minutes to Windermere's dining, shopping, and golf, and in the heart of Central Florida's most iconic attractions. On clear evenings, you don't even have to leave. The Magic Kingdom fireworks are visible right from the backyard. One gate leads to the best school in the area. The other view is Disney. Not many addresses can say both.

11821 Waterstone Loop Drive, Windermere
$385,000
3 Beds ⋅ 3 Baths ⋅ Summerport Ph 03 SubDv. ⋅ 34786 Zip Code
SUMMERPORT TOWNHOME IN A GREAT LOCATION. Back to the Market, Buyer's financing fell through- their loss is your gain. Brand new A/C unit for buyers' peace of mind. Beautiful 3-bedroom, 2.5 - bathroom townhome. SUMMERPORT Community in Windermere offers Residents to enjoy fantastic amenities, including a clubhouse, resort -style swimming pool, tennis and volleyball courts, basketball court, fitness center, multiple playgrounds and green spaces to enjoy nature - plus lake access with a sandy beach. The neighborhood offers a convenient nearby plaza with restaurants, an ice cream shop, a veterinary clinic, Publix, a pizza place, a coffee shop, and Aldi Supermarket. Located in a Top-Rated district, featuring Keene Crossing Elementary School, Bridgewater Middle School and Windermere High School, just a mile away. Perfect situated just 7 minutes from Historic Downtown Winter Garden Village, with easy access to Highway 429, Disney Parks, Orlando Airport, and Downtown Orlando. Easy to show. schedule your private tour today and see how can make your dreams come true.

13808 Ancilla Boulevard, Windermere
$700,000
5 Beds ⋅ 4 Baths ⋅ Westside Village SubDv. ⋅ 34786 Zip Code
5 BEDROOM energy-efficient home ready NOW! Enjoy the pond view in the rear of the Melville home. The home features a master suite on the main level with a spacious walk-in closet, study, huge game room, 2 sets of jack and jill walk-in closets,and more! Located in the highly desirable heart of Windermere, Westside Village is only minutes from access to multiple lakes, dining, shopping, and A-rated schools. Westside Village will also have fantastic community amenities including a resort-style pool, clubhouse, and playground. Known for our energy saving features, our homes help you live a healthier and quieter lifestyle, while saving you thousands of dollars on utility bills.

12779 Westside Village Loop, Windermere
$1,450,000
4 Beds ⋅ 4 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Waterfront Luxury in Keene’s Pointe – Fully Renovated & Priced to Move Welcome to resort-style living in one of Windermere’s most exclusive 24/7 guard-gated communities. Set on a quiet cul-de-sac with peaceful lake views, this bold, fully renovated masterpiece in Keene’s Pointe blends timeless elegance with modern design—and it’s move-in ready. Inside, you’ll find high-end imported cabinetry, a chef’s kitchen with an oversized quartz island, Italian gas range, wine cooler, and designer lighting throughout. Remote-controlled shades open to reveal sweeping lake views that frame the open-concept living space. Outside, entertain or unwind in your private paradise: a jetted spa, resort-style pool, covered lanai, and dramatic waterfall fire bowl—all set against a shimmering lake backdrop. Additional features include marble-tiled bathrooms, a newer roof (2021), and meticulously selected upgrades in every room. This home offers more than beauty—it’s part of a lifestyle. Keene’s Pointe features private lake access, a Jack Nicklaus golf course, boat/RV storage, and optional Golden Bear Club membership with tennis, fitness, dining, and more. Plus, you’re minutes from A-rated schools, upscale dining, and boutique shopping. Opportunities like this are rare—schedule your private showing today before it’s gone. "All Furniture excluded from sale; negotiable separately!!

8430 Woburn Court, Windermere
$356,000
3 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code
Welcome to your dream condo in the heart of Windermere! This stunning 3 bedroom, 2 bath unit boasts an open floor plan that is perfect for entertaining and comfortable living. The current owners updated the unit by adding Luxury vinyl flooring, a new garbage disposal, and fresh interior paint. You'll stay cool and comfortable year round with a new A/C unit installed in 2022. Once you enter, you will see the custom "mudroom" that was recently added, perfect for storing shoes, coats and bags, keeping your home clutter-free. The kitchen boasts brand new appliances, including a range, microwave, and garbage disposal. The primary bedroom features a custom closet, ensuring plenty of storage space for all your belongings .Additionally, new ceiling fans throughout the condo help keep the air circulation and energy costs down. Located just minutes from the area's top theme parks and Windermere's amenities, you'll never run out of things to do. Plus, with easy access to highways, commuting is a breeze. Relax and unwind on your enclosed patio, or take advantage of elevator access for added convienence. With valet trash service, you'll never have to worry about taking out the garbage again. In addition to the amazing features of the condo itself, the community offers even more amenities to enjoy. Take a dip in the community pool, perfect for relaxing on hot summer days. The gated entrance provides added security and peace of mind, while the volleyball court is ideal for friendly competitions and staying active. With all of these fantastic amenities, plus the convenience of the condo's location and upgrades, this is truly a place you'll be proud to call home. Don't miss out on the opportunity to live the Windermere lifestyle to its fullest. Most furniture items are available for purchase, please inquire. Schedule your showing today!

8180 Boat Hook Loop Unit 205, Windermere
$430,500
3 Beds ⋅ 3 Baths ⋅ Edens Hammock SubDv. ⋅ 34786 Zip Code
This corner unit townhouse located in the active community of Summerport has 3 bedrooms, 2.5 bathrooms, and a loft. It is completely remodeled and upgraded with ceramic tile floors downstairs and laminate flooring upstairs. The interior of the home was painted and the downstairs includes a spacious dining/living room, a fully equipped stainless steel kitchen with a quartz countertop island, a half-bathroom, and one of the master suites. A waterproof laminated staircase leads you upstairs to the open loft, a second master suite, and another bedroom. There is a covered porch at the front of the unit and in the back/side with a courtyard area. The back alley gives access to a paved path to the garage with a fenced side yard. The townhome is walking distance of all of the community amenities which includes the clubhouse, community pool, tennis and basketball courts, fitness center, dog park, fishing pier, pizzaria, ice cream shop, salon, and animal clinic. The A/C was replaced in 2018 and the roof was replaced in 2022. There is a HVAC UV/Elec filtration system and water softener system. It is zoned for the best schools in the area including the new Windermere High School. Conveniently located off 535 and 429 with quick access to shopping and dining at the Winter Garden Village, downtown Winter Garden, and Disney Springs. ALL OFFERS WILL BE ACCEPTED UNTIL 8:00 PM 09/11/23.

14059 Ancilla Boulevard, Windermere