Windermere Real Estate

Welcome to Windermere, a picturesque subdivision nestled in the heart of Florida’s enchanting landscape. Known for its serene atmosphere and stunning natural beauty, Windermere offers an idyllic retreat for families, professionals, and retirees alike. This charming community is situated just a stone's throw away from the bustling city of Orlando, providing residents with the perfect blend of tranquility and accessibility.

Windermere is renowned for its luxurious homes, many of which boast breathtaking views of pristine lakes and lush green spaces. The architectural styles vary from modern masterpieces to classic Mediterranean designs, ensuring that there’s something to suit every taste. The neighborhood is characterized by tree-lined streets, manicured lawns, and a strong sense of community, making it a welcoming place to call home.

Residents of Windermere enjoy a wealth of amenities, including top-rated schools, boutique shopping, and delightful dining options. The nearby Windermere Town Square is a hub of activity, featuring charming cafes and local shops that create a vibrant community atmosphere. For outdoor enthusiasts, the area is surrounded by beautiful parks and recreational opportunities, including boating, fishing, and hiking along the scenic trails.

Windermere is not just a place to live; it’s a lifestyle. With its friendly neighbors, family-oriented events, and a commitment to preserving the natural beauty of the area, this subdivision truly embodies the essence of Florida living. Whether you’re looking to settle down or invest in a vacation home, Windermere offers a unique opportunity to embrace the Florida sunshine in a welcoming and vibrant community. Come discover your dream home in Windermere today!

Newest Listings in Windermere

$7,500,000

6 Beds ⋅ 8 Baths ⋅ O6426995 MLS

Welcome to an extraordinary lakefront estate on the prestigious shores of Lake Butler with 182 feet of water frontage, where timeless architecture, exceptional craftsmanship, and resort-style amenities come together in one of Windermere's most coveted locations. Built in 2024 and spanning approximately 6,900 square feet under air (10,400 total square feet), this custom residence sits on a rare one-acre homesite along the iconic, paved Second Avenue, renowned for its festive holiday displays, spectacular sunsets, and unmatched charm. Designed for both everyday luxury and grand scale entertaining, this 6 bedroom, 7.5 bathroom home offers en-suite bedrooms with walk-in closets, including a private first floor guest suite. The stunning primary retreat features a spa inspired bathroom and a private balcony overlooking the lake, creating the perfect setting to enjoy breathtaking sunsets and nightly Disney fireworks. The heart of the home is a designer chef's kitchen featuring exquisite Cristallo countertops, premium Miele appliances, and seamless flow into the expansive living and entertaining spaces. A dramatic floating wood staircase with a striking stone accent wall serves as an architectural centerpiece, while an elevator provides effortless access to every level. Additional highlights include a custom onyx sink in the powder bath, elegant 8-foot solid wood core doors throughout, motorized blinds, and laundry rooms on both the first and second floors. Step outside to experience a true private resort. The heated infinity edge saltwater pool features a unique acrylic glass viewing wall, allowing swimmers to enjoy underwater lake views unlike anything else. The expansive summer kitchen is equipped with two oversized Big Green Egg grills, a hibachi grill, and generous entertaining areas perfect for hosting unforgettable gatherings. A spacious game room with a full bar, dedicated fitness room, and professionally designed dog run complete the home's exceptional lifestyle offerings. Boating enthusiasts will appreciate the impressive two story private dock with multiple lifts, providing direct access to the famed Butler Chain of Lakes. Car collectors will love the oversized four car garage with an automotive lift, an additional golf cart garage, and an exceptionally long driveway offering abundant guest parking, a rare luxury on Second Avenue. Constructed with impact-rated windows and doors, spray foam insulation, and energy-efficient systems, this home was thoughtfully built to provide superior comfort, security, and efficiency. Combining impeccable design, world-class amenities, spectacular waterfront views, and one of the finest addresses in Central Florida, this remarkable Lake Butler estate represents a rare opportunity to own a nearly new custom home in one of Windermere's most sought after neighborhoods. Be sure to click on the virtual tour links.

724 W 2nd Avenue, Windermere

Listing courtesy of THE SIMON SIMAAN GROUP. 407-558-1396

$290,000

3 Beds ⋅ 2 Baths ⋅ 2154180 MLS

**NEW APPLIANCES**LARGE LOT**PRIME LOCATION**NEW ROOF** Nestled in the highly coveted area of Mandarin, this 3 bed/2 bath home sits in a great neighborhood with NO HOA OR CDD! Inside, a gorgeous living room boasts a stone FIREPLACE and a vaulted ceiling, while the kitchen features a double sink, a breakfast bar, and NEW APPLIANCES. The spacious primary suite offers a large walk-in closet. Once the builder's model home, the garage retains its previous climate-controlled setup, making it incredibly easy to ADD over 400 sqft of bonus space that can be an extra bedroom, or whatever you need. Outside, enjoy a FENCED BACKYARD, a huge side yard with fruit trees, a storage shed, and plenty of room for your RV or boat. Commuting, shopping, and dining are a breeze with easy access to I-295! Plus, the listing price perfectly justifies the need for new flooring, especially since the roof and HVAC were both replaced within the last 5 years. Don't miss this opportunity!

4208 Queensway Drive, Jacksonville

Courtesy of CHAD AND SANDY REAL ESTATE GROUP

Listing courtesy of CHAD AND SANDY REAL ESTATE GROUP.

Listing courtesy of CHAD NEUMANN from CHAD AND SANDY REAL ESTATE GROUP.

$380,000

4 Beds ⋅ 3 Baths ⋅ 2151223 MLS

Nestled in the heart of Mandarin, this pool home features durable tile and vinyl flooring an expansive four-bedroom, three-bathroom layout. High ceilings flood the open-concept floor plan with natural light, seamlessly connecting the dining, living, and family spaces, which center around a cozy fireplace. Private backyard oasis complete with a large swimming pool, a low-maintenance paved seating area, and a jacuzzi that was freshly resurfaced in June 2024. Converted garage now serves as a spacious fourth bedroom with its own full bathroom. No HOA, New A/C and water heater (both installed June 2024) and Roof replaced in February 2021. Tour today!

10720 Knottingby Drive, Jacksonville

Courtesy of REDFIN CORPORATION

Listing courtesy of REDFIN CORPORATION.

Listing courtesy of HEATHER KRUAYAI from REDFIN CORPORATION.

$360,000

4 Beds ⋅ 2 Baths ⋅ 2139494 MLS

Welcome to this beautifully maintained home in the highly desirable Mandarin area of Jacksonville! Featuring soaring high ceilings and an open-concept floor plan, this property offers a bright, spacious, and inviting atmosphere perfect for both everyday living and entertaining. The remodeled kitchen is a true highlight, offering modern finishes and a seamless flow into the main living areas. Recent updates provide peace of mind, including a water heater just 2 years old, HVAC replaced in 2018, floors updated 3 years ago, and a roof approximately 8 years old. Fresh interior paint gives the home a clean, move-in-ready feel. Located in one of Jacksonville's most sought-after communities, this home combines comfort, style, and convenience with close proximity to shopping, dining, parks, and top commuter routes.

4235 Queensway Drive, Jacksonville

Courtesy of EXP REALTY LLC

Listing courtesy of EXP REALTY LLC.

Listing courtesy of DANIELLA OTTONE from EXP REALTY LLC.

$2,175,000

6 Beds ⋅ 6 Baths ⋅ O6368185 MLS

Architecturally refined and thoughtfully designed, this custom built Transitional Craftsman residence blends timeless craftsmanship with modern luxury in the heart of Historic Olde Windermere with excellent walkability. Rich wood detailing, exposed pecky cypress beams, and dramatic stonework create warmth and depth throughout. The chef’s kitchen is both functional and sculptural, featuring a stone-framed cooking alcove, premium JennAir® appliances, custom ceiling-height cabinetry, and a walk-in pantry designed for serious cooks and entertainers. The home offers six bedrooms and six bathrooms, with two main-level owner’s suites providing exceptional functionality and privacy. Multiple living spaces are anchored by a striking floor-to-ceiling stone fireplace and beautiful library with rolling ladder, while upstairs bedrooms and bonus room are thoughtfully designed for comfort and quiet, complemented by quality finishes throughout. Recent updates include a newly installed roof (2024) and windows (2025), enhancing both peace of mind and long-term value. A spacious three-car garage adds both convenience and functionality. Outdoors, the home transitions easily to an entertainer’s retreat with covered porches, fireplace, outdoor kitchen, circular firepit, cabana bath, Tiki hut and lush landscaping. The property also offers the opportunity to add a FRONT GATE for enhanced privacy and security, and allows for a FUTURE POOL ADDITION, giving buyers flexibility to further customize the outdoor living experience. Deeded town resident access to the Butler Chain of Lakes and a prime location within Windermere’s vibrant town center with its new redevelopment complete this rare offering where architectural integrity meets a fun and functional Florida lifestyle.

713 Main Street, Windermere

Listing courtesy of THE REAL ESTATE COLLECTION LLC. 407-656-7814

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