105 Pine St,
- Windermere, FL
5 Beds 6 Baths 5,696 Sq.Ft. 0.57 Acres
Extraordinary multigenerational living opportunity in the Town of Windermere, where mature oak trees and a quiet, established setting create a true sense of place just moments from the Butler Chain of Lakes. Set on an oversized, over half-acre corner lot in downtown Windermere, this custom home offers a rare blend of privacy, flexibility, and walkability to local dining, coffee shops, boutiques, and the weekly farmers market. Built in 2015 and thoughtfully expanded, this 5,696 square foot home features five bedrooms and five and a half bathrooms, including a fully separate casita ideal for in-law living, guests, or private quarters. From the moment you arrive, fresh landscaping and an exposed brick front porch create a warm and inviting entrance. Inside, the open living space is both spacious and comfortable, with high ceilings, wood beams, crown molding, and a gas fireplace, complemented by shiplap and exposed brick accents. The kitchen opens seamlessly to the main living area and overlooks the backyard, featuring a large Cambria quartz island, Kohler farm sink, walk-in pantry, Bosch double ovens, Viking gas cooktop, custom hood, LG refrigerator, soft-close cabinetry, under-cabinet lighting, and a dedicated coffee bar. The primary suite offers peaceful backyard views, two custom walk-in closets, and a well-appointed bath with dual vanities, a makeup station, a garden tub, and a large walk-in shower with floor-to-ceiling tile and dual showerheads. Additional bedrooms are thoughtfully placed, including one with an ensuite bath. A versatile flex room with a coffered ceiling, storage, and its own laundry setup connects to a private office with built-ins and a walk-in closet. A secondary primary suite provides a comfortable space for extended family or guests. In total, the home offers three separate laundry areas for added convenience. Outdoor living is designed for true Florida living. Two sets of sliding glass doors, including one from the flex room, open to a covered lanai with wood plank ceiling and fans, along with a fully equipped summer kitchen featuring an Artisan natural gas grill, vent hood, sink, and icemaker. The space extends to an expansive paver patio surrounding a heated saltwater pool and spa with water features, all overlooking a large fenced backyard. The casita, completed in 2023 and offering over 1,200 square feet, lives like a private residence with its own entrance and Spanish Mediterranean character, including wood beams, hardwood flooring, and a Kiva-style fireplace. It features a full living room, a kitchen with GE Café appliances and a quartz island, and a spacious bedroom suite with a custom walk-in closet and a beautifully finished bath. A screened lanai and separate fenced yard provide added privacy. A three-car garage with high ceilings includes an oversized RV-height door, 50-amp plug, and space for additional storage or lifts, along with a third laundry area. Additional features include dual AC systems, tankless water heaters, and a Generac generator. Residents of Windermere enjoy private access to the Butler Chain of Lakes, parks, tennis courts, and a boat ramp, all golf cart accessible. Golf cart friendly with tree-lined streets and a true small-town feel. No HOA and conveniently located near top-rated schools, major roadways, and world-class dining and entertainment. This is a truly unique Windermere home designed for modern multigenerational living. Schedule your private showing today!
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Established in 1889 and incorporated in 1925, Windermere seamlessly blends historic character with refined living in one of Central Florida’s most desirable locations. Nestled on a peninsula amid the Butler Chain of Lakes,13 interconnected lakes spanning over 1,800 acres, the town offers scenic beauty, elegant homes, and a tranquil residential atmosphere just minutes from Winter Garden, Dr. Phillips, and major highways. These pristine lakes provide abundant opportunities for boating, fishing, paddleboarding, and lakeside relaxation, making Windermere a haven for water enthusiasts.
Windermere’s lifestyle is characterized by exclusivity and sophistication. Gated golf communities like Isleworth and Keene’s Pointe offer luxury homes and world-class amenities, while other premier neighborhoods such as Lake Butler Sound, Reserve at Lake Butler Sound, Bellaria, Tilden’s Grove, Casabella at Windermere, and The Willows provide diverse architectural styles and serene, private settings. These neighborhoods are among the most sought-after in Central Florida, known for their estate homes, lush landscaping, and access to the area’s lakes and golf courses. The walkable town center features boutique shops, a weekly farmers’ market, and community events that foster a close-knit community spirit. The area is also known for its top-ranked public schools, including Windermere Elementary and Olympia High, as well as private options like Windermere Preparatory School.
Windermere’s allure extends to numerous celebrities and professional athletes who are drawn to its privacy, luxury, and proximity to Orlando’s attractions. Notable residents have included NBA legend Shaquille O’Neal, who owned a 31,000-square-foot mansion in Isleworth featuring a 6,000-square-foot indoor basketball court. Baseball star Johnny Damon and Westgate Resorts founder David Siegel have also called Windermere home. The town’s gated communities and expansive estates offer the seclusion and amenities that appeal to high-profile individuals seeking a retreat from the public eye.
Whether attracted by the waterfront estates, serene streetscapes, or the vibrant community atmosphere, Windermere offers an unparalleled blend of natural beauty, convenience, and prestige in the heart of Central Florida.
What county is Windermere, Florida in?
Windermere is located in Orange County, Florida.
What is the Windermere zip code?
Windermere’s zip code is 34786, placing Windermere just west of Orlando’s vibrant heart.
Is Windermere a good place to live?
Yes! Windermere is known for its safe neighborhoods, beautiful lakes, top-rated schools, and elegant homes, making it one of Central Florida’s most sought-after places to live.
Is Windermere considered Orlando?
No, Windermere is its own incorporated town. While it's part of the Greater Orlando area, it has its own local government and identity.
What school district is Windermere in?
Windermere falls under Orange County Public Schools. Public schools include Windermere Elementary, Gotha Middle, and Olympia High School, with several private school options nearby as well.
What are some popular neighborhoods in Windermere?
Keene’s Pointe, Isleworth, Windermere Downs, and Lake Butler Sound are just a few of the highly sought-after communities in the area.
How far is Windermere from Disney World?
Windermere is approximately 10-15 miles from Walt Disney World, depending on the specific neighborhood, making it a convenient spot for theme park enthusiasts.
Ready to find your dream home in Windermere?
Explore available listings and learn more about living in Windermere, one of Central Florida’s most prestigious communities.
Who is the best real estate agent in Windermere, Florida?
If you're looking to buy or sell in Windermere, Align Real Estate is here to help. From exploring top neighborhoods to understanding market trends, our team is here to guide you through the entire process.
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