Welcome to this exceptional traditional style home nestled along one of Windermere's iconic oak canopied dirt roads, where the charm of "Old Florida" meets the warmth of a true small town community. Located in the heart of Windermere proper, this beautifully updated two story residence offers 3 bedrooms, 2.5 bathrooms, 4 car garage, and combines timeless character with modern conveniences on an expansive 0.38-acre homesite. Surrounded by lush custom landscaping, the private cypress-fenced backyard is a true retreat. Meander along picturesque flagstone pathways to discover multiple outdoor seating areas, a detached studio/office perfect for working from home, and an oversized detached garage/workshop offering endless possibilities for hobbies, storage, classic cars, or creative projects. Inside, thoughtful upgrades have enhanced both style and functionality. Improvements include exterior paint, travertine flooring, custom trim work, oversized gutters with leaf guards, conversion of the fireplace to natural gas, additional gas hookups for a future summer kitchen and generator, and the transformation of the screened porch into a bright Florida room overlooking the beautifully landscaped backyard. Living in Windermere proper is about more than just the home it's a lifestyle. Enjoy an easy stroll to the town library, tennis and basketball courts, weekly farmers market, monthly food truck events, neighborhood cafes, brewery, and the soon to open Italian restaurant. Residents also enjoy exclusive access to private boat ramps leading to the renowned Windermere Chain of Lakes, including the pristine, sandy bottomed waters of Lake Butler and Lake Down, offering some of Central Florida's finest boating, skiing, and fishing. This is a rare opportunity to own a beautifully updated home in one of Central Florida's most sought after communities, where timeless charm, outdoor living, and an unmatched lifestyle come together.