Windermere is one of the nicest small towns in Florida. It resides about 12 miles west of downtown Orlando. Founded in 1889, Windermere is one of the oldest communities in Orange County. In the years before the big freezes of the 1890s and the 1980s, this small town was in the heart of one of the largest citrus regions in the world. Many of these old homes and buildings have been preserved and add to the charm of this little place nestled among the old oaks and clear lakes of Central Florida.

In the early days of the construction of Walt Disney World, the 1960’s and 1970’s, many Disney executives lived in Windermere.

Windermere’s location on the isthmus puts it on the shortest path between the east and west sides of the chain of lakes. The next lake crossing to the south is 7.5 miles away at Lake Buena Vista, where CR-535 and Apopka-Vineland Road intersect. The next lake crossing to the north is at Gotha, 2 miles north. This has made Windermere a busy little place for traffic, but the town has handled it beautifully with roundabouts and other traffic calming techniques.

An interesting little place to see while you are in town is the Windermere School. It is on the National Register of Historic Places. It is located at 113 West Seventh Avenue. Park your car and walk right up to it. Windermere is a pleasant and peaceful place to spend a day; you won’t feel like speeding through this pretty little town.

Located in Orange County, Oakland is a small town of about 2,500 people 31 min or 22 miles via Florida’s Turnpike and I-4 E just west of Orlando, Florida.  It is also on the southern shore of Lake Apopka and a stop on the West Orange Trail, a popular “rails to trail” bike and pedestrian path in this part of Central Florida. It is primarily a residential community, and the residents prefer the quiet serenity that now prevails. You will enjoy a visit to this quiet little Old Florida town. It’s one of the more affluent areas of metro Orlando but offers excellent schools and a small-town lifestyle.

The closest beaches to Oakland are Eatons Beach and Hampton Beach, which are 35 miles from town. Nearby attractions include the Winter Garden Heritage Museum, Orlando Metropolitan Museum of Art, Orlando Science Center, Mennello Museum of American Folk Art, and Orlando Museum of Art. Parks nearby are Irrgain Park and Lakeview Park, which are both about 3 miles away. In addition, the city has many places of worship within the city limits from multiple denominations.