By  Mike Miller  Updated June 12, 2024

Windermere, Florida Things To Do, Lodging, Dining, & Real Estate At End Of Article

The Town of Windermere is one of the nicest small towns in Florida.  It is located on the secondary roads about 15 miles west-southwest of downtown Orlando on the Butler Chain of Lakes.

These lakes are popular places for water skiing, boating and fishing.  Windermere is a residential community with a population in 2022 of less than 4,000.

Windermere Florida old 1890 school houseWindermere School

Even though it is a very small town, the greater Windermere area has been steadily growing.  Real estate prices are much higher here than most other sections of Orange County.


In the years  before the giant freezes of the 1890s and the 1980s, this small town was in the heart of one of the largest citrus regions in the world.

Vintage Postcard of Windermere GroveVintage Postcard of Windermere Grove

Founded in 1889,  Windermere is one of the oldest communities in Orange County.

By 1910, the Windermere Improvement Company had been formed, homes were built and thousands of acres of citrus planted all around the area.

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.

Windermere NeighborhoodWindermere Neighborhood

The quiet neighborhoods of Windermere are located on an isthmus between Lake Down and Lake Butler.  The downtown area has a small town feel.

Windermere Was Home To Disney Executives

In the early days of the construction of Walt Disney World, the 1960's and 1970's, many Disney executives lived in Windermere, including Don Edgren, Bob Allen and Admiral Joe Fowler.


In more recent years, plush golf course developments like Isleworth, home of Tiger Woods , Shaquille O'Neal and other celebrities, have popped up on the edges of Windermere.

Some of these luxury homes are on one of the many golf courses, and others are on Lake Butler and Lake Down.

Maybe these fancy new places have a Windermere address, but they are far removed from the laid back beautiful homes of what I guess I'll call "old Windermere".

Older Windermere HomeOlder Windermere Home

Windermere's location on the isthmus puts it on the shortest path between the east and west sides of the chain of lakes. 

Main Street is the route through downtown Windermere with charming tree shaded residential neighborhoods on either side.

The next lake crossing to the south is 7.5 miles away at Lake Buena Vista where Winter Garden Vineland Road (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.

They don't mind handing out speeding tickets, either.

Watercolor of Historic Windermere SchoolWatercolor of Historic Windermere School

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.  Just 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.  

Although the main drag is paved, most of the residential streets are not.  

Bird Island at Fernwood ParkBird Island at Fernwood Park

The Windermere residents want it that way and have resisted many times the efforts of some to lay down asphalt.

Very few tourists venture off the paved road into the unknown of the dirt trails that lead off through the tree canopies to who knows where.  

Most folks do not want to take the road less traveled.

Windermere folks seem to know that and treasure and protect their solitude.

Former home of NBA Legend Shaq O'Neal in Windermere, FloridaFormer home of NBA Legend Shaq O'Neal in Windermere, Florida

You can stop and buy some wine at Tim's Wine Market and have breakfast or lunch next door at the Dixie Cream Cafe.

There is also a nice coffee shop on Main Street that also serves good ice cream.  It is popular with local residents and visitors.

You can also take a short drive down the road to Gotha for lunch at one of the neatest restaurants in the area, Yellow Dog Eats Cafe.

Recommended Windermere Restaurant


1236 Hempel Avenue
Windermere, Florida
Tel: 407-296-0609

Yellow Dog Eats Cafe is owned by a former CIA man named Fish Morgan

Yellow Dog Eats Cafe in Gotha, FloridaYellow Dog Eats Cafe in Gotha, Florida

That's CIA as in Culinary Institute of America.  This quaint restaurant has an Orlando address but is really in Gotha, a small village west of Orlando near Windermere.

When I lived in Orlando many years ago a trip to Gotha was often on the Sunday ride agenda.

There were no restaurants back then, only the large century old ramshackle Gotha Country Store where you could get a beef jerky, Twinkie, or saran wrapped sandwich.

Read More About Yellow Dog Eats Cafe


Butler Chain of Lakes 
Windermere, Florida 

Begin your Windermere adventure with a serene boat ride on the Butler Chain of Lakes. Launch from one of the many access points and glide through crystal-clear waters surrounded by lush greenery.

Our favorite route? Explore Lake Butler, where luxurious waterfront estates dot the shoreline. It's a tranquil escape that showcases the natural beauty of Windermere and provides a glimpse into the town's upscale residential charm. 

Beck Brothers Blueberries U-Pick 
12500 Overstreet Road, Windermere, FL 34786.  (407) 656-4353 

Beyond their renowned citrus groves, the family-owned Beck Brothers Citrus offers a delightful twist with their u-pick blueberry fields.

The farm provides all the necessary equipment, making the experience accessible and enjoyable for visitors of all ages. As you stroll through the neatly manicured rows of blueberry bushes, the sweet aroma fills the air, bringing you closer to nature.

Enjoy the Florida agriculture particular to this part of the State.    

Windermere Farmers Market 
614 Main St, Windermere, FL 34786.  (407) 625-3818 

One of our favorite weekend activities is strolling through the Windermere Farmers Market on Main Street. Open on Fridays from 9 AM to 2 PM, this vibrant market is a treasure trove of locally sourced produce, artisanal crafts, and delectable treats.

Engage with friendly vendors, savor freshly baked goods, and discover unique handmade items. The market's lively atmosphere and the backdrop of charming downtown Windermere make it an ideal spot to immerse yourself in the community spirit while enjoying the best of local flavors. 

Florida Ski School 
10900 Chase Road, Windermere, FL 34786.  (407) 497-5550 

Located within the idyllic R.D. Keene Park, the Florida Ski School is a haven for water sports enthusiasts. This renowned school offers a unique opportunity to master the art of water skiing in the Sunshine State.

Whether you're a beginner or an experienced skier, their expert instructors provide personalized coaching to enhance your skills. They offer lessons in waterski, slalom, wakeboarding and 3 event coaching.

The pristine waters of Lake Isleworth provide the perfect backdrop for an exhilarating day on the waves, making the Florida Ski School a premier destination for those seeking aquatic adventures. 

Yellow Dog Eats 
1236 Hempel Ave, Windermere, FL 34786.  (407) 296-0609 

No Windermere journey is complete without indulging in the culinary delights of Yellow Dog Eats, as described earlier on this page. From inventive salads to unique sandwiches, each item on the menu is a culinary adventure.

The outdoor patio, adorned with whimsical art and surrounded by lush greenery, creates a laid-back ambiance. It’s worth your while to visit this local favorite. 


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