Pathway to Living Blog

Return To Blog

Living in Windermere, Florida

When people think of Orlando, they think of the usual things: Disney, crowds, heat and a bustling city. However, just outside of Orlando proper is a beautiful, quiet and incredibly exclusive suburb: Windermere, FL.


“Windermere is one of the most prestigious neighborhoods in the Orlando region,” says Tracy Deal, Executive Director of Azpira at Windermere, an Assisted Living and Memory Support community providing thoughtful and award-winning care to older adults. “We’re located right behind the Magic Kingdom, directly north of Disney, in a beautiful location with an upscale, historic feel. I absolutely love it here, and so do our residents – which is why they chose to make their home with us.”


History of Windermere, FL

Windermere was founded in 1889, making it one of the oldest communities in Orange County. The town was unofficially founded by Dr. Stanley Scott, who built his home on the shore of Lake Butler. It’s believed by many that he named this town “Windermere” after England’s famous Lake Windermere. In the 1970s, an influx of Disney employees moved to the sleepy suburb due to its proximity to Disneyworld. Today, Windermere is home to more than 2,300 people, but still retains its small-town, historic charm. The town is very focused on preserving its natural history – in fact, many town streets are unpaved in order to retain the pristine nature of the bordering Chain of Lakes.


Living in Windermere, FL

Living in Windermere is definitely a treat. Downtown Windermere is the smallest downtown of Orlando’s suburbs, which definitely gives it a charming, historic feel. It boasts brick-paved roads, large oak trees, roundabouts and mature landscaping. There are only a handful of stores and restaurants downtown, but all of them are local favorites and hangouts. There are two coffee shops, a café and several other boutiques.


While outsiders may think at first that the only parks in Windermere are the Disney kind, the town in fact has a wide variety of beautiful green spaces. There are 12 official town parks, many of which have gorgeous views of the lakes and opportunities to fish, boat and bird-watch the day away.


Things To Do in Windermere, FL

While visiting the various theme parks in Orlando tops the list of most individuals’ to-dos when they come to Windermere, the town itself actually has many delightful things to do. Here’s just a sampling of some of the local favorites:


Windermere Farmers Market

Every Friday, the Windermere Farmers Market is the place to be. Located on Main Street along Town Square Park, the Market offers a great place to shop local, stock up on unique gifts and enjoy delicious delicacies from local farmers and artisans.


Butler Chain of Lakes

The Butler Chain of Lakes is a group of 13 lakes, interconnected by small canals, that covers approximately 5,000 acres. Reserve a boat tour and you’ll get to enjoy the sights of Spanish-moss covered trees, local wildlife, a bird island and the magnificent celebrity mansions that line the lake.


Florida Ski School

Besides boating, what better thing to do on the lake than learn to water ski? The Florida Ski School is a local favorite and the place to go to learn about water skiing.


The Art Room

The Art Room is a teaching studio, located in downtown Windermere, that offers a variety of classes for all ages. Whether you’re a beginner or a master artist, you’ll find inspiration at The Art Room.


Tibet-Butler Preserve

You’d hardly expect to find a gorgeous spot of wilderness right outside of the busy urban mass of Orlando, but Tibet-Butler Preserve is a gorgeous haven from the hustle and bustle of the city. More than three miles of trails loop through different habitats, including longleaf pine forest and scrub, bayhead swamp, and cypress-lined lakeshore. It’s a great option to get outdoors and commune with nature, all within a stone’s throw of the Magic Kingdom.

Dixie Cream Cafe

This charming little restaurant has been serving made-from-scratch Southern comfort food in downtown Windermere for just over 10 years. Its 50s-style decor and location provide a funky yet nostalgic feel, which is echoed by the local art that hangs from the walls. You’ll be sure to see lots of locals enjoying breakfast and lunch at their usual spots if you pop in for a bite.


Paloma Coffee Co.

This teeny-tiny coffee shop is a must-stop spot for high-quality baked goods, tea, espresso, coffee and more.


Allen’s Creamery & CoffeeHouse

Ice cream and coffee? What could be more perfect? This little shop has it all, from tasty barbecue to gourmet coffee to sweet ice cream. There’s a little bit of everything here, and it’s a favorite for locals and visitors alike.




Pizza 14

This pie (pizza pie, that is) shop is still moderately new to the area but quickly becoming a favorite spot for New York-style pizza. The alfresco-style dining makes it a lovely place to spend a sultry Florida night.


Azpira at Windermere: Quality Senior Living in a Prime Location

“As you can see, our little town of Windermere may be quiet but has a world of opportunities to explore,” says Tracy. “Our community is situated on the east side of Lake Speer and is close to all your favorite Windermere and Orlando destinations. We love being able to provide a fulfilling, engaged lifestyle for our Assisted Living and Memory Support residents who call Windermere their home.”

Live Well. Age Well. Be Well.

At Azpira at Windermere, located in Windermere, FL, we’re redefining how older adults Live Well. Age Well. Be Well. Our lifestyle is far from “typical.” Our vibrant and engaging Assisted Living and uplifting A Knew Day® Memory Support inspires our residents to live passionately with purpose, every single day.

Step outside your apartment and you’ll experience a community offering thoughtful and award-winning VIVA!SM programs that are proven to enhance your life spiritually, mentally and physically. Azpira at Windermere’s team of specially trained wellness professionals are passionate about building unique relationships with every resident and guiding older adults as they set new goals, forge new relationships and live life at their own pace.

Azpira at Windermere is all about creating an environment that is ahead of the curve in wellness, fitness, spirituality, technology and preventative care. As the times and technology are changing, so are we. Residents and their families, along with our Resident Care Manager, will meticulously build a wellness plan that addresses medicine distribution, fitness objectives, nutrition needs and socialization goals.​

Get excited about life at Azpira at Windermere. Our team is eager to guide you on the path you want to live – whether it’s enjoying your own city, exploring new ones, spending time with old friends or spearheading a program of your own, this is your time to live the life you want with the luxury you deserve.​

To learn more or to schedule a personal visit, contact us at 407-278-8508.