Windermere Fall Events That Have Become Local Traditions

When fall comes around, the events around Orlando start ramping up, and Windermere is no exception. Windermere's fall events calendar for 2026 includes the Windermere Garden Club Flower Show, Run Among the Lakes 5K/10K, Windermere Oktoberfest, and the Halloween Costume Parade & Hayride. These local events have become annual traditions for residents and visitors to celebrate the change of seasons.

What's Happening this Fall in Windermere, FL?

Windermere Garden Club Flower ShowWindermere Garden Club Flower Show

This "Just for Fun" flower show will be celebrates National Constitution Day. The public is invited to see creativity through flowers and plants. 

  • Location: Windermere Town Hall at 520 Main Street.
  • Date:…

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Why Was Orlando Named The #1 Place to Retire?

With Florida's tax advantages, year-round recreation, warm climate, world-class attractions, easy travel, and a wide range of communities, Southwest Orlando offers an ideal lifestyle that matters most to many retirees. So, it should be no surprise that Orlando was recently named the #1 place to retire in the U.S. by WalletHub. Let's take a closer look at what makes Orlando a top choice for retirees.

What Makes Southwest Orlando a Great Place to Retire?

Southwest Orlando Golf CommunityLocation and lifestyle are two of the top reasons people choose Southwest Orlando for their retirement home base. Its Central Florida location makes it easy to travel throughout Florida to the east and west coasts for beaches and cruise ports. Port…

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A Local Look at Windermere Neighborhoods With Clubhouses & Pool Cabanas

Are there communities in Windermere, Florida with clubhouses or cabanas? Yes. For those seeking a neighborhood with community amenities, including a clubhouse, a cabana, or an amenity center with pools, sports courts, and playgrounds, Windermere has several options to explore. The Funk Collection has compiled this local guide to Windermere communities with clubhouses, cabanas, and shared resident amenities.

What is the Difference Between a Clubhouse and a Cabana?

Clubhouses and cabanas have many similarities and are often used interchangeably to describe a building in a neighborhood amenity area. Often, clubhouses have more interior amenities than cabanas. Clubhouses are…

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What Are Key Differences Between Keene’s Pointe and Isleworth?

Blog Author: Jen Durben | The Funk Collection, Brokered by eXP Realty

The Windermere communities of Keene's Pointe and Isleworth are both guard-gated luxury golf communities that are built around the Butler Chain of Lakes. What differentiates these two communities? Keene's Pointe is larger, covering more than 1,000 acres with over 1,050 homes, while Isleworth is slightly smaller overall, spanning over 600 acres with just over 350 homes. Lots and home sizes in Isleworth tend to be larger than Keene's Pointe. Homes in Keene's Pointe have a slightly lower entry price point, with available homes currently starting at just under $1 million, while Isleworth homes currently start at just…

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A Local Guide To Dog Parks, Pet-Friendly Dining, And Communities Across Southwest Orlando

Blog Author: Jen Durben | The Funk Collection, Brokered by eXP Realty

Waterbrooke Community Dog ParkRecently Orlando was named the #4 pet-friendly city in the U.S. by WalletHub. They compared 100 of the largest cities across 23 key metrics, including veterinary care costs, dog-friendly restaurants per capita, and dog parks per capita. Orlando stood out in the pet health & wellness category, as well as the number of veterinarians per capita, and dog-friendly restaurants per capita. 

Orlando’s latest pet-friendly ranking puts the spotlight on something locals already know: Southwest Orlando makes it easy to enjoy everyday life with a dog, from parks and trails to neighborhoods built…

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What Home Buyers Should Know About Golf Cart Access in Windermere

Blog Author: Jen Durben | The Funk Collection, Brokered by eXP Realty

The Windermere Golf Cart District is a network of approved streets in the Town of Windermere where residents can legally drive golf carts and low-speed vehicles between downtown businesses, parks, and neighborhoods. There is something special about being able to skip the car and cruise around town in a golf cart. Golf cart living in Windermere means being able to grab morning coffee, pick up a bite to eat, head to Windermere Elementary School, or enjoy a cool beverage in the evening. From the Friday farmers market and monthly food truck events to annual events like the Run Among the Lakes 5K/10K, experiencing…

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Trying to Decide Between Windermere and Winter Garden? 

Blog Author: Jen Durben | The Funk Collection, Brokered by eXP Realty

For buyers considering neighborhoods around Orlando, especially Southwest Orlando, the conversation usually includes a comparison of Windermere and Winter Garden. This makes sense in many ways. Located next to each other, with a great selection of communities to choose from, access to Walt Disney World, and a wide range of homes, from townhomes and condos to lakefront estates. Both are also appealing to those seeking access to downtown, the I-4 corridor, and beyond. 

Windermere is known for its lake-centered lifestyle among the Butler Chain of Lakes with a small-town vibe, established communities, and close proximity…

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What are Surprising Facts About Windermere, FL?

Blog Author: Renee Funk | Co-Founder, Speaker, Trainer

Windermere, Florida, has deep roots in Central Florida, with a quaint downtown and a setting among the lakes that feel almost untouched by time. Established decades before the area’s major growth, the town has maintained its small-town vibe while also collecting its share of odd but true facts.

1. The Infamous Dirt Roads of Windermere

Why does Windermere still have dirt roads downtown? Originally, when the town of Windermere was being built, paving downtown sand streets was not a priority. Funding fell short, so the town's sandy dirt roads became part of its charm. More than 100 years later, the sand roads are still part of Windermere’s…

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Trying to Decide Between Windermere and Dr. Phillips? 

Blog Author: Jen Durben | The Funk Collection, Brokered by eXP Realty

If you are looking for your next move in Orlando, whether relocating from out of state or across town, narrowing down the areas of the Orlando metro is typically one of the first decisions. And, if the decision is between Windermere and Dr. Phillips and you're not sure how they compare, this guide will help differentiate the two communities.

At a high level, these two areas feel like siblings. Both are located in Southwest Orlando and border each other (Windermere to the West, in the 34786 zip code, and Dr. Phillips to the East, in the 32836 & 32819 zip codes). Both offer well-established residential communities with a…

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The Latest Openings and Upcoming Developments in Windermere, Dr. Phillips, Winter Garden & Clermont

Blog Author: Jen Durben | The Funk Collection, Brokered by eXP Realty

If you've been asking what's new in Southwest Orlando in 2026, this post covers the latest restaurant openings, business arrivals, and development projects across Windermere, Dr. Phillips, Winter Garden, Horizon West, and Clermont.

From new restaurants and coffee shops to beloved re-openings and major mixed-use developments and lifestyle additions, Southwest Orlando continues to evolve in ways that make communities like Windermere, Dr. Phillips, Winter Garden, and Clermont some of the most talked-about cities in Central Florida real estate.

Whether you're already a local…

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