Orlando Real Estate Blog - Windermere events

Where Locals Are Celebrating America 250 Around Orlando

Orlando Area Community 4th of July Guide

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

From Windermere and Winter Garden to Downtown Orlando, Ocoee, Celebration, and beyond, Central Florida knows how to celebrate the 4th. In fact, Orlando was recently ranked the #3 city to spend the Independence Day holiday by WalletHub. Hometown events and city celebrations make it easy for locals to get out and commemorate the day, and especially with this year marking the 250th anniversary.

The Funk Collection has you covered with a local's guide to the 2026 Fourth of July celebrations happening in your community across Central Florida. We've also included ways you to commemorate the 4th at local theme parks, including Magic Kingdom…

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Art in Windermere Florida: Don't Miss the 11th Annual Windermere Fine Art Show

Experience Art In The Heart Of Downtown Windermere

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

If you're searching for art in Windermere Florida or researching Windermere events in 2026, the Annual Windermere Fine Art Show belongs on your calendar. Celebrating 11 years of art, this yearly event brings the community together for live art, music, and interactive experiences in historic downtown Windermere, with FREE admission.

2026 Windermere Fine Art Show Must-Know Info

This year's event will be held on Saturday, February 28, from 11 am - 5 pm and on Sunday, March 1, from 10 am - 5 pm in downtown Windermere at Town Hall (520 Main Street). Outdoor art vendors will line Main Street along with local food vendors.…

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Celebrating Past and Present at the Windermere Flower Show

What Makes the 2025 Flower Show Special

This year's Windermere Flower Show isn't just any event; it's part of the town's Centennial Celebration. Hosted by the Windermere Garden Club, "Celebrating Windermere Past and Present" is all about honoring 100 years of history, the present, and tomorrow. And honestly, what better way to celebrate Windermere than with flowers, trees, and plants that truly show off the place we call home?

What you will experience at the Show

From the moment you step inside the Windermere Town Hall, you'll find find entries in three divisions (Horticulture, Design, and Education). You'll experience everything from exhibits featuring horticulture that celebrate local flowers, trees, and plants to creative floral displays that…

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Top Orlando Events & Things to Do This Week | March 1 - 7

Can't believe it's March? Same here! Spring is around the corner and with that comes plenty of fun events to keep you entertained. From Carnaval celebrations to Festivals and everything in between, there are a ton of events right in your backyard. Whether you're exploring the vibrant streets of Downtown Orlando or enjoying the charm of Windermere, these communities offer more than just great events—they’re incredible places to call home. Learn more about living in these sought-after Orlando area communities and available places to call home.

Mar 1 | Carnaval, Lake Nona Town Center | A lively celebration featuring colorful entertainers, live music, and high-energy Samba dancing.

Mar 1 | Horizon West Fest, Green Space at Hamlin | A community event…

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Windermere Celebrates 100 Years: A Centennial To Remember

2025 marks a significant historical milestone for Windermere, Florida—its Centennial celebration! Over the course of the year, the community will honor its 100-year journey with special touches that highlight its unique charm, history, and community spirit.

Festive Updates Across Downtown

Downtown Windermere is ready to dazzle with:

• Centennial Banners: New flags now line the streets, adding a cheerful and celebratory vibe to the town’s heart.
• New Entry Signs: The town’s entryways have been updated with commemorative Centennial signs, welcoming everyone to this once-in-a-lifetime celebration.

These thoughtful touches remind residents and visitors alike of the rich history that makes Windermere so special.

The Centennial Lobby: A…

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Holiday Lights, Broadway Nights, and Sports Thrills: Orlando Events Nov 16 - 22

As November moves closer to the holiday season, Orlando is lighting up with festive events and family-friendly activities. From Jingle Eve in Ivanhoe Village to performances at the Dr. Phillips Center, this week is packed with culture, entertainment, and holiday spirit. Get ready to enjoy a mix of theater, sports, and community celebrations across Central Florida!

• Nov 16 - 24 | Jingle Eve, Ivanhoe Village | Kick off the holiday season in style at Ivanhoe Village's Jingle Eve! This weeklong celebration brings festive feelings with live entertainment, kid's holiday village, and plenty of local shopping and dining options to enjoy.

• Nov 16 | Annie Jr., Dr. Phillips Center | Bring the family to see this heartwarming performance of Annie…

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Pumpkins, Pedals, and Performances: Central Florida Events October 5 - 11

October is packed with vibrant events throughout the central Florida region, perfect for all ages! From scenic runs to pumpkin patches, soccer matches, and lively performances, there's something for everyone in and around Orlando this week. Let’s dive into the exciting happenings!

• Oct 5 | Windermere Run Among the Lakes, Windermere Town Hall | Get ready to lace up your sneakers and enjoy a scenic 5K or 10K run along Windermere’s beautiful lakes. Perfect for runners of all skill levels, this family-friendly event supports the Windermere Parks and Recreation Department.

• Oct 5 | Hamlin Pumpkin Patch, Hamlin | Kick off fall festivities at Hamlin’s charming pumpkin patch. Snap a few family photos, pick out the perfect pumpkin, and enjoy…

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Bunnies, Bears, and Boats: Orlando Area Events March 30 - April 5

As spring blooms across Central Florida, the Orlando area is gearing up for a week filled with vibrant celebrations and thrilling entertainment. From March 30th to April 5th, mark your calendars for these exciting events:

• Mar 30 | Operation Easter Bunny, Windermere | Join the Windermere Police Department for Operation Easter Bunny in Windermere, as the Easter bunny makes his way downtown delivering Easter goodies to the kiddos along the way.
  
  
• Mar 30 | Easter in the Parks, Winter Park | Head to Phelps & Ward Parks for Easter goodie bags, balloon artists, kids entertainment and at Winter Park's Easter celebration!
  
  
• Mar 30 | Orlando Holi Festival, Festival Park Orlando | Visit the Festival Park in downtown Orlando to celebrate the Holi Festival…

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