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Results for:

  • By Observer Staff |
  • April 2, 2017
GALLERY: WOCC Best Fest 2017

The West Orange Chamber of Commerce’s 15th annual Best Fest brought out more than 1,000 people and 60 vendors.

  • West Orange Times & Observer
  • News
  • By Annabelle Sikes |
  • February 25, 2024
PHOTOS: 2024 town of Windermere PetFest

The annual event featured a multitude of activities, including doggie games, a children’s bubble zone, awards for pets, vendors, K-9 demonstrations, story time and food trucks.

  • Southwest Orange
  • News
  • By Sam Albuquerque |
  • June 29, 2024
PHOTOS: Annual Independence Firework Spectacular in Horizon West

The Independence Village in Horizon West kicked off the Fourth of July celebrations with its annual fireworks event.

  • Southwest Orange
  • News
  • By Liz Ramos |
  • December 13, 2024
PHOTOS: St. Luke's United Methodist Church's Christmas concert spreads holiday joy

"Sounds of the Season" includes holiday classics performed in a new way.

  • West Orange Times & Observer
  • Neighborhood
  • By Michael Eng |
  • May 19, 2025
Windermere High employee placed on administrative leave following allegations

Principal Andrew Leftakis made the announcement just hours after a gun report disrupted school operations.

  • Southwest Orange
  • News
  • By Liz Ramos |
  • April 12, 2025
PHOTOS: Palm Lake Elementary School carnival makes a splash

The dunk tank was a fan-favorite activity at the carnival, which also had games, rock climbing and inflatables.

  • Observer School Zone
  • By Michael Eng |
  • April 6, 2025
PHOTOS: Town of Windermere’s Centennial Country Fair

The town of Windermere celebrated its 100th anniversary with a good old-fashioned fair Saturday, April 5.

  • Southwest Orange
  • Neighborhood
  • By Michael Eng |
  • May 5, 2025
PHOTOS: Rosen JCC’s Israel North to South

The Rosen JCC brought a slice of Israel to Southwest Orange with its Israel at Israel North to South event, which took place Sunday, May 4, at the center.

  • Southwest Orange
  • Neighborhood
  • By None |
  • March 7, 2024
Keene’s Pointe estate sells for $3,800,000

This lakefront home is sited on a 3-plus-acre lot. The sellers were represented by Angela Durruthy, Keene’s Pointe Realty.

  • Southwest Orange
  • Real Estate
  • By Michael Eng |
  • November 21, 2024
Eight Waves to host 2024 Holiday Tour of Homes

The event takes place Saturday, Nov. 23, beginning at the Oakland Park Amenity Center and Pool, 1000 Civitas Way, Winter Garden.

  • Arts + Entertainment
  • Things to Do
  • By Observer Staff |
  • December 4, 2024
Horizon High SGA spearheads Reading Reindeer donations

The Hawks collected more than 500 books for the Observer’s annual book drive.

  • Observer School Zone
  • By Michael Eng |
  • November 29, 2023
Light Up Winter Garden is Friday, Dec. 1

Winter Garden's annual Christmas kickoff will feature a plethora of holiday cheer.

  • Arts + Entertainment
  • Things to Do
  • By Debra Garcia |
  • May 13, 2025
Town of Windermere to host Armed Forces Day

The event takes place at 10 a.m. Saturday, May 17, at Town Hall, 520 Main St., Windermere.

  • Arts + Entertainment
  • Things to Do
  • By Leticia Silva |
  • August 2, 2025
PHOTOS: Foundation Academy seniors create art in parking spots

The FA families came together to help seniors paint their parking spots for the 2025-26 school year.

  • West Orange Times & Observer
  • By Sam Albuquerque |
  • August 10, 2025
PHOTOS: Global Not Local, Devin Jackson host basketball clinic, backpack giveaway

The Winter Garden-based nonprofit and The First Academy star football player partnered to host 200 kids at the West Orange Recreation Center for the free youth event.

  • Sports
  • Youth Sports
  • By Leticia Silva |
  • August 8, 2025
Crunch Fitness coming soon to Dr. Phillips

A new Cruch Fitness will soon open in Dr. Phillips at 7600 Dr Phillips Blvd, Suite 170, Orlando.

  • Southwest Orange
  • News
  • By Michael Eng |
  • October 3, 2024
Dueling pianos show set for Oakland

Doors for the Music Under the Oaks event open at 5 p.m. Saturday, Oct. 5, at Vanderley Park, 117 E. Gulley Ave., Oakland.

  • Arts + Entertainment
  • Things to Do
  • By Annabelle Sikes |
  • October 8, 2024
Town to maintain boat ramp access for residents to remove, secure vessels

The town of Windermere is taking extra precautions to prepare for Hurricane Milton.

  • Southwest Orange
  • News
  • By Leticia Silva |
  • August 27, 2025
Oakley's Trailside Treats

Oakland has treats! Oakley's Trailside Treats is a snack stand built for walkers, bikers and families in the Oakland area.

  • West Orange Times & Observer
  • News
  • By Leticia Silva |
  • August 29, 2025
Windermere High's new money management course

Windermere High School has a new mandatory finance and money management course.

  • Southwest Orange
  • News
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