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By Observer Staff |
September 12, 2025

PHOTOS: West Orange Times & Observer celebrates 120 years

The West Orange Times & Observer, West Orange’s only hyperlocal community newspaper, threw a birthday party to celebrate its 120th anniversary. And the whole community was invited.

West Orange Times & Observer
News

By Liz Ramos |
March 19, 2026

Keene's Pointe home tops Windermere sales from March 9-15

The home at 9733 Carillon Park Drive, Windermere, sold March 12, for $5,000,000.

Southwest Orange
Real Estate

By Michael Eng |
July 22, 2015

The Road to Recovery

West Orange Times & Observer
News

By Annabelle Sikes |
May 4, 2023

Windermere pavilion continues to face opposition

The proposed outdoor pavilion project planned for downtown Windermere continues to face opposition from residents following a virtual Town Council workshop Tuesday, April 25.

Southwest Orange
News

By Josh Garrick |
May 22, 2013

Josh Garrick: Culture Worthy of Your Calendar

Under the enlightened new leadership of Flora Maria Garcia, United Arts of Central Florida has launched power2give.org.

Winter Park - Maitland Observer
Neighborhood

By Gabby Baquero |
October 26, 2016

Orange County smacks down proposal to develop Windermere Country Club

The Board of County Commissioners denied a developer the rights to build 95 homes on the property.

Southwest Orange
News

By Danielle Hendrix |
June 2, 2021

Former West Orange High a cappella group wins awards

The 2018-19 members of West Orange High a cappella group Noise Complaint racked up some awards for their 2020 album, ‘Vibe.’

West Orange Times & Observer
News

By Amy Quesinberry Price |
February 21, 2018

Erin Matherne checks one off bucket list

The Winter Garden resident tried her luck at all things trivia on a popular game show, and although she didn't win, she did know the Final Jeopardy! question.

West Orange Times & Observer
Neighborhood

By Gabby Baquero |
August 17, 2018

Achilles Art Cafe celebrates 10 years

The cafe, which opened Aug. 8, 2008, has had its fair share of struggles.

Southwest Orange
News

By Annabelle Sikes |
February 15, 2024

Unidentified bones leave case open in Winter Garden

The Winter Garden Police Department is asking the community for information regarding unidentified remains found in 2004.

West Orange Times & Observer
News

By Sam Albuquerque |
December 11, 2024

Early Byrd special: L.J. Byrd leads TFA boys basketball to statement start

TFA’s L.J. Byrd scored 24 points to lead the Royals to an overtime win against Windermere Prep to break seven-game losing streak.

Sports
High Schools

By Sam Albuquerque |
April 25, 2024

Windermere, Horizon compete at WGI World Championships

Both Windermere High and Horizon High color guard teams qualified for and competed in the 2024 WGI Scholastic A World Championships.

Sports

By Amy Quesinberry Price |
May 8, 2024

House fire destroys Winter Garden home

The home occupied by Patricia Oliver and her son, Darryl Merchant was gutted following a kitchen fire March 1. She is temporarily living in a rental home, and the work is taking longer than expected.

West Orange Times & Observer
News

By Sam Albuquerque |
May 23, 2024

Practice makes perfect: How Windermere softball survived extra innings in regional finals

After seven scoreless innings in the regional softball finals between, the Wolverines leaned on a practice drill called chaos to help them win.

Sports
High Schools

By Amy Quesinberry Price |
November 26, 2024

Orlando Torah Center project draws community’s ire

Orange County staff is scheduling a second meeting in December so more residents have a chance to ask questions and share their opinions on the synagogue project in Sand Lake Hills.

West Orange Times & Observer
News

By Megan Bruinsma |
October 10, 2025

Horizon's lighting speed placed girls and boys cross-country in first

Horizon High’s girls and boys cross-country teams both placed first in the Metro West Championship.

Sports
High Schools

By Megan Bruinsma |
February 17, 2026

Girls wrestling looks towards regionals after success in districts

The Knights finished as the district runners-up, and Windermere High’s wrestler Emily McCormack became the school’s first girl wrestler to reach 100 wins.

Sports
High Schools

By Gracie Santiago-Mazanec |
January 28, 2016

Students fight procrastination with simple strategies

Here are six steps to inspire and achieve results.

Winter Park - Maitland Observer
News

By Amy Quesinberry Price |
April 7, 2016

THESE TIMES: Thanks for the journey, Odyssey

Saying good-bye to my trusted family vehicle wasn't easy.

West Orange Times & Observer
Neighborhood

By Troy Herring |
October 28, 2020

Ocoee approves project budget, amendment for new city hall

The amendment covers the guaranteed maximum price for City Hall at $17,255,537.

West Orange Times & Observer
News

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