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By Amy Quesinberry Price |
September 17, 2025

Church of the Messiah in Winter Garden celebrates 75 years of faithful service

The Episcopal church is celebrating its anniversary with the Sunday evening service of supper and a one-minute message.

West Orange Times & Observer
News

By Steven Ryzewski |
August 3, 2016

Wave of recruiting commitments leads into start of fall practice

A combined four star student-athletes from Dr. Phillips and West Orange announced their intended college destinations last week.

Sports
High Schools

By Steven Ryzewski |
September 4, 2014

Prep volleyball roundup: West Orange, Legacy off to strong starts

Sports

By Troy Herring |
April 21, 2021

Orange Observer: High 5 — Thursday, April 22

In Windermere Prep softball’s 15-0 win over Orlando Christian Prep Thursday, April 15, Sophie Shaik led the way for the Lakers, going 3-fo-3 with two doubles, two RBIs and three-runs scored.

Sports

By Megan Bruinsma |
September 19, 2025

PHOTOS: Windermere Prep’s winning season came to a close

The Lakers lost their first game of the season, but rather than sulking, they’ll learn and grow.

Sports

By Annabelle Sikes |
August 18, 2021

Disney World parks update

Cirque du Soleil new show sets opening date and new Disney Genie+ reservation system.

West Orange Times & Observer
News

By Brittni Larson |
July 2, 2013

Senior builds homes for Habitat

This 71-year-old Orlando woman hasn’t let age stop her from volunteering or hopping on roofs.

Winter Park - Maitland Observer
Neighborhood

By Leticia Silva |
October 16, 2025

Oktoberfest brewing at Crooked Can

Crooked Can Brewing Co. is bringing back the biggest Oktoberfest in Central Florida for three days full of beer, food and entertainment as well as a new VIP area.

West Orange Times & Observer

By Amy Quesinberry Price |
August 3, 2022

SunRidge Middle getting edible garden

Fleet Farming and Fresh Kitchen have teamed up to bring the urban agriculture program to the Winter Garden school.

West Orange Times & Observer
News

By Isaac Babcock |
April 24, 2013

Rain stalls Tars comeback

Rollins came back just in time to tie St. Leo in their final meeting of a three game series.

Winter Park - Maitland Observer
Sports

By Tim Freed |
February 6, 2019

BREAKING NEWS: Winter Park woman charged with murder of husband

Danielle Redlick faces charges of second degree murder with a weapon and tampering with evidence.

Winter Park - Maitland Observer
News

By Megan Bruinsma |
December 18, 2025

FHSAA finalizes football classifications for 2026-28

FHSAA finalizes removing Class 7A for the 2026-28 seasons, placing four local schools in the same district.

Sports
High Schools

By Steven Ryzewski |
September 29, 2016

Undefeated Lakers readying for Legacy -- Observer Preps

After surviving its first close game of the season, Windermere Prep will travel to Ocoee to face the Eagles Friday.

Sports
High Schools

By Andrea Mujica |
September 22, 2023

ATHLETE OF THE WEEK: Sam Hoenstine

Hoenstine placed second in the 500-meter freestyle and the 200-meter IM during a tri-meet against Master’s Academy and Windermere Prep Thursday, Sept. 7.

Sports
Athlete of the Week

By Doug Kinson |
May 6, 2010

Maitland City Talk

I have always believed that our destinies are not driven solely by our desire to succeed, but by a higher force

Winter Park - Maitland Observer
News

By Isaac Babcock |
July 14, 2016

Winter Park Diamond Dawgs slowly rising in FCSL standings

The Winter Park Diamond Dawgs are still in trouble, despite having one of their best weeks so far this season.

Winter Park - Maitland Observer
Sports

By Troy Herring |
August 28, 2019

West Orange Observer: Sports Spotlight — Logan Jerrells

Logan Jerrells loves the game of golf and perfecting his technique at Windermere High School.

Sports

By Catherine Kerr |
December 8, 2015

Windermere school trains animators of tomorrow

Elite Animation's goal is to bring out students’ natural talent for digital and traditional animation while training them on the latest technology.

Arts + Entertainment
Arts + Culture

By Megan Bruinsma |
January 30, 2026

Ocoee youth basketball league recognizes Week 2 player and team of the week

Rock ‘N Rev’s Week 2 player of the week is Corbin Householder and team of the week is coach Massey.

Sports
Youth Sports

By Zak Kerr |
March 10, 2016

ATHLETE OF THE WEEK: Evan Anderson

Anderson has played center for Windermere Prep’s football team but more recently has dominated the 238-pound weight class for the boys weightlifting team. He has won his class in all four meets for the Lakers this season.

Sports
Athlete of the Week

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