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By Michael Eng |
April 16, 2024

Winter Garden voters return to polls today

District 2 voters will select between incumbent Ron Mueller and challenger Iliana Ramos Jones in a runoff election.

West Orange Times & Observer
News

By Leticia Silva |
November 17, 2025

Support small businesses at Winter Garden's Small Business Saturday

The event will take place all day long Saturday, Nov. 29, in Downtown Winter Garden.

Arts + Entertainment
Things to Do

By Annabelle Sikes |
August 1, 2023

Dwight Jones celebrates 20 years with Baldwin Park

Dwight Jones started with Baldwin Park as the only maintenance employee in 2004. He celebrates his 20th anniversary with the community next month.

Baldwin Park Living

By Danielle Hendrix |
October 23, 2019

Windermere High legacy fund to host 'Downton Abbey' themed social

Guests at this year’s Windermere High Legacy Social will be transported to a 20th-century British tea room in honor of the ‘Downton Abbey’ theme.

Southwest Orange
News

By Eric Gutierrez |
November 13, 2019

Influencer of the Week: Kelley Bell, Horizon West Middle School

Kelley Bell enjoys being the go-to individual when students at HWMS need someone to talk to.

Southwest Orange
News

By Danielle Hendrix |
March 8, 2017

Keene's Crossing Elementary fourth-grader begins battle with osteosarcoma

Daniel Roberts, a fourth-grader at Keene’s Crossing Elementary, was diagnosed with osteosarcoma in his right leg in February.

Southwest Orange
News

By Leticia Silva |
October 1, 2025

Canine Companions celebrates 25 years of service

The organization has trained more than 8,300 service dogs since 1975.

West Orange Times & Observer
News

By Liz Ramos |
March 16, 2026

INFLUENCER OF THE WEEK: Debbie DiPrato, Sand Lake Elementary School

Debbie DiPrato is a third-grade teacher at Sand Lake Elementary School.

Observer School Zone
Influencer

By Isaac Babcock |
November 17, 2010

Knights tripped up by Eagles

On an undefeated conference streak, the Knights saw it end with a dramatic Southern Miss comeback

Winter Park - Maitland Observer
Sports

By Isaac Babcock |
November 2, 2011

Wildcats fight Wolves Nov. 4

The Wildcats are back in the win column and coming home for a district showdown against Timber Creek on Friday, Nov. 4.

Winter Park - Maitland Observer
Sports

By Observer Staff |
December 9, 2016

Local players help power West to victory in Central Florida All-Star Game -- Observer Preps

Wekiva's Trey McGee threw three touchdowns and Apopka's Deshawn Massey was the West Offensive MVP.

Sports
High Schools

By Steven Ryzewski |
November 19, 2015

Olympia football ends successful season with bowl win

Titans finish with 7-4 record in first season under head coach Kyle Hayes.

Sports

By Zak Kerr |
July 15, 2015

Primrose developers add wall, lighting limitations to plans

West Orange Times & Observer
News

By Emilee Jackson |
July 22, 2015

Haecker brothers share field for Squeeze, Auburn Tigers

Sports

By Troy Herring |
March 31, 2021

Sports Spotlight: Brianna Kulich, Windermere High flag football

Windermere High’s Brianna Kulich is the first Wolverine to commit to playing flag football at the collegiate level.

Sports

By Danielle Hendrix |
January 3, 2019

Sports Spotlight - Windermere Observer: Abdoulaye Thiam

Thiam, a junior guard for the Dr. Phillips boys basketball team, is off to a great start this season.

Sports

By Steven Ryzewski |
December 10, 2017

A well-earned state title for Dr. Phillips' Rodney Wells | Observer Preps

The Panthers' 17-7 victory in the FHSAA Class 8A State Championship Game Dec. 9 was also the culmination of a journey for the team's head coach that began when he was a teenager.

Sports

By Steven Ryzewski |
April 12, 2018

Sports Spotlight - Windermere Observer: Mia Williams

Seventh-grader Mia Williams is verbally committed to the Florida Gators and is making an impact for Windermere Prep this spring.

Sports

By Sam Albuquerque |
July 25, 2025

Windermere Prep hires state champion track-and-field coach

Former Olympia and Windermere coach Jason Greer returns to Southwest Orange to take over the Lakers’ programs.

Sports
High Schools

By Zak Kerr |
December 8, 2015

Windermere roads make the grade

Report gives town's paved roads a 77 on 100 scale, a mark many places could never achieve.

Southwest Orange
News

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