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By Steven Ryzewski |
February 1, 2018

Legacy High hoops having success under first-year coach | Observer Preps

Ahead of the 2017-18 season, Caio Santos was promoted to head coach. The Eagles have rewarded their new coach with a program-best 13 wins.

Sports

By Michael Eng |
August 6, 2025

GET YOUR TICKETS: Winter Garden Heritage Foundation to present ‘All Is Calm: The Christmas Truce of 1914’

Performed by Opera Orlando, this holiday event will take place at 7:30 p.m. Saturday, Dec. 20, and 2 p.m. Sunday, Dec. 21, at the Garden Theatre, 160 W. Plant St., Winter Garden.

Arts + Entertainment
Things to Do

By Amy Quesinberry Price |
August 24, 2022

West Orange community honors its hero, supports Fitzgibbon family

Foundation Academy held a candlelight vigil and Windermere organized a processional through town to honor fallen U.S. Army 1st Lt. Evan Patrick Fitzgibbon.

West Orange Times & Observer
News

By Catherine Kerr |
August 22, 2015

GALLERY: Back to School Bash at Zanders Park

West Orange Times & Observer
News

By Steven Ryzewski |
July 2, 2015

GALLERY: 11-Year-Old All-Stars at Bailey Park

West Orange Times & Observer
News

By Annabelle Sikes |
May 23, 2022

Parents speak out on new school development in Horizon West

With the upcoming opening of several new relief schools in Horizon West, parents offer their thoughts on how one, Hamlin Middle, will affect Bridgewater Middle.

West Orange Times & Observer
News

By Steven Ryzewski |
June 25, 2014

Girls lacrosse helmet mandate stirs controversy

West Orange Times & Observer
News

By Annabelle Sikes |
August 19, 2023

PHOTOS: Foundation Academy hosts Welcome Back BBQ

The school’s family fun event included live music, barbecue, photo opportunities and the chance to purchase fan gear from the shop.

Observer School Zone
Photos

By Annabelle Sikes |
April 6, 2023

DG Doughnuts hosting first Pop Up Ocoee Makers Market

Small business owners will gather in the city of Ocoee to sell items including candles, cookies, house plants, jewelry, candy and pies.

West Orange Times & Observer
News

By Megan Bruinsma |
February 10, 2026

West Orange high schoolers learn CPR from firefighters

Winter Garden Professional Firefighters Local 4947 taught CPR at West Orange Tuesday, Feb. 10.

Observer School Zone

By Zak Kerr |
August 25, 2015

More details confirmed for Dillard-S.R. 50 plaza

West Orange Times & Observer
News

By Sarah Wilson |
September 25, 2013

SunRail sneak peak

Winter Park’s railway station got its first visit from SunRail this Saturday.

Winter Park - Maitland Observer
News

By Amy Quesinberry Price |
March 18, 2015

Oakland residents attend work session for update on 'mold house'

West Orange Times & Observer
News

By Amy Quesinberry Price |
February 15, 2017

Is Oakland's ZIP code 34760 or 34787? Yes

In Oakland, the Winter Garden ZIP code is also used, but officials are worried about even more confusion as more residents and businesses come to the small town.