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By Liz Ramos |
November 25, 2025

Winter Garden, Ocoee fire departments help Santa come to town

Winter Garden’s Santa Run and Ocoee’s Operation Santa bring joy to the community.

West Orange Times & Observer
Neighborhood

By Clyde Moore |
July 24, 2012

Tuesdays Are In!

I think Tuesdays have finally arrived! I've noticed more and more Local stores promoting specials FOR Tuesdays. And with Totally LOCAL Tuesday set to go weekly . . . watch for more!

Winter Park - Maitland Observer
Opinion

By Tim Freed |
January 3, 2019

Winter Park's new library and event center to take shape in 2019

The Winter Park Canopy, the city’s new library and event center, will continue forward in the new year.

Winter Park - Maitland Observer
News

By Observer Staff |
February 8, 2012

Winter Park/Maitland real estate briefs

Cuhaci & Peterson Architects Engineers Planners did the design work for the new Truffle’s Grill restaurant that recently opened at the Winter Park Village.

Winter Park - Maitland Observer
Business

By Troy Herring |
July 1, 2020

Montgomery and Hefner join West Orange High School athletic department

New Athletic Director Lisa Montgomery returns to West Orange High School, while newcomer Jordan Hefner takes over the school’s volleyball program.

Sports

By Steven Ryzewski |
July 20, 2018

Ocoee Little League decides to transition, rebrand as West Orange Babe Ruth

Parents and board members from Ocoee Little League voted July 9 to transition the league from operating under Little League to Babe Ruth Baseball, where it will now be known as West Orange Babe Ruth.

Sports

By Danielle Hendrix |
January 17, 2018

Matthew's Steakhouse set to open in downtown Winter Garden

Matthew’s Steakhouse is one of the first tenants to open in the new building at 360 W. Plant St., across from Crooked Can Brewing Company and the Plant Street Market.

West Orange Times & Observer
News

By Tim Freed |
May 4, 2018

Orlando Ballet School dancers shine in New York

The Orlando Ballet School had an amazing showing at the Youth America Grand Prix finals in New York last month as Jolie Rose Lombardo finished first in the Junior Women division and Joseph Markey finished among the top 12 Senior Men.

Winter Park - Maitland Observer
News

By Tim Freed |
August 30, 2018

Trinity Preparatory School welcomes new senior chaplain the Rev. Richard Towers

The new Trinity Preparatory School senior chaplain arrives at the school after eight years as a military chaplain.

Winter Park - Maitland Observer
News

By Annabelle Sikes |
November 14, 2024

Orlando Health installs new tech for patients

Orlando Health is the first health care system in Florida to use the Hercules Patient Repositioning system, an automated device that repositions patients more efficiently in a hospital bed.

Southwest Orange
News

By Megan Bruinsma |
October 29, 2025

Ocoee waits on electing a firm for Forest Lake Golf Club

The Ocoee City Commission will select either Hampton Golf, Tamarack Golf Management or Ocoee Golf Holdings to run the club.

West Orange Times & Observer

By Sam Albuquerque |
August 31, 2025

West, Southwest Orange high school football Week 2 scores

Miss any of the area's Week 2 high school football action? Catch up with all the scores and notes from each area game right here.

Sports
High Schools

By Liz Ramos |
March 11, 2026

Windermere Prep students experience a whole new world

Students lived and worked alongside members of the Maasai for the first time while visiting Tanzania.

Observer School Zone

By Louis Roney |
May 4, 2011

Play On!

Differentiating between the truth and a lie is an art that every citizen of a free country should assiduously acquire

Winter Park - Maitland Observer
Opinion

By Michael Eng |
November 3, 2021

Observer goes BIG, makes move to broadsheet

While some newspapers across the country are shrinking — either by personnel, circulation, publication frequency or all-of-the-above — we are doing quite the opposite.

West Orange Times & Observer
Opinion

By Steven Ryzewski |
August 18, 2016

Challenge accepted: New West Orange offensive coordinator settles into role

Replacing one of the top offensive coordinators in Central Florida is no small task, but West Orange High O.C. Vernon Mitchell has made himself right at home in Winter Garden.

Sports
High Schools

By Steven Ryzewski |
August 25, 2016

Winter Garden Little League recognized for growing the game

Little League International informed Winter Garden Little League that it is one of the top leagues for new-player growth in the state and the nation over the past two years.

Sports
Youth Sports

By Tim Freed |
June 23, 2016

Mead Botanical Garden finishes Lake Lillian restoration project

City officials and residents gathered at Mead Botanical Garden last Thursday to celebrate the restoration of one acre of the Lake Lillian wetlands, as well as a new boardwalk path opening to the public.

Winter Park - Maitland Observer
News

By Steven Ryzewski |
August 2, 2016

Football fall practice begins with new regulations

New rules set by the FHSAA will limit how often and for how long teams can stage live contact drills at practice.

Sports
High Schools

By Sarah Wilson |
May 5, 2016

Maitland downtown goes back to drawing board

The Maitland City Council is again second-guessing what Independence Lane should look like, frustrating developers.

Winter Park - Maitland Observer
News

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