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By Troy Herring |
August 19, 2017

PHOTOS: Bishop Moore dominates Timber Creek -- Observer Preps

The Hornets enjoyed a solid 27-7 win over the Wolves in the Kickoff Classic

Winter Park - Maitland Observer
Sports

By Steven Ryzewski |
November 22, 2017

PHOTOS: Windermere High boys hoops debuts with preseason win | Observer Preps

In the program's first preseason game, the Wolverines defeated Cypress Creek 56-48.

Sports

By Troy Herring |
February 27, 2018

PHOTOS: Orangewood falls in 4-0 loss to Windermere Prep | Observer Preps

A big fourth-inning sparks the Lakers past the Rams

Winter Park - Maitland Observer
Sports

By Troy Herring |
August 25, 2018

PHOTOS: Winter Park blasts Lake Nona in 48-7 win | Observer Preps

An offensive explosion in the second quarter boosted the Wildcats to an easy win.

Winter Park - Maitland Observer
Sports

By Amy Quesinberry Price |
July 25, 2024

Horizon West Kids Expo returns

The back-to-school event in Hamlin will feature games and booths sharing available services for families.

West Orange Times & Observer
News

By Annabelle Sikes |
December 10, 2023

PHOTOS: 2023 city of Ocoee Jolly Jamboree

The event festivities included the Holiday Dog Parade, tree lighting, pictures with Santa and Mrs. Claus, games, carnival rides, downtown merchants, food trucks, and special performances.

West Orange Times & Observer
News

By Michael Eng |
December 15, 2023

PHOTOS: Santa’s Wonderland Village

Santa's Winter Wonderland Village is offering plenty of holiday fun for a few more days.

Arts + Entertainment

By Annabelle Sikes |
May 10, 2024

Burger King building undergoing renovations in Winter Garden

The previous Burger King building was demolished to rebuild a new 3,349-square-foot building with an expanded drive-thru.

West Orange Times & Observer
News

By Sam Albuquerque |
October 25, 2024

PHOTOS: Dillard Street Elementary's Boo Ball 2.0

Students filled Dillard Street Elementary for an evening full of candy, music and Halloween fun for the school's Boo Ball 2.0 event.

Observer School Zone
Photos

By Michael Eng |
November 12, 2024

Pedestrian dies in Southwest Orange crash

The 31-year-old woman from Germany was pronounced dead at Orlando Regional Medical Center.

Southwest Orange
News

By Michael Eng |
September 22, 2025

PHOTOS: West Orange High School 2025 Homecoming Parade

Warrior Nation took over downtown Winter Garden as West Orange High School celebrated its 2025 Homecoming Parade Thursday, Sept. 18.

Observer School Zone

By Megan Bruinsma |
September 17, 2025

PHOTOS: Water Spring's boys soccer surpasses Hamlin, 2-0

Water Spring Middle School’s boys soccer team shined bright in its first home game.

Sports

By Leticia Silva |
October 18, 2025

PHOTOS: Windermere Prep celebrates with homecoming parade and pep rally

Windermere Preparatory School held a parade and pep rally on the morning of Friday, Oct. 17 to celebrate homecoming.

Southwest Orange
Neighborhood

By Leticia Silva |
October 30, 2025

Windermere Prep to donate candy to U.S. troops

The school’s Parent Volunteer Association and the Wounded Warrior club organized Treats for Troops to gift U.S. Troops.

Southwest Orange
News

By Amy Quesinberry Price |
July 12, 2023

Windermere student earns Rotary’s first Global Grant

Sid Kasi, a student at Lake Highland Prep, has created a nonprofit organization with a network of other students to improve medical conditions in underdeveloped countries.