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By Steven Ryzewski |
July 25, 2018

Final few days of regular season loom large for Squeeze

Depending upon how the Winter Garden Squeeze fare in their final five games, they could ascend as high as third place — or fall out of the Florida Collegiate Summer League Playoffs, completely.

Sports

By Steven Ryzewski |
August 24, 2017

Observer Preps 2017 Football Preview: Dr. Phillips Panthers

Exciting mix of returners, newcomers keep expectations high on campus in Dr. Phillips.

Sports

By Gabby Baquero |
May 27, 2017

3 injured in east Winter Garden shooting

West Orange Times & Observer
News

By Sam Albuquerque |
August 23, 2024

Severe weather postpones area season opening high school football games

Thanks to rain and lightning around West, Southwest Orange County area high school football games have been postponed or canceled.

Sports
High Schools

By Michael Eng |
March 31, 2025

Cypress Shores home tops Southwest Orange sales from March 24 to 30

The home at 10409 Trout Road, Orlando, sold March 24, for $3,750,000.

Southwest Orange
Real Estate

By Michael Eng |
April 3, 2025

Isleworth estate tops Windermere sales from March 24 to 30

The home at 5518 Worsham Court, Windermere, sold March 28, for $6,175,000.

Southwest Orange
Real Estate

By Leticia Silva |
June 16, 2025

Bird center to host event on bald eagles in Oakland

The town of Oakland will hold an event to inform the community on the bald eagle community.

West Orange Times & Observer

By Michael Eng |
July 31, 2025

Isleworth estate tops Windermere sales from July 21 to 27

The home at 9724 Chestnut Ridge Drive, Windermere, sold July 25, for $4,330,000.

Southwest Orange
Real Estate

By Leticia Silva |
October 7, 2025

Car crashes into 77-year-old man's house; sends him to hospital

A 20-year-old man is now facing charges of leaving the scene of a crash with injuries and hit-and-run involving property damage.

West Orange Times & Observer
News

By Megan Bruinsma |
April 3, 2026

OARS opens championship season strong at FSRA Central District Championship

The FSRA Central District Championship was held at Lake Minneola Waterfront Park in Clermont Saturday, March 28.

Sports
Youth Sports

By Amy Quesinberry Price |
May 15, 2024

1946-2024: Richard Hudson ran neighborhood tire shop for 36 years

The businessman operated Hudson Tire on Story Road in Winter Garden for more than two decades.

West Orange Times & Observer
News

By Annabelle Sikes |
February 18, 2022

County decision could solve Bird Island dilemma

The Orange County Commission is scheduled to discuss a measure regarding the loud, alcohol-infused parties, illegal Jet skis and littering on the island.

West Orange Times & Observer
News

By Zak Kerr |
March 26, 2015

Windermere native, former Olympia teacher sets course record at marathon in Antarctica

Southwest Orange
Neighborhood

By Tim Freed |
April 9, 2014

Mead Garden restoration plans could transform wetland

A restoration project for the Lake Lillian Wetlands at Mead Botanical Garden could bring new life to the dark, murky habitat – an effort that would eliminate other wildlife and vegetation in the process.

Winter Park - Maitland Observer
News

By Eric Gutierrez |
April 22, 2020

Garden Theatre hires first education director

Nick Bazo spent the last 11 years in Boston serving as the director of programs for The Theater Offensive.

Arts + Entertainment
Arts + Culture

By Troy Herring |
June 17, 2020

New bill could affect high school athletes

A recent bill signed by Florida Gov. Ron DeSantis would go into effect July 1, 2021, and allow college athletes to be paid for name, image and likeness.

Sports

By Amy Quesinberry Price |
July 17, 2024

Residents speak out against downed trees in Oakland

Folks argue the the town of Oakland, a Tree City USA for more than 20 years, has an obligation to keep its foliage intact when it allows developers to come into the town to build neighborhoods.

West Orange Times & Observer
News

By Megan Bruinsma |
November 11, 2025

Playoffs are set for West, Southwest Orange football teams

Three West and Southwest Orange teams enter the 7A Regional Quarterfinals, while Foundation Academy and Windermere Prep wrap up the SSAA brackets.

Sports
High Schools

By Annabelle Sikes |
April 15, 2022

F45 celebrates first anniversary in Baldwin Park

In its first year, owners Robert and Tara Strauss have seen their fitness program create a community.

Baldwin Park Living

By Andrea Mujica |
September 28, 2022

THE EQUALIZER: Horizon High School kicker equalizes field position for the Hawks.

Currently ranked a top kicker in the nation, Horizon High kicker Daniel Case Melo Porto is one of the Hawks’ most potent weapons.

West Orange Times & Observer
News

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