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By Megan Bruinsma |
September 18, 2025

Windermere Prep's offseason growth is reflecting this season

At the core of Windermere Prep’s success this season is restarting their mentality after each game and offseason growth.

Sports

By Observer Staff |
May 20, 2022

Legacy High School: Note from the principal

All of us at Legacy are so proud of you and we believe in you. Congratulations and Soar High!  

West Orange Times & Observer
Neighborhood

By Observer Staff |
February 16, 2017

Rollins College to host candidate forum

Winter Park's political season is heating up, with another candidate forum between incumbent City Commissioner Greg Seidel and challenger Wes Naylor.

Winter Park - Maitland Observer
News

By Annabelle Sikes |
March 22, 2024

School upgrades spark contrasting opinions

Holy Family Catholic School is proposing to upgrade its existing track-and-field and sports facilities. However, some neighbors have concerns.

Southwest Orange
News

By Liz Ramos |
August 20, 2025

Windermere Town Hall bathroom plans no longer clogged

Windermere Town Council votes to have the restrooms constructed adjacent to the library.

Southwest Orange
News

By Megan Bruinsma |
February 11, 2026

Winter Garden Heritage Foundation serves up community through pickleball

WGHF will host the inaugural Paddles for the Past pickleball tournament Saturday, Feb. 28.

West Orange Times & Observer
Neighborhood

By Louis Roney |
December 1, 2010

Play On!

Obama’s thoughts and words

Winter Park - Maitland Observer
Opinion

By Isaac Babcock |
February 9, 2011

Get money to stay

The City Commission will decide whether to offer incentives to businesses that stay in town

Winter Park - Maitland Observer
Business

By Observer Staff |
April 6, 2011

Our Observation

Stop the thought police

Winter Park - Maitland Observer
Opinion

By Josh Garrick |
December 21, 2011

Culture Worthy of your calendar

Culture for the holidays

Winter Park - Maitland Observer
Neighborhood

By Danielle Hendrix |
August 29, 2016

Gotha campground to host peace camp

The Church of the Brethren’s Action for Peace team is hosting its 10th annual Family Peace Camp at Camp Ithiel in Gotha.

West Orange Times & Observer
News

By Christina Rordam |
June 12, 2013

Smart homes: Products for the digital age

When I look back 10, even 5 years ago, I am amazed at how modern and automated our world has become.

Winter Park - Maitland Observer
Neighborhood

By Bob Franken |
November 6, 2013

Bob Franken: Covert health care

The excuse that the all-important website was a massive undertaking doesn’t hold a lot of water when we remember that there have been three full years to get it up and running.

Winter Park - Maitland Observer
Neighborhood

By Sarah Wilson |
June 25, 2015

Budget balloons for Maitland boardwalk project

The boardwalk will connect residents living to the west of the railroad tracks to the station by cutting through the wooded area where Marion Way intersects with Robinhood Drive in the Greenwood Gardens neighborhood through to the SunRail station plat...

Winter Park - Maitland Observer
News

By Isaac Babcock |
December 12, 2012

Four projects pass in Winter Park

Construction is one step closer to reality for four projects in Winter Park after the City Commission voted in favor of a YMCA expansion, an affordable senior living facility, a tavern and a road beautification project Monday.