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By Danielle Hendrix |
January 20, 2021

Winter Garden, church reach right-of-way agreement

The city will trade an acre of land near Tilden Road to First Baptist Winter Garden in exchange for right-of-way needed for the Dillard Street project.

West Orange Times & Observer
News

By Amy Quesinberry Price |
November 13, 2019

Windermere Union celebrates six decades of early education

The school began as a kindergarten program before OCPS added the grade to its elementary schools.

Southwest Orange
Neighborhood

By Danielle Hendrix |
December 19, 2019

Sibling duo aims to help preserve Windermere history

Windermere siblings Charles and Janine Matteson are working on their respective scouting projects, which will help preserve Windermere town history.

Southwest Orange
News

By Troy Herring |
June 26, 2017

Maitland 12U All-Stars pumped for pool play

Maitland has improved its pitching and hitting in anticipation of facing Oviedo in District 23 pool play.

Winter Park - Maitland Observer
News

By Harry Sayer |
January 19, 2019

Dommerich Elementary Storytelling Troupe students win state competition

Winter Park - Maitland Observer
News

By Tim Freed |
March 1, 2019

Winter Park hosts State of the City Luncheon

The event gave residents an update on the city and honored some of its hardest working employees.

Winter Park - Maitland Observer
News

By Gabby Baquero |
September 28, 2017

Westside Shoppes in Horizon West nearly tenant-ready, developer says

The long-awaited Westside Shoppes center is less than two weeks away from being turned over to its tenants, who will open for business soon.

Southwest Orange
News

By Annabelle Sikes |
October 27, 2024

City of Winter Garden Fiscal Year ’24-’25 budget breakdown

City commissioners voted to set the budget at $158,251,629 with a millage rate of 4.5.

West Orange Times & Observer
News

By Troy Herring |
November 26, 2019

West Orange Times basketball preview: West Orange Warriors have big plans for new season

It’s a new year, new coach and basically new team for the West Orange High girls basketball team, which has its sights on a playoff run.

Sports

By Tim Freed |
January 5, 2018

Winter Park City Commissioners weigh in on development and preserving the city's charm

The Observer reached out to all five members of the Winter Park City Commission to get their thoughts.

Winter Park - Maitland Observer
News

By Michael Eng |
October 9, 2014

Windsor Landing home tops September sales in Ocoee

West Orange Times & Observer
Real Estate

By Sam Albuquerque |
February 19, 2025

Fly like the Eagles: CFCA boys hoops’ new culture leads incredible turnaround

In 2023-24, Central Florida Christian Academy boys basketball finished the season 6-19. This year, with a new coach and culture, the Eagles are three wins from a state title.

Sports
High Schools

By Liz Ramos |
July 24, 2025

First West Orange High graduating class to celebrate 50 years

The Class of 1976 reflects on being the first to graduate from West Orange High.

West Orange Times & Observer
News

By Liz Ramos |
November 3, 2025

INFLUENCER OF THE WEEK: Alyson Hupp, Windermere Elementary School

Alyson Hupp is in her first year as a board member for Windermere Elementary School’s Parent-Teacher Organization serving as the school improvements director.

Observer School Zone
Influencer

By Andrea Mujica |
September 1, 2022

Foundation alum Denzel Irvin joins the Lions coaching staff

Only four months after he received a new heart, Denzel Irvin is helping current Lions as defensive back coach.

West Orange Times & Observer
News

By Danielle Hendrix |
January 5, 2017

FORECAST: Building Windermere Wolverine pride

With Windermere High School set to open its doors this August, shaping tradition and Wolverine pride is on the agenda as a community effort.

Southwest Orange
News

By Isaac Babcock |
April 20, 2017

The Golden Ticket

College Park pastrami man on the verge of his TV debut

Winter Park - Maitland Observer
News

By Annabelle Sikes |
July 13, 2024

Will new Florida law reduce street racing?

Residents hope a new Florida law pertaining to harsher and swifter consequences for street racing will serve as a deterrent for offenders in Horizon West and beyond.

Southwest Orange
News

By Liz Ramos |
August 6, 2025

PopStroke opens in Hamlin

Hamlin's PopStroke, which opened Wednesday, Aug. 6, will feature new technology and food and drink items unique to the location.

Southwest Orange
News

By Amy Quesinberry Price |
March 22, 2023

Agoraphobia: Bound by home's four walls

For people like Ye’vette Toms, who has agoraphobia, getting an identification card is nearly impossible. A mobile unit will be in Winter Garden next week to assist residents who are unable to visit the DMV.

West Orange Times & Observer
News

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