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By Leticia Silva |
December 9, 2025

New manager of HR and payroll at Oakland

Ashly Woosypiti will serve as the town's new human resources and payroll manager.

West Orange Times & Observer
News

By Amy Quesinberry Price |
January 20, 2021

A life fit for a King

The King family has been in Winter Garden for more than a century after Jimmy and Eddie Mae King established roots here. Many of their descendants continue to break barriers.

West Orange Times & Observer
Neighborhood

By Sam Albuquerque |
October 3, 2024

TFA football’s Evan James, Demetrice McCray key to historic passing attack

The First Academy receivers Evan James, Demetrice McCray and QB Salomon Georges Jr. are having a historic year through the air.

Sports
High Schools

By Annabelle Sikes |
October 9, 2024

Horizon West resident flies to North Carolina, delivers essential items

Resident Corbin Clouser, with the help of his family and other community members, flew essential supplies and resources to those in need in North Carolina following Hurricane Helene.

Southwest Orange
Neighborhood

By Observer Staff |
December 1, 2010

Our Observation

Reporting, or espionage?

Winter Park - Maitland Observer
Opinion

By Amy Quesinberry Price |
September 2, 2020

"Hello, Dolly!" marks return of live shows to Garden Theatre

“Hello, Dolly!” is the Garden Theatre's first stage production after the pandemic forced the temporary closure of businesses and activities this summer.

Arts + Entertainment
Arts + Culture

By Zak Kerr |
June 4, 2015

Spring Lake Elementary walks to support one of its own

West Orange Times & Observer
Neighborhood

By Troy Herring |
April 28, 2021

County updates Ocoee on intersection upgrades

Four problematic intersections in city limits will be getting upgrades to make them safer and more efficient.

West Orange Times & Observer
News

By Harry Sayer |
May 10, 2019

Winter Park Farmers’ Market celebrates 40th Anniversary

These days, the Winter Park Farmers’ Market draws thousands of locals and tourists alike — a far cry from its humble beginnings on a gravel parking lot.

Winter Park - Maitland Observer
News

By Eric Gutierrez |
December 18, 2019

Custom cupcakery sweetens Winter Garden

Sweet Dee’s Cupcakery and Custom Cakes opened Nov. 9 on Main Street.

West Orange Times & Observer
News

By Amy Quesinberry Price |
August 16, 2017

Gracemarie Howland is new principal at Lakeview Middle

Howland wants to inspire her students to strive to be the best during the 2017-18 school year.

West Orange Times & Observer
Neighborhood

By Eric Gutierrez |
January 16, 2019

Pizzeria heats up W.G. dining scene

1000 Degrees Pizza owner Matthew Peach went from sweeping sidewalks at Walt Disney World to owning a number of businesses throughout the country.

West Orange Times & Observer
News

By Steven Ryzewski |
April 13, 2017

Olympia water polo seniors complete journey to the top, one step at a time -- Observer Preps

The Titans' Class of 2017 lost in the state quarterfinals as freshmen, in the state semifinals as sophomores, in the state championship as juniors — and now they're FHSAA State Champions.

Sports

By Annabelle Sikes |
October 5, 2023

Windermere to host first Daddy Daughter Dance

Mothers in Windermere are coming together to plan the first Daddy Daughter Dance hosted by the town.

Southwest Orange
News

By Amy Quesinberry Price |
September 25, 2014

Winter Garden offers new beginning for thrift store

West Orange Times & Observer
Business

By Sam Albuquerque |
April 22, 2024

PHOTOS: Dr. Phillips Little League’s grand opening ceremony for new $9.25 million facility

After years of playing its games next door to the Dr. Phillips YMCA, DP Little League has moved into a brand new ball field complex on Bissell Street.