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By Danielle Hendrix |
October 4, 2018

Windermere jeweler creates $200,000 Hope Tiara to benefit Runway to Hope

Windermere resident Virginia Ann Rodriguez, owner of Gianni Vincent Jewellers, designed and is renting out the $200,000 Hope Tiara for pediatric research.

Southwest Orange
News

By Amy Quesinberry Price |
June 26, 2024

Oakland Society aims to aid others

Anne Fulton started the group in the town after discovering residents had small needs that weren’t being met. She decided to rally her neighbors to assist those in need.

West Orange Times & Observer
News

By Sam Albuquerque |
September 16, 2024

FRIDAY NIGHT FIVE: Olympia football's young core gaining experience, maturity

Observer Sports Editor Sam Albuquerque serves up his top five observations from the area's high school football games, every Monday morning.

Sports
High Schools

By Liz Ramos |
February 10, 2026

Nonprofits to host inaugural Boots and Salutes in Windermere

Proceeds from the event will go toward sponsoring the travel for local first responders and veterans to go to the ranch for Healing Warriors Week at Wind River Ranch in Estes, Colorado.

Southwest Orange
Neighborhood

By Leticia Silva |
March 11, 2026

Fostering creativity through children's books

Windermere’s Megan Morris wrote “How to Catch a Leprechaun,” teaching kids to have fun while celebrating St. Patrick’s Day.

Southwest Orange

By Andrea Mujica |
June 15, 2022

THRICE IS NICE: Windermere Prep 4x800 track and field team breaks school record

The Lakers 4x800 track-and-field boys relay team broke the school record three times and already is planning on doing it a fourth time.

Southwest Orange
News

By Isaac Babcock |
February 5, 2014

Where did 'Lakemont Jack' go?

He’s probably waved at you before and you didn’t know it. He’s the man in tennis shoes taking those remarkably spritely steps as cars blur by.

Winter Park - Maitland Observer
Neighborhood

By Isaac Babcock |
February 5, 2014

Winter Park's Lakemont Jack says hello

He’s probably waved at you before and you didn’t know it. He’s the man in tennis shoes taking those remarkably spritely steps as cars blur by.

Winter Park - Maitland Observer
Neighborhood

By Amy Quesinberry Price |
January 6, 2021

FORECAST: Tucker Ranch to become health, wellness park

A partnership between the city of Winter Garden and local health care stakeholders will turn Tucker Ranch into the first comprehensive physical and mental wellness park in the nation.

West Orange Times & Observer
News

By Brittany Gaines |
January 8, 2018

FORECAST 2018: Bobby Olszewski

Since elected as the House Representative for District 44, Bobby Olszewski has filed five bills, three appropriations and plans to run for re-election in 2018.

West Orange Times & Observer
News

By Amy Quesinberry Price |
February 21, 2018

Calendar for the week of 2-22-18

Find out what's going on this week in West Orange County.

West Orange Times & Observer
Neighborhood

By Annabelle Sikes |
October 10, 2024

Garden Theatre's closure shocks community

The Winter Garden theater has announced it is closing due to insurmountable financial challenges.

West Orange Times & Observer
News

By Megan Bruinsma |
November 11, 2025

At 13, Noah O'Brien's making waves in wakeboarding

The First Academy student Noah O’Brien’s hobby led him to winning the Wakeboarding World Championship four years later.

Sports
Youth Sports

By Liz Ramos |
October 30, 2025

Winter Garden nonprofits help woman build her future

With the help of Matthew's Hope and West Orange Habitat, Sherry Easley will have a place to call her own for the first time in her life.

West Orange Times & Observer
Neighborhood

By Liz Ramos |
November 18, 2025

Windermere still waiting for state, federal reimbursement funds

Windermere Town Council approved additional funding of up to $2 million to cover reimbursable costs for town projects as the town waits for funding from the state and federal government.

Southwest Orange
News

By Andrea Mujica |
June 1, 2023

Foundation Academy softball poised for success next season

For the first time in school history, the Lions softball team made it all the way to the Final Four.

Sports

By Annabelle Sikes |
September 3, 2023

Winter Garden hosts first FY 2023-24 budget workshop

The General Fund revenues budget for Fiscal Year 2023-24 totals $82,768,911. This is an increase of $31,920,525, or 63%, when compared to the budget for the prior year.

West Orange Times & Observer
News

By Observer Staff |
October 27, 2010

Letters to the Editor

Letters from Herbert Weiss, Robert S. Lemon, Jr., Marti Miller, David Akins and Nancy Rudner Lugo

Winter Park - Maitland Observer
Opinion

By Louis Roney |
March 4, 2010

Play on

Carolyn Cooper gets kicks from hard jobs

Winter Park - Maitland Observer
Opinion

By Annabelle Sikes |
April 13, 2023

Windermere Prep leaders discuss safety, growth at State of the School

Head of School Dr. Mitchell Salerno shared highlights from the year, areas of opportunity and growth, academic insights, and campus improvements.

Observer School Zone
News

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