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By Troy Herring |
May 12, 2021

Brian Simmons ready to lead Lakers football into new era

As Windermere Prep kicks off spring football, first-year head coach Brian Simmons is ready to put his mark on the program.

Sports

By Zak Kerr |
December 30, 2015

Computation education

With a focus on preparing children for the technological future, Ashley Moore has taught many students computer coding from her Windermere home — some for free.

Southwest Orange
Neighborhood

By Liz Ramos |
January 14, 2026

Good & faithful servant: Winter Garden's First Baptist Church pastor retires

Tim Grosshans says goodbye to the "sweetest fellowship" after nearly 17 years serving as pastor.

West Orange Times & Observer
Neighborhood

By Sam Albuquerque |
July 30, 2025

Trio of West Orange alums thrive as Winter Garden Squeeze interns

With three of the Winter Garden Squeeze’s four interns being locals, the group was crucial in the team’s operations in 2025.

Sports

By Harry Sayer |
January 11, 2019

Mead Botanical Garden to debut renovated clubhouse

The botanical garden’s clubhouse will open Jan. 22 with a ribbon-cutting ceremony.

Winter Park - Maitland Observer
News

By Howard Schieferdecker |
June 5, 2013

Maitland City Talk

We dare you to make the right choices.

Winter Park - Maitland Observer
Opinion

By Gabby Baquero |
July 19, 2017

Windermere braces for tighter budget

The Windermere town manager predicts the council might need to put some projects on hold due to insufficient funding and a need to prioritize.

Southwest Orange
News

By Amy Quesinberry Price |
March 27, 2024

Development coming to Colonial in Oakland

Two projects totaling nearly 27 acres have come before the Oakland Town Commission for approval.

West Orange Times & Observer
News

By Annabelle Sikes |
October 14, 2023

City of Winter Garden sets Fiscal Year 2023-24 budget

City commissioners voted to set the budget at $138,019,903 with a millage rate of 4.5.

West Orange Times & Observer
News

By Amy Quesinberry Price |
January 3, 2024

FORECAST 2024: Meet new West Orange Chamber president Stephen Lewis

Stephen Lewis is hoping his age will be a benefit to the chamber and his experience can help him bridge the gap between the generations of business men and women who are members of the organization.

West Orange Times & Observer
News

By Andrea Mujica |
June 8, 2022

Spring games offers glimpse into fall football

West Orange- and Southwest Orange-area teams are moving into summer conditioning to prepare for the 2022 season.

West Orange Times & Observer
News

By Carmen Carroquino |
June 3, 2010

Putting community in Winter Park

A 38,000-square-foot, $9.1 million community center is being built at the former center's site

Winter Park - Maitland Observer
News

By Jim Carchidi |
November 23, 2021

Habitat for Humanity brings West Orange family home for the holidays

Thanks to the organization, a mother and daughter are settling in for a better future.

West Orange Times & Observer
News

By Tim Freed |
November 12, 2015

Winter Park Commission makes first vote on historic preservation ordinance

Property rights and historic preservation clashed on Monday night as Winter Park City Commissioners took their first look at a new controversial historic preservation ordinance – and made several policy-shaking votes.

Winter Park - Maitland Observer
News

By Brittni Larson |
October 1, 2014

Rollins College students live-tweet history

A Rollins College class took social media’s “throwback” posting theme to the next level last week, treating the public to a day of tweeting and instagramming the news like it was 1893.

Winter Park - Maitland Observer
Neighborhood

By Troy Herring |
December 5, 2018

Brian Hoff takes helm of Lakers basketball program | Observer Preps

New Windermere Prep head coach Brian Hoff ushers in a new era of Lakers basketball.

Sports

By Harry Sayer |
February 9, 2019

Will Watts takes helm at Maitland Fire-Rescue

Will Watts has served the city for nearly 18 years. He takes over for Kim Neisler, who retired Jan. 4.

Winter Park - Maitland Observer
News

By Observer Staff |
December 29, 2015

Best of news 2015

Revisit the stories that had your neighbors talking in 2015.

Winter Park - Maitland Observer
Neighborhood

By Observer Staff |
July 27, 2011

Obituaries

We remember

Winter Park - Maitland Observer
Neighborhood

By Michael Eng |
December 22, 2024

Foundation Academy mourns loss of football coach

Foundation alum Denzel Irvin received a heart transplant in 2022 and returned to his alma mater to coach. He died Sunday, Dec. 22, 2024, due to heart complications.

West Orange Times & Observer
News

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