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By Megan Bruinsma |
September 4, 2025

Construction to begin on extension project connecting Orange and Lake counties

Orange County Public Works proceeding with construction on New Independence Parkway extension project to connect Lake and Orange county.

Southwest Orange
News

By Leticia Silva |
November 4, 2025

New shops coming to Winter Garden

Winter Garden is getting new shops in the spring of 2026 at 186 S. Main Street.

West Orange Times & Observer
News

By Amy Quesinberry Price |
July 13, 2023

Oakland celebrates citrus history through art

Forty adult and youth artists are participating in the heritage center’s current exhibition that pays tribute to the town’s citrus history.

West Orange Times & Observer
News

By Leticia Silva |
September 25, 2025

Car purchase in Ocoee leading to lawsuits

Winter Garden family purchased a vehicle for a struggling college student from an Ocoee car lot. Days later, its transmission failed.

West Orange Times & Observer
News

By Observer Staff |
August 12, 2020

LaunchED@Home presents teaching, learning challenges

Teachers and students are back to school and learning their way around OCPSLaunchED@Home.

West Orange Times & Observer
News

By Steven Ryzewski |
August 19, 2018

Windermere Prep welcomes new strength coach, athletic trainer to campus | Observer Preps

The athletic community at Windermere Prep has been abuzz about two high-profile hires from this summer — new athletic trainer Nathan Peck and strength coach Micah Kurtz.

Sports

By Steven Ryzewski |
April 26, 2016

SIDELINE SCENE: Attempting perspective on the ‘school choice bill’

The massive education bill signed into law recently by Gov. Rick Scott has important implications for high school sports in Florida.

Sports

By Tim Freed |
August 29, 2019

Safety, traffic changes coming to Horizon West Middle School

New signage and potentially more crossing guards are coming to Horizon West Middle School to assuage traffic and safety concerns.

Southwest Orange
News

By Christina Rordam |
May 12, 2016

Christina Rordam: Condominium conundrum

Condos have gotten a bad rap since the crash, but do they really deserve it?

Winter Park - Maitland Observer
Neighborhood

By Troy Herring |
October 14, 2020

Disney layoffs take toll on locals, economy

Two weeks ago, thousands of Disney employees were laid off as the company deals with financial challenges caused by COVID-19. The impact — on both individuals and the local economy — is devastating.

Southwest Orange
News

By Danielle Hendrix |
June 22, 2017

Adopted Windermere siblings defy odds, graduate from Olympia High

Tori and Jayden Steele have defied the odds all their lives — most recently, that includes graduating from Olympia High.

Southwest Orange
News

By Amy Quesinberry Price |
April 7, 2016

THESE TIMES: Thanks for the journey, Odyssey

Saying good-bye to my trusted family vehicle wasn't easy.

West Orange Times & Observer
Neighborhood

By Steven Ryzewski |
August 18, 2016

Dr. Phillips alumni now teammates on UCF football team

Freshman receiver Jaquarius "Q" Bargnare and senior quarterback Nick Patti are each competing for starting jobs in the new-look Knights offense.

Sports
High Schools

By Sarah Wilson |
September 1, 2016

City approves Maitland Estate apartments

Twelve years ago redeveloping Maitland’s downtown was still a dream. That vision came closer to reality last week with the approval of Maitland Estates.

Winter Park - Maitland Observer
News

By Sarah Wilson |
November 19, 2014

Maitland approves downtown redevelopment plan

The project will transform the block between Packwood and Horatio avenues sandwiched between U.S. Highway 17-92 and Independence Lane.

Winter Park - Maitland Observer
News

By Amy Quesinberry Price |
March 19, 2019

Landeavor assures residents: No changes to Oakland Park

The new developer of Oakland Park, which lies in both Oakland and Winter Garden, is vowing to stick to the agreement signed by previous owners of the project.

West Orange Times & Observer
News

By Michael Eng |
November 27, 2017

Jackie Fanara named new publisher of Winter Park/Maitland Observer

Jackie Fanara, a veteran community newspaper executive, served as publisher of the East County Observer in Manatee County.

Winter Park - Maitland Observer
News

By Isaac Babcock |
March 23, 2011

Seeing green in Hannibal Square

Wine filled glasses and beer made a brief appearance at The Hannibal Square Wine Tasting & St. Patrick’s Day Street Party on March 17 on New England Avenue.

Winter Park - Maitland Observer
Neighborhood

By Jeffrey Blydenburgh |
July 13, 2011

Mead from the sky

Mead Garden from a ladder truck

Winter Park - Maitland Observer
Neighborhood

By Tim Freed |
August 13, 2019

PHOTOS: Keene's Crossing Elementary School bike rodeo

The elementary school hosted a bike safety event leading up to the new school year.

Southwest Orange
News

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