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By Brittany Gaines |
October 29, 2017

PHOTOS: Windermere High "Truck"-or-Treat

The Windermere High's PTO hosted a trick-or-treat event on Thursday, Oct. 26

Southwest Orange
Neighborhood

By Michael Eng |
July 23, 2025

Cars and Coffee to celebrate third anniversary

The party will take place from 8 to 1030 a.m. Saturday, July 26, at 3118 Daniels Road, Winter Garden.

Arts + Entertainment
Things to Do

By Observer Staff |
January 23, 2013

Family Calendar

The Seasons 52 Park Avenue 5.2K presented by Florida Hospital will be Saturday, Jan. 26.

Winter Park - Maitland Observer
Neighborhood

By Observer Staff |
October 23, 2014

Southwest Fest opens Thursday

West Orange Times & Observer
Neighborhood

By Josh Garrick |
April 17, 2013

Josh Garrick: Culture Worthy of Your Calendar

“All Night Strut” is a combination of harmony and unbeatable energy opening at the Winter Park Playhouse on April 18.

Winter Park - Maitland Observer
Neighborhood

By Troy Herring |
June 30, 2021

Orange Observer: High 5 — Thursday, July 1

The Winter Garden Squeeze slipped by the Leesburg Lightning in a 1-0 win Saturday, June 26.

Sports

By Eric Gutierrez |
April 27, 2019

PHOTOS: Whispering Oak Elementary Spring Carnival 2019

Whispering Oak Elementary held its annual spring carnival on Friday, April 26.

West Orange Times & Observer
News

By Liz Ramos |
January 23, 2026

Portion of Tremaine Street in Winter Garden to be closed

Tremaine Street between South Boyd Street and South Main Street will be closed starting Monday, Jan. 26.

West Orange Times & Observer
News

By Tony Judnich |
September 4, 2014

Winter Garden WIC moves to new home

West Orange Times & Observer
News

By Kristy Vickery |
December 23, 2010

Leave it to the experts

Orange County Public Schools pilot a new program that has chefs serving up healthier cafeteria food

Winter Park - Maitland Observer
News

By Annabelle Sikes |
September 25, 2024

OCLS branches to close ahead of hurricane Helene impacts

All library branches and book drops will be closed beginning Sept. 26. OCLS plans to reopen Sept. 27 for normal business hours, conditions permitting.

West Orange Times & Observer
News

By Danielle Hendrix |
October 16, 2017

BLACK TIE: Central Florida Navy League’s Navy 242nd Birthday Ball

The ball, hosted by the Central Florida Navy League, celebrated the U.S. Navy’s 242nd birthday and also honored local U.S. Naval Sea Cadets.

Black Tie

By Michael Eng |
October 2, 2025

Isleworth mansion tops Windermere sales from Sept. 22 to 29

The home at 9743 Chestnut Ridge Drive, Windermere, sold Sept. 26, for $3,250,000.

Southwest Orange
Real Estate

By Observer Staff |
April 24, 2013

Calendar

See “Starbuck,” a Florida Film Festival award-winning film, at the Enzian.

Winter Park - Maitland Observer
Neighborhood

By Michael Eng |
February 27, 2016

GALLERY: Windermere Prep Spring Festival

One day after winning a state championship in basketball, the Windermere Prep community celebrated of night of family fun and fundraising at the school’s annual Spring Festival Feb. 26.

Southwest Orange
Neighborhood

By Eric Gutierrez |
March 27, 2020

PHOTOS: Keene’s Crossing Elementary Cougar Staff Parade

Keene's Crossing teachers and staff paraded through the Summerport community on Thursday, March 26.

West Orange Times & Observer
News

By Amy Quesinberry Price |
October 27, 2019

PHOTOS: Oakland Heritage & Wildlife Festival

Oakland Heritage & Wildlife Festival attendees had a fun and educational experience during the event held Saturday, Oct. 26.

West Orange Times & Observer
Neighborhood

By Steven Ryzewski |
May 26, 2018

PHOTOS: Legacy High Class of 2018 Graduation

Seniors for Legacy High School in Ocoee celebrated the conclusion of their high-school careers on-campus May 26.

West Orange Times & Observer
Neighborhood

By Michael Eng |
October 22, 2024

Crossline Community Church to host Fall Festival

The event will take place from 4 to 7 p.m. Saturday, October. 26, at Crossline Park, 17922 Old YMCA Road, Winter Garden.

Arts + Entertainment
Things to Do

By Observer Staff |
July 24, 2014

Calendar

Watch a free outdoor screening of “Muscle Beach Party” at this month’s Popcorn Flick in the Park, starting at 8 p.m. on Thursday, July 24, in Winter Park’s Central Park.

Winter Park - Maitland Observer
Neighborhood

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Results for:

PHOTOS: Windermere High "Truck"-or-Treat

Cars and Coffee to celebrate third anniversary

Family Calendar

Southwest Fest opens Thursday

Josh Garrick: Culture Worthy of Your Calendar

Orange Observer: High 5 — Thursday, July 1

PHOTOS: Whispering Oak Elementary Spring Carnival 2019

Portion of Tremaine Street in Winter Garden to be closed

Winter Garden WIC moves to new home

Leave it to the experts

OCLS branches to close ahead of hurricane Helene impacts

BLACK TIE: Central Florida Navy League’s Navy 242nd Birthday Ball

Isleworth mansion tops Windermere sales from Sept. 22 to 29

Calendar

GALLERY: Windermere Prep Spring Festival

PHOTOS: Keene’s Crossing Elementary Cougar Staff Parade

PHOTOS: Oakland Heritage & Wildlife Festival

PHOTOS: Legacy High Class of 2018 Graduation

Crossline Community Church to host Fall Festival

Calendar

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