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By Michael Eng |
June 10, 2025

Village Point Church plans first Summer Blitz

The weekend-long event will feature a Night of Worship, Village Party and Father’s Day BBQ.

Arts + Entertainment
Things to Do

By Leticia Silva |
July 10, 2025

PHOTOS: Windermere Prep School hosts summer camp

On Thursday, July 10, kids attending camp were able to go on water inflatables and enjoy the sun.

Southwest Orange
Neighborhood

By Leticia Silva |
July 26, 2025

PHOTOS: Cars and Coffee celebrates its three-year anniversary

Located at 3118 Daniels Road, the car show featured a variety of cars and trucks.

West Orange Times & Observer
Neighborhood

By Sam Albuquerque |
November 15, 2024

Foundation Academy Athletics celebrates historic National Signing Day

With its first-ever D-I softball signee and biggest class of baseball players heading to college for the sport, Foundation Academy saw nine total athletes sign to play at the next level.

Sports
High Schools

By Amy Quesinberry Price |
October 17, 2024

Horizon West Middle has new principal

Andrew Agudo has assumed the top role at the school near Windermere.

West Orange Times & Observer
News

By Megan Bruinsma |
October 21, 2025

Two West, Southwest Middle Schools bring home soccer district titles

SunRidge Middle School’s girls soccer team won championship and Horizon West Middle School's boys soccer finished as runner ups.

Sports
Youth Sports

By Leticia Silva |
September 25, 2025

Jaleo at Disney Springs to host cooking event

The Disney Springs restaurant will celebrate National Paella Day with a cooking event Sunday, Sept. 28, at 1482 E Buena Vista Drive, Orlando.

Southwest Orange
News

By Megan Bruinsma |
October 1, 2025

Crooked Can teaming up with the Orlando Magic for kickoff party

Crooked Can Brewing Company is hosting an Orlando Magic season kickoff party with a DJ, trivia and special guests.

Arts + Entertainment
Things to Do

By Megan Bruinsma |
February 20, 2026

Dr. Phillips hires Darryl Monroe as offensive coordinator

The Dr. Phillips alumni will step on the Panthers’ football team’s sideline as an offensive coordinator.

Sports
High Schools

By Megan Bruinsma |
January 8, 2026

Olympia High athletic director Russell Wambles retires

After almost 29 years in athletic administration, Russell Wambles retired.

Sports
High Schools

By Liz Ramos |
January 12, 2026

Windermere residents under precautionary boil water advisory

Residents on West Second Avenue and Pine Street are under the advisory from 7 a.m. to 7 p.m. Tuesday, Jan. 13.

Southwest Orange
News

By Liz Ramos |
March 5, 2026

Windermere Preparatory School announces head of school

Alex Birchenall has been appointed as the next head of school. He has been serving as the interim head of school and previously served as the assistant head of school.

Observer School Zone
News

By Leticia Silva |
April 12, 2026

PHOTOS: Spring Fever in the Garden 2026

Thousands came to Plant Street to enjoy the annual festival bloom for two days.

West Orange Times & Observer
Neighborhood

By Leticia Silva |
April 6, 2026

Orange County Commissioners to discuss zoning tobacco shops

The discussion will take place during the Board of County Commissioners meeting at 9 a.m., Tuesday, April 7.

West Orange Times & Observer
News

By Megan Bruinsma |
April 10, 2026

West Orange celebrates boys lacrosse team awards

The Warriors named the MVP, offensive and defensive player of the year, and more for the 2025-2026 season.

Sports
High Schools

By Zak Kerr |
February 25, 2016

Windermere Town Council candidates Q&A

Three candidates vie for two spots in the March 15 election. Here are their answers to some of the most pressing questions facing the town of Windermere. Candidates are in alphabetical order.

Southwest Orange
News

By Observer Staff |
January 18, 2012

Calendar of events

Self-taught and nationally recognized African-American artist “Missionary” Mary Proctor will speak at the opening reception for an exhibit of her highly distinctive work.

Winter Park - Maitland Observer
Neighborhood

By Observer Staff |
September 15, 2016

Calendar

For the 12th year in a row, the Winter Park Public Library will hold its annual Bash for Books.

Winter Park - Maitland Observer
Neighborhood

By Gabby Baquero |
September 28, 2017

Eddy Dominguez replaces Paul Chandler in HD 44 race

Democrats chose Dominguez to face Robert “Bobby”Olszewski in the District 44 special election.

West Orange Times & Observer
News

By Andrea Mujica |
May 12, 2022

TWICE AS NICE: Windermere High School and The First Academy captured district titles in baseball and softball last week

The baseball and softball teams from Windermere High and The First Academy moved on to the regional semifinals.

West Orange Times & Observer
News

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