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By Michael Eng |
February 18, 2025

Roper Y to offer Healthy YOU Day

The celebration will take place from 10 a.m. to 1 p.m. Saturday, Feb. 22, at the Roper YMCA Family Center, 100 Windermere Road, Winter Garden.

Arts + Entertainment
Things to Do

By Troy Herring |
December 7, 2017

Soccer look in: Wildcats, Hornets start strong | Observer Preps

The high-school soccer season is in full swing in the Winter Park/Maitland area. Here is a run down of the action thus far.

Winter Park - Maitland Observer
Sports

By Michael Eng |
July 9, 2024

Enclave home tops Horizon West sales from July 1 to 7

The home at 11708 Hampstead St., Windermere, sold July 5, for $997,500.

Southwest Orange
Real Estate

By Observer Staff |
December 11, 2014

WOT office will close for holidays

West Orange Times & Observer
Your Town

By Amy Quesinberry Price |
December 2, 2018

PHOTOS: Light Up Oakland

The town of Oakland held its annual Light Up Oakland event Saturday, Dec. 1.

West Orange Times & Observer
Neighborhood

By Tim Freed |
October 20, 2017

PHOTOS: Edgewater High School vs. East Ridge High School -- Observer Preps

The Edgewater High School Eagles defeated the East Ridge High School Knights 41-21 on Friday, Oct. 20 to move up to a 7-1 record.

Winter Park - Maitland Observer
Sports

By Zak Kerr |
October 22, 2015

Cops Corner 10.22.15

West Orange Times & Observer
Cops Corner

By Megan Bruinsma |
September 26, 2025

West, Southwest Orange’s Week 6 high school football schedule

District games commence as Dr. Phillips hosts Olympia, West Orange travels to Apopka and Lake Buena Vista meets Windermere.

Sports
High Schools

By Observer Staff |
May 4, 2012

Fit for the Fourth: Day 8

Diets that give you a cheat day make it a little easier, but the day after is not as fun!

Winter Park - Maitland Observer
Opinion

By Troy Herring |
February 8, 2020

PHOTOS: West Orange holds on late in 3-2 victory over East Ridge to claim Class 7A, District 5 crown

Despite a frantic finish, a three goal lead in the first half was enough to help the Warriors clinch a district title.

Sports

By Michael Eng |
November 9, 2023

Waterfront property tops Windermere sales from Oct. 30 to Nov. 5, 2023

The home and property at 803 W. Second Ave., Windermere, sold Nov. 1, for $2,550,000.

Southwest Orange
Real Estate

By Annabelle Sikes |
March 25, 2022

Town of Windermere hosting second round of Lakes Cleanup Day

The event will take place from 1:30-3:30 p.m. on Saturday, March 27, at Fernwood Park.

West Orange Times & Observer
News

By Annabelle Sikes |
March 25, 2022

Community Health Centers Inc. holding hiring event

The hiring event will be for various positions in the healthcare field from 9 a.m. to 1 p.m. on Saturday, March 26.

West Orange Times & Observer
News

By Annabelle Sikes |
May 3, 2022

Horizon West hosting Hamlin Hoedown

The event will take place from 10 a.m. to 1 p.m. on Saturday, May 14, outside Cinepolis in Hamlin.

West Orange Times & Observer
News

By Steven Ryzewski |
August 28, 2015

GALLERY: Area volleyball teams return to action

Southwest Orange
News

By Danielle Hendrix |
May 3, 2016

Universal Orlando Resort announces addition of 2,500 jobs

The theme park and resort is also increasing hourly pay to $10 on June 1.

Southwest Orange
News

By Amy Quesinberry Price |
March 11, 2020

Obituary: George Malone Traywick

Obituary: George Malone Traywick, 77, of Winter Garden, died Sunday, March 1, 2020.

West Orange Times & Observer
Obituaries

By Steven Ryzewski |
March 9, 2017

PHOTOS: Freedom tops Dr. Phillips 2-1 in pitchers' duel -- Observer Preps

Justin Driscoll's six strong innings on the hill helped elevate the Patriots to victory March 8.

Sports
Game Film

By Troy Herring |
February 27, 2018

PHOTOS: Orangewood falls in 4-0 loss to Windermere Prep | Observer Preps

A big fourth-inning sparks the Lakers past the Rams

Winter Park - Maitland Observer
Sports

By Michael Eng |
August 21, 2024

Make-A-Wish to host Winter Garden fundraiser

The annual Wish-A-Thon takes place from 5 a.m. to 1 p.m. Friday, Aug. 23, at the Winter Garden Village Clock Tower.

Arts + Entertainment
Things to Do

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