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By Peter Gordon |
July 2, 2015

Winter Garden leaders discuss ordinance to restrict pamphlets

West Orange Times & Observer
News

By Tim Freed |
July 30, 2015

Winter Park and Maitland mull over raising millage rates

After raising taxes for the first time in seven years last year, Maitland is on its way to bumping rates again. Across city lines, Winter Park City Commissioners also considered an uptick in the millage on Monday.

Winter Park - Maitland Observer
News

By Steven Ryzewski |
August 6, 2014

A look back: One season in books for Winter Garden Squeeze

Sports

By Steven Ryzewski |
September 5, 2014

Ocoee's Cody Beesley has gone from beginner to leader for Knights

Sports

By Troy Herring |
November 4, 2020

Garden Theatre has new managing director

Elisa Spencer-Kaplan, who most recently was executive director of The Acting Company in New York City, started virtually Nov. 1.

West Orange Times & Observer
News

By Danielle Hendrix |
May 23, 2021

Windermere OKs agreement for new pavilion

The Rotary Club of Windermere has been awarded a $1 million grant from the West Orange Healthcare District to construct an outdoor entertainment pavilion.

Southwest Orange
News

By Troy Herring |
May 18, 2019

Olympia water polo falls in state final to end season | Observer Preps

The Titans finished the season with a record of 29-2.

Sports

By Steven Ryzewski |
June 2, 2018

PHOTOS: Dr. Phillips baseball ends season in state semifinal | Observer Preps

The Dr. Phillips High School baseball team fell 5-1 to Timber Creek High School in a battle of Orlando-area programs in the FHSAA Class 9A State Semifinals at Hammond Stadium in Fort Myers June 2.

Sports

By Gabby Baquero |
August 23, 2017

Ocoee Charter Review Commission proposes future ballot questions

The charter review commission presented eight ballot questions it recommended for inclusion in the city’s 2018 election.

West Orange Times & Observer
News

By Troy Herring |
January 30, 2019

Windermere Prep girls soccer brings home SSAC state title | Observer Preps

A year of dominating success has led the Windermere Prep girls soccer team to its first SSAC Independent State title.

Sports

By Troy Herring |
November 18, 2017

PHOTOS: Winter Park stays perfect in 34-27 win over Apopka in regional semifinal | Observer Preps

Thanks to a five-touchdown night from receiver Brian Gomez, the Wildcats move on to the regional final against Wekiva.

Winter Park - Maitland Observer
Sports

By Steven Ryzewski |
February 1, 2018

Dr. Phillips swimming alumna Cindy Cheng piles up collegiate accolades | Observer Preps

Emory University senior and Dr. Phillips High alumna Cindy Cheng already has national titles and program records to her credit — and most recently some ink in Sports Illustrated.

Sports

By Troy Herring |
February 22, 2018

The Maitland Public Library will be hosting its annual Astronomy Week

From Feb. 26 through March 2, the library will put on a series of programs aimed to educate the community on space.

Winter Park - Maitland Observer
News

By Sam Albuquerque |
February 21, 2024

Athlete of the Week: Aida Bell, Horizon girls soccer

In her senior season, Aida Bell, a Centre College girls soccer signee, has continued to add to her already-special legacy at Horizon.

Sports
Athlete of the Week

By Amy Quesinberry Price |
January 17, 2024

Winter Garden captain graduates from FBI National Academy

Anthony Dawkins is the first person to earn his diploma while working with the city of Winter Garden’s police department.

West Orange Times & Observer
News

By Sam Albuquerque |
July 11, 2024

Ocoee High football star Joshua Guerrier on why he committed to Pitt

The Knights' three-star prospect talks about his choice to become a Panther over Iowa, Tennessee, Wake Forest and others.

Sports
High Schools

By Michael Eng |
December 8, 2023

Deer Island home tops Winter Garden sales from Nov. 27 to Dec. 3, 2023

The home at 17667 Deer Isle Circle, Winter Garden, sold Nov. 27, for $1,750,000.

West Orange Times & Observer
Real Estate

By Michael Eng |
September 9, 2025

Waterside home tops Horizon West sales from Sept. 1 to 7

The home at 16821 Broadwater Ave., Winter Garden, sold Sept. 5, for $2,670,000.

Southwest Orange
Real Estate

By Leticia Silva |
October 16, 2025

Oktoberfest brewing at Crooked Can

Crooked Can Brewing Co. is bringing back the biggest Oktoberfest in Central Florida for three days full of beer, food and entertainment as well as a new VIP area.

West Orange Times & Observer

By Observer Staff |
February 23, 2011

Calendar and Family Calendar

Tax help at the Winter Park Library; Morse Museum free through March 20; award-winning comic book artist visiting shop on Semoran

Winter Park - Maitland Observer
Neighborhood

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