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By Observer Staff |
June 3, 2015

Calendar

The Winter Park Diamond Dawgs’ season opener will be played against the Sanford River Rats at 7 p.m. on Friday, June 5, at Rollins College Alfond Stadium.

Winter Park - Maitland Observer
Neighborhood

By Observer Staff |
February 5, 2015

Calendar

Sip wine and stroll downtown Winter Park in an evening of wine and hors d’oeuvres with the first Winter Park Sip, Shop & Stroll of 2015 on Thursday, Feb. 5.

Winter Park - Maitland Observer
Neighborhood

By Tim Freed |
April 16, 2014

Wounded soldier to receive new home in Winter Park

Sgt. Bacary Sambou nearly lost his life in Afghanistan. Now he's found a place to call home: a donated house in Winter Park.

Winter Park - Maitland Observer
News

By Danielle Hendrix |
July 29, 2020

COVID-19 and classrooms: How childcare facilities keep children, staff safe

As K-12 schools grapple with the idea of reopening to students, some West Orange-area childcare centers never closed. And they’ve also never had an outbreak.

West Orange Times & Observer
News

By Troy Herring |
September 16, 2020

2020 Football preview: Public and charter schools

The area’s public schools finally are returning to the field as the football season begins this week.

Sports

By Eric Gutierrez |
June 12, 2019

County OKs Kerina Parkside, O-Town West developments

County leaders voted on June 4 to approve requests related to the Kerina Parkside and O-Town West development projects in Dr. Phillips.

Southwest Orange
News

By Tim Freed |
January 10, 2020

FORECAST: The cost of keeping Windermere's roads dirty

It’s hard work maintaining the town’s dirt roads, but Windermere hopes to create a master plan for its roadways.

Southwest Orange
News

By Chris Martucci |
September 23, 2021

Local volleyball squads prep for Metro West Conference tournament

The tournament takes place from Oct. 1 to 2.

West Orange Times & Observer
News

By Danielle Hendrix |
January 8, 2017

FORECAST: West Orange area to see multitude of new health care options

Local health care providers have seen the increase in West Orange’s population. Now, they’re here to compensate for that growth.

West Orange Times & Observer
News

By Tim Freed |
December 30, 2018

Maitland family and police chief form friendship after near tragedy

A Maitland family and Police Chief David Manuel have a close, ongoing friendship – 28 years after Manuel saved their 2-year-old’s life.

Winter Park - Maitland Observer
News

By Eric Gutierrez |
January 3, 2019

FORECAST: Church planting season in West Orange

As the population of West Orange continues to grow, the number of churches in the area are growing with it.

Southwest Orange
News

By Troy Herring |
January 5, 2019

FORECAST: Dr. Phillips Little League looks to grow

Dr. Phillips Little League is growing in attendance but has found itself at a crossroads as it waits for the development of a new facility to call home.

Sports

By Steven Ryzewski |
February 1, 2018

West Orange softball standout Lexie Blair comes full circle | Observer Preps

A four-year starter for the West Orange softball team, Lexie Blair has grown from a wide-eyed freshman on the varsity squad to a senior leader for the Warriors.

Sports

By Liz Ramos |
January 16, 2025

Old Glory returns to Windermere in honor of hometown hero

A town icon has been dedicated as a memorial for U.S. Army 1st Lt. Evan Fitzgibbon.

West Orange Times & Observer
News

By Sam Albuquerque |
February 9, 2024

Soccer playoffs: Everything you need to know about the area’s postseason teams

With district tournaments done and dusted, 10 West Orange, Southwest Orange County teams had a shot to hunt for state championship glory.

Sports

By Leticia Silva |
August 20, 2025

Magical Dining 2025: All you need to know

West Orange and Southwest Orange foodies have a plethora of local options in this year’s Magical Dining.

Arts + Entertainment
Things to Do

By Sam Albuquerque |
September 28, 2024

FRIDAY NIGHT ROUNDUP: Everything you need to know from Week Six of high school football

Did you miss your favorite West or Southwest Orange County high school football team's game? Catch up here with all the scores and notes from the area's Week Six action.

Sports
High Schools

By Annabelle Sikes |
September 12, 2024

Winter Garden resident creates Celiac Cruise

Winter Garden resident Connie Saunders and co-founder Maureen Basye have created Celiac Cruise, which provides a gluten-free, educational cruise vacation experience for those with celiac disease.

West Orange Times & Observer
Neighborhood

By Liz Ramos |
January 26, 2026

INFLUENCER OF THE WEEK: Carly Orenstein, Keene's Crossing Elementary School

Carly Orenstein is a reading instructional coach at Keene’s Crossing Elementary School.

Observer School Zone
Influencer

By Liz Ramos |
January 13, 2026

Winter Garden educator leads with purpose in new microschool

Lea Thompson created Purpose Prep Academy to provide individualized education to students after experiencing a childhood of not being academically challenged.

Observer School Zone
News

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Results for:

Calendar

Calendar

Wounded soldier to receive new home in Winter Park

COVID-19 and classrooms: How childcare facilities keep children, staff safe

2020 Football preview: Public and charter schools

County OKs Kerina Parkside, O-Town West developments

FORECAST: The cost of keeping Windermere's roads dirty

Local volleyball squads prep for Metro West Conference tournament

FORECAST: West Orange area to see multitude of new health care options

Maitland family and police chief form friendship after near tragedy

FORECAST: Church planting season in West Orange

FORECAST: Dr. Phillips Little League looks to grow

West Orange softball standout Lexie Blair comes full circle | Observer Preps

Old Glory returns to Windermere in honor of hometown hero

Soccer playoffs: Everything you need to know about the area’s postseason teams

Magical Dining 2025: All you need to know

FRIDAY NIGHT ROUNDUP: Everything you need to know from Week Six of high school football

Winter Garden resident creates Celiac Cruise

INFLUENCER OF THE WEEK: Carly Orenstein, Keene's Crossing Elementary School

Winter Garden educator leads with purpose in new microschool

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