Your Town | Southwest Orange

Southwest Orange | Your Town

Michael Eng
August 26, 2025

SAVE THE DATE: Windermere High Fall Bash set for Sept. 17

Attendees will enjoy drinks, food, music and a silent auction — all to raise funds for faculty and club grants for the school.

Arts + Entertainment
Things to Do

Michael Eng
August 5, 2025

Observer wins awards for journalism, advertising

The West Orange Times & Observer and Southwest Orange Observer won awards for its journalism, design and advertising at the 2025 Florida Media Conference.

West Orange Times & Observer
Your Town

Sam Albuquerque
July 24, 2025

Match play magic: Fundraiser pits golfers against NBA legends

Headlined by Hall-of-Fame basketball player Vince Carter, Windermere Elementary’s first fundraising tournament offers golfers the chance to play 18 holes against former Orlando Magic players.

Arts + Entertainment
Things to Do

Sam Albuquerque
June 19, 2025

Winter Garden Squeeze announces free tickets for kids for remainder of 2025

In partnership with local preschool The Learning Experience, all kids 12 and under get in free to the Squeeze’s remaining home games.

Sports

By None
June 11, 2025

Winter Garden to celebrate Juneteenth at Charlie Mae Wilder Park

The annual event honors legacy and community with music, speakers and family activities.

Arts + Entertainment
Things to Do

Michael Eng
May 28, 2025

HarborChase of Dr. Phillips to honor local heroes

The community’s BBQ for Badges takes place from 11 a.m. to 3 p.m. Saturday, May 31, at 7233 Della Drive, Orlando.

Arts + Entertainment
Things to Do

Michael Eng
May 28, 2025

Winter Garden's Churchill Room pockets two-day pool masterclass

Two of the best pool players in the world will be in Winter Garden this weekend.

Arts + Entertainment
Things to Do

Sam Albuquerque
April 21, 2025

PHOTOS: Family Church’s Brazilian Community presents its annual Easter play

The annual drama production, directed by Paulo and Micheline Guerreiro, portrays Jesus Christ’s final days, death and resurrection in celebration of the Easter holiday.

Southwest Orange
Neighborhood

Michael Eng
April 9, 2025

Latest podcast episode features former Duke, WBNA star

This week’s episode of “Between Faith and Reason” is an in-depth interview with Krystal Thomas Smith.

West Orange Times & Observer
Your Town

Sam Albuquerque
March 29, 2025

PHOTOS: Evening at the Pops returns to Winter Garden

The Rotary Club of Winter Garden filled the lawns of Newton Park for its annual Evening at the Pops concert headlined by Winter Garden's own Plant Street Pops Orchestra.

Southwest Orange
News

Sam Albuquerque
March 29, 2025

PHOTOS: Relay for Life of Lake Buena Vista 2025

The American Cancer Society fundraiser returns to Lake Buena Vista for the 40th anniversary of the national event.

Southwest Orange
News

Sam Albuquerque
March 26, 2025

Relay for Life of Lake Buena Vista returns March 29

From 2-10 p.m. at District Fire Station No. 4, locals affected by cancer come together to celebrate survivors and caregivers, remember lost loved ones and raise funds to fight against the disease.

Southwest Orange
News

Amy Quesinberry Price
March 5, 2025

Cheers to the Engaged Couple

Two former high school and college cheerleaders are tying the knot in April.

West Orange Times & Observer
News

Amy Quesinberry Price
March 5, 2025

Time change: Get ready to spring forward

It’s time to turn your clock ahead one hour this weekend.

West Orange Times & Observer
News

Sam Albuquerque
March 3, 2025

PHOTOS: Windermere Fine Arts Show

Local artists filled downtown Windermere with a variety of original and unique works of art for the town's annual fine arts show.

Southwest Orange

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