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News | All

    By
  • Liz Ramos
  • February 18, 2026
Annual Winter Garden Musical Fest returns

It takes about 40 city employees and 260 volunteers to pull off Winter Garden’s annual Music Fest. The 12-hour concert festival returns Saturday, Feb. 21.

  • West Orange Times & Observer
  • News
    By
  • Megan Bruinsma
  • February 18, 2026
Oakland presents fourth-quarter officer awards

The Oakland Town Commission recognized the accomplishments of its police officers at the meeting Tuesday, Feb. 10.

  • West Orange Times & Observer
  • News
    By
  • Leticia Silva
  • February 17, 2026
More downtown Winter Garden businesses unable to renew leases

Polka Dotz and Driftwood Market announced closure is near because of new building owners.

  • West Orange Times & Observer
  • News
    By
  • Leticia Silva
  • February 17, 2026
Founder and CEO of Hi-Lite Academy announces separation from school

Jessica Villegas and her coaching team are no longer involved in the leadership or day-to-day operations of Hi-Lite Academy.

  • West Orange Times & Observer
  • News
    By
  • Leticia Silva
  • February 17, 2026
New ambassador at Oakland Nature Preserve

ONP welcomed Buttercup, a Virginia Opossum to its ambassador team.

  • West Orange Times & Observer
  • News
    By
  • Liz Ramos
  • February 16, 2026
Three Birds Café to close in Winter Garden

The final day for the café will be Thursday, Feb. 26.

  • West Orange Times & Observer
  • News
    By
  • Liz Ramos
  • February 16, 2026
Meet Commissioner Nicole Wilson in Windermere

The Orange County Board of County Commission member is hosting in-person office hours from 11:30 a.m. to 2 p.m. Thursday, Feb. 19, at Town Hall.

  • Southwest Orange
  • News
    By
  • Liz Ramos
  • February 16, 2026
Windermere to experience road closures

Several roads throughout downtown Windermere could experience closures through Friday, Feb. 20.

  • Southwest Orange
  • News
    By
  • Liz Ramos
  • February 13, 2026
Ocoee Neighborhood Matching Grant Program applications available

The grant program assists residents with making improvements to their neighborhoods.

  • West Orange Times & Observer
  • News
    By
  • Liz Ramos
  • February 12, 2026
Traffic signal for Schofield and Avalon roads in Horizon West nears completion

The project includes three new signal mast arm assemblies expected to be complete in March.

  • Southwest Orange
  • News
    By
  • Liz Ramos
  • February 12, 2026
Winter Garden warns of scam

The scam involved false city Planning and Zoning invoices requesting a wire transfer.

  • West Orange Times & Observer
  • News
    By
  • Liz Ramos
  • February 12, 2026
Orange County Sheriff's Office arrests teen in Horizon West

A deputy conducted a traffic stop on a 14-year-old who was riding an electric bicycle when the teen fled from the stop.

  • Southwest Orange
  • News
    By
  • Amy Quesinberry Price
  • February 12, 2026
1931-2026: Anne Bailey built community through local newspaper

Anne and George Bailey bought The Winter Garden Times in 1970 and shared the ins and outs of small-town living for 44 years.

  • West Orange Times & Observer
  • Obituaries
    By
  • Megan Bruinsma
  • February 11, 2026
Oakland’s deadline is approaching to request a vote-by-mail ballot

The deadline to request a vote-by-mail ballot is Thursday, Feb. 26.

  • West Orange Times & Observer
  • News
    By
  • Leticia Silva
  • February 11, 2026
Central Florida Diaper Bank receives four-month supply from Huggies

The Winter Garden-based bank has served local families for more than 30 years.

  • West Orange Times & Observer
  • News
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