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Orange Observer | Orange Observer

    By
  • Liz Ramos
  • February 23, 2026
Town of Windermere faces road closures

Several roads throughout downtown Windermere could experience closures through Friday, Feb. 27.

  • Southwest Orange
  • News
    By
  • Liz Ramos
  • February 23, 2026
Property purchases signal major changes to downtown Winter Garden

One individual — James Larweth — has spent more than $40 million since 2015 to buy 36 residential and commercial properties — all in downtown Winter Garden. No one knows his plans.

  • West Orange Times & Observer
  • News
    By
  • Leticia Silva
  • February 22, 2026
PHOTOS: Young Star Musical Theatre presents ‘In the Heights’

The children’s theater in Winter Garden presented the “In the Heights” musical for three nights in a row.

  • West Orange Times & Observer
  • Neighborhood
    By
  • Liz Ramos, Michael Eng
  • February 21, 2026
PHOTOS: 2026 Winter Garden Music Fest

Residents enjoyed sunshine, good eats and plenty of music during the 2026 Winter Garden Music Fest, held Saturday, Feb. 21, downtown.

  • West Orange Times & Observer
  • Neighborhood
    By
  • Leticia Silva
  • February 21, 2026
Winter Garden Little League celebrates largest season opener

The Winter Garden Little League celebrated its season opener Friday, Feb. 20, with more than 600 players.

  • Sports
  • Youth Sports
    By
  • Leticia Silva
  • February 20, 2026
Windermere Police Department gets reaccredited

Police Chief David Ogden took to social media to celebrate the department’s accomplishment.

  • Southwest Orange
  • News
    By
  • Leticia Silva
  • February 20, 2026
Orange County plans warming centers as cold front approaches

Orange County is closely monitoring the weather as temperatures are expected to drop below 40 degrees early next week.

  • Southwest Orange
  • News
    By
  • Leticia Silva
  • February 20, 2026
Dead fish surface at Newton Park

Multiple tilapia fish were found dead along Lake Apopka's shoreline at Newton Park, 31 W. Garden Ave., Winter Garden, due to cold weather.

  • West Orange Times & Observer
  • News
    By
  • Michael Eng
  • February 20, 2026
Hickory Hammock home tops Winter Garden home sales from Feb. 9 to 15

The home at 15851 Turkey Island Circle, Winter Garden, sold Feb. 12, for $2,700,000.

  • West Orange Times & Observer
  • Real Estate
    By
  • Leticia Silva
  • February 19, 2026
Williams Holiday House resolves code enforcement issues

The holiday house owners announced many issues have been positively resolved.

  • West Orange Times & Observer
  • News
    By
  • Leticia Silva
  • February 19, 2026
Ruby and Rust to close doors by end of the month

The Winter Garden houseplant boutique has announced it will be closing its doors by the end of February.

  • West Orange Times & Observer
  • News
    By
  • Liz Ramos
  • February 19, 2026
Matthew's Hope receives matching donation

An anonymous donor has made up to $35,000 in matching money available to help replace funds the nonprofit used to operate its freeze warning emergency shelters.

  • West Orange Times & Observer
    By
  • Liz Ramos
  • February 19, 2026
Orlando Health — Health Central to expand cardiology services

Advanced electrophysiology and arrhythmia care will be available in the spring.

  • West Orange Times & Observer
  • News
    By
  • Liz Ramos
  • February 19, 2026
Outback Steakhouse in Hamlin to open soon

The restaurant will host a grand opening at 3 p.m. Tuesday, March 3.

  • Southwest Orange
  • News
    By
  • Michael Eng
  • February 19, 2026
Three Birds Café supporters plan demonstration

The demonstration is planned for 10:30 a.m. Friday, Feb. 20, outside the cafe, 2 W. Plant St., Winter Garden.

  • Arts + Entertainment
  • Things to Do
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