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Ward Trail will make Windermere safer

Construction has begun on Phase 1 of the Windermere Ward Trail, a path to provide a wider, safer route to Windermere Elementary.

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Latest News

1
  • April 10, 2026
CFX to close State Road 429 throughout April 12-16
2
  • April 9, 2026
Dr. Phillips High student arrested for bringing handgun to school
3
  • April 9, 2026
Winter Garden woman arrested for grand theft
4
  • April 9, 2026
Orlando Health hosted its second-annual 407 Day
5
  • April 9, 2026
Road closures scheduled in downtown Winter Garden for Spring Fever

Neighborhood

  • April 4, 2026
PHOTOS: Windermere Easter Egg Hunt Extravaganza 2026
  • April 4, 2026
PHOTOS: Ocoee Easter Eggstravaganza 2026
  • April 1, 2026
Orange County to host food giveaway at Lake Buena Vista High
  • April 1, 2026
Oakland Nature Preserve in need of books
  • March 29, 2026
PHOTOS: 2026 Evening at the Pops
  • March 29, 2026
PHOTOS: Hamlin Craft Beer Fest 2026
  • March 29, 2026
PHOTOS: Mayor Jim O'Brien Farewell Party
  • March 29, 2026
PHOTOS: St. Luke's Easter Hop
  • March 28, 2026
PHOTOS: 2026 Tildenville Elementary Tigers’ Ball
  • March 28, 2026
PHOTOS: Celebration Among the Oaks 2026
  • March 28, 2026
PHOTOS: Healthy West Orange Ocoee Block Party
  • March 28, 2026
PHOTOS: Lake Buena Vista Relay for Life 2026

Arts & Entertainment

  • April 9, 2026
Oakland Nature Preserve illuminates the night with Firefly Hike
  • April 9, 2026
SAVE THE DATE: Arts at the J to present Comedy For Peace
  • April 9, 2026
Flamingo Crossings block party set for Friday
  • April 8, 2026
Spring Fever to return to Winter Garden

Winter Garden Livestream of the Downtown Area

House Wise

  • March 26, 2026
Outdoor kitchens help complete Florida lifestyle

Spring has sprung, and that means it’s the perfect time to consider adding or revamping your outdoor kitchen.

Sponsored Content
  • March 26, 2026
Downtown Winter Garden business changes will affect nearby residents

RE/MAX real-estate adviser Carmelo Nuccio has built his business on intimate knowledge of Winter Garden.

Sponsored Content
  • February 26, 2026
Local insurance agent Jo Barsh says regular insurance reviews are critical to ensuring you have the right amount of coverage for your home.

Be proactive now to prevent major heartbreak later

Sponsored Content
  • February 26, 2026
To start your gardening journey

Have you ever wanted to plant a garden but didn’t know how to start?

Sponsored Content

Schools

  • April 9, 2026
Dr. Phillips High student arrested for bringing handgun to school

Joshua Brown, a 17-year-old, was arrested Thursday, April 9, after police were notified he had a gun in his possession.

  • April 9, 2026
Olympia High School heading to national speech competitions
  • April 8, 2026
CFCA students serve others on two mission trips
  • April 8, 2026
Horizon West Middle to present ‘The Lightning Thief: The Percy Jackson Musical'
  • April 8, 2026
New club at Ocoee Middle empowers students

Sports

  • April 10, 2026
Horizon High boys volleyball team wins 2026 Metro Championship

The Hawks earned the program's first Metro Champions title by topped Freedom 3-0 Thursday, April 9.

  • April 10, 2026
Two The First Academy girls lacrosse players reach career milestones
  • April 10, 2026
West Orange celebrates boys lacrosse team awards
  • April 10, 2026
The First Academy's baseball head coach reaches 250th career win
  • April 8, 2026
Ocoee baseball's winning culture reignited by its legendary coach

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Things to Do

  • April 9, 2026
Oakland Nature Preserve illuminates the night with Firefly Hike

The event will take place at7 p.m. Friday, April 10, at ONP, 747 Machete Trail, Oakland.

  • April 9, 2026
SAVE THE DATE: Arts at the J to present Comedy For Peace
  • April 9, 2026
Flamingo Crossings block party set for Friday

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Opinion

1
  • February 12, 2026
  • By Michael Eng
OBSERVED: New digs! Observer returns to Dillard Street
2
  • September 18, 2025
  • By Megan Bruinsma
Introducing myself to you: The Observer's new writer, Megan Bruinsma
3
  • September 17, 2025
  • By Jeff Lawrence | Between Faith & Reason
MY VIEW: How then shall we live?

Real Estate

  • April 10, 2026
Hickory Hammock home tops Winter Garden home sales from March 30 to April 5
  • April 9, 2026
Isleworth West home tops Windermere-area home sales from March 30 to April 5
  • April 8, 2026
Wynwood home tops Ocoee home sales from March 30 to April 5
  • April 7, 2026
Independence/Signature Lakes home tops Horizon West home sales from March 30 to April 5

Photo Galleries

  • April 4, 2026
PHOTOS: Windermere Easter Egg Hunt Extravaganza 2026
  • April 4, 2026
PHOTOS: Ocoee Easter Eggstravaganza 2026
  • March 29, 2026
PHOTOS: 2026 Evening at the Pops
  • March 29, 2026
PHOTOS: Hamlin Craft Beer Fest 2026
  • March 29, 2026
PHOTOS: Mayor Jim O'Brien Farewell Party
  • March 29, 2026
PHOTOS: St. Luke's Easter Hop
  • March 28, 2026
PHOTOS: 2026 Tildenville Elementary Tigers’ Ball
  • March 28, 2026
PHOTOS: Celebration Among the Oaks 2026
  • March 28, 2026
PHOTOS: Healthy West Orange Ocoee Block Party
  • March 28, 2026
PHOTOS: Lake Buena Vista Relay for Life 2026

Contact

  • 210 S. Dillard St.,
  • Winter Garden, FL 34787
  • Phone: 407-656-2121
  • Email: [email protected]

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