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Tucker Ranch addition to open later this year

The city of Winter Garden is moving the historic West Orange Country Club arch. It will serve as a centerpiece for the Tucker Ranch addition.

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Latest News

1
  • March 4, 2026
Winter Garden leaders approve AI answering system
2
  • March 4, 2026
Tucker Ranch addition to open later this year
3
  • March 4, 2026
Winter Garden residents protest recent property purchases
4
  • March 4, 2026
Oakland Town Commission says goodbye to longtime commissioner
5
  • March 4, 2026
Horizon West Fest to take place this Saturday

Neighborhood

  • March 4, 2026
PHOTOS: Purim in the Stadium
  • March 4, 2026
Central Florida puzzlers find community through puzzle swaps
  • March 4, 2026
Oakland Town Commission says goodbye to longtime commissioner
  • March 3, 2026
Passion to community: The nonprofit Empowering Teens United is unlocking students' potential
  • March 3, 2026
Covered by Christ to raise $50k for Ocoee church
  • March 2, 2026
PHOTOS: Orange County Fire Rescue Station 32 ribbon cutting
  • March 1, 2026
PHOTOS: Big Orange Awards 2026
  • February 28, 2026
PHOTOS: Winter Garden Heritage Foundation's Paddles for the Past
  • February 27, 2026
Matthew's Hope in need of volunteers
  • February 26, 2026
Savannah's 5K raises more than $15k
  • February 23, 2026
Windermere High's Dance Marathon to take place this weekend
  • February 22, 2026
PHOTOS: Young Star Musical Theatre presents ‘In the Heights’

Arts & Entertainment

  • March 4, 2026
Horizon West Fest to take place this Saturday
  • March 2, 2026
Oakland Nature Preserve to host Pours at the Preserve
  • February 27, 2026
Windermere High choir to participate in Choir of Distinction performance
  • February 27, 2026
Horizon High School Theatre to present Beetlejuice Jr.

Winter Garden Livestream of the Downtown Area

House Wise

  • 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
  • February 26, 2026
Ocoee resident Michelle Finley has brought Cincinnati-based WOW Windowboxes to West Orange.

WOW factor!

  • October 30, 2025
Counter Intelligence

Viewpoint seeks to offer homeowners a better option between the chaos of a big-box DIY store or paying a premium to hire a high-end custom design firm

Sponsored Content

Schools

  • March 4, 2026
Foundation Academy robotics team competes on national level

Gov. Ron DeSantis selected the Ducks in a Row robotics team from Foundation Academy to represent the state at the inaugural Governors Cup.

  • March 2, 2026
OCPS superintendent invites community to town hall meeting
  • March 2, 2026
INFLUENCER OF THE WEEK: Jackie Archer, Lake Whitney Elementary School
  • February 28, 2026
PHOTOS: Innovation Montessori Ocoee Spring Festival
  • February 27, 2026
The First Academy raises nearly $62k for Arnold Palmer Hospital for Children

Sports

  • March 3, 2026
The 2026 Arnold Palmer Invitational kicks off at Bay Hill

The PGA has made its way back to Southwest Orange for competition play from Thursday, March 5, to Sunday, March 8.

  • March 3, 2026
Athlete of the Week: Richelle Ruiz, Olympia High softball
  • March 3, 2026
Regional Finals wrap up as State Semifinals picture is set for local basketball teams
  • March 3, 2026
Windermere's boys soccer players show grit in run to the 7A State Semifinals
  • March 3, 2026
Registration open for The Real McCoy X Shuler Elite Exposure Camp

Newsletter

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Things to Do

  • March 4, 2026
Horizon West Fest to take place this Saturday

The annual festival will include live music, local vendors and activities for children and adults alike.

  • March 2, 2026
Oakland Nature Preserve to host Pours at the Preserve
  • February 27, 2026
Windermere High choir to participate in Choir of Distinction performance

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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

  • March 4, 2026
Hammocks home tops Ocoee home sales from Feb. 23 to 29
  • March 3, 2026
Palms at Windermere home tops Horizon West home sales from Feb. 23 to 29
  • March 2, 2026
Cypress Point home tops Dr. Phillips home sales from Feb. 23 to 29
  • February 27, 2026
Estates at Lakeview home tops Winter Garden home sales from Feb. 16 to 22

Photo Galleries

  • March 2, 2026
PHOTOS: Orange County Fire Rescue Station 32 ribbon cutting
  • March 1, 2026
PHOTOS: Big Orange Awards 2026
  • February 28, 2026
PHOTOS: Winter Garden Heritage Foundation's Paddles for the Past
  • February 24, 2026
Fire emerges at Winter Garden recycling facility
  • February 22, 2026
PHOTOS: Young Star Musical Theatre presents ‘In the Heights’
  • February 21, 2026
PHOTOS: 2026 Winter Garden Music Fest
  • February 21, 2026
Winter Garden Little League celebrates largest season opener
  • February 16, 2026
PHOTOS: Rotary Club of Winter Garden's 100th anniversary exhibit
  • February 16, 2026
PHOTOS: Boots and Salutes
  • February 14, 2026
PHOTOS: 2026 Night to Shine
  • February 12, 2026
PHOTOS: Tildenville Elementary School Family Science Night
  • February 12, 2026
1931-2026: Anne Bailey built community through local newspaper

Contact

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

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