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‘This place will leave a mark on you’: Windermere mayor reflects on 15 years of service

After serving as mayor of Windermere for six years, Jim O’Brien says now is the right time to step away because the town has talented people prepared to lead.

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Latest News

1
  • January 20, 2026
Ocoee Commissioner seeks Orange County seat
2
  • January 20, 2026
Six local high schoolers named 2026 MLK Humanitarians
3
  • January 20, 2026
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  • January 20, 2026
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  • January 20, 2026
Winter Garden to host first cars and coffee of 2026

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Good & faithful servant: Winter Garden's First Baptist Church pastor retires
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‘This place will leave a mark on you’: Windermere mayor reflects on 15 years of service
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Spreading holiday joy through decor

Arts & Entertainment

  • January 20, 2026
Winter Garden to host first cars and coffee of 2026
  • January 19, 2026
Windermere to host first Food Truck Night of the new year
  • January 17, 2026
PHOTOS: OCPS All-County Dance Gala
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Live Well in Horizon West set for Sunday

Winter Garden Livestream of the Downtown Area

House Wise

  • 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

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A Florida homeowner’s guide to bug-free outdoor living

Living in Florida means sunshine, warm breezes and beautiful backyards. But it also means mosquitos, gnats and lovebugs that make it hard to enjoy the outdoors.

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News flash: You live in Florida, and it’s summertime. And yes, the sunshine is beautiful, but the heat and humidity can be unbearable. Luckily, A1 Aluminum can help you beat the heat.

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Schools

  • January 20, 2026
Want to name the new Horizon West elementary school?

Fill out an OCPS survey that will be available until 4 p.m. Friday, Feb. 6.

  • January 17, 2026
PHOTOS: OCPS All-County Dance Gala
  • January 16, 2026
8-year-old Winter Garden boy writes, publishes book
  • January 15, 2026
INFLUENCER OF THE WEEK: Terrance Washington, Windermere Preparatory School
  • January 15, 2026
Dr. Phillips Dance Magnet presents ‘Celebration of Dance’

Sports

  • January 20, 2026
Olympia's Titan Trot 5K returns to blossom soccer and community growth

The girls soccer team began the Titan Trot last year to help fund the program. After a successful inaugural year, the 5K is back to foster team and community growth.

  • January 20, 2026
Athlete of the Week: Jonah Bryan, Windermere Prep boys soccer
  • January 20, 2026
Foundation Academy girls basketball player commits to college in Italy
  • January 15, 2026
Windermere High boys soccer claims Metro Champions title
  • January 15, 2026
Ocoee High welcomes a new football assistant coach

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Things to Do

  • January 20, 2026
Winter Garden to host first cars and coffee of 2026

The event will take place from 8 to 10:30 a.m. Saturday, Jan. 24, at 3118 Daniels Road, Winter Garden.

  • January 19, 2026
Windermere to host first Food Truck Night of the new year
  • January 15, 2026
Live Well in Horizon West set for Sunday

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Opinion

1
  • September 18, 2025
  • By Megan Bruinsma
Introducing myself to you: The Observer's new writer, Megan Bruinsma
2
  • September 17, 2025
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MY VIEW: How then shall we live?
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  • September 10, 2025
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Celebrating 120 years of the West Orange Times & Observer: The weight of it all

Real Estate

  • January 20, 2026
Providence home tops Horizon West home sales from Jan. 12 to 18
  • January 19, 2026
Cypress Point estate tops Dr. Phillips-area home sales from Jan. 12 to 18
  • January 16, 2026
Hull Island home tops Winter Garden/Oakland home sales from Jan. 5 to 11
  • January 15, 2026
Casabella estate tops Windermere-area home sales from Jan. 5 to 11

Photo Galleries

  • January 20, 2026
PHOTOS: Winter Garden's MLK Celebration 2026
  • January 19, 2026
PHOTOS: Ocoee's 18th annual MLK parade
  • January 11, 2026
PHOTOS: Horizon West Theater Company grooves through the decades
  • January 5, 2026
2025 Year in Photos
  • January 2, 2026
2025 Year in Photos: December
  • January 1, 2026
2025 Year in Photos: November
  • December 31, 2025
2025 Year in Photos: October
  • December 30, 2025
2025 Year in Photos: September
  • December 29, 2025
2025 Year in Photos: August
  • December 28, 2025
2025 Year in Photos: July
  • December 26, 2025
2025 Year in Photos: May
  • December 25, 2025
2025 Year in Photos: April
  • December 24, 2025
2025 Year in Photos: March
  • December 23, 2025
2025 Year in Photos: February
  • December 22, 2025
2025 Year in Photos: January

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