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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.

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Latest News

1
  • February 26, 2026
Reclaimed water only available intermittently in the city of Winter Garden
2
  • February 26, 2026
Soccer stadium no longer planned for Winter Garden
3
  • February 26, 2026
Healthy West Orange Arts and Heritage Center looking for submissions
4
  • February 25, 2026
Caribbean Sunshine Eatery’s outdoor patio catches fire
5
  • February 25, 2026
Shepherd's Hope receives $10k in grant

Neighborhood

  • 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’
  • February 21, 2026
PHOTOS: 2026 Winter Garden Music Fest
  • February 21, 2026
Winter Garden Little League celebrates largest season opener
  • February 18, 2026
Arts at the J program unveils the future of its arts in the Pargh Event Center
  • 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 11, 2026
Winter Garden Heritage Foundation serves up community through pickleball
  • February 10, 2026
Nonprofits to host inaugural Boots and Salutes in Windermere
  • February 8, 2026
PHOTOS: Legacy Events for Education’s Central Florida Chili Cookoff 2026

Arts & Entertainment

  • February 26, 2026
County to celebrate Fire Rescue Station 32 with ribbon-cutting
  • February 26, 2026
Winter Garden Heritage Foundation serves up first pickleball tournament
  • February 26, 2026
SAVE THE DATE: Arts at the J presents CFCArts’ Hand-Drawn Jazz
  • February 26, 2026
Chamber to host Big Orange Awards Saturday

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

  • February 25, 2026
Windermere Prep raises more than $35k for American Heart Association

Windermere Preparatory School announced the school raised the most amount it ever has raised for this cause.

  • February 24, 2026
Attention students: Win a $5,000 scholarship from new nonprofit
  • February 24, 2026
West Orange High charter class to host celebrations
  • February 23, 2026
Windermere High's Dance Marathon to take place this weekend
  • February 23, 2026
INFLUENCER OF THE WEEK: Gabriela Cardani, Water Spring Elementary School

Sports

  • February 26, 2026
Florida Athletic Coaches Association awards roll in for local basketball coaches

Olympia’s Justin Shipp and TFA’s Tarrik Mabon are producing talent on the hardwood.

  • February 26, 2026
Winter Garden Heritage Foundation serves up first pickleball tournament
  • February 25, 2026
Lake Buena Vista welcomes new head football coach
  • February 25, 2026
Athlete of the Week: Giulia Belardo, Top Gun cheer
  • February 25, 2026
Baseball and softball players to look out for on the plate

Newsletter

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Things to Do

  • February 26, 2026
County to celebrate Fire Rescue Station 32 with ribbon-cutting

The event takes place at 9 a.m. Monday, March 2, at the station, 13826 Luna Harvest Ave., Winter Garden.

  • February 26, 2026
Winter Garden Heritage Foundation serves up first pickleball tournament
  • February 26, 2026
SAVE THE DATE: Arts at the J presents CFCArts’ Hand-Drawn Jazz

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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

  • February 26, 2026
Isleworth estate tops Windermere home sales from Feb. 16 to 22
  • February 25, 2026
Hammocks home tops Ocoee home sales from Feb. 16 to 22
  • February 24, 2026
Summerlake home tops Horizon West home sales from Feb. 16 to 22
  • February 23, 2026
Sand Lake Sound home tops Dr. Phillips home sales from Feb. 16 to 22

Photo Galleries

  • 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
  • February 11, 2026
Frigid temperatures hit Southern Hill Farms hard
  • February 8, 2026
PHOTOS: Legacy Events for Education’s Central Florida Chili Cookoff 2026

Contact

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

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