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Orange Observer | Orange Observer

By

Liz Ramos
January 14, 2026

‘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.

Southwest Orange
Neighborhood

By

Michael Eng
January 14, 2026

Wesmere home tops Ocoee home sales from Jan. 5 to 11

The home at 427 Dunoon St., Ocoee, sold Jan. 9, for $415,000.

West Orange Times & Observer
Real Estate

By

Leticia Silva
January 14, 2026

Theatre South Playhouse to perform "Alice by Heart"

The performances will take place from Thursday, Jan. 15 to Sunday, Jan. 18 at Theatre South Playhouse, 7601 Della Drive, Suite 15, Orlando.

Arts + Entertainment
Things to Do

By

Leticia Silva
January 14, 2026

Green PLACE acquires 28-acre Winter Garden property

The Wintersweet property was recently purchased for $1.9 million.

West Orange Times & Observer
News

By

Leticia Silva
January 14, 2026

West Orange Venezuelans speak on Maduro's capture

Nicolas Maduro's capture was a shock to the world, but more importantly, to Venezuelans, it was a step in the right direction.

West Orange Times & Observer
News

By

Liz Ramos
January 13, 2026

Winter Garden expands Golf Cart District

The city also approved an ordinance regulating the operation of electric bicycles, motorized scooters and wheeled devices on the city’s streets, trails and sidewalks.

West Orange Times & Observer
News

By

Megan Bruinsma
January 13, 2026

The City of Ocoee's centennial year closes, changes gears to 2026

During its State of the City, Ocoee highlighted upcoming projects that will shape the future for its next 100 years and improvements for residents’ quality of life.

West Orange Times & Observer
News

By

Liz Ramos
January 13, 2026

Winter Garden to host community meeting on Johns Lake Urban Village Planned Unit Development

The meeting will be at 6:30 p.m. Wednesday, Jan. 14, in the cafeteria of SunRidge Middle School, 14955 SunRidge Blvd., Winter Garden.

West Orange Times & Observer
News

By

Leticia Silva
January 13, 2026

Matthew's Hope to open as cold weather shelter for third time

The homeless ministry is asking for help with cots, clothes and food.

West Orange Times & Observer
News

By

Leticia Silva
January 13, 2026

ONP's opossum ambassador crosses Rainbow Bridge

The Oakland Nature Preserve announced Pepper's passing on Facebook.

West Orange Times & Observer
News

By

Leticia Silva
January 13, 2026

Town of Windermere faces multiple road closures

The town announced multiple road closures from Monday, Jan. 12 to Friday, Jan. 16.

Southwest Orange
News

By

Michael Eng
January 13, 2026

Lake Star at Ovation home tops Horizon West home sales from Jan. 5 to 11

The home at 17378 Glossy Pomelo Way, Winter Garden, sold Jan. 5, for $1,585,480.

Southwest Orange
Real Estate

By

Liz Ramos
January 12, 2026

Multi-vehicle crash near Windermere High sends two to hospital

The crash occurred at approximately 6:43 a.m. Monday, Jan. 12, on Summerport Village Parkway and Winter Garden Vineland Road in Windermere.

Southwest Orange
News

By

Liz Ramos
January 12, 2026

Windermere residents under precautionary boil water advisory

Residents on West Second Avenue and Pine Street are under the advisory from 7 a.m. to 7 p.m. Tuesday, Jan. 13.

Southwest Orange
News

By

Liz Ramos
January 12, 2026

Windermere to welcome new mayor, council member

Andy Williams will be the next mayor of Windermere with CT Allen taking his seat on Windermere Town Council.

Southwest Orange
News

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