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By Megan Bruinsma |
September 25, 2025

Winter Garden Cracker Barrel to change its logo again

Winter Garden’s Cracker Barrel was one of four stores to undergo renovations, but it won’t be sticking.

West Orange Times & Observer
News

By Megan Bruinsma |
November 25, 2025

Dr. Phillips football team advances to the regional semifinals

Dr. Phillips is the last local team standing in the FHSAA football playoffs.

Sports
High Schools

By Sam Albuquerque |
September 3, 2025

Athlete of the Week: Gavin Pritzkau, Central Florida Christian Academy football

As an eighth-grader, Gavin Pritzkau is playing a crucial role on CFCA’s varsity football team and its early-season success.

Sports
Athlete of the Week

By Michael Eng |
September 5, 2025

Five-acre horse farm tops Winter Garden sales from Aug. 25 to 31

The home and property at 9201 Tower Pine Drive, Winter Garden, sold Aug. 25, for $2,625,000.

West Orange Times & Observer
Real Estate

By Megan Bruinsma |
October 9, 2025

Athlete of the Week: Kayla McKinney, West Orange swim

West Orange’s swimmer, Kayla McKinney, is a state medalist and continues to make waves in the water her senior year.

Sports
Athlete of the Week

By Liz Ramos |
October 14, 2025

Windermere Isle home tops Horizon West sales from Oct. 6-12

The home at 8379 Vivaro Isle Way, Windermere, sold Oct. 9, for $1,200,000.

Southwest Orange
Real Estate

By Michael Eng |
November 11, 2025

Watermark home tops Horizon West sales from Nov. 3 to 9

The home at 9574 Meadow Hunt Way, Winter Garden, sold Nov. 7, for $1,250,000.

Southwest Orange
Real Estate

By Michael Eng |
December 12, 2025

Oakland Park home tops Winter Garden sales from Dec. 1 to 7

The home at 1224 Union Club Drive, Winter Garden, sold Dec. 1, for $1,665,000.

West Orange Times & Observer
Real Estate

By Megan Bruinsma |
January 27, 2026

Local cheer teams compete in FHSAA States

Windermere High competitive cheer team has won back-to-back state championships and will compete in nationals this weekend.

Sports
High Schools

By Leticia Silva |
January 27, 2026

Crossline Community Church's construction soon to begin

The project, which includes a church, preschool, gym and athletic fields, should be completed in 2027 or 2028.

Southwest Orange
News

By Leticia Silva |
January 27, 2026

Beyond the books: How Thornebrooke Elementary cultivates lifelong friendships

The program brings fourth- and fifth-graders together with students with special learning needs through Barracuda Buddies.

Observer School Zone

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 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 Megan Bruinsma |
March 3, 2026

Athlete of the Week: Richelle Ruiz, Olympia High softball

Olympia High softball team’s Richelle Ruiz is batting in success during her senior season.

Sports
Athlete of the Week

By Megan Bruinsma |
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.

Sports

By Justice Covert |
March 4, 2026

Winter Garden leaders approve AI answering system

Winter Garden will implement an AI system to answer calls for non-emergency police assistance.

West Orange Times & Observer
News

By Michael Eng |
April 10, 2026

Hickory Hammock home tops Winter Garden home sales from March 30 to April 5

The home at 15986 Johns Lake Overlook Drive, Winter Garden, sold March 31, for $1,962,500.

West Orange Times & Observer
Real Estate

By Michael Eng |
March 9, 2016

Keene’s Pointe estate sells for $2.925 million

A home in the Keene’s Pointe community in Windermere topped all West Orange-area residential real-estate sales from Feb. 19 to 25.

West Orange Times & Observer
Real Estate

By Michael Eng |
June 5, 2020

Windermere Club estate sells for $1.6 million

A home in the Windermere Club community in Windermere topped all West Orange-area residential real-estate transactions from May 21 to 28.

West Orange Times & Observer
Real Estate

By Michael Eng |
June 22, 2020

Keene’s Pointe estate sells for $2.75 million

A home in the Keene’s Pointe community in Windermere topped all West Orange-area residential real-estate transactions from June 5 to 11.

West Orange Times & Observer
Real Estate

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