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By Observer Staff
February 17, 2026

Obituary: Annie Esther Gooch Heise

Annie Esther Gooch Heise, 29, formerly of Winter Garden, passed away on Feb. 12, 2026, after a brief battle with gastric cancer.

West Orange Times & Observer
Obituaries

By

Michael Eng
February 17, 2026

Casabella home tops Horizon West-area home sales from Feb. 9 to 15

The home at 13125 Casabella Drive, Winter Garden, sold Feb. 10, for $3,075,000.

Southwest Orange
Real Estate

By

Liz Ramos
February 16, 2026

Three Birds Café to close in Winter Garden

The final day for the café will be Thursday, Feb. 26.

West Orange Times & Observer
News

By

Amy Quesinberry Price
February 16, 2026

PHOTOS: Rotary Club of Winter Garden's 100th anniversary exhibit

A new exhibition at the Winter Garden Heritage Foundation pays tribute to the Rotary club’s dedication to its mission of Service Above Self and making a difference in Winter Garden.

West Orange Times & Observer
Neighborhood

By

Liz Ramos
February 13, 2026

Ocoee Neighborhood Matching Grant Program applications available

The grant program assists residents with making improvements to their neighborhoods.

West Orange Times & Observer
News

By

Michael Eng
February 13, 2026

Oakland Park home tops Winter Garden/Oakland home sales from Feb. 2 to 8

The home at 8123 Fenton St., Orlando, sold Feb. 5, for $1,174,620.

West Orange Times & Observer
Real Estate

By

Michael Eng
February 12, 2026

PHOTOS: Tildenville Elementary School Family Science Night

From computer programming and meteorology to biology and chemistry, Tildenville Elementary School made science come alive at its Family Science Night Thursday, Feb. 12, at the school.

Observer School Zone

By

Liz Ramos
February 12, 2026

Winter Garden warns of scam

The scam involved false city Planning and Zoning invoices requesting a wire transfer.

West Orange Times & Observer
News

By

Michael Eng
February 12, 2026

Windermere rolls out red carpet for Night to Shine

Night to Shine 2026 will take place from 6 to 9 p.m. Friday, Feb. 13, at the church’s Windermere campus, 300 Main St., Windermere.

Arts + Entertainment
Things to Do

By

Amy Quesinberry Price
February 12, 2026

1931-2026: Anne Bailey built community through local newspaper

Anne and George Bailey bought The Winter Garden Times in 1970 and shared the ins and outs of small-town living for 44 years.

West Orange Times & Observer
Obituaries

By

Michael Eng
February 12, 2026

OBSERVED: New digs! Observer returns to Dillard Street

We left our longtime home at 720 S. Dillard St. in 2018 and now have found a new one at 210 S. Dillard St.

West Orange Times & Observer
Opinion

By

Megan Bruinsma
February 11, 2026

Oakland’s deadline is approaching to request a vote-by-mail ballot

The deadline to request a vote-by-mail ballot is Thursday, Feb. 26.

West Orange Times & Observer
News

By

Leticia Silva
February 11, 2026

Central Florida Diaper Bank receives four-month supply from Huggies

The Winter Garden-based bank has served local families for more than 30 years.

West Orange Times & Observer
News

By

Leticia Silva
February 11, 2026

MEET THE CANDIDATES: Oakland Town Commission

Joseph McMullen and Anne Fulton are vying for the District 4 seat on the Oakland Town Commission.

West Orange Times & Observer
News

By

Leticia Silva
February 11, 2026

MEET THE CANDIDATES: Joseph McMullen, Oakland Town Commission District 4

Incumbent Joseph McMullen will face Anne Fulton in the race for the Oakland Town Commission District 4 seat.

West Orange Times & Observer
News

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