Winter Garden, a historic downtown with room to grow
A city of about 48,000 people in west Orange County, with a historic downtown on Plant Street, a large Saturday farmers market and the West Orange Trail. Fabiola helps families, first-time and move-up buyers here.
Your Orlando REALTOR®
Fabiola Meneses
The Pozek Group · Real Broker, LLC
FIU civil engineering graduate · English & Español
The market right now
Redfin, City of Winter Garden, three months ending August 2026 (median up 4.6% from a year earlier; homes sold at 97.9% of list price). Population: U.S. Census Bureau estimate for July 1, 2025. Ask Fabiola for a current report for the area you like.
See Winter Garden with Fabiola
Tours and neighborhood guides from Fabiola’s YouTube channel. Press play to watch them right here.
Living in Winter Garden
Winter Garden’s small-town downtown, history and lifestyle, just west of Orlando.
Winter Garden · 2024 · YouTube ↗
What Winter Garden offers
Winter Garden was established in 1903 and incorporated in 1908. Its downtown was listed on the National Register of Historic Places in 1996, and today it is the center of the city’s social life.
Around it are older neighborhoods and newer communities, many of them close to Horizon West and the SR 429.
- Farmers Market. Every Saturday from 8 a.m. to 1 p.m. at the Downtown Pavilion, with more than 100 vendors.
- West Orange Trail. 22.4 miles for walking and biking through Oakland, Winter Garden and Apopka.
- Garden Theatre. A 1935 theater restored in 2008, now owned by the city.
- Plant Street. Restaurants, shops and Plant Street Market, with a new boutique hotel under construction since July 2026.
Four things to check before you buy in Winter Garden
Fabiola, a civil engineering graduate from FIU, checks these before you make an offer.
CDD or no CDD
Some communities have one, such as Stoneybrook West and Winter Garden Village at Fowler Groves. Others do not. She gets the exact amount for each home.
City or county
Some homes with a Winter Garden address are outside city limits. That can change taxes, utilities and rules.
Older vs. newer homes
Homes near downtown can be decades old; newer ones may have builder warranties. She reviews the inspection either way.
Commute and tolls
The Turnpike, SR 429 and SR 408 are all toll roads. Add them to your monthly budget if you commute every day.
Schools and getting around
Schools are part of Orange County Public Schools. Always confirm the assigned schools by address.
- Schools often listed: West Orange High, SunRidge Middle and elementary schools such as Dillard Street, Tildenville, Whispering Oak and Maxey.
- Dual language: Tildenville Elementary’s two-way dual language magnet program was recognized by Magnet Schools of America in 2026.
- Disney: about 20 minutes via SR 429. Downtown Orlando: about 20 to 25 minutes.
- Orlando International Airport: about 30 to 35 minutes via the Turnpike.
“I met Fabiola at my kids school and was wondering to myself why is there a Real Estate Company here at my kids Open House, but thank God she was. I was only interested in renting a property, but she gave me the confidence that I needed to go through the lending process and now we own our own newly built home. She stood by me the whole time through the good, ugly, stressful, and anxious periods of the process. Her knowledge in her field was spot on. I would recommend Fabiola for anyone looking for a Realtor.”
Winter Garden: common questions
How much does a home in Winter Garden cost?
The median sale price was about $599,000 for the three months ending August 2026, according to Redfin. Townhomes and older homes start lower.
When is the Winter Garden Farmers Market?
Every Saturday from 8 a.m. to 1 p.m. at the Downtown Pavilion, 104 S. Lakeview Ave.
Do Winter Garden homes have a CDD?
Some do and some do not. Communities like Stoneybrook West have a CDD. Fabiola confirms it for each home before you make an offer.
How far is Winter Garden from Disney?
About 20 minutes via SR 429, depending on traffic.
Find the right neighborhood in Winter Garden
Prices, costs, schools and commute for the homes you like. In English or Spanish.
Where these numbers come from
Checked in October 2026. Some figures come from market data and broker sites; confirm before you make a decision.