Braddock Park & George Bailey Park: Public Sports Fields Serving Winter Garden
Two parks, two jurisdictions, and where Winter Garden families actually play ball
Braddock Park and George Bailey Park are the two main public sports fields serving the Winter Garden, FL area. Braddock Park, at 13460 Lake Butler Blvd, is a City of Winter Garden park with two soccer fields and two softball fields, home to the City's Youth Soccer League and Adult USSSA Softball. George Bailey Park, at 11974 Roberson Rd with a Winter Garden 34787 mailing address, is actually a 15-acre Orange County park and the home field for Windermere Little League. Both parks share the 34787 zip code but fall under different jurisdictions — Braddock is city-managed, George Bailey is county-managed.
If you're moving to Winter Garden with kids who play sports, you'll hear two park names on repeat: Braddock Park and George Bailey Park. They're where youth soccer practices on Tuesday nights, where Little League runs all spring, and where adult softball fills the diamonds under the lights Monday through Thursday.
Here's the wrinkle: only one is actually a Winter Garden city park. The other shares a Winter Garden mailing address but is run by Orange County and hosts a league called Windermere Little League. Welcome to West Orange, where city limits, zip codes, and league names don't always line up.
Braddock Park: The City of Winter Garden Park on Lake Butler Boulevard
Braddock Park sits at 13460 Lake Butler Blvd on the south side of Winter Garden, near the Horizon West edge. It's owned and operated by the City of Winter Garden Parks and Recreation Department, which means this is where your tax dollars work if you live inside city limits.
The park was built as a roughly 20-acre community athletic complex with two multi-purpose fields, two softball fields, around 130 parking spaces, a 1,600-square-foot covered playscape, and a 1,200-square-foot concession building with restrooms. Lighting on the fields means evening games run well past sunset — useful in Florida, where the only reasonable practice time half the year is after the sun drops.
What plays there:
- City of Winter Garden Youth Soccer League — recreational program for ages 4–13, with an eight-week season, team jerseys, and end-of-season awards. Games typically start in early September.
- Adult Slow-pitch USSSA Softball — spring and fall leagues, Monday through Thursday evenings, split into church, men's, and co-ed divisions.
- Drop-in use — the playground and picnic area are open to the public when fields aren't reserved.
Honest assessment: parents universally praise the field maintenance and the cleanliness of the restrooms. The most common complaint is parking on game days — 130 spaces sounds like a lot until four soccer games and two softball games are all wrapping up at the same time. Arrive early or carpool. The playground is on the smaller side and better suited for younger kids than for older siblings burning energy between sibling games.
Registration, league schedules, umpire/scorekeeper jobs, and field rentals all run through the Winter Garden Parks and Recreation office at (407) 656-4155, headquartered at the Jessie Brock Community Center on N. Dillard Street.
George Bailey Park: The Orange County Park That Sounds Like a City Park
Now here's where it gets fun. George Bailey Park is at 11974 Roberson Rd with a Winter Garden, FL 34787 mailing address — but it's an Orange County Parks and Recreation facility, not a City of Winter Garden one. It sits in unincorporated Orange County right at the geographic meeting point of Winter Garden, Windermere, and Horizon West.
The 15-acre park is built around baseball and softball — multiple ball diamonds, all with lights, plus a fenced-in playground, two pavilions, and a concession stand that opens for league games. The fields are well-shaded, well-maintained, and consistently rated among the best youth ball complexes in West Orange.
The league that actually plays there: Windermere Little League. Yes, "Windermere" — even though the park is mailed Winter Garden. The league's boundary covers a wide swath of West Orange County, so plenty of families from inside Winter Garden city limits, the Horizon West villages, and the Windermere area all funnel their kids onto these diamonds.
Hours: 8 a.m. to 8 p.m. summer / 8 a.m. to 6 p.m. winter, Sunday through Saturday. Reservations require 30 days' advance notice through Orange County Parks. Park direct line: (407) 254-9086.
Why the City/County Split Matters to You
If you're new to 34787, the practical takeaway is this: when you sign your kid up for a city league, you'll likely play at Braddock Park (soccer/softball) or another City of Winter Garden facility. When you sign up for Little League baseball, you're probably with Windermere Little League at George Bailey Park, regardless of which side of which boundary line your house actually sits on.
This trips people up. A family in a Winter Garden subdivision will ask, "Where's the city's baseball program?" The answer: Winter Garden runs youth soccer, basketball, football, and adult softball — but for Little League baseball, most families register with Windermere Little League at the county park. That's how the West Orange youth sports map has settled.
For broader context on what the city itself runs versus what's outsourced to the county or to nonprofit leagues, our guide to city athletic programs walks through the registration calendar and which sports are offered each season.
Who Lives Closest to Each Park
For house-hunters, proximity to the right park can be a real factor — Friday-night practices add up over a season.
Closest to Braddock Park (Lake Butler Blvd area): the southern Winter Garden subdivisions along Winter Garden-Vineland Road and Lake Butler Boulevard. Many Stoneybrook West, Black Lake Park, and southern-corridor neighborhoods are a 5–10 minute drive.
Closest to George Bailey Park (Roberson Rd area): Horizon West villages (especially Bridgewater and Lakeside) and the Hamlin/Avalon Road corridor, plus several Windermere neighborhoods near Lake Butler. Most Horizon West families end up at George Bailey simply because it's the closest baseball complex.
For a fuller look at non-sports parks in town, see our companion piece on Winter Garden's neighborhood parks.
What the Locals Know
A few things that don't show up on the city or county websites:
- Game-day parking at Braddock gets ugly when soccer and softball overlap. Locals know to use the back lot near the maintenance building or to park along Lake Butler and walk in.
- George Bailey's entrance is genuinely confusing the first time. There's no big sign pointing to the playground versus the diamonds — turn in off Roberson and bear right for the kid stuff.
- Concession stands are open during league play at both parks and the prices are actually reasonable — pack snacks for practices, but plan to buy at games.
- Dogs: not allowed at George Bailey, even leashed. This is a recurring sore point in reviews. Braddock is more dog-friendly, but always check current park rules before bringing one.
- Field closures after heavy rain are common from June through September. The City of Winter Garden posts updates on its Athletics page; Windermere Little League posts on the league's field-status page.
If your family's sports life will extend beyond ball fields, our Winter Garden sports and athletics guide covers golf, cycling, pickleball, and the West Orange High School athletic program — and our Winter Garden parks and recreation guide rounds out the trails, lakefront, and neighborhood-park picture.
For league registration, fees, and current season schedules, visit the official City of Winter Garden Athletics page.
Thinking about which Winter Garden neighborhood works best for your family's sports schedule? Browse our Winter Garden homes for sale or contact us for relocation help tailored to where your kids will actually be playing. ⚾
