Winter Garden Sports & Athletics at a Glance

22 Miles of Trail
2 Golf Courses
10+ Fitness Centers
8+ City Sports Programs

🚴 Florida's Trail Town: Winter Garden is one of Florida's official designated Trail Towns — the only city where the West Orange Trail runs directly down the brick-lined main street rather than parallel to it. That single piece of infrastructure shapes Winter Garden's sports identity more than any country club: cycling, running, walking, and rolling are how this community moves. Add a public championship course at Stoneybrook West, the long-standing private West Orange Country Club, and a fast-growing pickleball scene, and you have one of West Orange County's most well-rounded athletic communities. Browse Winter Garden homes for sale.

"Plant Street isn't just Winter Garden's main street — it's a Florida Trail Town corridor where the West Orange Trail runs through the heart of downtown, turning a casual ride into lunch on a brick-lined patio."
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Sports & Athletics Highlights of Winter Garden

Winter Garden's sports profile is unusual for West Orange County. While neighboring communities like Horizon West are built around large planned-community amenity centers, Winter Garden's athletic life is anchored in three things — the West Orange Trail running through historic downtown, two distinct golf clubs serving very different memberships, and an unusually robust city Parks & Recreation department running youth and adult leagues year-round. For families considering this active community, explore our Winter Garden homes for sale.

🏆 Top Sports & Athletic Destinations

1West Orange Trail

22 miles of paved rail-trail from Killarney Station to Apopka — and the only at-grade urban segment runs directly through downtown Winter Garden's brick-lined Plant Street. The trail's most active hub.

2West Orange Country Club

Winter Garden's only private country club. An 18-hole Lloyd Clifton course built in 1967, plus tennis, pickleball, swimming, and dining — the city's traditional members' club since the 1960s.

3Stoneybrook West Golf Club

An Arthur Hills-designed public championship course wrapped by the gated Stoneybrook West community. Reopened in 2023 with new ownership and a fresh practice facility.

4Veterans Memorial Park Pickleball

Free public open-play pickleball courts at 420 South Park Avenue. The center of Winter Garden's growing pickleball scene with skilled play and open play sessions throughout the week.

🚴 Cycling Capital of West Orange

Winter Garden is a designated Florida Trail Town — the West Orange Trail runs through Plant Street, drawing roughly 150,000 trail users a month. Two on-trail bike rental shops (Wheelworks at Winter Garden Station, and West Orange Trail Bikes & Blades at Killarney Station) keep the corridor active year-round.

⛳ Two Golf Profiles

Unlike the membership-only Horizon West model, Winter Garden gives golfers a clear choice: West Orange Country Club for traditional private membership, or Stoneybrook West Golf Club for daily-fee public play on a championship Arthur Hills design.

🏓 Pickleball Everywhere

Free open-play courts at Veterans Memorial Park, member courts at West Orange Country Club, and city league play through Jessie Brock Community Center make pickleball one of Winter Garden's fastest-growing community sports.

🧒 City-Run Youth Sports

The City of Winter Garden operates one of West Orange's deepest municipal recreation programs — basketball, football, soccer, baseball, softball, archery, swim lessons, and tennis — coordinated out of Jessie Brock Community Center on North Dillard Street.

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Winter Garden Sports & Athletics Map

Explore golf courses, fitness centers, sports facilities, and athletic venues in Winter Garden using this interactive map:

Cycling & the West Orange Trail in Winter Garden

If Winter Garden has a single defining sports asset, it's the West Orange Trail. The 22-mile paved rail-trail runs from Killarney Station in Oakland east through downtown Winter Garden, then turns north toward Apopka — and the segment that defines the city is the at-grade run down brick-paved Plant Street, where the trail and the historic main street are the same corridor. That makes Winter Garden one of Florida's officially designated Trail Towns, and it's why daily cycling, running, and walking volume here is unlike anywhere else in West Orange County.

🚴 Trail Stations & Bike Rentals in Winter Garden

Facility Type Location Details
Winter Garden Station Trail Station 455 E Plant Street, Winter Garden The signature on-trail station in the heart of historic downtown — restrooms, water, and a bike rental shop on site (Wheelworks). Mile marker 5.2 of the 22-mile West Orange Trail.
Chapin Station Trail Station 501 Crown Point Cross Road, Winter Garden Family-oriented station with playground, picnic areas, basketball court, and tennis courts. Mile 7.2. Anchors the Crown Point neighborhoods to the trail.
Tildenville Outpost Trail Outpost 1064 Tildenville School Road, Winter Garden Smaller rest stop with a butterfly garden and shaded seating between Oakland and downtown Winter Garden. Mile 3.8.
Wheelworks Bike Rental & Sales 455 E Plant Street, Winter Garden (at Winter Garden Station) Full-service bike shop offering rentals, sales, repairs, and accessories — directly on the West Orange Trail. Open Tues–Sun.
West Orange Trail Bikes & Blades Bike Rental 17914 SR 438 (Killarney Station) Western trailhead rental fleet — bikes, tandems, and skates. The traditional starting point for first-time trail riders heading into Winter Garden. Open daily.

🚴 Trail Quick Facts

  • Length: 22 miles, fully paved (12–15 ft wide), Killarney Station to Apopka
  • Hours: Sunrise to sunset daily
  • Cost: Free
  • Surface: Asphalt
  • Connections: South Lake-Lake Minneola Scenic Trail (west), part of the Florida Coast-to-Coast Trail
  • Use: Cycling, running, walking, rollerblading, dog walking
  • Helmet law: Required for cyclists under 16 (recommended for all)

For the broader trail context — including connections, mileage, and how Plant Street earned its Florida Trail Town designation — see the West Orange Trail guide.

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Golf Courses in Winter Garden

Winter Garden's golf scene is defined by two courses with very different identities. The West Orange Country Club has been the city's traditional private members' club since 1967, founded by West Orange citrus families and still defined by that family-oriented, low-key atmosphere. Stoneybrook West Golf Club — the public daily-fee championship course wrapped by the gated Stoneybrook West community — closed in 2018, reopened in 2023 under new operators, and is back in the rotation for area public golfers. Together they cover the spectrum from old-school private to championship public play. Many Winter Garden homebuyers are drawn here specifically for the golf-course-adjacent neighborhoods.

🏌️ Golf Courses & Country Clubs

Course Name Type Location Details
West Orange Country Club Private Country Club 3300 W Orange Country Club Drive, Winter Garden 18-hole, par-71 Lloyd Clifton design (1967), 6,418 yards. Tree-lined fairways, small ponds, no tee times for members, walkable course. Greens rebuilt in 2006 with TifDwarf grass. Includes tennis, pickleball, pool, and dining. Membership-only.
Stoneybrook West Golf Club Public Championship 15501 Towne Commons Boulevard, Winter Garden 18-hole, par-72 Arthur Hills design (2000) with water on 14 holes. Aqua driving range, chipping area, and putting green. Public — no membership required. Reopened 2023 under new operations after a 2018–2023 closure. Located within gated Stoneybrook West.

⛳ A Note on Recent Course Status: Stoneybrook West Golf Club closed abruptly in December 2018 and remained dark for nearly five years before reopening in July 2023 with new course management leasing the property from the Stoneybrook West HOA. The course is currently open daily for public play. Verify current tee time availability and conditions directly with the operator before visiting.

For golf enthusiasts looking to live near these courses, browse Winter Garden homes for sale, explore luxury homes in Winter Garden, or look specifically at Stoneybrook West homes wrapped around the public course.

People Also Ask

What golf courses are in Winter Garden?

Winter Garden has two golf courses: the private West Orange Country Club (18 holes, par 71, Lloyd Clifton design from 1967) and the public Stoneybrook West Golf Club (18 holes, par 72, Arthur Hills design from 2000) located inside the gated Stoneybrook West community. WOCC requires membership; Stoneybrook West is open to daily public play.

Are there public golf courses in Winter Garden?

Yes. Stoneybrook West Golf Club is the city's public championship course — an Arthur Hills design that reopened in July 2023 after a multi-year closure. It's located at 15501 Towne Commons Boulevard inside the gated Stoneybrook West neighborhood. The other course in town, West Orange Country Club, is private and requires membership.

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Pickleball & Tennis in Winter Garden

Pickleball has exploded in Winter Garden, and the city has met the demand with free public open-play courts at Veterans Memorial Park, organized league play through the Recreation Department, and member courts at West Orange Country Club. Tennis is more concentrated — primarily WOCC for members and city-run lessons at Jessie Brock — but Chapin Station's public tennis courts on the West Orange Trail add free public access for casual players.

🏓 Pickleball & Racquet Sports Facilities

Facility Name Type Location Details
Veterans Memorial Park Pickleball Courts Public Pickleball 420 South Park Avenue, Winter Garden Free public courts — Open Play Mon/Wed/Sat mornings 8–11 am and Tues/Thurs evenings 6–8 pm; Skilled Play Mon/Wed evenings. Self-organized; not a city-sponsored program. The hub of Winter Garden's growing pickleball community.
West Orange Country Club Private Tennis & Pickleball 3300 W Orange Country Club Drive, Winter Garden Member tennis courts and pickleball courts alongside the golf course. Includes resort-style pool. Membership required.
Chapin Station Tennis & Basketball Public 501 Crown Point Cross Road, Winter Garden Public tennis courts and basketball court adjacent to the West Orange Trail at Mile 7.2. Free, sunrise to sunset.
Jessie Brock Community Center — Pickleball & Tennis Programs City Program 310 N Dillard Street, Winter Garden City-run pickleball lessons and adult tennis instruction. Resident and non-resident rates. Multiple sessions per year.
Where can I play pickleball in Winter Garden?

The center of Winter Garden's public pickleball scene is Veterans Memorial Park at 420 South Park Avenue, with free open-play sessions multiple days per week. The City of Winter Garden also runs pickleball lessons through the Recreation Department at Jessie Brock Community Center. Members of West Orange Country Club have access to private courts. Note that Veterans Memorial open play is self-organized — it is not a city-sponsored program.

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Gyms & Fitness Centers in Winter Garden

Winter Garden's fitness scene runs the full spectrum: budget chains on the SR 50 corridor, full-service health clubs, a YMCA family center on Roper, 24-hour studios for shift workers, and a cluster of boutique studios near Plant Street offering yoga, Pilates, infrared HIIT, and CrossFit. Most of the larger gyms sit along the West Colonial Drive (SR 50) retail corridor. For more wellness context, see our Winter Garden health and wellness guide.

💪 Gyms, Fitness Centers & Studios

Facility Name Type Location Amenities
Crunch Fitness National Chain 14150 W Colonial Drive, Winter Garden 24-hour access, group fitness studio, HIITZone, cycling studio, cardio and strength equipment, dry sauna, HydroMassage, tanning. Memberships from $9.99/month. Opened 2023.
LA Fitness National Chain SR 50 / West Colonial corridor, Winter Garden Full-service club with pool, basketball court, cycle studio, group exercise, free weights, and personal training.
Roper YMCA Family Center Family YMCA Roper Road, Winter Garden area Family-focused facility with pool, group classes, youth programs, swim lessons, and after-school care. Sliding-scale membership.
Anytime Fitness 24-Hour Gym Multiple Winter Garden locations 24/7 keycard access. Compact gym format with free weights, machines, and personal training. Convenient for early-morning or late-night training.
HOTWORX Infrared HIIT Winter Garden Infrared sauna fitness studio offering 30-minute HIIT, yoga, Pilates, cycle, and Iso sessions in heated private suites.
Mili's Gym Powerlifting / Independent Winter Garden Independent serious-training facility known for powerlifting equipment, plates, and a no-frills hardcore atmosphere.
Iron Core Gym Independent Winter Garden Local independent gym focused on strength training and bootcamp-style group classes.

🧘 Specialized Fitness & Wellness Studios

Plant Street and the surrounding downtown core host a cluster of boutique fitness studios — yoga, Pilates, barre, and martial arts — that complement the larger SR 50 chains. For specifics on this downtown studio cluster, see the dedicated downtown Winter Garden fitness and wellness guide.

What fitness centers are in Winter Garden?

Winter Garden has a deep fitness inventory along the SR 50 / West Colonial corridor — Crunch Fitness, LA Fitness, Anytime Fitness, HOTWORX, plus the Roper YMCA Family Center for families. Independent options like Mili's Gym (powerlifting) and Iron Core Gym serve more serious training. Boutique studios cluster near Plant Street downtown. For deeper coverage of downtown fitness studios, see our downtown fitness and wellness guide and our Winter Garden health and wellness guide.

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Team Sports & Youth Leagues in Winter Garden

Winter Garden's organized sports scene is unusually city-driven. The City of Winter Garden Parks & Recreation Department — based at Jessie Brock Community Center — runs an exceptionally broad slate of youth and adult leagues, from recreational basketball, football, soccer, and baseball to less-common offerings like archery, kickball, and esports. Most program registration runs through enroll.wgplay.com or 407-656-4155. For more on local schools and their sports programs, visit our Winter Garden schools guide.

⚽ Youth & Adult Sports Programs

Organization / Facility Type Sports Offered Details
City of Winter Garden Athletics Municipal — Youth & Adult Basketball, football, soccer, baseball, softball, kickball, archery, tennis, pickleball, esports Coordinated through Jessie Brock Community Center, 310 N Dillard Street. Resident and non-resident rates. Seasonal registration through enroll.wgplay.com.
Braddock Park & George Bailey Park Public Sports Fields Baseball / softball diamonds, multi-purpose fields The city's primary public sports field complexes — host most city youth baseball and softball league games. Maintained by City of Winter Garden Parks & Recreation.
Jessie Brock Community Center Recreation Center Indoor program HQ for all city sports, fitness classes, and youth camps 310 N Dillard Street. The administrative and program home of the Winter Garden Parks & Recreation Department. Outdoor walking trail with fitness stations, pond, and pavilion. 407-656-4155.
Striker Soccer Academy — Adult Leagues Adult Soccer 4v4 men's, women's, co-ed, over-35 Recreational adult soccer leagues run locally. Register as individual free agent or full team. soccerinorlando.com.
Super Soccer Stars / Amazing Athletes Youth Development Soccer (12 mo–3 yr), multi-sport (preschool) Early-childhood movement and sport-skill programs run through Jessie Brock Community Center.
West Orange High School Athletics High School Athletics Football, basketball, soccer, baseball, softball, lacrosse, track, more The Warriors have anchored Winter Garden Friday-night football since 1975. Multi-generational alumni base; the city's primary OCPS high school for most of 34787.
SunRidge Middle School Middle School Athletics Middle school sports feeders to West Orange High Winter Garden's primary OCPS public middle school athletic program — see our Winter Garden schools guide for zoning details.
What youth sports leagues are available in Winter Garden?

The City of Winter Garden Parks & Recreation Department runs the broadest slate of youth sports in West Orange County — recreational basketball, football, baseball, soccer, softball, archery, tennis, and pickleball — coordinated out of Jessie Brock Community Center on North Dillard Street. Registration is through enroll.wgplay.com. School-age players also have West Orange High School athletics, the city's primary OCPS high school program. For more family resources, see our Winter Garden schools guide.

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Water Sports & Boating in Winter Garden

Winter Garden's relationship to water sports runs through one major asset: Lake Apopka, Florida's fourth-largest lake. The city's southeastern shoreline is anchored by Newton Park at the western end of Plant Street — home to the public boat ramp, fishing pier, and Tanner Hall. Bass fishing and pontoon boating are the dominant water sports here. Smaller paddle-sport access exists at Tucker Recreational Park on Johns Lake. For waterfront living, explore our Winter Garden waterfront homes.

🚤 Boat Ramps & Lake Access

Facility Type Location Services
Newton Park Boat Ramp Public Boat Ramp 251 W Plant Street, Winter Garden (on Lake Apopka) The city's primary access point to Lake Apopka. Boat ramp, fishing pier, paddle-craft launch, Tanner Hall (event space), and the lakefront boardwalk that anchors downtown sunset views. Free public access.
Tucker Recreational Park & Nature Preserve Paddle-Craft Launch Off Tilden Road on Johns Lake, Winter Garden 200-acre conservation park along the Johns Lake shoreline. Canoe and kayak launch, nature trails, large playground, picnic areas, and preserved cattle-ranch heritage. Free.

🏄 Water Sports & Recreation

Winter Garden's water sports are predominantly paddle-based and angling-focused rather than ski- or jet-ski-driven — Lake Apopka's shallow average depth and protected ecology favor pontoons, kayaks, and bass fishing over high-speed water sports. There is no full-service marina inside Winter Garden city limits; for that scale of facility, residents typically travel to the Butler Chain (Windermere) or further south to Tibet-Butler.

🎣 Lakes Around Winter Garden

Winter Garden's 34787 ZIP code is dotted with named lakes — many small, some neighborhood-anchored — that support fishing, paddling, and lakefront living. Notable lakes include Johns Lake, Brandy Lake, Lake Roper, Lake Tilden, Lake Avalon, Lake Mac, Hickorynut Lake, Huckleberry Lake, Lake Luntz, Lake Roberts, Lake Speer, Saw Grass Lake, and Panther Lake — though Panther Lake's water sports profile sits primarily within Horizon West.

For outdoor enthusiasts, also explore our Winter Garden parks and recreation guide.

Where can I go boating near Winter Garden?

The Newton Park boat ramp at the western end of Plant Street is Winter Garden's primary access to Lake Apopka — Florida's fourth-largest lake — for fishing, pontoons, and paddle craft. Johns Lake has paddle-craft access through Tucker Recreational Park. There is no full-service marina within Winter Garden city limits; for that, residents typically head south to the Butler Chain in Windermere. Explore waterfront homes in Winter Garden.

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Specialized Sports & Athletic Activities in Winter Garden

Beyond the major categories, Winter Garden offers a handful of specialized athletic options — most run through the City Recreation Department or a small number of independent operators.

🎯 Specialized Athletic Programs & Facilities

Activity Type Location Details
City of Winter Garden Archery Archery Jessie Brock Community Center, 310 N Dillard Street Barebow archery courses for youth and adults — beginners through advanced. Equipment provided. Resident and non-resident rates per session.
Bouler Pool Public Pool 362 11th Street, Winter Garden City pool offering free youth swim lessons in summer (limited scholarships available). Registration on-site at the pool.
Karate / Martial Arts Martial Arts Jessie Brock Community Center & private studios in Winter Garden Karate classes through City Recreation; multiple independent martial arts schools (Brazilian jiu-jitsu, taekwondo, karate) operate in the SR 50 corridor.
Esports Club (City Program) Esports Jessie Brock Community Center, 310 N Dillard Street One of the more unusual offerings in West Orange — a city-run esports club for youth, alongside a Video Game Club for casual players.
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Athletic Lifestyle in Winter Garden

Why Choose Winter Garden for Sports & Athletics?

Winter Garden residents enjoy:

  • Trail-Town Cycling Culture — The West Orange Trail runs through downtown Plant Street, not parallel to it; daily cycling and running is built into the rhythm of the city.
  • Two Distinct Golf Options — Membership-only tradition at West Orange Country Club (1967) and public championship play at the reopened Stoneybrook West Golf Club inside Stoneybrook West.
  • Free Public Pickleball — Open-play pickleball at Veterans Memorial Park is one of the few free, regularly-used public pickleball venues in West Orange County.
  • Deep City Recreation Department — One of the broadest municipal sports slates in West Orange — youth basketball, football, baseball, soccer, plus archery, tennis, esports — all coordinated through Jessie Brock Community Center.

Sports & Athletic Culture in Winter Garden

🚴 Bike-First Downtown

The West Orange Trail draws an estimated 150,000 trail users a month through downtown. Bike racks line Plant Street. Wheelworks at Winter Garden Station rents bikes directly trailside.

⛳ Old-School Country Club Culture

WOCC has remained a multi-generational members' club founded by citrus families in 1967. Walkable, no tee times, and known for a non-pretentious atmosphere.

🏈 Friday Night Warriors

West Orange High School football has been a Winter Garden community event since 1975. The Warriors are the city's primary OCPS athletic identity.

🏊 Lake Apopka Sunsets

Newton Park at the foot of Plant Street is the city's signature water access — the boat ramp, fishing pier, and the boardwalk where downtown comes to watch the sun drop over Lake Apopka.

Quick Sports & Athletics Facts

  • Trail Access: 22 miles of paved West Orange Trail with downtown urban segment along Plant Street
  • Golf: Two courses — private West Orange Country Club and public Stoneybrook West Golf Club
  • Fitness Centers: 10+ along the SR 50 corridor including Crunch, LA Fitness, Anytime Fitness, HOTWORX, plus Roper YMCA
  • City Sports Programs: Basketball, football, baseball, soccer, softball, tennis, pickleball, archery, esports — all through Jessie Brock Community Center
  • Water Access: Lake Apopka via Newton Park boat ramp; Johns Lake via Tucker Recreational Park
  • High School Athletics: West Orange Warriors since 1975
"Winter Garden's sports identity isn't built around an exclusive amenity — it's built around what residents do every day on the West Orange Trail, on Plant Street, on the courts at Veterans Memorial Park, and at the Newton Park boat ramp."
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Nearby Sports & Athletic Facilities

Winter Garden residents have easy access to sports and athletic facilities in adjacent and nearby West Orange communities — many sit within a 15-minute drive:

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Frequently Asked Questions About Winter Garden Sports

What golf courses are in Winter Garden?

Winter Garden has two courses: the private West Orange Country Club at 3300 W Orange Country Club Drive (18 holes, par 71, Lloyd Clifton design from 1967), and the public Stoneybrook West Golf Club at 15501 Towne Commons Boulevard (18 holes, par 72, Arthur Hills design from 2000) inside the gated Stoneybrook West community. Stoneybrook West reopened in July 2023 after a multi-year closure.

Does Winter Garden have good fitness centers?

Yes — the SR 50 (West Colonial) corridor hosts a deep mix of national chains (Crunch Fitness, LA Fitness, Anytime Fitness, HOTWORX) and independent options (Mili's Gym, Iron Core), plus the family-focused Roper YMCA. Boutique studios cluster near Plant Street downtown. For more detail see our downtown fitness studios guide. Active residents can explore Winter Garden homes for sale.

What youth sports leagues are available in Winter Garden?

The City of Winter Garden Parks & Recreation Department runs an unusually broad municipal slate — basketball, football, baseball, soccer, softball, archery, tennis, and pickleball — out of Jessie Brock Community Center on North Dillard Street. Registration runs through enroll.wgplay.com. Public sports fields at Braddock Park and George Bailey Park host most game play. School-age athletes also have West Orange High School athletics. See our Winter Garden schools guide for related school zoning.

Where can I bike or run in Winter Garden?

The 22-mile West Orange Trail is the answer — and Winter Garden is the only city where the trail runs at-grade through historic downtown along brick-paved Plant Street, earning the city a Florida Trail Town designation. Trailheads at Winter Garden Station (455 E Plant Street), Chapin Station (Crown Point Cross Road), and Tildenville Outpost give multiple access points within city limits. Bike rentals are available trailside at Wheelworks (Winter Garden Station) and West Orange Trail Bikes & Blades (Killarney Station).

Are there water sports opportunities near Winter Garden?

Yes — primarily on Lake Apopka, Florida's fourth-largest lake. Winter Garden's public access is at Newton Park (251 W Plant Street), with a boat ramp, fishing pier, and paddle-craft launch directly downtown. Johns Lake offers a kayak/canoe launch at Tucker Recreational Park. Note that Lake Apopka's profile favors fishing, pontoons, and paddle craft over high-speed water sports. Explore waterfront homes in Winter Garden.

What makes Winter Garden good for sports-minded residents?

Three things set Winter Garden apart in West Orange: (1) Florida Trail Town status, with the West Orange Trail running through Plant Street downtown — daily cycling and running is built into the city's rhythm; (2) the choice between traditional private golf at West Orange Country Club and public championship play at Stoneybrook West Golf Club; and (3) one of the deepest municipal recreation programs in West Orange, with city-run leagues across nearly every popular sport. Ready to make Winter Garden home? Browse Winter Garden real estate listings.

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Find Your Home in Winter Garden

Ready to enjoy the trail-town cycling, country-club golf, free pickleball, and city sports leagues of Winter Garden? Our team at Florida Neighborhood Realty can help you find the perfect home in this active, historic community. Browse Winter Garden homes for sale or contact us for personalized assistance.

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Contact Us About Winter Garden Call/Text: 407.801.3286

*Disclaimer: The information on this page is for general informational purposes only. Facility hours, membership fees, programs, and access may change. Stoneybrook West Golf Club closed in 2018 and reopened in 2023 — verify current operations directly with the club before visiting. Please verify current details directly with each facility before visiting. The inclusion of sports facilities, golf courses, gyms, and links on this site does not imply endorsement by the site owner. We are not responsible for the content, accuracy, or services of any linked sites. Private clubs and facilities may require membership or fees for access.

Last Updated: May 8, 2026