Winter Garden Insider
Your Guide to Living in Winter Garden, Orange County
Explore our neighborhood guides to Winter Garden — dining, schools, parks, shopping, things to do and more. Browse by topic below to find the stories that matter to you.
Schools & Education
- Dillard Street Elementary: Pre-K Through 5th Grade in Downtown Winter Garden
- Foundation Academy: Winter Garden's Top-Rated Private Christian School Across Three Campuses
- SunRidge Middle School: Winter Garden's Public Middle School Option
- West Orange High School: A Winter Garden Institution Since 1975
- Westside Tech and Valencia College West: Career Training and Higher Education in Winter Garden
- William S. Maxey and Tildenville Elementary: Two Neighborhood Schools Serving Winter Garden Families
Restaurants & Dining
- Coffee Shops, Bakeries, and Ice Cream in Downtown Winter Garden
- Date Night on Plant Street: Romantic Restaurants in Historic Downtown Winter Garden
- Fine Dining in Winter Garden: Chef's Table at the Edgewater, Matthews Steakhouse, and More
- Global Flavors in Winter Garden: Thai Blossom, The Whole Enchilada, and International Cuisine
- The Historic Edgewater Hotel: Tasting Room Brunch and a 1927 Downtown Landmark
- Plant Street Market and Crooked Can Brewing: Winter Garden's Food Hall Experience
Fun Things to Do
- Fridays on the Plaza: Winter Garden's Free Weekly Outdoor Concert Series
- From Winter Garden to the Orlando Theme Parks: A Family Guide to Disney, Universal, and SeaWorld Day Trips
- Light Up Winter Garden and the Annual Christmas Parade: Holiday Traditions Downtown
- Spring Fever in the Garden: The Bloom & Grow Festival on Plant Street
- Winter Garden Farmers Market: Why This Saturday Tradition Was Voted Best in the USA
- The Winter Garden Halloween Experience: 14 Days of Family-Friendly Festivities Downtown
Parks & Recreation
- Fishing and Boating on Lake Apopka: Florida's Fourth-Largest Lake from Winter Garden's Shore
- The Jessie Brock Community Center: Recreation Programs, Classes, and Events in Winter Garden
- Newton Park: Lake Apopka Sunsets, Tanner Hall, and Downtown Winter Garden's Waterfront
- Oakland Nature Preserve: The 128-Acre Lake Apopka Boardwalk Minutes from Winter Garden
- The West Orange Trail Through Winter Garden: A Florida Trail Town Guide
- Winter Garden's Neighborhood Parks: Maple Street, Chapin Station, and Family-Friendly Playgrounds
Shopping Guide
- Big Box Shopping Along SR 50: The West Colonial Drive Retail Corridor in Winter Garden
- Boutique Shopping on Plant Street: Independent Retailers in Historic Downtown Winter Garden
- Grocery Store Options in Winter Garden: Publix, Walmart, ALDI, and Target Groceries
- Home Goods and Specialty Retail: Driftwood Market, Adjectives, and The Ancient Olive
- Shop Small in Winter Garden: Small Business Saturday and Year-Round Local Retail
- Winter Garden Village at Fowler Groves: A Guide to the 80+ Store Open-Air Shopping Center
Health & Wellness
- AdventHealth Winter Garden: The Full-Service Hospital on Fowler Grove Boulevard
- Fitness Studios and Wellness Centers Near Historic Downtown Winter Garden
- The New AdventHealth Winter Garden Baby Place: Labor & Delivery Arrives in Town
- Orlando Health Health Central Hospital: Winter Garden's Closest Full-Service Hospital in Neighboring Ocoee
- Senior Care and Family Health Resources in Winter Garden: What's Available in 34787
- Urgent Care Options in Winter Garden: Centra Care, Walk-In Clinics, and 24-Hour Services
Sports & Athletics
- Braddock Park and George Bailey Park: Winter Garden's Public Sports Fields
- City of Winter Garden Athletic Programs: Youth Basketball, Football, Soccer, and Baseball Leagues
- Cycling in Winter Garden: Rentals, Routes, and Riding the West Orange Trail
- Pickleball in Winter Garden: Public Courts, Private Clubs, and the Growing Local Scene
- West Orange Country Club: Winter Garden's Private Golf, Tennis, and Pickleball Club Since the 1960s
- West Orange High School Athletics: Warriors Football, Basketball, and Community Sports Tradition
Arts & Culture
- Arts in April in Winter Garden: Exhibitions, Performances, and Community Celebrations
- Central Florida Railroad Museum: Inside the 1913 Tavares and Gulf Depot on Boyd Street
- Garden Theatre: Downtown Winter Garden's Restored 1935 Performing Arts Venue
- SOBO Art Gallery and the Winter Garden Art Association: A Hub for Local Artists
- Winter Garden Downtown Historic District: Walking the National Register Streets
- Winter Garden Heritage Museum: Citrus, Railroads, and the Story of West Orange County
Roads & Highways
- Commuting from Winter Garden: Drive Times and Routes to Downtown Orlando, the Theme Parks, and Major Employment Centers
- Daniels Road and Winter Garden-Vineland Road (CR 535): The North-South Arteries South of SR 50
- Florida's Turnpike at Winter Garden: The SR 50 Interchange and Statewide Access
- Plant Street: The Brick-Lined Main Street of Historic Downtown Winter Garden
- SR 429 (Daniel Webster Western Beltway): Winter Garden's Toll Road Connection to I-4, Apopka, and Beyond
- State Road 50 / West Colonial Drive Through Winter Garden: The Primary East-West Retail Corridor
Thinking About a Move to Winter Garden?
Beyond the reading, we can help you find the right neighborhood and home.
David Myers
