Winter Garden Living
A Local's Guide to Life Beyond the Move
Welcome to Winter Garden Living—your insider peek into what it's really like to build a life here. Whether you're still planning your relocation or already unpacking boxes, this page is your go-to guide for family-friendly favorites, local gems, and everything in between (real estate optional, community essential).
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Where Locals Love to Live
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Independence
Known for its lakeside trails, community pools, top-rated schools, and active lifestyle, Independence is perfect for families who want space to grow and neighbors who feel like friends. With seasonal events, sports programs, and plenty of sidewalks to stroll, it's the kind of place that makes relocation feel like a fresh start.
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Hamlin
One of the most walkable communities in the area, Hamlin offers newer construction homes, great schools nearby, and easy access to restaurants, shopping, and entertainment. Families love the lake views, bikeable streets, and convenience of having everything close by—without sacrificing a strong community feel.
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Oakland Park
Steps from Downtown Winter Garden and the West Orange Trail, Oakland Park blends new homes with old Florida charm. Families love the golf cart-friendly streets, top-rated schools, and tight-knit community events. It's perfect for those wanting front porch living with walkable convenience and small-town warmth.
Winter Garden offers a wide range of school options to fit your family’s needs—from public and charter to private and special needs-friendly programs. Whether you're looking for strong academics, faith-based values, or a smaller classroom environment, there’s something here to support every student.
Families often choose from top-rated public schools like Water Spring Elementary, Bridgewater Middle, and Windermere High. For those exploring charter options, schools like Renaissance Charter, Imagine Schools, and Hope Charter are popular for their innovative programs and close-knit communities.
If you're considering a private school, local favorites include Foundation Academy, Cranium Academy, and Windermere Preparatory School, each offering unique approaches to education—from faith-based curriculums to global-focused academics.
Special Abilities
If your child has special needs, Florida's Family Empowerment Scholarship for Students with Unique Abilities (FES-UA) can provide funding for educational options outside of the traditional public system. This scholarship helps cover tuition for eligible private schools, therapies, and instructional materials—giving families the flexibility to customize their child's education based on their specific needs. For more information, visit the scholarship website.
Want more school info? Our ‘Living Like a Local’ guide takes a deeper dive into public, private, and charter options around town—plus tips for choosing the right fit!
Education in Winter Garden
Youth Sports
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West Orange Wildcats (Pop Warner)
i9 Sports – Flag Football
Central Florida Youth Football League
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i9 Sports – Basketball
YMCA of Central Florida
Winter Garden Hoops Academy
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Winter Garden Little League
West Orange Babe Ruth Baseball
Windermere Little League
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Winter Garden Soccer Club
Florida Kraze Krush
i9 Sports – Soccer
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Top Gun Cheerleading – Competitive all-star cheer program
Shooting Stars School of Performing Arts – Dance, cheer, and performance teams
Gymnastics USA – Recreational and competitive gymnastics for all ages
Orlando Metro Gymnastics (Baldwin Park/Clermont) – Expansive classes and team programs
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Victory Martial Arts – Winter Garden
Tiger Rock Martial Arts
Championship Martial Arts – Horizon West
Winter Garden is packed with opportunities to keep your kids active, social, and having fun outside of school. Whether they love team sports, martial arts, or more creative outlets, here are some of the most popular local programs!
You’ll also find programs for volleyball, swim, ninja-style obstacle training, and more. Whatever your child’s interests, Winter Garden makes it easy to plug in and feel part of the community.
Parent Tip: Registration for many leagues opens early. Let me know if you want my seasonal sports calendar!
Kid-Friendly Eats & Local Fun
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Restaurants To Try
Whether you're grabbing lunch after a game or enjoying a low-key dinner with the kids, these Winter Garden spots are tried-and-true family favorites.
Mangoni Italian Market — Pizza, gelato, and a turf field where the kids can play while you relax.
Plant Street Market — Food hall with something for everyone + plenty of outdoor seating.
Rosallie Le French Cafe — Cozy, charming, and perfect for a sweet treat or brunch date.
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Things To Do
Winter Garden is packed with simple ways to spend quality time with your kids. From outdoor adventures to family-friendly entertainment, there’s no shortage of local fun to explore together.
Tucker Ranch Park — Wide open space, nature trails, and one of the best playgrounds in town.
Downtown Pavilion Splash Pad — A favorite for little ones to cool off and play.
Garden Theatre — Kid-friendly plays and seasonal performances to spark their imagination.
Shop Local
Shop Local
Winter Garden is full of small businesses that make this community feel personal, connected, and unique. Whether you're shopping for a gift, treating yourself, or simply exploring downtown, these local gems bring big heart to our small town.
Adjectives Market — Home decor + gifts
Shoo Shoo Baby Boutique — Stylish finds for littles
The Sacred Olive — Gourmet oils and vinegars (great housewarming gift!)
Pilars Martini — Date night spot with live piano
Swing by the Winter Garden Farmers Market every Saturday from 8 AM to 1 PM — it’s the perfect way to support local vendors, grab fresh finds, and soak up small-town charm.
Upcoming & Recently Opened
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PopStroke Winter Garden
Opened August 6, 2025, PopStroke is a family-friendly mini-golf experience backed by Tiger Woods. Located at 5487 Hamlin Groves Trail, it features two 18-hole putting courses, a full-service restaurant, ice cream bar, and on-site playground—perfect for both kids and adults.
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Luxe Suite Spot Salon
Now pre‑leasing in Winter Garden, Luxe Suite Spot Salon offers luxury salon‑suite rentals for independent beauty professionals—perfect for new residents wanting professional services in a boutique setting. Currently still under construction at 1015 South Dillard St.
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Agave Bandido (Hamlin Town Center)
Opened June 9, 2025 at 5365 Hamlin Groves Trail, this modern Mexican concept offers table‑side guacamole, birria tacos, a large patio and branded “Maya Speakeasy” lounge—a hot new dinner destination for families and weekend date nights.
Annual Events & Seasonal Fun
One of the best parts about living in Winter Garden? There’s always something to celebrate. From festive parades to cozy outdoor concerts and magical seasonal displays, this town knows how to bring the community together. Whether you’re new to the area or a long-time local, these events are the perfect way to get plugged in, meet your neighbors, and make lasting memories with your family.
From live music on Friday nights to trick-or-treating in October and dazzling holiday lights in December, there’s a little something for everyone—no matter the season. These events are family-friendly, walkable, and full of heart. Many take place right in the heart of downtown Winter Garden, so you can grab a bite, bring the kids, and enjoy the charm that makes this town feel like home.
Here are just a few favorites to mark on your calendar:
Halloween Light Show at City Hall
Fridays on the Plaza (Live Music Weekly!)
Winter Garden Christmas Parade
4th of July Celebration + Fireworks
Fall Festival + Market Events
Want the full monthly list of events? Download our “Living like a Local” guide and sign up for our monthly newsletter!
Why I Love Living Here
As a mom of four, a local business supporter, and someone who's moved more times than I can count—Winter Garden just feels like home. It's walkable, warm, family-focused, and filled with community. I love that my kids can ride their bikes to the farmer's market, that we know our neighbors by name, and that there’s always something fun (and free!) happening on the weekend.
Whether you’re strolling Plant Street on a Saturday morning, taking the golf cart for a spin, or cheering from the sidelines at a youth game, you feel the heart of this town everywhere you go. It's a place where families grow, friendships stick, and memories are made around every corner.
& I’m so glad you're here!
Need help settling in or figuring out the best local spots? I’ve got you covered—reach out anytime here!