ABOUT WINTER GARDEN
Homeowners love Winter Garden’s character: brick-lined streets, historic storefronts, and a strong sense of community. The revitalized downtown and nearby lakes give the city its signature feel—authentic, welcoming, and easy to enjoy on foot or bike. The West Orange Trail runs right through downtown, connecting Winter Garden to neighboring areas and making outdoor time part of everyday life.
Amenities Of The Winter Garden Community
The heart of town is Plant Street—boutiques, cafés, weekly markets, and family-friendly events. Plant Street Market anchors the scene with artisan vendors and the locally loved Crooked Can Brewing Company, a popular gathering spot for casual meals and craft beer.
On Saturdays, the Winter Garden Farmers Market draws residents from across Central Florida for fresh produce, baked goods, flowers, and live music—regularly recognized among the best markets in the state and country.
Stroll the shops downtown, then head to the lakes and parks for a change of pace. If you’re exploring by bike, the trail and downtown paths make it simple to take in the sights at your own speed.
Culinary Scene and Craft Breweries
From quick bites to chef-driven spots, Winter Garden’s dining scene has range. Plant Street Market offers an easy “try-a-little-of-everything” experience, while Crooked Can pours award-winning brews steps from the action—perfect before or after a show at the Garden Theatre.
Parks, Trails & Lakes
The West Orange Trail is a community favorite—biking, jogging, skating, or leisurely walks on a wide, paved path that links downtown to neighboring towns. Trailheads offer rentals and conveniences, making it accessible for all ages.
Nature lovers also frequent the Lake Apopka Wildlife Drive for birding and scenic views—a peaceful weekend loop just minutes away.
Annual Festivals and Events
From seasonal celebrations and holiday performances to the weekly Farmers Market, Winter Garden’s calendar keeps the community connected. Downtown events, theatre productions, and family activities fill weekends throughout the year.
Outdoor and Recreational Activities
Hot days call for shaded trail rides, lakeside picnics, and relaxed strolls along Plant Street. The West Orange Trail’s central route through downtown makes it easy to combine errands, dining, and outdoor time in one trip
Arts and Entertainment in Winter Garden
The historic Garden Theatre on Plant hosts plays, concerts, films, and special events in an intimate, beautifully restored space—an arts anchor for residents and visitors alike.
Why Buying in Winter Garden Is Right For You
Winter Garden offers that rare mix of neighborhood warmth, vibrant downtown energy, and everyday outdoor living. With a variety of home styles and easy access to parks, schools, and local favorites, it’s a smart fit for families, first-time buyers, and anyone seeking a connected Central Florida lifestyle.
Chris Silberlight has a proven, client-first approach in Winter Garden and neighboring communities. If you’re considering a move, Chris can help you navigate the market and find the right home—on your timeline and budget.
Learn about other neighborhoods:
- Windermere
- Celebration
NEIGHBORHOOD LISTINGS
With years of experience and a focus on helping families and relocation clients, Chris Silberlight’s insight into the Central Florida real estate market is invaluable. His portfolio of single-family homes and new construction properties reflects both quality and care.
CONTACT
OFFICE
700 Celebration Avenue, Suite 300
Celebration, FL 34747
Chris Silberlight | FL LIC# SL3616521
Keller Williams Realty At The Lakes | FL LIC# CQ1034987
©2025 Chris Silberlight All rights reserved.
Keller Williams Realty At The Lakes® and the Keller Williams Realty At The Lakes logo are service marks licensed to Keller Williams Realty At The Lakes World Holdings, Inc. and used with permission. Chris Silberlight fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Any services or products provided by independently owned and operated brokerages are not provided by, affiliated with, or related to Keller Williams Realty At The Lakes® or any of its affiliated companies.
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ABOUT US
ABOUT US
FULL STACK DESIGNER
TURNED BRAND BUILDER.
I'm Matt thorne, aka sketchy.
i help companies find their place in culture and go from business to brand, earning attention online and skyrocketing sales.
Read how i helped build urban culture in the UK, growing a website and YouTube channel to over 9 Billion YOUTUBE views.
