Winter Garden

The private community of Winter Garden is part of West Orange County in Central Florida.

Welcome to Winter Garden


A quaint, homespun neighborhood lush with culture.

Recognized on the National Registry of Historic Places, the private community of Winter Garden is part of West Orange County in Central Florida. Their fitting slogan is “Where Good Things Grow.” Locals flock to the downtown historic district for frequent events centered around farmers' markets. They also have the choice of venturing to Orlando for even more excitement or escaping to nature via the West Orange Trail.

What to Love 

  • Daily and weekly community markets
  • Nature is preserved and restored 
  • The West Orange Trail 
  • Private community

Local Lifestyle 

Winter Garden is a charming small town, and a treasure trove of arts and culture kept alive by institutions such as the Winter Garden Heritage Foundation Museum. The Foundation serves to protect the architectural and cultural integrity of the historic district. Patrons of the SoBo Art Gallery will discover exquisite rotating exhibitions, and local businesses are decorated with exterior wall murals painted by local artists. 

Dining, Entertainment & Shopping 

Restaurants in downtown Winter Garden aim to transport their customers to different parts of the world. For traditional Thai food, visit Thai Blossom and try one of the New Zealand steamed green mussel dishes from the chef’s special menu. Those passionate about pasta will be impressed by the selections at Bella Italia. A European dining atmosphere is created at Rosallie French Cafe. To impress a date, Matthew’s Steakhouse sets the mood for a romantic dinner.
Not to be confused with the Netflix series, Chef’s Table is an award-winning restaurant where the chef orchestrates a three-course prix fixe menu with wine pairings for an additional charge. A connected property, The Tasting Room exudes a more casual vibe with small plates and craft beers. 
Craft beer aficionados will favor The Crooked Can brewing company to take a tour of this local brewery and nurse a glass dispensed straight from the tap. The talented brewmaster concocts multiple unique batches in different styles. Non-beer drinkers can discover something they like at the attached Plant Street Market, an indoor facility where local vendors sell their wares seven days a week.

Things to Do 

Winter Garden always has weekend plans. Kicking things off is Fridays on the Plaza for two hours of live music. The genre of music is varied to appeal to all music tastes, one night you might hear a bluegrass band and the next night will have rock, for instance.
The Farmer’s Market is downtown every Saturday morning. Crowds gather to peruse the wide assortment of fresh vegetables, specialty foods, artisanal craft items, and general merchandise sold by over 100 vendors, a fifth of which are local farms. On certain dates, you will find sponsored special events like cooking demonstrations and holiday celebrations at the Farmer’s Market in Winter Garden. 
Oakland Nature Preserve is thirty minutes removed from the commercial frenzy of Orlando. Its mission is to restore the natural habitat to its original conditions before explorers made landfall in the Americas. Visitors have free access to hiking trails and environmental education provided by the Preserve’s Museum center. 
Bikers seize the opportunity of traversing the tremendous West Orange Trail paved for smooth riding. This segment of Florida’s Coast-to-Coast Connector stretches 22.26 miles within Winter Garden and across several counties. Travelers will pass through points of interest such as the historic Winter Garden and Oakland, the Preserve, and Lake Apopka. Along the route are outposts and stations where parking, water, and restrooms are available.


The community of Winter Garden is served by Orange County School District

Search Homes

Work With Us

Florida Golf & Beaches is a leader among the most prestigious real estate companies in Orlando. Having listed and sold the most expensive home in Central Florida, we can help you market and sell your home for it’s highest possible value, or we can help you find your ideal residence in sunny Florida’s most splendiferous communities as we have done consistently for more than two decades.