Winter Garden is a tale of two cities. One steeped in history, one poised for the future—each with a unique set of charms to recommend them.
Positioned less than 20 miles west of downtown Orlando, Winter Garden is a bedroom community for people who crave more than just a pretty house to call home at the end of the day. And while yes, finding a pretty house is a guarantee here, what really sets this city of more than 45,000 apart from the pack is its emphasis on art, culture, history and outdoor recreation. (Plus, residents say it’s a really fun place to drive a golf cart!)
Historic Winter Garden
First settled by farmers seeking out its famously fertile muck and incorporated way back in 1908, Winter Garden today is better known for other features. Its placement along the 22-mile paved West Orange Trail makes the city a beloved hotspot for bikers, joggers and nature lovers. Meanwhile, a legendary weekend farmers market draws crowds from all over Central Florida for a chance at the perfectly picked pastries, produce and even pickles! And the heart of downtown serves an exemplary throwback to old-Florida style featured on the National Register of Historic Places. This strip includes shops, restaurants and cafes. On any given weekend you’ll see tourists hitting breweries on bikes while locals zip their guests around town for dinner on electric golf carts that are the town’s signature vehicle of choice.
The area is also home to museums and performing arts spaces like the SoBo Art Gallery and Garden Theatre—where top notch regional productions of Broadway plays rotate through.
Living in Downtown Winter Garden
The brick lined streets surrounding downtown encompass the Winter Garden Historic Residential District. Bounded by Plant, Boyd, Tilden and Central Streets, this neighborhood is where homebuyers go to find old Florida architecture—solid wood frame craftsmanship complete with covered porches —and even fireplaces.
This section attracts a crowd that want to be close to the action and values walkability (plus the ability to take their golf carts downtown).
These neighborhoods have exploded with newfound popularity in recent years as more and more buyers seek out downtown spaces. Still, homes abound and deals can be found!
The New Winter Garden
Outside the city center is the newer and much larger Winter Garden. Spanning over 18 miles from its northern to southern ends, this huge area is home to over 50 plannned developments of varying size, amenities and level of grandeur.
With easy access to Disney World, Sea World and Universal Studios, this area draws in industry professionals and park enthusiasts alike. (Just about every resident in Winter Garden can claim ownership of at least one season pass and many can see nightly fireworks displays from their porches).
These neighborhoods attract home buyers looking for newer builds and larger single/family homes with all the bells and whistles of a planned community. From multiple pools and gyms to splashpads and playgrounds for the kids and fire pits and golf courses for the adults— residents are spoiled for choice.
Newer communities such as Oakland Park combine amenities with nature, offering homes abutting the West Orange Trail.
Winter Garden Homes for Sale
Sorry we are experiencing system issues. Please try again.