Located about 25 minutes west of downtown Orlando, Winter Garden offers residents the perfect combination of an Old Florida feel and plenty of modern amenities.
You’ll love strolling through the historic downtown district but will also enjoy the lake lifestyle, the thriving cultural scene, shopping at the weekly farmers’ market, and dining at the impressive collection of modern restaurants.
Let’s dive in and take a close look at retirement in Winter Garden!
Nearby Communities
Del Webb Oasis in Winter Garden, located just minutes from Orlando area theme parks and attractions, is a highly anticipated new Del Webb community in the Orlando area.
Like most Del Webb communities, Del Webb Oasis will have a long list of amenities for residents to enjoy, including a 12,000 sq. ft. resort-style amenity center.
Del Webb will be offering 13 different floorplans here from their “Scenic”, “Distinctive”, and “Echelon” home series, plus the “Ellenwood” from their attached villa series.
You can request a full brochure with pricing, HOA fees and more here.
Here are some other homes for sale around Winter Garden (just FYI, most are not 55+):
Winter Garden History
After just over 50 years of settlers moving to the area along Lake Apopka, the modern history of Winter Garden started when the city was officially established in 1903 and incorporated in 1908.
The new community grew quickly during the roaring 20s, but that growth slowed considerably during the 1960s due in part to the pollution of Lake Apopka. Things started to pick up again in the 1970s, and the area has seen tremendous growth in the years that followed.
After placing its downtown district on the National Register of Historic Places in 1996, Winter Garden has evolved as a model for combining a rich history with modern amenities.
Winter Garden Lifestyle
Being so close to Orlando and all it has to offer has a huge impact on the lifestyle in Winter Garden. You are just minutes to the theme parks and other entertainment options, shopping, healthcare options, golf courses, great restaurants, and everything else Orlando has to offer.
The lifestyle in Winter Garden has always revolved around embracing the benefits of living among several local lakes. Whether you are interested in boating, fishing, swimming, or kayaking, there is something for everyone to enjoy.
Winter Garden is also one of the stops on the West Orange Trail, which is a part of the massive 250-mile Coast-to-Coast Connector Trail that runs across Central Florida. This makes it an ideal location for cycling enthusiasts.
Winter Garden Culture
You can’t have a historic Old Florida town without a historic theater, and that is exactly what Winter Garden residents have in the Garden Theatre. This old movie theater has taken on a new life as the center of the cultural scene in Winter Garden by hosting live performances of all kinds throughout the year.
Other important cultural attractions in Winter Garden include the Winter Garden Heritage Museum and the SoBo Art Gallery. Both offer a unique insight into what life can be like here in Winter Garden.
Winter Garden Shopping
Shopping in Winter Garden revolves around the unique stores and boutiques you will find in the historic downtown district.
In addition to the regular shopping options, there is the Winter Garden Farmers’ Market, which is held downtown every Saturday throughout the entire year. Here you can find everything from fresh produce to handmade soap, and usually some type of live entertainment as well.
And again, since the community is located only a short drive from Orlando, there are more than a few options for designer stores and outlets just minutes away from Winter Garden.
Winter Garden Dining
Any destination near a major city like Orlando is going to have fabulous dining options, but Winter Garden goes above and beyond in that respect with a vast array of delicious high-end choices like Market to Table Cuisine, Chef’s Table at the Edgewater, Rosallie Le French Cafe, and Matthew’s Steakhouse.
But Winter Garden is much more than just fancy restaurants because there are also casual options to choose from like Melts on Main Street, Plant St Market, This Little Piggy, and 4 Locos Tacos.
For those looking to enjoy a few adult beverages, Crooked Can Brewing is the local spot for craft beers. The brewery is located inside Plant Street Market, a local community market with 20 vendors featuring natural, organic food and handmade products all inside of one building.
Whether you are passionate about life on the lake, excited to dig into the local restaurant options, or just want to be close to Orlando without feeling overwhelmed by tourists, Winter Garden is a perfect retirement destination for anyone looking for Old Florida charm matched with modern amenities.
