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Retirement in Winter Garden, FL

by Andrew Selby | Originally Published: August 6, 2019 | Last Updated: March 14, 2021

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!

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 lakeside 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

The lifestyle in Winter Garden has always revolved around embracing the benefits of living along the banks of Lake Apopka. Whether you are interested in boating, fishing, swimming, or kayaking, there is something for everyone to enjoy out on the lake. 

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 since the community is located only a short drive from the booming Orlando area, 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. 

And for residents looking to enjoy a few adult beverages, The Tasting Room serves outstanding craft cocktails and Crooked Can Brewing is the local spot for craft beers. 

Nearby Communities

At Stanton Estates in Winter Garden you’ll find authentic, old world charm and craftsmanship combined with contemporary convenience. From the colonial style baseboards to the 8ft wood doors included throughout your home, to the open living areas and huge designer kitchens great for entertaining, all homes by Jones Homes USA provide you with more style and value as the standard features are considered upgrades from other builders.

These rare and spacious home sites are in a desirable urban setting close to close to eclectic shopping, dining and entertainment options of the historic downtown Winter Garden area and only minutes from the popular West Orange Trail and Farmers Market. You’ll live amidst the vibrant downtown, yet be surprisingly secluded with “living room” usually reserved for much more suburban locations.

You can request more information here.

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. 

Pick the Right Place for YOU!

Do you dream of finding the perfect location, community, and home for you? It’s easier than you think! In my book called Pick the Right Place, I show you exactly how to do it, step-by-step. Click Here to get started.

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