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Learn more about this historic city with a classic, small-town vibe.
If you’re looking for a great place to raise a family, look no further than Winter Garden, Florida! The Winter Garden, real estate market, is booming and with great reason. In 2019, Winter Garden made the Top 10 on Money.com’s list of the 100 best places to live in the U.S. What an achievement!
This beautiful city serves as the hub of West Orange County, one of the fastest-growing regions in Central Florida. Founded in 1903 and once home to acres of orange groves, Winter Garden is a historic city with plenty of personality and charm. Whether you’re looking for the culture and conveniences of big-city life or you’re hoping to settle in a small-town environment, you’ll find the best of both worlds here.
As Winter Garden’s premier real estate team, we have an insider’s perspective on this remarkable city. We not only know Winter Garden’s diverse neighborhoods inside and out, but we are also well-acquainted with local businesses, schools, and sources of entertainment. Read on for the many reasons we know Winter Garden is an amazing place to raise a family!
#1 – It’s got top-rated schools
One of the best reasons to raise a family in Winter Garden, Florida, is the diverse, highly-rated schools in the area. A 2021 Quality Counts report by Education Week shows Florida ranking third nationally in K-12 Achievement, demonstrating the state’s focus on education. A current U.S. News report also shows Florida ranking third nationally in overall education and #1 in the nation in higher education. In short, Florida has some of the best schools in the country!
Orange County Public Schools rank in the Top 25 in the state. In West Orange County, families have their choice of multiple A+ rated schools, including public, private, technical, Montessori, and charter options. When you raise a family in Winter Garden, you can be confident you’ll find an excellent school to meet your children’s needs!
#2 – Back-to-School shopping is a breeze
There are so many great places to shop in Winter Garden. You’ll never have to spend much money on gas when making sure your family has everything they need, whether it’s for back-to-school shopping or replacing those clothes and shoes the kids have outgrown. Families have the option of shopping in local boutiques like The Boutique on Plant or Apricot Lane Boutique in downtown Winter Garden or hitting up the convenient outdoor mall in the Winter Garden Village for popular chain stores like Target, Ross, and Beall’s.
#3 – The local restaurants are family-friendly
Right alongside the convenient, eclectic shops in Winter Garden is a wide variety of restaurants. When it comes to raising a family, we know having restaurant options that will please even the pickiest eaters is a MUST. This is definitely the right city for that!
Winter Garden is home to many chain restaurants families love. Some of the most popular include Red Robin Gourmet Burgers and Brews, Cracker Barrel Old Country Store, Romano’s Macaroni Grill, UNO Pizzeria and Grill, FirstWatch, LongHorn Steakhouse, and Chili’s Grill & Bar. Each of these restaurants offers menus that are very family friendly!
Winter Garden has many of those if you prefer to eat in local independent restaurants. Head over to The Big Easy for Cajun Creole cuisine, Winter Garden Restaurant for home-style cooking, Pammie’s Sammies for a casual meal of sandwiches and pizza, or Market to Table if you’re looking for modern American Fare. You’ll find something for everyone among Winter Garden restaurants!
#4 – You’ll love the thriving Farmer’s Market
Every Saturday, rain or shine, Central Florida residents flock to the Winter Garden Farmer’s Market. This Winter Garden staple was voted “Best of the Best” by Orlando Family in 2021 and features everything from fresh, locally sourced food to artwork and handmade crafts. The Market focuses on the environment and sustainability, insisting that all products sold be in biodegradable bags to discourage the use of plastics. Children also love the Farmer’s Market with its wide variety of offerings, which makes this one more reason Winter Garden is a such wonderful place to raise a family!
#5 – Less time in the car, more time at home
Winter Garden, Florida is in such a convenient Central Florida location that it’s hard to believe it wasn’t a boomtown well before now! Less than thirty minutes to downtown Orlando, the Disney and Universal theme parks, and the most popular area attractions and destinations, Winter Garden is perfectly situated on the west side of Orlando to minimize most commutes. We can all agree that’s a big plus when it’s time to raise a family!
#6 – You can all reconnect with nature
These days, many parents are trying to get their kids off their phones, computers, and television screens and out enjoying the world. That’s easy to do here in Winter Garden! Even with the many new residential developments cropping up around the city, you’ll find nature everywhere. From the Oakland Nature Preserve and West Orange Trail to the Lake Apopka Wildlife Trail and the Tucker Ranch Recreation and Nature Complex, you and your family can visit and enjoy a new park, trail, or nature preserve every month of the year.
#7 – Your pets are welcome
Winter Garden is such a pet-friendly city! You can bring your dogs with you to restaurants like Crooked Can Brewing Co., Hagan O’Reilly’s Pub, 4 Rivers Smokehouse, Winter Garden Pizza Company, and Moon Cricket. If you live in Winter Garden and have out-of-town guests traveling with their pets, they’ll be welcome at establishments such as TownePlace Suites Orlando at Flamingo Crossings, Stage Stop Campground, and numerous local Airbnbs. And be sure to check out our Dog Lover’s Guide to Dog Parks in Winter Garden to decide where you’ll next bring your furry friend for a day of play!
#8 – There’s entertainment for everyone
The many entertainment options around Winter Garden also make this a great place to raise a family! From highly reviewed plays at the historic Garden Theater downtown to blockbuster movies on the big screen at Cinepolis in Winter Garden’s Hamlin community, there are multiple ways families can enjoy a theatrical experience. If your kids don’t want to sit still that long, that’s okay! There are many more entertainment options for them.
Head over to Escape Goat and see if you and your family can defeat one of their fun escape rooms. Take a tour of the Central Florida Railroad Museum and learn more about the rich history shared there. Hit the lanes at Winter Garden Bowl for a few hours of family fun.
And during the hot summer months, kids love the splash pad in downtown Winter Garden! There is often live entertainment for parents to enjoy, too. For the foodies out there, Winter Garden also hosts multiple food truck events throughout the city’s neighborhoods all month long. You’ll find delicious cuisine options for everyone in your family at these festive gatherings. In short, you’ll never have to venture far to find entertainment in Winter Garden! There’s no question Winter Garden, Florida is a wonderful place to raise a family. If you’re ready to call this fun, welcoming city your new home, you’ll want to work with a knowledgeable Winter Garden real estate agent to guide you to the ideal neighborhood for your family. We are here to help you buy a home in Winter Garden, Florida and enjoy Central Florida living to its fullest! When it comes to raising a family, choosing the right home and community is of the utmost importance. We would love to help you find the perfect place to raise yours! Contact us today for all the help you’ll need to navigate the Winter Garden real estate market and find the home of your dreams.
