Exploring Winter Garden’s Neighborhoods

Winter Garden is a picturesque and historic city located in the western suburbs of Orlando. It is known for its beautiful downtown area, which boasts a wide variety of shops, restaurants, charming ice cream shops, shady playgrounds, and miles of bike trails. But Winter Garden is much more than just its downtown. The city is made up of several unique neighborhoods, each with its own unique character and personality. By exploring Winter Garden’s neighborhoods, you can determine which one would be right for you.

Downtown Winter Garden

Downtown Winter Garden is the heart of the city, a quiet city center with tree-lined brick streets, locally owned businesses, gorgeous landscaping, and intriguing public art. This vibrant and bustling area is filled with unique shops, restaurants, and events, and is home to the Winter Garden Farmers Market which is held every Saturday. Here locals socialize, support local businesses, listen to live music and shop for locally grown produce, crafts, and other goods. Plant Street runs through the heart of Downtown Winter Garden and is a vibrant mix of historic single-family homes, brand-new townhomes, and high-end apartments. 

Oakland Park

Just south of Downtown Winter Garden is Oakland Park. This shady neighborhood is a favorite for families, has several parks and playgrounds, and is within walking distance to Oakland Avenue Charter School. From Oakland Park, it’s easy to hop on major highways and toll roads, which is a plus for those commuting throughout the Orlando area. It is also conveniently located near major highways, making it easy to commute to other areas of Orlando. There are 28 different neighborhoods nestled in the Oakland Park area, and houses range anywhere from $129K to $2.9M. Depending on the neighborhood. This is a popular area for busy families because it’s close to great schools, local grocery stores and restaurants, and the West Orange Trail. 

Stoneybrook West

Stoneybrook West is a luxurious gated community located on the southeastern edge of Winter Garden. It is known for its luxurious homes and amenities, including a golf course, clubhouse, and fitness center. The homes here are elegant and spacious, with many featuring upgraded features such as granite countertops, stainless steel appliances, and hardwood floors. The community is made up of several different subdivisions, each with its own unique character and charm. Golfers love living here because the neighborhood is home to a championship-style golf course that is open to residents and their guests.

Living in Stoneybrook West also means having exclusive access to resort-style amenities, including a fitness center, clubhouse, playground, and tennis courts. This highly sought-after neighborhood is conveniently located near several shopping centers and restaurants, making it easy to enjoy all that Winter Garden has to offer. 

Summerlake

Summerlake is part of the larger Horizon West area, a master-planned community in Winter Garden made up of six self-sustaining villages. This innovative concept created a place where thousands of families could put down roots, really get to know their neighbors, enroll their kids in high-performing schools, and enjoy resort-style amenities all year long. Nestled on the shores of Lake Hannock, Ski Lake, and SawGrass Lake, living in Summerlake has resort-style living vibes. Families here like to take their boats out onto the water, spend hot afternoons in the resort-style pools, ride down the miles of bike trails, and meet friends for dinner or drinks in Downtown Winter Garden.

Summerlake is made up of 1231 single-family homes, 36 lakefront properties, and 178 modern townhomes. Residents of this sprawling community have access to a pool, fitness center, dog park, clubhouse, sports courts, and a calendar packed with social events and activities. The houses in Summerlake vary in size and style, and the average home price here is $758,060. 

Another thing locals love about this neighborhood is its location. Minutes from highways, toll roads, and the interstate, it is easy to get home from anywhere in the greater Orlando area. Families with annual passes to Disney also appreciate how easy it is to get to the Happiest Place on Earth from the neighborhood. Wide sidewalks and bike paths are perfect for exploring the neighborhood on two wheels and getting to the local elementary school.

Tildenville

Known for its small-town charm and friendly community, Tildenville is a quaint and historic neighborhood located in Winter Garden, Florida. This established neighborhood is a unique blend of old and new, combining historic homes and modern amenities. Locals love being so close to the nearby nature trails and it’s common to see families taking a stroll through one of the community’s parks on warm afternoons. The proximity to lake Apopka is a plus for those who like to spend time outdoors and on the water, and it’s home to many locally owned restaurants, sidewalk boutiques, health and beauty stores, and businesses. 

Tildenville is home to Tucker Ranch Recreation and Nature Complex, a sprawling outdoor space with a wooden playground, shady picnic pavilions, a kayak launch nature trails, and plenty of room to play. Tucker Ranch is a relatively new addition to the Winter Garden area, and there are plans to expand the outdoor recreation complex to include multi-purpose buildings, campsites,  and a state-of-the-art working and teaching farm that will function as a regional food hub.

Homes in Tildenville come in a variety of shapes and sizes. Some have been built recently while others have been part of the Winter Garden story for decades. The average home price in Tildenville is $249k and is close to a handful of public, private, and charter schools. 

Bottom Line

Whether you’re looking for a charming first-time home, a modern townhome, or a million-dollar lakefront estate, you can find your home in Winter Garden. Locals love the friendly neighborhoods, the idyllic downtown area, the vibrant art and music scene, the highly-rated schools, and the small-town feel. Winter Garden is more than just a neighborhood, it’s a lifestyle.

If you need help exploring Winter Garden’s neighborhoods and finding the right one for you, contact the Erica Diaz team. We’re ready to welcome you home.