Here is where you want to be

A profound sense of community runs deep through the veins of this historic and charming neighborhood that offers something for everyone. When you need to get to downtown Orlando, the theme parks, or beyond, you’ll love the convenient access to SR 408, SR 429, and Florida’s Turnpike. From the quaint streets of downtown Winter Garden to the lively Plant Street Market, to endless dining, entertainment, and shopping opportunities that capture the spirit of Winter Garden, you’ll find all the ingredients to an incredible day just minutes away from your front door.

A brick road in front of a gazebo and a strip of shops and restaurants all surrounded by trees

Prepare to be Charmed

Winter Garden is one of the most popular neighborhoods in the Orlando area with its wide sidewalks, shady canopies of palms and oaks, and year-round calendar of community events where you can mix and mingle.

Explore Winter Garden

Rendering of a bright and welcoming neighborhood cafe at Smith + Main with bohemian and natural elements

Meet us for a cup

Whether heading to work, meeting up with friends for an overdue chat, or taking a well-deserved break, you’ll love the convenience, personal service and airy environment of our in-house café. Open to Smith + Main residents and the public, our café invites you to linger longer with a cup of coffee made just for you.

Browse Our Amenities

Exterior image of a brick brewery Crooked Can with people sitting at tables under umbrellas

Head to the Market

With its red brick exterior, The Plant Street Market is a sprawling market that features delicious food hall selections and handmade products from 20 vendors. The award-winning Crooked Can Brewery offers live entertainment and a shady, pet-friendly patio.

Visit Plant Street Market

A woman stretching on a bicycle path in between two trees

Blaze a trail

Just footsteps from your front door at Smith + Main, the 22-mile West Orange Trail is perfect for strolling, running, or bicycling alongside the towering oaks and scenic picnic areas, and it’ll soon be part of the Coast to Coast Connector Trail across Florida.

Explore the West Orange Trail

A closeup of a row of clothes on hangers

Discover new finds

When you’re on a quest for a unique gift, that just-right table for your new apartment, a new pair of kicks for the trail or a night out, or even a luscious dessert, the shops, restaurants, and cafés of Downtown Winter Garden have you covered.

Shop, Dine + Be Entertained