Coffee Shops, Bakeries, and Ice Cream in Downtown Winter Garden
A Plant Street guide to where the locals get their caffeine, sugar, and scoops
Downtown Winter Garden, FL is a four-block historic district along Plant Street with a concentrated cluster of coffee shops, bakeries, and ice cream parlors. Anchor coffee shops include Axum Coffee at 146 W Plant Street, Foxtail Coffee at The Exchange (276 W Plant Street), and Way Chocolate & Coffee at 50 W Plant Street. Top bakeries include Rosallie Le French Café at 141 W Plant Street and Sweetland Bakery & Tea House at The Exchange. Ice cream is served at Kelly's Homemade Ice Cream inside Foxtail Coffee and at Scoops Old Fashion Ice Cream at 99 W Plant Street in the historic Edgewater Hotel. The West Orange Trail runs directly through downtown, making it one of the most walkable and bike-friendly small-town downtowns in Central Florida.
If there's one Central Florida downtown that nailed the trifecta of coffee, baked goods, and ice cream, it's Winter Garden. Plant Street is one of those rare Orlando-area places where you can park once and walk five blocks to a flat white, a fresh croissant, and a scoop of homemade pistachio. Not an accident — two decades of careful downtown planning and a community that shows up for its small businesses.
Whether you're scoping out Winter Garden as a place to live or you're already nearby and want to know where the locals actually go, here's our field guide to the sweet stuff downtown.
A Quick Word on Plant Street Right Now
Heads up: Downtown Winter Garden is in real flux. Several long-time downtown businesses — including Three Birds Café — have closed or are closing in 2026 after a wave of building sales and lease non-renewals. This guide sticks to spots confirmed open as of the date above; a quick social check before you go never hurts.
The Coffee Lineup
Axum Coffee — The Original
If Downtown Winter Garden has a flagship coffee shop, it's Axum. The flagship café sits at 146 W Plant Street, and the Axum Roastery occupies a corner of Plant Street Market at 426 W Plant Street, where you can watch beans roast while you sip. Locally founded, locally roasted, with a portion of profits funding humanitarian work in Ethiopia — the country the brand is named after. The closest thing Winter Garden has to a community living room.
Foxtail Coffee at The Exchange
Foxtail is the Orlando-grown chain that scaled without losing the indie feel. The Downtown Winter Garden location at 276 W Plant Street sits inside The Exchange, a 2021 mixed-use building that intentionally blended into the historic streetscape with red brick and small-town proportions. Indoor and outdoor seating, beer and wine, and — this is the move — a built-in Kelly's Homemade Ice Cream counter. Cold brew with an affogato? One register, done.
Way Chocolate & Coffee
The newcomer of the three, Way Chocolate & Coffee at 50 W Plant Street is part café, part dessert shop, part chocolate counter. Hours run later than most coffee places — until 10 p.m. on weekdays, midnight on Friday and Saturday — making it a legitimate after-dinner option, not just a morning stop.
The Bakery Scene
Rosallie Le French Café
Rosallie at 141 W Plant Street is the Plant Street bakery that takes French baking seriously — laminated croissants, fresh baguettes, brunch service, espresso that doesn't apologize for being European-style. Same ownership runs Mangoni's Italian Market at The Exchange. If you only have one breakfast in Winter Garden, this is a defensible pick.
Sweetland Bakery & Tea House
Tucked into The Exchange alongside Foxtail and Kelly's, Sweetland is the destination if your sweet tooth leans Asian-inspired. Japanese-style chiffon cakes, mousse cups, milk and bubble teas with adjustable sweetness, and a Japanese ice cream sandwich shaped like a fish (red bean and vanilla). Not cheap, but it's the kind of place where you take a photo before the first bite.
Sweet Dee's Cupcakery and P.S. My Treat
For cupcakes and custom cakes, two options sit a block apart. Sweet Dee's Cupcakery at 21 S Main Street offers a make-your-own cupcake bar plus brownies, macarons, and cakes — strong birthday and event play. P.S. My Treat is the second downtown cupcakery, with its own loyal following for custom cakes. Locals tend to pick a side; both are legitimate.
Ice Cream: Two Very Different Vibes
Kelly's Homemade Ice Cream at Foxtail
Kelly's is the Orlando-area handcrafted ice cream brand spread across Central Florida — Orlando, Maitland, Lake Mary, Oviedo, Horizon West, and the Winter Garden counter inside Foxtail at The Exchange. They make their ice cream and sorbets at their shops, with oat-based non-dairy options on the menu. Signature flavors like O-Dough and Banana Pudding are the move; espresso milkshakes and affogatos take advantage of the Foxtail-Kelly's mashup.
Scoops Old Fashion Ice Cream
Scoops at 99 W Plant Street lives inside the historic Edgewater Hotel building — the same building housing The Chef's Table and Thai Blossom. It's a more traditional parlor experience: Hershey's ice cream, hot dogs, soup, cookies, small-town charm you can't engineer. If you're showing visiting family the "is this real?" version of Winter Garden, this is the stop.
How Locals Actually Use This District
Here's the thing about Downtown Winter Garden that visitors miss: it's not really about any one shop. It's about the loop. The West Orange Trail runs straight through downtown, so a typical Saturday morning looks like: bike in from Oakland or Ocoee, lock up, grab a cortado at Axum, browse the Saturday farmers market, swing through Plant Street Market, finish at Kelly's. The whole district is engineered for that pace.
That walkability is also why housing nearby costs more than housing in adjacent areas like Horizon West or Gotha — buyers pay a real premium for bike distance to Plant Street. Worth understanding upfront if downtown lifestyle is what you're after.
Pros and Cons of the Plant Street Sweet Scene
The Pros:
- Genuinely walkable — most spots are within 5 minutes of each other on foot
- Mix of locally founded (Axum, Kelly's, Foxtail) and small independents
- The Exchange and Plant Street Market concentrate options under one roof
- West Orange Trail integration means coffee-and-bike is a real lifestyle here
- Late-night options exist (Way Chocolate, Plant Street Market until midnight on weekends)
The Cons:
- Saturday morning parking is rough — get here before 9 a.m. or plan to walk a few blocks
- Prices have crept up; tourist-adjacent rates at peak times
- The current wave of building sales and lease non-renewals means the lineup is in flux
- Limited late-night dessert if Way Chocolate is closed (most spots wrap by 9 p.m.)
What the Locals Know
The unwritten rule of Downtown Winter Garden's sweet scene: Saturday before 9 a.m. is when locals own the district. Park easily, beat the farmers market crowd, get your Axum order without a 15-minute wait, and you'll understand why people pay the premium to live nearby. By 11 a.m. it's everyone's downtown — by 7 a.m. it's still the locals'. Same with ice cream on a Sunday afternoon: wait until after the dinner rush and Kelly's lines drop dramatically.
The other thing locals know — worth saying plainly — is that Plant Street's character is built on its small businesses, and that character is being tested right now. The shops above are the ones we're confident are operating. If a place you love isn't listed, it's either outside our scope or we couldn't confirm operating status as of publication.
For current downtown events, hours, and the official directory of open businesses, visit Downtown Winter Garden.
Thinking about putting down roots near Plant Street? Whether you're looking at Winter Garden, nearby Windermere, or surrounding West Orange County communities, we can help you find the right neighborhood. Get in touch for personalized West Orange relocation advice. ☕
