Whether you’re a Winter Park local who knows Park Avenue like the back of your hand, a visitor exploring the city’s charm for the first time, or planning a dreamy date night with something sweet at the end—this guide is for you.
Winter Park is more than oak-lined streets and lakefront views—it’s home to some of Central Florida’s most beloved dessert spots. From melt-in-your-mouth chocolate to handcrafted gelato and picture-perfect pastries, there’s a treat here for every kind of sweet tooth. And yes, we’ve included the hidden gems and the Insta-famous favorites (because sometimes you really can have both).
Ready to satisfy your craving? Let’s dig in—one bite at a time.
1. The Glass Knife
📍 276 S Orlando Ave, Winter Park, FL
💻 theglassknife.com
Elegant, cozy, and always serving something beautiful—the Glass Knife is where art meets pastry. Known for its handcrafted cakes, glazed donuts, and seasonal desserts, this spot is ideal for an afternoon pick-me-up or a classy after-dinner treat. It’s popular for date nights, thanks to its sophisticated atmosphere and decadent bites like the Chocolate Onyx or the Lemon Blueberry Petite Cake.
✅ Try this: Their famous Strawberry Tall Cake and any of their rotating seasonal donuts.
☕ Bonus: Great coffee and brunch options, too.
2. Kilwins Chocolates & Ice Cream
📍 122 N Park Ave, Winter Park, FL
💻 kilwins.com
Walking down Park Ave? Follow the smell of fresh waffle cones, and it’ll lead you straight to Kilwins. This old-school chocolate and ice cream shop feels like stepping into a sweet memory. It’s the perfect spot for families, couples, or anyone craving a scoop (or three) of creamy, house-made ice cream and hand-paddled fudge.
✅ Must-try: Toasted Coconut ice cream + Sea Salt Caramel Fudge.
🍦 Local tip: Grab your cone and stroll the avenue.
3. Peterbrooke Chocolatier of Winter Park
📍 300 S Park Ave, Winter Park, FL
💻 peterbrookewp.com
Chocolate lovers, meet your match. Peterbrooke is all about indulgence—European-style truffles, chocolate-covered popcorn, hand-dipped Oreos, and gift boxes galore. It’s a date night favorite for grabbing something to go—or building a custom box for someone sweet.
✅ Pro move: Pick up the chocolate-dipped strawberries. Trust us.
🍫 Great for: Holiday gifts, Valentine’s Day, or a Tuesday.
4. Gelato-Go Winter Park
📍 513 S Park Ave, Winter Park, FL
💻 gelatogo.net
Imported ingredients from Italy? ✔
Silky-smooth, handmade gelato? ✔
Cute corner shop on Park Ave? ✔✔
Gelato-Go brings an authentic Italian gelateria experience to Winter Park. The flavors are bold, creamy, and rotated often—so you’ll always find something new to fall in love with.
✅ Fan favorites: Pistachio, Stracciatella, and Mango Sorbetto.
🍨 Bonus: They offer dairy-free and vegan options, too.
5. Buttermilk Bakery
📍 1198 Orange Ave, Winter Park, FL
💻 buttermilk-bakery.com
This cozy, Instagram-worthy bakery is where locals line up early for fresh pastries, buttery croissants, and their famous lemon bars. Everything is made from scratch daily, and it shows. Buttermilk’s vibe is laid-back, warm, and smells like your dream kitchen on a Sunday morning.
✅ Don’t miss: The seasonal danishes and the soft-baked chocolate chip cookie.
🥐 Heads-up: They often sell out before noon, so go early.
6. Choulala Fine Pastries
📍 340 N Park Ave, Winter Park, FL
💻 choulala.com
Refined and ridiculously good, Choulala is a boutique French pastry spot that specializes in cream puffs and macarons. Their pastries are not only delicious—they’re beautiful. It’s the kind of place where even a quick snack feels fancy.
✅ Must-order: Salted Caramel Cream Puff + Pistachio Macaron.
🎯 Best for: Date nights and special occasions.
7. Crumbl Cookies – Winter Park
📍 501 N Orlando Ave, Ste 309, Winter Park, FL
💻 crumblcookies.com
If you like your cookies oversized, gooey in the center, and served warm—Crumbl is your spot. The menu rotates weekly, so every visit brings a new surprise. Perfect for dessert runs with friends, family cookie nights, or a sweet treat after dinner.
✅ Always a win: Their classic Milk Chocolate Chip never disappoints.
🍪 Fun fact: You can order a 4-pack sampler to try more.
8. Light on the Sugar Bakery Café
📍 4270 Aloma Ave, Winter Park, FL
💻 lightonthesugar.com
This bakery fuses Asian-style sweets with European flair. From fluffy Japanese cheesecakes to mochi donuts and milk teas, Light on the Sugar is as pretty as it is tasty. Every dessert is carefully crafted and picture-perfect. Expect crowds on weekends—it’s that good.
✅ Fan favorites: Thai Tea Cream Puff + Oreo Cheesecake
🍵 Bonus: Their Boba Tea game is strong.
9. Kelly’s Homemade Ice Cream – Winter Park
📍 111 N Orlando Ave, Winter Park, FL
💻 kellyshomemadeicecream.com
Kelly’s brings small-batch, handcrafted charm to the local ice cream scene. With rotating seasonal flavors and classics that never miss, this bright pink shop feels playful and nostalgic. It’s a neighborhood favorite with a loyal following—and once you go, you’ll understand why.
✅ Must-try: Maple Bourbon Pecan (when it’s in season!)
🍦 Local tip: Follow them on social for flavor drops.
10. Mynt Fine Indian Cuisine – For a Sweet Finish
📍 535 W New England Ave, Winter Park, FL
💻 myntorlando.com
Not your typical dessert spot—but if you’re dining here, do not skip dessert. Mynt blends modern Indian cuisine with traditional sweets, offering treats like Gulab Jamun, Rasmalai, and homemade Kulfi. Their desserts are rich, aromatic, and full of flavor—perfect after a spicy meal.
✅ Try this: Mango Kulfi or the warm Gulab Jamun.
🥂 Ideal for: A romantic dinner + sweet finish.
Final Thoughts: Sweet Spots That Steal the Show
Whether you’re a local hunting for your new favorite cookie, a couple chasing the perfect after-dinner treat, or a traveler looking to taste the best of Winter Park—this list covers it all. Each of these dessert spots offers a unique experience, and yes, you can absolutely plan an entire afternoon or evening around dessert here. No judgment.
🍰 Pro tip: Make it a “dessert crawl” and hit a few in one day. Start with pastries, grab gelato mid-afternoon, and end with fudge or cookies after dinner. Your future self will thank you.
