Winter Park Shopping Districts

Winter Park is a gem of a town that blends upscale shopping with small-town charm. From its brick-lined streets and boutique-lined avenues to its vibrant dining scene, this stylish destination invites you to shop, stroll and savor. Whether you're planning a day trip or a weekend escape, here's your guide to discovering the best shopping districts --and delicious bites -- in Winter Park, Florida. For more Winter Park recommendations, click here.

Park Avenue District

Park Avenue is the heart and soul of Winter Park shopping. This picturesque, walkable strip is lined with boutiques, restaurants, and historic charm. Here are some standout shops you won’t want to miss:

• Almut Belote Jewelry – Handmade fine jewelry with elegant European flair.
• Be On Park – A stunning jewelry boutique offering designer collections and custom creations.
• Bobbles + Lace – Trendy, affordable fashion for the stylish modern woman.
• The Collection Bridal – Elegant wedding gowns and accessories in a charming boutique setting.
• Current by John Craig – A contemporary men’s boutique with polished, casual looks.
• Dear Jane – A modern women’s boutique featuring chic, curated pieces.
• frank. – A minimalist boutique offering modern essentials and timeless wardrobe staples with an elevated edge.
• John Craig Clothier – Upscale menswear with classic Southern sophistication.
• Lauren Sigman Collection – Playful, colorful fine jewelry with a personal touch. Watch the B Student podcast episode featuring Lauren Sigman, where she shares how she built the courage to pursue her passion—and shows us how to style layered necklaces like a pro.
• Leonard 5th Avenue – Upscale men's and women's fashion with a cosmopolitan edge.
• Orlando Watch Company – Fine timepieces and expert service for watch enthusiasts.
• Rieker Shoes – Comfortable, stylish footwear designed with European craftsmanship.
• SEE Eyewear – Unique, fashion-forward glasses and sunglasses with a boutique feel.
• Siegels – Timeless style with a mix of upscale men’s and women’s clothing.
• Southern Tide – Preppy and casual clothing inspired by coastal living.
• Synergy – A contemporary boutique featuring trendy, comfortable fashion.
• Tuni – A fashion-forward women’s boutique known for luxurious, trendsetting pieces.
• The Vintage Vault – A curated collection of fine wines, wine accessories and wine pairings.
• Warby Parker – Stylish, affordable eyewear with modern flair and a try-on experience.
• Writers Block Bookstore – A beloved indie bookstore offering author events, local finds and literary treasures.

Where to Eat on Park Avenue:

After a day of browsing the boutiques, unwind and refuel at one of these standout dining spots:

• AJ Chocolate House – Handmade chocolates, truffles and gourmet sweets. Make your reservation for AJ Chocolate House here.
• Atlantic Beer & Oyster – Fresh oysters and craft beer in a relaxed, patio-friendly setting.
• AVA MediterrAegean – Elegant Mediterranean cuisine in a stylish setting. Make your reservation for AVA MediterrAegean here.
• Barnie’s Coffee & Tea Co. – A beloved local spot with artisan coffee, teas, breakfast, lunch and a cozy vibe.
• Boca – Farm-to-table dishes with fresh, locally sourced ingredients. Make your reservations for Boca here.
• BoVine Steakhouse – A sleek steakhouse serving prime cuts and upscale American fare. Make your reservation for BoVine here.
• Bricks and Bowls – A quick, healthy stop for flavorful rice bowls, noodles, and wraps.
• The Chapman – Elevated American cuisine with a Southern twist in a charming setting. Make your reservation for The Chapman here. 
• ÔMO by Jônt – A refined, intimate experience featuring an omakase-style tasting menu. Make your reservation for ÔMO by Jônt here. 
• Park Avenue Smoothie Cafe – A quick, refreshing stop for smoothies and light bites.
• Power House Café – Health-conscious dishes and smoothies in a casual café vibe.
• Prato – A stylish Italian eatery known for wood-fired pizzas, handmade pastas and a trendy, bustling atmosphere. Make your reservation for Prato here.
• Tabla – Indian, Thai, and Chinese fusion in a chic and modern space. Make your reservation for Tabla here. 
• The Wine Room on Park Avenue – A wine lover’s paradise with self-serve tasting stations and gourmet bites.

Hannibal Square

Just a few steps from Park Avenue, Hannibal Square offers a slightly quieter, artsy vibe with boutiques nestled among historic buildings. It’s a great spot to discover local charm and unique finds.

• Monkee’s of Winter Park – A chic boutique offering high-end fashion, footwear, and accessories in a friendly, personalized environment.
• Novella Needlepoint – A specialty shop for high-end needlepoint canvases, threads, and accessories.
• Rifle Paper Co. – A stationery lover’s dream. Find whimsical prints, planners, and home accessories.

Where to Eat in Hannibal Square:

After exploring these charming shops, take a break and enjoy a bite at one of the area's favorite local spots:

• Corner Chophouse – This beautiful space set right in the heart of Hannibal Square brings fresh energy to the classic steakhouse experience. With a buzzing bar, comfortable dining room and a outdoor sidewalk tables, it's a great spot for quick bite, a celebratory dinner or a perfect martini.

Winter Park Village

This open-air lifestyle center combines big-name convenience with boutique elegance. It’s the perfect place to shop, stroll, and dine in style.

Where to Eat in Winter Park Village:

Once you've explored the shops, treat yourself to a delicious meal or refreshing drink at one of these inviting eateries:

• The Grove Bar + Kitchen – Florida-focused fare with inventive dishes and bold flavors, crafted by Food Network celebrity chef Mario Pagán, known for his vibrant culinary creativity and global influence. Make your reservation here.
• Crisp & Green – A fast-casual spot offering fresh, healthy salads and grain bowls.
• 480N Wine Bar – An elegant space for a glass of wine, live music and enjoying light bites.

Additional Shopping Throughout Winter Park

Beyond the main shopping districts, Winter Park is home to even more specialty shops worth exploring:

• Cami Monet – Whimsical hand-painted gifts, paper goods, and home décor.
• Majestic Jewelers – Fine jewelry with custom design services and expert craftsmanship.
• SIMPLY CHEESE. – A gourmet shop offering artisan cheeses and accompaniments for every palate.