407 FYI · Winter Springs
407 FYI · A District FinderWinter Springs is the Seminole County city between Oviedo and the Lake Jesup shore, and its eating gathers in two clusters: the Town Center at 434 and Tuskawilla, where a restaurant row runs down Tree Swallow Drive, and the older west 434 strip of family rooms that have held their corners for decades. A wine bar, a destination sushi counter, Detroit style deep dish, and a roughly 100 acre park that hosts the Highland Games each January give it more range than its quiet streets suggest.
16 places
Top Picks
New to the district? Start with these three, then work down the full list below.
5248 Red Bug Lake Rd, Winter Springs, FL 32708
Agave Azul's Winter Springs room is festive and high-energy, a family-owned Mexican kitchen where the noise is part of the fun. Guests rave about birria tacos and birria brisket, chicken fajitas, queso they call to die for, and spicy margaritas that keep pace with the kitchen. It is the kind of place where tables order widely and linger, stylized but grounded.
Boba Garden, 1184 E State Rd 434, Winter Springs, FL 32708
A family owned bubble tea cafe in Town Center, pouring made to order milk teas and fruit teas in a nature inspired room with board games and a claw machine. The blue cheese foam is the signature, over Thai tea, taro, and Kagoshima matcha lattes.
Central Winds Park, 1000 Central Winds Dr, Winter Springs, FL 32708
The city's sports and festival hub on about 100 acres, with baseball and softball fields, basketball, fishing, a three story playground, and a dog park split for small and large dogs. The Cross Seminole Trail runs through it, and each January it hosts the Central Florida Scottish Highland Games, the largest community event in Seminole County.
Start Here
Winter Springs eats well in two clusters, but the city's other life runs through its big park, the trail that crosses it, and the wild lake on its northern edge.
Each January, Central Winds Park hosts the Central Florida Scottish Highland Games, organized by the Scottish-American Society of Central Florida and described as the largest community event in Seminole County. The 48th edition ran in January 2026: caber toss, hammer throw, stone lift, Highland dance, bagpipes, a clan village, and a Ceilidh with Celtic rock bands. The same park also hosts the Hometown Harvest Festival.
The paved Cross Seminole Trail runs about 22 to 23 miles between the Oviedo and Lake Mary directions, straight through Winter Springs and through Central Winds Park, crossing Gee Creek on a bridge and passing Winter Springs High School. It is part of the Florida National Scenic Trail. The city counts 12 park sites in all, including Trotwood Park and the Bear Creek Nature Trail.
The city sits just south of Lake Jesup, one of the area's great wild lakes. A road by the Central Winds Park dog park leads to a boardwalk with a panorama across the lake, which is known for alligators, and the Lake Jesup Conservation Area offers birdwatching, fishing, and hiking.
Most of this list sits in two clusters: the Town Center at SR 434 and Tuskawilla, where Ristorante Positano, Sushi Delight & Bowl, and Spill Wine Bar line Tree Swallow Drive, and the west 434 strip, where Victorio's II has been serving since 1989.
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The Full List
Full cards for the whole district, Local Picks first, then A to Z. Every name opens its own page, with directions and more nearby. The map, filters and export live in the full finder.
5248 Red Bug Lake Rd, Winter Springs, FL 32708
Agave Azul's Winter Springs room is festive and high-energy, a family-owned Mexican kitchen where the noise is part of the fun. Guests rave about birria tacos and birria brisket, chicken fajitas, queso they call to die for, and spicy margaritas that keep pace with the kitchen. It is the kind of place where tables order widely and linger, stylized but grounded.
Boba Garden, 1184 E State Rd 434, Winter Springs, FL 32708
A family owned bubble tea cafe in Town Center, pouring made to order milk teas and fruit teas in a nature inspired room with board games and a claw machine. The blue cheese foam is the signature, over Thai tea, taro, and Kagoshima matcha lattes.
Central Winds Park, 1000 Central Winds Dr, Winter Springs, FL 32708
The city's sports and festival hub on about 100 acres, with baseball and softball fields, basketball, fishing, a three story playground, and a dog park split for small and large dogs. The Cross Seminole Trail runs through it, and each January it hosts the Central Florida Scottish Highland Games, the largest community event in Seminole County.
Greek Eatery, 1188 E State Rd 434, Winter Springs, FL 32708
A family owned Greek kitchen in the Town Center with more than 15 years behind it, turning out gyros, souvlaki, pastitsio, and moussaka. Reviewers call the gyros the best they have had, and the room runs on dine in, takeout, and delivery.
Khaos Sports Bar and Grill, 178 W State Rd 434, Winter Springs, FL 32708
A lively dive bar sports hub on west 434 that expanded in 2026 with a new kitchen, more pool tables, and a smoke free interior. Wings are the draw, with darts, karaoke, and domestic beer buckets on game day.
Kiko Japanese Cuisine, 5661 Red Bug Lake Rd, Winter Springs, FL 32708
A neighborhood sushi spot on Red Bug Lake Rd that opened in 2023 and built a devoted following fast, with fresh sashimi, inventive rolls, and one of the deepest vegan sushi menus around. The sushi and sashimi boat and surf and turf ramen show the range.
Napoli's Pizza & Italian Restaurant, 122 W State Rd 434, Winter Springs, FL 32708
A simple family pizzeria on west 434 and the cheapest sit down Italian in Winter Springs, with garlic knots, baked mussels, and eggplant Campania beside the pies. Chicken parmesan, piccata, and marsala round out a menu that punches past its price.
Ristorante Positano Authentic Italian, 1168 Tree Swallow Dr, Winter Springs, FL 32708
Winter Springs' Italian escape in the Town Center, where owner Salvatore greets guests personally and the room runs cozy and family like. Campania pizza, fettuccine alla panna, chicken piccata, and carbonara anchor the menu, with tiramisu to finish.
Senor Tequila Mexican Grill, 855 E State Rd 434, Winter Springs, FL 32708
A spacious, family friendly Mexican grill in the Villaggio plaza on 434, with one of the deepest review followings in Winter Springs. Carne asada, molcajete, fajitas, and the Sangrita, a sangria and frozen margarita mashup, lead a menu with a big seafood bench.
Spill Wine Bar, 1196 Tree Swallow Dr, Suite 1314, Winter Springs, FL 32708
A locals first wine bar in the Town Center, started by a local for the locals, pouring 100 plus wines and a deep craft beer list. Live music, trivia and bingo nights, flatbreads, and a patio make it Winter Springs' living room after dark.
Stefano's Trattoria, 1425 Tuskawilla Rd, Winter Springs, FL 32708-4703
A cozy, old-school Italian dining room tucked into a Tuskawilla Road shopping center, easy to miss and worth finding. Live piano drifts through the room while gnocchi della nonna in pink sauce, lobster ravioli, and veal piccata land in generous portions, with tiramisu cheesecake to finish. Longtime fans still prize it, though recent regulars say the cooking has turned uneven under new ownership.
Sushi Delight & Bowl, 1172 Tree Swallow Dr, Winter Springs, FL 32708
A pan-Asian counter on the Tree Swallow Dr restaurant row in Town Center, rolling sushi and building rice bowls to order. Spicy beef bowls, the Hama roll, and crispy pork belly make it the row's quick lunch move.
Taiwan Cafe, 158 W State Rd 434, Winter Springs, FL 32708
A family Chinese kitchen on west 434 doing classic stir fries, noodles, and rice plates with fresh ingredients. General Tso's, honey glazed chicken, and salt and pepper chicken lead a menu that mixes English and Chinese dish names.
Taqueria Las Cazuelas Winter Springs, 162 W State Rd 434, Winter Springs, FL 32708
A second room for the East Colonial taqueria, on west 434 in Winter Springs, with tacos, milanesa de res and pollo, chips and guacamole, and queso dip at counter prices.
The Cuban Sandwich Cafe, 140 W State Rd 434, Winter Springs, FL 32708
A small breakfast and lunch cafe on west 434 opened in 2025 by a veteran local Cuban restaurateur, scaled down on purpose. Cubanos, ham croquettes, bistec empanizado, and carne con papas, with pastries, smoothies, and coffee.
Victorio's II Italian Restaurant & Pizzeria, 200 E State Rd 434, Winter Springs, FL 32708
Serving Winter Springs since 1989, Victorio's II is known for Detroit style deep dish baked in pans imported from Detroit, sauce ladled on after the bake. Hand tossed pies, the sealed Nero Sub, and a lasagna over a pound and a half make it a family standby on 434.
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List last checked October 2026
Answers only from the guide's own listings.