Italian Dining in Windermere: Bella Tuscany and Family Favorites
From the Wine Spectator list at Bella Tuscany to the neighborhood pizzerias every Windermere kid knows
Italian dining in Windermere, FL is anchored by Bella Tuscany Ristorante Italiano at 13424 Summerport Village Pkwy, a family-owned restaurant operating since 2012 with a Wine Spectator-recognized wine list of more than 700 selections. The Cornerstone at Summerport plaza alone houses both Bella Tuscany and Stromboli's NY Pizzeria, giving residents two Italian options in one shopping center. Windermere is also roughly 10 minutes from Sand Lake Road's Restaurant Row in Dr. Phillips, which includes Christini's Ristorante Italiano. Surrounding neighborhood pizzerias include Castello's Pizza, Piesanos Stone Fired Pizza, and Pie-Fection.
Here's the thing about Italian food in Windermere: for a town of just over 3,400 residents on a peninsula in the Butler Chain of Lakes, the Italian dining bench is deeper than it has any right to be. You've got a chef-driven, Wine Spectator-recognized neighborhood ristorante. You've got NY-style pizzerias run by families that have been doing this for decades. And you're 10 minutes from one of Florida's most famous restaurant corridors.
Whether you're a future resident scoping out the area or a local who's only ever ordered the same thing from the same place (no judgment, we've all been there), this is your guide to where Windermere actually eats Italian.
Bella Tuscany: Windermere's Italian Anchor
If you only have time to try one Italian restaurant in Windermere, make it Bella Tuscany Ristorante Italiano. Tucked into the Cornerstone at Summerport shopping center off CR 535, this family-owned spot has been the area's go-to Italian restaurant since 2012.
What separates Bella Tuscany from the dozens of generic Italian-American chains around Central Florida is genuine ambition. The wine list runs more than 700 selections deep and has earned recognition from Wine Spectator — a tough thing to pull off in a strip-mall location. The kitchen turns out chef-driven specials alongside the expected pasta lineup: linguine carbonara with applewood bacon, chicken saltimbocca, ricotta-and-pear-stuffed pasta with Maytag blue cheese, frutti di mare, and wood-fired pizza for the kids (or, fine, for you).
The patio is the move when the weather cooperates, which in Central Florida is most of the year. They also do a Sunday brunch that quietly competes with the better breakfast spots in town — handmade waffles, eggs benedict variations, and the same wine list waiting for you at noon.
Address: 13424 Summerport Village Pkwy, Windermere, FL 34786
Phone: (407) 656-2355
Style: Casual upscale, family-friendly, patio dining, full bar
The Pizzeria Scene: Windermere's Casual Italian Lineup
Windermere's pizza game punches above the town's weight class. A few you should know:
Stromboli's NY Pizzeria
Walk literally next door to Bella Tuscany in the same Cornerstone at Summerport plaza and you'll find Stromboli's at 13518 Summerport Village Pkwy. Open daily 11 AM to 9 PM, this is the weeknight workhorse — NY-style pies, calzones, classic baked pasta dishes, and a kids' menu that won't blow up your Tuesday. It's the kind of spot you end up at after soccer practice, then somehow keep coming back to.
Castello's Pizza
Family-owned since 2009 and serving the Windermere, Gotha, Ocoee, and Metro West side of Dr. Phillips, Castello's has the longest tenure of any pizzeria in the immediate area. Hand-tossed, fire-oven-baked, NY-style — the playbook is simple and they've been running it for 16+ years.
Piesanos Stone Fired Pizza – Windermere
A bigger casual-dining footprint than the neighborhood pizzerias above, Piesanos is the spot for groups that want a sit-down meal without committing to a special-occasion price point. Stone-fired pizzas, a full pasta menu, and a vibe that works equally well for family dinner and watching a game.
Pie-Fection
Operating since 2011, Pie-Fection brings an artisan-pizza approach with handcrafted dough and premium mozzarella. Quieter than the bigger names but a steady favorite among residents who've done their pizza homework.
Sand Lake Road: Where Windermere Goes for Upscale Italian
Here's the Windermere advantage no one talks about enough: you're 10 minutes from one of Central Florida's premier dining corridors. Conroy-Windermere Road feeds you straight into the Sand Lake Road Restaurant Row in Dr. Phillips, a 1.5-mile stretch with more than 24 acclaimed restaurants. For Italian specifically, this is where the special-occasion dinners happen.
Christini's Ristorante Italiano is the one to know. Open since 1984 in the Marketplace at Dr. Phillips, Christini's is one of Orlando's longest-running white-tablecloth Italian restaurants — strolling violinists, tableside Caesar salad, the whole tuxedoed-server experience. It is exactly the place you take in-laws who fly down for the holidays and want to be impressed.
If you want a step down in price but still cinematic Italian energy, Maggiano's Little Italy on International Drive is roughly 15 minutes from most of Windermere — family-style portions, classic-American Italian menu, and the sort of place that handles a 12-person birthday dinner without flinching. Manzzo Cuisine, a newer casual-elegant Italian spot inside Windermere itself, is also worth a look for date night when you don't feel like driving to Sand Lake.
Picking the Right Spot: Our Take by Occasion
- Weeknight family dinner: Stromboli's NY Pizzeria or Piesanos. Fast, kid-tested, no reservation drama.
- Date night you actually want to talk through: Bella Tuscany's patio. Quieter than Sand Lake, real wine list, no valet circus.
- Holiday dinner with the in-laws: Christini's. Worth the 10-minute drive and the price tag.
- Birthday party for 10+: Maggiano's on I-Drive — they've been doing big-table Italian for 30+ years.
- Tuesday-night pizza craving: Castello's or Pie-Fection. Both deliver.
Why This Matters If You're Moving Here
Windermere's reputation skews lakefront-luxury — Isleworth, Keene's Pointe, the Butler Chain. What gets undersold is the everyday infrastructure: the schools, the medical pavilion on CR 535, and yes, the dining. A community that supports a Wine Spectator-recognized Italian restaurant in a strip mall is a community where the residents care about food. That's a quality-of-life signal worth noticing.
It's also a community where you don't sacrifice variety for the small-town feel. You get the brick-street, English-village character of Main Street Windermere, plus 10-minute access to one of Florida's most acclaimed dining corridors. That combination is hard to replicate.
What the Locals Know
Bella Tuscany is the answer when someone asks for "good Italian in Windermere" — full stop. Reservations are smart on Friday and Saturday nights. The Cornerstone at Summerport parking lot fills up; come early or be patient. The pizzerias are interchangeable enough that loyalty here is more about what's on your way home than which pies are objectively best.
And remember: when the occasion is bigger than what Windermere proper can handle — anniversary, milestone, business dinner — you've got Sand Lake Road right next door. Most newcomers don't realize how close it is until they make the drive once. Then it becomes the default.
Explore more dining options in our complete Windermere restaurants and dining guide, and check out our casual and family dining guide for non-Italian neighborhood-center options at The Grove at Isleworth, Lakeside Village, and Summerport.
For menus, hours, the wine list, and online ordering, visit Bella Tuscany Ristorante Italiano.
Thinking about moving to Windermere or curious which neighborhoods get you closest to your favorite restaurants? Browse Windermere homes for sale or contact us for personalized relocation advice. 🍝
