407 FYI · Windermere
407 FYI · A District FinderWindermere is the lakeside village west of the parks: a brick Main Street under a heavy oak canopy, a Friday market in front of Town Hall, and a moneyed quiet that never needed to shout. The food follows the register: a Southern breakfast cafe, a hometown brewery, wood-fired pizza, a serious wine shop and Tuscan dinners out in Summerport. Paloma anchors the morning.
10 places
Lake Down Park in Windermere. Photo: “Lake Down Park” by Town of Windermere, Florida, public domain, via Wikimedia Commons.
Top Picks
New to the district? Start with these three, then work down the full list below.
13424 Summerport Village Pkwy, Windermere, FL 34786
A family-owned Tuscan room in Summerport with a wine list past 700 bottles and Wine Spectator recognition to show for it. Beef carpaccio and a lobster and pumpkin risotto served in the pumpkin itself lead the menu, with chicken parm for the traditionalists. The patio keeps date night outside when the weather behaves.
434 Main St, Windermere, FL 34786
An independently owned Main Street room with 1950s diner warmth and a from-scratch Southern kitchen. Smoked brisket hash, Bananas Foster French toast and biscuits under sausage gravy run the morning. The dog-friendly patio keeps it a neighborhood ritual.
527 Main St, Windermere, FL 34786
A wood-fired pizzeria from the Scialoia family, whose Dr. Phillips Italian kitchens go back to 2006. Pies come off 48-hour dough with blistered edges, and the handmade pastas hold their own against them. Main Street's family dinner anchor.
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The Full List
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13424 Summerport Village Pkwy, Windermere, FL 34786
A family-owned Tuscan room in Summerport with a wine list past 700 bottles and Wine Spectator recognition to show for it. Beef carpaccio and a lobster and pumpkin risotto served in the pumpkin itself lead the menu, with chicken parm for the traditionalists. The patio keeps date night outside when the weather behaves.
434 Main St, Windermere, FL 34786
An independently owned Main Street room with 1950s diner warmth and a from-scratch Southern kitchen. Smoked brisket hash, Bananas Foster French toast and biscuits under sausage gravy run the morning. The dog-friendly patio keeps it a neighborhood ritual.
527 Main St, Windermere, FL 34786
A wood-fired pizzeria from the Scialoia family, whose Dr. Phillips Italian kitchens go back to 2006. Pies come off 48-hour dough with blistered edges, and the handmade pastas hold their own against them. Main Street's family dinner anchor.
14387 Bridgewater Crossings Blvd, Windermere, FL 34786
The Windermere scoop shop of the Orlando-born ice cream maker that started in Audubon Park. Small-batch flavors rotate through salted caramel Oreo, PB&J potato chip and guava cheese, and flights exist for the undecided. A Summerport evening ritual in the making.
Mikado, 6417 Raleigh St, Orlando, FL 32835-5739, United States
An unassuming Raleigh Street room in Metrowest that guests call a little gem, and the sashimi is why. Cuts arrive large, tender, and ultra fresh, from toro and yellowtail to Scottish salmon and unagi, with the omakase, the Mikado Roll, and buttery uni toast as the standing orders. Cozy and old-school, it is the quiet room locals name when only real sushi will do.
507 Main St, Windermere, FL 34786
The coffee shop Windermere regulars treat as their own now trades as Paloma Parlor at 507 Main St, a small, plant-filled spot with a contemporary, small-town charm. The lattes come strong, smooth, and never bitter, with lavender, rose, and the Lucky Latte keeping the menu playful beside house-baked croissants and macarons. Ice cream joined the lineup after the move, and guests call it worth the short trip out of Orlando.
Teak Neighborhood Grill, 6400 Time Square Ave, Orlando, FL 32835-6453
Teak is MetroWest's tucked-away neighborhood grill, chill and laid-back, with a burger menu deep enough to keep regulars rotating through it. The Glazed Donut Burger and Kobe Burger get the headlines, but insiders point to the loaded pierogies and the soft pretzel with beer cheese, which one guest called perfection. Dogs are welcome on the patio, the staff reads like family to the regulars, and when the room fills the kitchen can take its time, so settle in.
428 Main St, Windermere, FL 34786
The Windermere storefront of Orlando's long-running independent wine shop, with shelves in Orange Avenue and Sanford siblings. Small-producer bottles are the point, and the staff teach as they pour. On Fridays the Wine Down pours free tastes for whoever wanders in.
111 W 5th Ave, Windermere, FL 34786
Windermere's hometown brewery, a block off Main Street with a dog-friendly backyard and a food truck rotation. The Watermann helles and Orange Grove Outlaw IPA pour beside a peach wheat called Party Boat. Trivia and bingo nights give the week a rhythm.
520 Main St, Windermere, FL 34786
Every Friday, Town Square Park in front of Windermere's Town Hall fills with a small hometown market: fresh produce and seafood, breads and pastries, homemade pasta, local honey, plants and hanging baskets. Live music drifts over the brick street and leashed dogs are part of the crowd; pairing it with coffee at Paloma down the block is the local routine.
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List last checked October 2026
Answers only from the guide's own listings.