15 Best Restaurants in Windermere (FL)

Windermere is one of the oldest residential towns in Orange County, Florida, USA. Over 3000 residents call the town home.

Many Disney executives lived in Windermere in the 1970s, including Don Edgren, Bob Allen, and Admiral Joe Fowler, to mention a few.

The town is known for its close-knit community values. Over the years, tourism has stimulated the development of Windermere and aided its growth to become a popular destination for tourists worldwide.

The town is perfect for those who want to experience a renewed spark in their love life, a change of scenery, and a relaxing haven to explore.

Windermere restaurants are at the forefront of the welcome party for new visitors and those who call it home, making the town a lively and exciting place for everyone.

Planning a trip to Windermere? Here are the best restaurants in Windermere, FL.

Best Restaurants in Windermere, FL 

1. Chipotle Mexican Grill

Chipotle Mexican Grill

Chipotle Mexican Grill is an excellent Mexican restaurant that caters to customers who want to experience the awesomeness of incredible Mexican cuisine. 

This fantastic restaurant has a well-illustrated Mexican-themed interior decoration that makes it stand out with its pleasant atmosphere, making it appear cozy and beautiful.

Chipotle Mexican Grill takes excellent care of its customers and ensures they enjoy every minute spent dining at the restaurant.

Thanks to its great effort to please customers, the Grill rose to stand alongside the best places to eat in Windermere, FL. It is known to serve tasty meals and offer genuine hospitality.

This fabulous place is home to the most exquisite meal specials that have won the restaurant praises over the years.

If you find yourself at this restaurant, try out meals like Burritos, Quesadillas, Salad, Vegan Bow, Tortilla On The Side, Chips & Guacamole, Large Side Of Queso Blanco, and Tacos.

Chipotle Mexican Grill is open every day from 8:00 am–2:30 pm.

Address: 9100 Conroy Windermere Rd Ste 120, Windermere, FL 34786, United States. Phone: +1 407-909-6267.

2. Josie’s Pizza and Wings

Josie's Pizza and Wings

Josie’s Pizza and Wings is a family-owned American restaurant, inarguably one of the most hospitable restaurants in Windermere. 

It offers outstanding hospitality, authentic American cuisine, and friendly atmosphere that makes it comfortable for customers.

The restaurant is a great place to treat yourself to an array of well-prepared dishes that are incredibly satisfying in a very cozy dining environment.

The menu at Josie’s Pizza and Wings offers surprising combinations of dishes like Bobby’s Bread Sticks, Metro west Salad, Meatballs With Sauce & Cheese, Fried Ravioli, Chicken Tenders, Jamie’s Cheese Fries, Jalapeno Poppers, and Cheesy Bread.

Josie’s Pizza and Wings is open to receive orders daily from 11:00 am – 9:00 pm.

Address: 5855 Winter Garden Vineland Rd Suite #150, Windermere, FL 34786, United States. Phone: +1 407-395-9794.

3. Dixie Cream Cafe

Dixie Cream Cafe

Dixie Cream Cafe is one of the best places to eat in Windermere, FL, due to its tasty offerings, and the incredible hospitality guests enjoy while dining at the cafe.

The cafe was set up to cater to the food needs of Windermere residents who want to enjoy some peaceful dining alone or with family and friends.

Dixie Cream Cafe has a serene environment and is suitable for lone diners who want to sit with a book while they enjoy the sweet meals served by the cafe.

Every meal listed on its outstanding menu will leave your mouth asking for more as you savor the deliciousness long after your food is digested. The cafe is famous for the diversity of its meals.

Some dishes served at the restaurant include Fried green tomatoes, Belgium waffles, Pancakes with blueberries, Buffalo Bill chicken sandwiches, Fried Green, Tomato Sandwiches, Tuna Melt, biscuits, Sawmill gravy, etc.

Dixie Cream Cafe is open to welcome everyone from 8:00 am – 2:30 pm every Tuesday to Sunday, and it is closed on Mondays.

Address: 434 Main St, Windermere, FL 34786-8648. Phone: +1 407-217-5047.

4. My French Cafe

My French Cafe

My French Cafe is a fantastic restaurant that provides customers with meals curated with hearty French and sophisticated European recipes and prepared by an award-winning chef.

This incredible cafe is one of the top restaurants in Windermere, FL. You can visit with your pet as it has a pet-friendly facility and policies to ensure that you and your fur babies have a blast of excitement.

Guests are welcomed and ushered into the serene dining spot with warm smiles from the ever-hospitable staff that is on hand to give them the time of their life, all at a great price.

With an array of tasty menu entries, this restaurant has no shortage of surprises regarding food.

There are tasty meals like Swiss hot chocolate, Julius Meindl Coffee, ham and cheese omelet, vegetable quiche, The Quiche Lorraine, homestyle potatoes, mimosas, and so much more to eat.

The doors to the restaurant open to customers at 7:00 am and close at 7:00 pm every other day of the week but close at 6:00 pm on Sundays.

Address: 7782 Winter Garden Vineland Rd Suite #100, Windermere, FL 34786-5931. Phone: +1 407-347-8945.

5. Bella Tuscany

Bella Tuscany

You cannot choose a better place to dine with friends, family, or vacation buddies in Windermere than Bella Tuscany. It is the right place to celebrate your wedding anniversary, birthday, promotions, and more.

The best decision you can make while vacationing at Windermere is to visit Bella Tuscany, one of Windermere restaurants with premium customer service.

Bella Tuscany is not your average Italian restaurant; it is decorated to show Italian heritage, the music is complementary, and the interior colors are enchanting.

Bella Tuscany is different from your average Italian restaurant; you would have only one wish after your first visit, which will be to visit again because you will need more of the spread of Italian dishes on the menu.

You will be impressed with fantastic offerings like duck pasta, pappardelle, calamari and fried zucchini chips, Blue cheese Fiocchi, Spaghetti and shrimp, Linguine carbonara, and Baked Penne Eggplant Rollatini.

It is open from 10:00 am – 10:00 pm every day.

Address: 13424 Summerport Village Pkwy, Windermere, FL 34786. Phone: +1 407-656-2355.

6. Jeremiah’s Italian Ice

Everything about Jeremiah’s Italian Ice is inspired by its rich history, from its treats to its decor and ambiance.

Jeremiah’s Italian Ice should be your favorite stop after a long walk or sightseeing with your friend or family while in Windermere.

Jeremiah’s Italian Ice is on hand to satisfy you with a collection of tasty treats such as pumpkin pie, soft custard ice cream, chocolate and swirl ice cream, gelatos, vanilla ice cream, Black Raspberry, Cafe Latte, and a lot more delicacies.

The restaurant is open from 12:00 pm – 10:00 pm every day.

Address: 4750 The Grove Dr. Ste 108, Windermere, FL 34786. Phone: +1 407-217-7800.

7. BurgerFi


BurgerFi is an American fast-food restaurant passionate about burgers that will get you hooked from the first bite until your meal is consumed.

It is a gem of a place that commands respect from every visitor; the palette of colors used to paint the restaurant artistically is commendable.

Suppose you want an exciting alternative to regular drive-by fast-food restaurants. In that case, you have to visit to try out their competitively priced fast food options at BurgerFi.

BurgerFi menu includes custard shakes, Chili cheese fries, Draught, stir Fries, Cheeseburger, BurgerFi burgers, The red Velvet milkshake, and a lot more that will keep you hooked on every bite.

BurgerFi is open from 11: 00 am – 9:00 pm on Sundays to Thursdays and closes at 10:00 pm on Fridays and Saturdays.

Address: 4750 The Grove Dr, Windermere, FL 34786-8425. Phone: +1 407-217-7612.

8. Allen’s Creamery and Coffee House

Allen's Creamery and Coffee House

Allen’s Creamery and Coffee House is an extraordinary place at the heart of Windermere.

The establishment provides an enjoyable atmosphere serenaded with music. Customers meet the smiling faces of the homely owners.

You can choose your choice of treats from the star-studded menu that includes chocolate fudge ice cream, chocolate shakes, a slowly pulled barbecue, coffee, donuts, pumpkin ice cream, and a sandwich.

Allen’s Creamery and Coffee House is very welcoming and open from 11:00 am every day and closes at 9:00 pm on Sundays to Thursdays while closing at 9:30 pm on Fridays and Saturdays.

Address: 523 Main St, Windermere, FL 34786-3562. Phone: +1 407-876-3558.

Are you considering more exploration of Florida? Here is our list of things to do in Wesley Chapel, and things to do in Fernandina Beach for a fun vacation.

9. Agave Azul Cocina Mexicana – Windermere

Agave Azul Cocina Mexicana - Windermere

This restaurant is a fantastic find with an eclectic feel brimming with great character and exceptional staff.

Agave Azul Cocina Mexicana, which is one of the top restaurants in Windermere, FL, serves a range of food and drinks, including the freshest brews that excite customers’ taste buds.

This fantastic Mexican restaurant has a spacious interior and well-arranged dining hall.

The restaurant brings Mexican cuisine’s authentic feel and taste to the table of its customers at affordable prices

You can treat yourself by dining at Agave Azul Cocina Mexicana to enjoy its vast selection of tasty dishes.

The restaurant offers meals like enchiladas and empanadas, chicken tamale, chicken quesadillas, chicken tacos, Ahi Tuna Ceviche Stack, beef Burrito, Mazapan French Toast, chicken enchilada, and so much more.

The restaurant is open on Sundays to Thursdays from 11:00 am – 10:00 pm and extends its closing time to 11:00 pm on Fridays and Saturdays.

Address: 5855 Winter Garden Vineland Rd #100, Windermere, FL 34786-6125. Phone: +1 407-395-8350.

10. Little Greek Fresh Grill – Windermere

Little Greek Fresh Grill - Windermere

Little Greek Fresh Grill – Windermere is a fantastic restaurant with a mix of American and Greek cuisine served to the delight of its customers.

The restaurant provides first-class dining service and can seat numerous customers in its comfortable dining halls with all the right features to make you feel welcome and at ease.

At Little Greek Fresh Grill, every meal is tasty and arrives on time as you take in the beautiful sights and interiors of the restaurant.

With over 35 years of experience catering to customers and their food needs, Little Greek has offered premium service at affordable rates and has become tested and trusted by its customers. Little Greek is no doubt one of the outstanding Windermere restaurants.

If you find yourself at this restaurant, try out some of its incredible offerings like steak, chicken kebabs, salmon, gyro platter, potato salad, Greek salad, Pitas, and more.

Little Greek Fresh Grill opens its doors daily from 10:45 am – 9:00 pm.

Address: 6536 Old Brick Road Ste. 130, Windermere, FL 34786. Phone: +1 407-612-5952.

11. Bruster’s Real Ice Cream

Bruster's Real Ice Cream

Bruster’s Real Ice Cream provides tasty treats to the delight of its numerous customers.

Bruster’s Real Ice Cream is a child and pet-friendly fast-food spot that understands the value of family. The food is prepared in clean contemporary surroundings with a fantastic view of the Windermere streets.

This beautiful restaurant is a place to visit repeatedly with your friend, fiancé, or business colleagues for a taste out of this world. It has seen thousands of customers return to enjoy its delicious meals.

Bruster’s Real Ice Cream serves numerous customers daily with unique recipes such as custard shakes, Chili cheese fries, stir Fries, cheeseburgers, vegan burgers, and milk.

Buster’s is open from 12:00 pm – 10:00 pm from Sunday to Thursday, while they close at 11:00 pm on Fridays and Saturdays.

Address: 5855 Winter Garden Vineland Rd Ste 110, Windermere, FL 34786-6125. Phone: +1 407-347-9578.

12. Panera Bread

Panera Bread

Panera Bread is one of the top places for mouth-watering breakfast, lunch, and dinner in Windermere.

It is worth a visit when you try their exclusive variety of dishes that would transport you across the world in a matter of minutes while also catering to people who desire customizable vegan dishes. 

Panera Bread brings life and action to the saying “We are here to serve you” because the scent of craftsmanship permeates the clean restaurant space.

The food served at the restaurant is exceptional. It includes meals like Bacon, Scrambled eggs, Cheese on Ciabatta, and so much more you would wish you could live in Windermere.

Panera Bread opens daily from 6:30 am – 9 pm.

Address: 6537 Old Brick Rd, Windermere, FL 34786. Phone: +1 407-217-2915.

13. Clean Juice

Clean Juice

Clean Juice is a highly sought-after establishment that provides excellent customer service to its customers alongside delicious food that soothes the soul.

In addition to its tasty edibles, the restaurant’s environment is warm and welcoming enough for customers to sit in while they enjoy the delicious meals at their fingertips.

It is best to visit this restaurant with a friend or loved one to share the wholesome experience.

Clean Juice has exciting menu options like The Avocado Toast, BBQ Chicken Wrap, Almond Butter Toast, The Cold Brew Bowl, The Berry Bowl, Just Got, and delicious Smoothie.

They are open every Monday through Sunday from 7:00 am – 8:00 pm.

Address: 5855 Winter Garden Vineland Rd Suite 130, Windermere, FL 34786, United States. Phone: +1 407-347-7814.

14. Stromboli’s NY Pizzeria

Stromboli's NY Pizzeria

Stromboli’s NY Pizzeria is a fabulous place to visit in Windermere. It is known for its freshly prepared pizzas that leave a lasting impression of delicious tastes on customers’ taste buds.

The pizza served by the restaurant has a rich and satisfying taste that is worth your time and money.

For a more enjoyable feel, it is best to pair Stromboli’s pizza with a delicious milkshake to get the most out of your dining experience at one of the finest Windermere restaurants in town.

The exceptional pepperoni pizza headlines the menu, and there are over ten different toppings for variety and customer satisfaction.

They are open from 11:00 am – 9:00 pm on Monday to Thursday while it closes at 10:00 pm on Fridays and Saturdays.

Address: 13518 Summerport Village Pkwy, Windermere, FL 34786-7366. Phone: +1 407-654-5291.

15. Gator’s Dockside

Gator's Dockside

Gator’s Dockside is a fantastic restaurant and inarguably one of the best restaurants in Windermere, FL. It will capture your heart and make an impression on you after you step foot in its beautiful dining hall.

It is an excellent restaurant to explore authentic American flavors that are delicious and highly satisfying.

Using only the freshest ingredients to make its meals in a spotless kitchen, this restaurant has an array of tasty offerings that will leave your taste buds wanting more.

Gator’s Dockside Windermere serves various dishes such as gator tail and wings, breaded white meat, burgers, Grilled sandwiches, Salt Beef Brisket Sandwiches, and Triple Cheese sandwiches paired with beer or wine.

Gator’s Dockside opens from 11:00 am to 11:00 pm every day from Sunday to Thursday while closing later by 11:00 on Fridays and Saturdays.

Address: 6516 Old Brick Rd, Windermere, FL 34786-5838. Phone: +1 407-217-5191.

Map of the Best Restaurants in Windermere, FL 

To get around during your trip to Windermere, here is a map of the best restaurants in Windermere with markers of the top places to eat in Windermere, FL.


Are you considering more exploration of Florida? Here is our list of things to do in Tallahassee, things to do in Miramar Beach and things to do in Sebring for a fun vacation.

Plan a Visit to Windermere 

These Windermere restaurants are the best places to experience the hospitality that the city has to offer.

Whether you visit these restaurants to dine by yourself or in the company of loved ones you have the assurance of getting valuable service worth every penny.