Josie's Pizza & Wings-Windermere Menu

Welcome to Josie's Pizza & Wings-Windermere, a family-owned gem located at 5855 Winter Garden Vineland Rd. This establishment masterfully combines warmth and deliciousness in every dish. Their menu showcases some of the best pizza and wings in Florida, beloved by locals and visitors alike.

Highlights include:

  • Honey Hot Wings: Known for their unique flavor, these wings are a must-try.
  • Fresh Pizza: Always loaded with quality ingredients that tantalize taste buds.
  • Family-Friendly Atmosphere: An inviting space perfect for sharing meals with loved ones.

Dining here is not just about the food; it’s about support for a hardworking establishment where the staff, like the attentive Lacey, make your experience memorable. Josie's Pizza & Wings is not your typical pizza place. It's a community staple where you can feel at home while enjoying top-notch cuisine!

Desserts

Homemade Key Lime Pie

The official state pie of Florida! Sweet and grainy graham cracker crust, with a creamy, tangy lime filling.

US$12.99

Semi-Sweet Chocolate Ganache Cake

Layered chocolate cake with chocolate ganache filling topped with decadent dark chocolate frosting. Finished with semi sweet chocolate chips. A true chocolate lovers dessert!!!

US$12.99

Fresh Baked Cookies

Oven-baked gooey goodness, made fresh throughout the day. Chocolate chip flavor.

US$0.90

Tiramisu

Lady fingers soaked in espresso. Topped with whipped mascarpone cream and dusted with semi sweet cocoa. A Josie's favorite!!!

US$12.99

Creamy NY Style Cheesecake

Creamy cheesecake with graham cracker crust.

US$11.99

Kid's Pizza

Eight-inch pizza. toppings are available for an additional charge.

US$6.99

Kid's Spaghetti

With marinara.

US$9.99

Kid's Chicken Tenders With French Fries

With French fries.

US$7.99

Kids Menu

Pizza

Cheese Pizza - 10"

6 slices. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$11.99

Cheese Pizza - 17"

10 slices. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$19.99

Cheese Pizza - 14"

8 slices. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$16.99

Cheese Pizza - 12"

8 slices. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$13.99

Fountain Soda

20 ounce cup of soda: Coca Cola Diet Coke Coke Zero Sprite Minute Maid Lemonade Fanta Orange Barq's Root Beer Fuze Raspberry Tea .

US$4.75

2-Liter Soda

Cold two liter bottles of: Coca Cola, Diet Coke, Sprite.

US$6.99

Milk

US$4.75

Chocolate Milk

US$4.75

Beverages

Specialty Pizzas - 17"

17"-MetroWest Gourmet Pizza

10 slices. Roasted peppers, spinach, sun-dried tomatoes and fresh garlic. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$23.99

17"-Mediterranean Pizza

10 slices. Banana peppers, red onions, fresh tomatoes, Greek olives and Feta. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$23.99

17"-White Pizza

10 slices. Ricotta cheese blended with fresh garlic, olive oil, oregano, black pepper and Mozzarella. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$21.99

17"-Margherita Pizza

10 slices. Light tomato sauce, fresh basil, fresh sliced tomatoes, Mozzarella and Provolone, sprinkled with oregano. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$23.99

17"-BBQ Chicken Pizza

10 slices. BBQ sauce, chicken, banana peppers, mushrooms and red onions. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$25.99

17"-Vegetarian Pizza

10 slices. Onions, black olives, mushrooms, green peppers, broccoli and fresh tomatoes. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$24.99

17"-Mexican Pizza

10 slices. Ground beef, fresh tomatoes, black olives, jalapenos, Cheddar and Mozzarella. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$24.99

17"-Italiana Pizza

10 slices. Salami, sun-dried tomatoes, artichoke hearts, fresh garlic and olive oil. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$23.99

17"-Pesto Special Pizza

10 slices. Pesto sauce, fresh tomatoes, red onions and Feta cheese. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$23.99

17"-Josie's Specialty Pizza

10 slices. Sausage, green peppers, onions, black olives, pepperoni and mushrooms. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$25.99

17"-Hawaiian Pizza

10 slices. Ham and pineapple. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$21.99

17"-Rustic Mushroom Pizza

10 slices. Quartered fresh mushrooms, marinated in extra virgin olive oil, fresh garlic and Italian spices and sprinkled with shredded Parmesan. Goes great with sausage or chicken. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$24.99

17"-Meat Lover's Pizza

10 slices. Italian sausage, pepperoni, ham, ground beef and bacon. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$26.99

17"-Buffalo Pizza

10 slices. Buffalo style chicken, banana peppers, Mozzarella and Cheddar. Hand-tossed New York style, made from scratch, with the freshest ingredients. Try it with a Ranch or Blue Cheese Dressing Drizzle!

US$26.99

17"-Hot Italian Pizza

10 slices. Light tomato sauce, prosciutto, hot capicolla, fresh basil, abruzzese sausage, sweetie peppers, Provolone and Mozzarella. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$26.99

17"-3 Cheeses Pizza

10 slices. Mozzarella, Cheddar and Parmesan. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$21.99

17"-BBQ Meatball Pizza

10 slices. BBQ sauce, meatballs, banana peppers, mushrooms and red onions. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$25.99

Jalapeno Poppers

Choice of cheddar or cream cheese. Served with ranch dressing.

US$7.99

12" Garlic Bread

12 inches of our fresh bread topped with butter garlic. Served with marinara. Add cheese for additional charge.

US$7.99

Jamie's Cheese Fries

Our fresh made French fries topped with mozzarella and cheddar cheese. Goes great with bacon or jalapenos for a nominal charge.

US$9.99

Fried Ravioli

Five breaded ravioli filled with ricotta, mozzarella and parmesan cheeses. Served with marinara.

US$8.99

Meatballs With Cheese

Three of our housemade meatballs served with marinara & mozzarella cheese.

US$11.99

6" Garlic Bread

6 inches of our fresh bread topped with butter garlic. Served with marinara. Add cheese for additional charge.

US$5.99

Onion Rings

Beer battered served with our housemade chipotle mayo dip.

US$11.99

Chicken Tenders

Five breaded chicken breast tenderloins. Served with honey mustard.

US$15.99

Cheese Sticks

Breaded mozzarella cheese sticks (5). Served with marinara.

US$8.99

Fries

Our delicious French fries fried fresh and never under a heat lamp! Feeling adventurous? Try our in housemade fry seasoning.

US$7.99

Buffalo Chicken Tenders

Five breaded chicken breast tenderloins tossed in your choice of wing sauce. Served with Blue cheese and celery.

US$19.99

Bobby's Bread Sticks

Bread sticks made from our fresh dough topped with herbed butter garlic & parmesan cheese. Served with marinara.

US$7.99

Cheesy Bread

Fresh baked, made to order, soft baked pizza dough covered with fresh garlic, mozzarella and spices, served with marinara.

US$7.99

Appetizers

Pizza by the Slice

Cheese Slice

Hand-tossed New York style slices.

US$2.25

Cheese Calzone

Mozzarella, seasoned Ricotta, Parmesan served with marinara sauce on the side.

US$13.99

Specialty Calzone

Make any calzone a specialty calzone!! Served with marinara sauce on the side.

US$16.99

Calzones

Sides

Honey & Hot Wing Sauce

US$0.75

BBQ Wing Sauce

US$0.75

Medium Wing Sauce

US$0.75

Hot Wing Sauce

US$0.75

Raspberry Vinaigrette Dressing

US$0.75

Italian Dressing

US$0.75

Teriyaki Wing Sauce

US$0.75

Herbed Butter Garlic Wing Sauce

A sauce crafted with butter and garlic, enhanced with a selection of herbs, designed to accompany wings.

US$0.75

Butter Garlic Parmesan Wing Sauce

US$0.75

Greek Dressing

US$0.75

Blue Cheese Dressing

US$0.75

Balsamic Vinaigrette Dressing

US$0.75

Honey Mustard Wing Sauce

US$0.75

Mild Wing Sauce

US$0.75

Creamy Caesar Dressing

US$0.75

Citrus Chipotle BBQ Wing Sauce

US$0.75

Ranch Dressing

US$0.75

Honey Mustard Dressing

US$0.75

Oil & Vinegar Dressing

US$0.75

Florentine Stuffed Shells

Covered in our homemade meat sauce, which can be substituted with marinara sauce. Baked to mouth-watering perfection. Served with garlic bread.

US$17.99

Pasta Combo

Lasagna, and stuffed shells. Covered in our homemade meat sauce, which can be substituted with marinara sauce. Baked to mouth-watering perfection. Served with garlic bread.

US$17.99

Lasagna

Covered in our homemade meat sauce, which can be substituted with marinara sauce. Baked to mouth-watering perfection. Served with garlic bread.

US$17.99

Spaghetti

With meatballs and covered in our homemade meat sauce, which can be substituted with marinara sauce. This item is not baked. Served with garlic bread.

US$15.99

Pastas

Specialty Pizzas - 14"

14"-Pesto Special Pizza

8 slices. Pesto sauce, fresh tomatoes, red onions and Feta cheese. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$21.99

14"-Josie's Specialty Pizza

8 slices. Sausage, green peppers, onions, black olives, pepperoni and mushrooms. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$21.99

14"-Buffalo Pizza

8 slices. Buffalo style chicken, banana peppers, Mozzarella and Cheddar. Hand-tossed New York style, made from scratch, with the freshest ingredients. Try it with a Ranch or Blue Cheese Dressing Drizzle!

US$22.99

14"-Mexican Pizza

8 slices. Ground beef, fresh tomatoes, black olives, jalapenos, Cheddar and Mozzarella. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$21.99

14"-Vegetarian Pizza

8 slices. Onions, black olives, mushrooms, green peppers, broccoli and fresh tomatoes. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$21.99

14"-Meat Lover's Pizza

8 slices. Italian sausage, pepperoni, ham, ground beef and bacon. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$24.99

14"-MetroWest Gourmet Pizza

8 slices. Roasted peppers, spinach, sun-dried tomatoes and fresh garlic. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$21.99

14"-Italiana Pizza

8 slices. Salami, sun-dried tomatoes, artichoke hearts, fresh garlic and olive oil. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$21.99

14"-Hawaiian Pizza

8 slices. Ham and pineapple. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$21.99

14"-Mediterranean Pizza

8 slices. Banana peppers, red onions, fresh tomatoes, Greek olives and Feta. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$21.99

14"-BBQ Meatball Pizza

8 slices. BBQ sauce, meatballs, banana peppers, mushrooms and red onions. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$21.99

14"-BBQ Chicken Pizza

8 slices. BBQ sauce, chicken, banana peppers, mushrooms and red onions. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$21.99

14"-Hot Italian Pizza

8 slices. Light tomato sauce, prosciutto, hot capicolla, fresh basil, abruzzese sausage, sweetie peppers, Provolone and Mozzarella. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$24.99

14"-Margherita Pizza

8 slices. Light tomato sauce, fresh basil, fresh sliced tomatoes, Mozzarella and Provolone, sprinkled with oregano. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$21.99

14"-White Pizza

8 slices. Ricotta cheese blended with fresh garlic, olive oil, oregano, black pepper and Mozzarella. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$21.99

14"-Rustic Mushroom Pizza

8 slices. Quartered fresh mushrooms, marinated in extra virgin olive oil, fresh garlic and Italian spices and sprinkled with shredded Parmesan. Goes great with sausage or chicken. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$21.99

14"-3 Cheeses Pizza

8 slices. Mozzarella, Cheddar and Parmesan. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$21.99

6 Wings

Our famous deep fried made to order chicken wings come in many different flavors! Buffalo: hot, honey & hot, medium & mild (add fresh garlic to any flavor), butter garlic, butter garlic parmesan, BBQ (sweet), citrus chipotle BBQ (BBQ with a kick), teriyaki, honey mustard. Ranch or blue cheese is available for a nominal fee. Carrots or celery is available for a nominal fee.

US$10.99

20 Wings

Our famous deep fried made to order chicken wings come in many different flavors! Buffalo: hot, honey & hot, medium & mild (add fresh garlic to any flavor), butter garlic, butter garlic parmesan, BBQ (sweet), citrus chipotle BBQ (BBQ with a kick), teriyaki, honey mustard. Ranch or blue cheese is available for a nominal fee. Carrots or celery is available for a nominal fee.

US$35.99

10 Wings

Our famous deep fried made to order chicken wings come in many different flavors! Buffalo: hot, honey & hot, medium & mild (add fresh garlic to any flavor), butter garlic, butter garlic parmesan, BBQ (sweet), citrus chipotle BBQ (BBQ with a kick), teriyaki, honey mustard. Ranch or blue cheese is available for a nominal fee. Carrots or celery is available for a nominal fee.

US$17.99

Wings

Six Pack of Cold Beer, Seltzer, or Hard Ciders

Six Pack Of Rekordelig Swedish Cider

Choose from the following flavors of Rekordelig Hard Ciders: Blood Orange Mixed Berries Strawberry Lime Mango Raspberry Pear

US$20.99

Six Pack Of Corona

Cold bottles of Corona

US$16.99

Six Pack Heineken

Cold bottles of Heineken

US$15.99

Six Pack Of Michelob Ultra

Cold bottles of Michelob Ultra

US$15.99

6 Wings With French Fries

Includes a small portion of French fries, fresh celery, carrots, ranch or Blue cheese and a soft drink or tea.

US$13.99

Family Large Cheese Pizza Special

US$12.99

10" Personal Pizza

Includes 2 free (single) toppings and a soft drink.

US$9.99

6" Sub

Includes chips and a soft drink.

US$7.99

Chicken Tenders With Fries

Three chicken tenders with side of french fries, includes a soft drink..

US$10.25

2 Cheese Slices

Includes a soft drink.

US$6.99

Small Garden Salad & Garlic Bread

Includes a 6" garlic bread and a soft drink or tea.

US$9.99

Lunch Specials

Salads

Josie's Cobb Salad

Mixed romaine and iceberg lettuce with red onion, cucumber, tomatoes, black olives, and green peppers. Served with warm chopped bacon and hare boiled eggs. Choice of feta cheese, blue cheese crumbles or mozzarella cheese.

US$10.99

Greek Salad

Mixed Iceberg & Romaine lettuce, topped with banana peppers, cucumbers, tomatoes, red onions, Kalamata olives and Feta cheese. Dressing is served on the side.

US$10.99

Buffalo Chicken Salad

Josie's awesome Buffalo tenders over a bed of lettuce with green apples, topped with crumbled Blue cheese and dried cranberries. Goes great with Raspberry Vinaigrette or Blue Cheese dressing.

US$11.99

Caesar Salad

Mixed Iceberg & Romaine lettuce topped with fresh shredded parmesan cheese and croutons. Served with Creamy Caesar dressing.

US$9.99

Metrowest Salad

Mixed Romaine and Iceberg lettuce with Blue cheese crumbles, candied pecans, dried cranberries and mandarin oranges. Goes great with Raspberry Vinaigrette dressing.

US$10.99

Garden Salad

Iceberg and Romaine lettuce, tomatoes, green peppers, black olives, red onions and cucumbers. Dressing is served on the side.

US$9.99

Chef Salad

Iceberg and Romaine lettuce topped with turkey, ham, topped with mozzarella cheese, tomatoes, green peppers, black olives, red onions and cucumbers. Dressing is served on the side.

US$10.99

12"-Mexican Pizza

8 slices. Ground beef, fresh tomatoes, black olives, jalapenos, Cheddar and Mozzarella. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$18.99

12"-Hawaiian Pizza

8 slices. Ham and pineapple. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$17.99

12"-BBQ Chicken Pizza

8 slices. BBQ sauce, chicken, banana peppers, mushrooms and red onions. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$18.99

12"-Vegetarian Pizza

8 slices. Onions, black olives, mushrooms, green peppers, broccoli and fresh tomatoes. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$18.99

12"-Josie's Specialty Pizza

8 slices. Sausage, green peppers, onions, black olives, pepperoni and mushrooms. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$18.99

12"-3 Cheeses Pizza

8 slices. Mozzarella, Cheddar and Parmesan. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$17.99

12"-Italiana Pizza

8 slices. Salami, sun-dried tomatoes, artichoke hearts, fresh garlic and olive oil. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$18.99

12"-Margherita Pizza

8 slices. Light tomato sauce, fresh basil, fresh sliced tomatoes, Mozzarella and Provolone, sprinkled with oregano. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$17.99

12"-MetroWest Gourmet Pizza

8 slices. Roasted peppers, spinach, sun-dried tomatoes and fresh garlic. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$18.99

Hot Italian Pizza

8 slices. Light tomato sauce, prosciutto, hot capicolla, fresh basil, abruzzese sausage, sweetie peppers, Provolone and Mozzarella. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$22.99

Buffalo Pizza

8 slices. Buffalo style chicken, banana peppers, Mozzarella and Cheddar. Hand-tossed New York style, made from scratch, with the freshest ingredients. Try it with a Ranch or Blue Cheese Drizzle!!!!

US$21.99

12"-Meat Lover's Pizza

8 slices. Italian sausage, pepperoni, ham, ground beef and bacon. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$22.99

12"-Rustic Mushroom Pizza

8 slices. Quartered fresh mushrooms, marinated in extra virgin olive oil, fresh garlic and Italian spices and sprinkled with shredded Parmesan. Goes great with sausage or chicken. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$19.99

12"-White Pizza

8 slices. Ricotta cheese blended with fresh garlic, olive oil, oregano, black pepper and Mozzarella. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$17.99

12"-Pesto Special Pizza

8 slices. Pesto sauce, fresh tomatoes, red onions and Feta cheese. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$18.99

12"-Mediterranean Pizza

8 slices. Banana peppers, red onions, fresh tomatoes, Greek olives and Feta. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$18.99

12"-BBQ Meatball Pizza

8 slices. BBQ sauce, meatballs, banana peppers, mushrooms and red onions. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$18.99

12"-Hot Italian Pizza

8 slices. Light tomato sauce, prosciutto, hot capicolla, fresh basil, abruzzese sausage, sweetie peppers, Provolone and Mozzarella. Hand-tossed New York style, made from scratch, with the freshest ingredients.

US$22.99

12"-Buffalo Pizza

8 slices. Buffalo style chicken, banana peppers, Mozzarella and Cheddar. Hand-tossed New York style, made from scratch, with the freshest ingredients. Try it with a Ranch or Blue Cheese Drizzle!!!!

US$21.99

Specialty Pizzas - 12"

Subs

Chicken BBQ Sub

Chicken topped with BBQ sauce, red onions, mushrooms, banana peppers and Mozzarella. Served hot with side choice.

US$11.99

Ham & Cheese Sub

Ham, lettuce, tomatoes, green peppers, red onions, black olives, banana peppers, mayo, mustard, salt, pepper, vinegar and oil. Served hot with side choice.

US$11.99

Turkey & Cheese Sub

Turkey, lettuce, tomatoes, green peppers, red onions, black olives, banana peppers, mayo, mustard, salt, pepper, vinegar and oil. Served hot with side choice.

US$11.99

Chicken Caesar Sub

Chicken tenders topped with creamy Caesar, Provolone cheese, Romaine lettuce and shredded Parmesan. Served hot with side choice.

US$11.99

Spicy Italian Sub

Light tomato sauce, prosciutto, hot capicola, Abruzzese sausage, sweetie peppers, fresh basil and Provolone. Served hot with side choice.

US$11.99

Buffalo Style Chicken Sub

Choice of mild, medium or hot, served with Mozzarella, Cheddar and Parmesan. Served hot with side choice.

US$11.99

Meatball BBQ Sub

Meatballs topped with BBQ sauce, red onions, mushrooms, banana peppers and Mozzarella. Served hot with side choice.

US$11.99

Chicken Parmesan Sub

Chicken smothered in pizza sauce and Mozzarella. Served hot with side choice.

US$11.99

Meatball Parmesan Sub

Meatballs smothered in pizza sauce and Mozzarella. Served hot with side choice.

US$11.99

Metro Turkey Sub

Turkey, sliced green apples, crumbled Blue cheese, lettuce, dried cranberries and sun-dried tomato mayo. Served hot with side choice.

US$11.99

Italian Combo Sub

Ham, salami pepperoni, lettuce, tomatoes, green peppers, red onions, black olives, banana peppers, mayo, mustard, salt, pepper, vinegar and oil. Served hot with side choice.

US$11.99