Restaurants in Winchester

Best Restaurants in Winchester

Karma in Winchester 16 Thompson St, Winchester Asian Fusion • $$$$

Customers` Favorites

Amazing
Sashimi
Salmon on Fire
GF Hamachi w Banana Pepper 2
GF Lemon Basil Salmon Maki
Salmon Avocado Maki
Spicy Yellowtail
Duck Bao Buns 2

“We love this style of Asian fusion cuisine so we came by for dinner and were not disappointed. Staff are helpful, attentive, and super friendly. The cocktails are great, and the food was incredible. It's a higher end spot in a wealthy area so you have to expect costs to reflect that.”

4.9 Superb58 Reviews
Playa Bowls 600 Main St, Winchester Health Food • $

Customers` Favorites

Nutella
Coconut
Vegan
Pura Vida
Stupid Cupid
Coco Bowl
Peanut Butter Banana Smoothie
Acai Energy Mermaid Fuel
Playa Bowls Fruit Tray
Blueberry Strawberry

“Andres makes the best bowls! And their customer service is amazing!!”

4.7 Superb117 Reviews
A Tavola Restaurant 34 Church St, Winchester Italian • $$$

Customers` Favorites

Burrata
Ravioli
Ragu Bolognese
Gnocchi
Salted Caramel Gelato
Antipasto
Octopus
Chocolate Chip Cookies
Sticky Toffee Pudding
Spaghetti Carbonara

“Superb restaurant, one of my Top Three Favorites.”

4.4 Superb37 Reviews
D'Agostino's Delicatessen 11 Waterfield Rd, Winchester Sandwich Shop • $

Customers` Favorites

Meatball
Italian
Chicken Parm Sub
Chicken Cutlet
Pastrami
Turkey & Cheese

“I called last minute due to a family death. I needed multiple food platters and D'Agostino was all too happy to help out even with such short notice. I called at 9 AM and the food was ready for pick up at 11:30. It was all delicious and nicely presented. Thank you, D'Agostino's in Winchester for coming to the rescue!”

4.5 Superb39 Reviews
Eleni's Mediterranean Grille 599 Main St, Winchester Mediterranean • $

Customers` Favorites

Greek Salad
Wrap
Lamb Shish Kebab
Roasted Potatoes
Rice Pudding
Mixed Grill
Kabobs
Chicken Shish Kebab
Or Meatballs
Gyro Plate

“Some of the best Greek food I have ever had in all of Massachusetts! Would gladly return 😇🇬🇷”

4.4 Superb42 Reviews

Customers` Favorites

Greek Salad
Grilled Chicken Salad
Meat Lovers
Grilled Chicken with Rice Pilaf and Broccoli
Large Meatball Grinder
Chicken Broccoli Ziti
Cheese Steak Pizza
Cheese Pizza
Meatball Sub
Greek Pizza

“If you’re in Winchester, MA, you must check out this hidden gem! From the moment you walk in, you know you’re in for something special. The atmosphere is welcoming, and the staff is friendly and attentive — but it’s the food that really steals the show.

The pizza here is absolutely fantastic. The crust is perfectly crispy, the sauce has just the right balance of tangy and savory, and the toppings are fresh and generous. But what truly makes this place stand out is the Greek twist on everything. Whether you’re enjoying a classic Greek salad or one of their specialty pies (pizzas), the flavors are unique and mouthwatering.

The grilled chicken is another standout — it’s tender, juicy, and seasoned to perfection. I’ve also had the pasta dishes, and they’re just as amazing. Rich, flavorful, and cooked to perfection. Every bite feels like a little piece of Greece in every dish.

From the pizza to the pasta to the grilled chicken, every meal here is bursting with flavor and made with high-quality ingredients. If you’re craving Greek-inspired pizza or just want a meal that’s both delicious and satisfying, this is the place to go in Winchester. Highly recommend it to anyone who loves great food!

Dietary restrictions: I know they offer gluten free pizza”

4.3 Superb53 Reviews

Customers` Favorites

Calamari
Cannoli
Chicken Marsala
Lasagna
Chicken Cutlet Parmigiana
Handmade Italian Pasta
Veal Cutlet Parmigiana
Shrimp Appetizer
Pollo Parmigiana
Parmesan Cheese

“Nice place for a celebration! Great food and customer service!!”

4.2 Good126 Reviews
Bagels N Brew 748 Main St, Winchester Cafe • $

Customers` Favorites

Bagels
Iced Latte
Lox Scallion Bacon Cream Cheese Red Onion Capers on a Toasted Poppy Seed Bagel
Bacon Egg & Cheese
Bacon & Cheese
Prime

“Their customer service, bagels, coffee, muffins… all top notch!! Will be back soon!!”

4.2 Good35 Reviews
Swanton Street Diner 72 Swanton St, Winchester Diner • $

Customers` Favorites

Steak
Home Fries
Lobster Eggs Benedict
French Toast
Sausage
The Contractor's Breakfast
Breakfast Sandwich
Lobster Benedict
Steak & Eggs
Side Salad

“Just had Swanton Street Diner's food (via GrubHub). for the first time. Delicious, huge quantities, all top Notch ingredients.and prices that remind me of the good old days before the pandemic. My Wife LOVED the chicken stir fry and she is picky about food I was impressed by my contractor's breakfast. Best home fries I've had in twenty years. looking forward to working our way through your menu one item at a time. Five***** stars”

4.1 Good55 Reviews
Black Horse Tavern 32 Waterfield Rd, Winchester Bar • $$

Customers` Favorites

Burger
Sandwich
Tips
Eggplant Fries
Chicken Wings
Onion Rings
Turkey Avocado and Cheese
Cheeseburger and Fries
Mozzarella Sticks
Fried Mozzarella

“Good food, atmospheric; good selection of seasonal beers/ales. Can get very busy during peak dining hours.”

3.9 Good64 Reviews

Customers` Favorites

Buffalo Chicken Pizza
Steak Bomb

“We always get the salads with chicken. They are always good. They are a little dry without extra dressing so ask for extra. People that work there are very friendly and accommodating.”

3.8 Good18 Reviews
Nourish Your Soul 15 Thompson St #2903, Winchester Juice • $

Customers` Favorites

Muffin of Day
Acai Berry

“Unbelievably delicious! From the juices to the smoothies and the milks...nothing has been a disappointment. My absolute favorites are the Lavender Charcoal Lemonade, PPM & Cashew Milk. Everything is so fresh and my body begs for more :)”

3.6 Good8 Reviews
Gloria's Pizzeria & Grill 920 Main St, Winchester Italian • $

Customers` Favorites

Steak Tip
Cheese Pizza
French Fries and Onion Rings
Stuffed Shells Pasta Dinner
Veggie Calzone Sans Cheese
Buffalo Chicken Pizza
Chicken Caesar
Cheese Slice
Veggie Pizza

“Good pizza and great service. The people who work here are very nice and really go the extra mile to make sure you know that they appreciate your business. There is nothing wrong with the 'atmosphere' but it is really the people working here that have me coming back for more.

Vegetarian options: It's as vegetarian as you would expect a pizza restaurant to be....if you don't want to eat meat, just don't order it on your pizza.

Dietary restrictions: The staff can tell you whatever you need to know.

Wheelchair accessibility: Wheelchair ramp at the entrance.”

3.8 Good40 Reviews
China Sky 27 Converse Pl, Winchester Chinese • $$

Customers` Favorites

Sushi
Hot and Sour Soup
A01 Vegetable Spring Rolls 2
Tangerine Chicken Hunan
General TSO's Chicken
Boneless Ribs
Sesame Shrimp
Dumplings

“Fresh food with good portions. Enjoyed a quiet lunch.”

3.8 Good44 Reviews
First House Pub 528 Main St, Winchester Pubs • $$

Customers` Favorites

Wings
Potato Salad
Gloucester Reuben
Tater Tots
Steak
Bacon Cheeseburger and Fries
3 Pulled Pork Sliders
Baked Potatoes
Oreo Cheesecake
French Fries

“Great drinks! Relaxing atmosphere!”

3.7 Good42 Reviews

More Restaurants in Winchester

Customers` Favorites

Baguette
Croissant and Chocolate Croissant
Assorted Bread
Rye Bread
Ciabatta

“We went for the first time today and were not disappointed! We had the brioche roll, baguette and a croissant and they were all PERFECT. Soft, buttery and delicious. The owner was so kind and friendly too! My fiancé and I will be going every Sunday as a new tradition now!”

4.8 Superb64 Reviews

Customers` Favorites

Blueberry
Strawberry Shortcake Muffin
Gingerbread Men and Women
Chocolate Chip Cookie
Banana Cream Muffins
Gingerbread People
Carrot Cake Muffin
Gingerbread Girl
Lemon Poppy Seed
Chocolate Dreme

“I’ve loved this place since I was a little girl and the recipe has been the same, from what I can tell, this whole time. Their sugar cookies are the best in the world I’ve NEVER tried sugar cookies that measure up. However I have one suggestion! Please stop using the heavily dyed sugar Crystal sprinkles on top of the sugar cookies. Not because I’m anti dye or anything; it’s because it stains really badly. And the stain lasts forever on my lips. I’ve essentially had to take a Brillo pad to my lips so I don’t walk out of the house looking like I’m wearing green lipstick!! Don’t get me wrong I love the crunch of the sugar crystals on top- I just wish there was a clear non dyed option so I can enjoy these cookies without looking funny afterwards lol.”

4.3 Superb74 Reviews

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