Winston's Cafe
1412 Greenbrier Pkwy #133, Chesapeake
(757) 420-1751
Customers' Favorites
Cranberry Walnut Chicken Salad
Winston’S Jumbo Wings
French Dip Sandwich
Winston’S Burger
Winston’S Nachos
French Onion Soup
Chicken Parmesan
Chicken Tenders
Steamed Shrimp
Caesar Salad
Menu
Photos
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Recent Reviews
Winston's Cafe is located in the Crossways Shopping Center in Chesapeake. It is near the intersection with Greenbrier Pkwy and Eden Way N. It's in the same group of buildings such as Michael's (around the corner). My visit here was on October 27, 2025.\n\nThe outside view of the business is simple, but effective. They have a specials chalkboard next to the entrance. Parking wasn't an issue on this visit, but I'm sure it can fill up at busier times. My...
We stopped by today for the famous reuben sandwich. It was delicious and the coleslaw was a pleasant surprise. It was some of the best I've had. We even ordered a second bowl. We will definitely be back. Mike was a great server.
I do enjoy and recommend Winston’s, but would like to also give a shout out to our waitress and cook working 10/18/25 around 11:30, and also a concern to one gentleman who showed up for work around then as well.
I wish I had names, especially for the amazing waitress who served us (she was blond, I know that!). I came in with my daughter and elderly father who has dementia. Dad wanted an egg sandwich. We had already driven by some of the usual breakfast spots and naturally...
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