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Kenilworth Shores 

A neighborhood located in the southeast part of Winter Park. It's mostly middle-class, but compared to the lakeside estates and other rich-people neighborhoods in town? This place is a fucking slum.
Kenilworth is fine, but there's just less than nothing to do around here.
Kenilworth Shores by KRHimself October 3, 2004

Kenilworth 

Kenilworth is a very wealthy white christian suburb located along Lake Michigan in the north shore of Chicago. The residents have more money than they know what to do with. Most own multiple homes and a boat. Their children attend New Trier High School, one of the top three best high schools in Illinois. Not to mention one of the filthiest rich schools in the country, due to the fact they enroll over 4,000. For a reference to the outsiders, Kenilworth is the Greenwich or Orange County of the Midwest.
Girl: Hey come to Kenilworth for my party Friday on my yatch. We'll pregame on my beach.
Guy: Yeah for sure. You bring a case. I'll bring the bong.
Kenilworth by John Hagan October 15, 2006

Kenilworth 

a small town on the North Shore of Lake Michigan. It is only 1 km in size and is made up entirely of houses (except a beach, church, and school) Kenilworth is know though out the country as the orange county of the mid west. Being from Kenilworth I can say it is not true. First yes there are big house, HUGE houses even, but the lot they sit on can barely hold them and they are a regular lot size. Not some over sized jumbo, I cant even see the neighbors house size! There are only a handful of families that are the real rich bitches that everyone thinks reside in Kenilworth. A lot of them are just families looking for the nicest neighborhood that fits their lifestyle. I live in Kenilworth and I am going to have to buy my own car AND pay for the insurance. Most kids ANYWHERE get help with that! The kids of Kenilworth can be another story. Most of them can be real pieces of shit, but they are not all the pop-collared driving big fancy car kids. Some are just like everyone else cause there parents dont want them to be rich little bitches! And if we were all like that we would all be sent off to those boarding schools out east for $50,000 a year. so stop all the bitching about how Kenilworth kids are so damn arrogant and rich. Come talk to me. My dad is a god damn wine merchant! You think that pays well? please!!
I live in Kenilworth, the Average income is $800,000 a year!
Kenilworth by Mark Mesrobian September 14, 2007

kenilworth 

a small rich-ass town in northern chicago.
that brat from kenilworth is so fucking rich

Kenilworth 

An extremely wealthy suburb of Chicago that spans around 1km in total with a private beach along the coast of Lake Michigan. It is one of the top ten safest neighborhoods in America due to its many police offers for such a small area. People who live in Kenilworth are generally white and christian, although there has been some more variety lately. The town is filthy rich, with most residents owning houses over 5million. Children who live here can be seen as spoiled and their lives closely resemble those of famous celebrities living in LA, such as the Kardashians. Kenilworth is a part of the North Shore and most students attend New Trier High School.
Bob: Hey, is she from Kenilworth?
Joe: Haha, yes! I almost got lost in her house.
Kenilworth by Christina Ryan's January 17, 2017

Kenilworth Guys 

They're scared of girls and just get high with each other and then they have an orgy. They smoke their dads cuban cigars.
"Are the Kenilworth Guys coming to the party?"
"No, they're too busy smoking weed and fingering each other."
"What could I expect?"
Kenilworth Guys by hunwilbah August 28, 2017