Streeterville real estate offers the lifestyle that most people envision when they think about moving into luxury Chicago condos. The great shopping, dining and nightlife of the location coupled with the luxurious real estate of Streeterville and the nearby areas make it a desirable and distinctly Chicago place to live. The famous neighborhood has an interesting history along with its current cachet. Here are some of our favorite quirky facts about the famous Chicago neighborhood.
The Streeterville Real Estate Story: How the Neighborhood Got Its Start
Until you take an architectural tour of the city, you might never know the story behind the name Streeterville– but it’s one you don’t want to miss. The lakefront Near North Side neighborhood started as nothing but a sandbar and a landfill, and yet now it is some of the most sought after real estate in the country.

In the late 1880s, George “Cap” Streeter and his wife parked their houseboat on the sandbar, which had formed naturally from silt accumulation but hadn’t yet been put to use. Formerly, Streeter had been a lumberjack, a Civil War soldier and a circus performer, but along with his second wife, he decided to try to find his fortune in gunrunning. So he bought a boat and planned to take it Honduras to sell guns illegally. However, when taking a test-drive on the waters of Lake Michigan, Streeter and his wife stopped on the sandbar on the coastline of Chicago.
The couple claimed they had been shipwrecked there during a storm. They lived in the “marooned” boat and proclaimed the entire sandbar as their own land, creating what technically could be called the first Streeterville real estate!
Streeterville Real Estate: From Sandbar to Shantytown
Until this point in time, the Lake Michigan coastline was as far west as current day Michigan Avenue and was where many of Chicago’s elite had their lakeside mansions. The “shipwrecked” couple, upon establishing themselves on the sandbar east of the Gold Coast, started allowing construction companies to use the island as a place to dump construction materials.
By underselling legal dumps, Streeter quickly became prosperous, and his island began to grow. Garbage and leftover construction materials from the new skyscrapers being built in the city were dumped on the shoreline and built up the area where Lake Shore Drive now runs. Suddenly, Streeter had real estate that he could actually sell. He began selling lots on the island, and soon enough, an entire community of squatters lived in the area.
Streeter, of course, knew exactly what he was doing and was a criminal of the highest degree. He claimed the valuable lakefront land as his own and dubbed himself the mayor of the newly created District of Lake Michigan. He harbored criminals, sold prohibited liquor and ran brothels from that claimed tract of land. It wasn’t long before the wealthy Gold Coast dwellers became furious with these squatters obscuring their view of the Lake and sullying the cachet of their neighborhood. Plus, they realized a thoroughfare on the new tract of land would be beneficial for the city. They enlisted the police of Chicago to evict the squatters and Streeter.
When the city tried to evict Streeter, he waged epic gun battles against them. His second wife poured boiling water over cops to keep her husband from being arrested, and his third wife went after cops with a meat cleaver. For years, Streeter would be arrested and then released — the mayor of Chicago even pardoned him after he was convicted of murder, saying that he had been framed.
Finally, Streeter was arrested in 1918 for selling alcohol without a license and assaulting an officer. The squatters were ousted from his shantytown, and the land was returned to the city to be developed into Lakeshore Drive and the surrounding neighborhood. As the years passed, this lakefront land became some of the most valuable property in Chicago. Despite its literally and figuratively trashy origins, Streeterville real estate is now the height of luxury in Chicago– and George Streeter at least maintains his legacy in the name of the neighborhood.
Tags: george streeter, lake shore drive, luxury Chicago condos, streeterville history, streeterville real estate



