A rare five-lot parcel on Halsted Street in the heart of Boystown is listed for an eye-watering $7.5 million — a figure almost certainly aimed at builders who see a redevelopment opportunity in the site. Among the establishments on the strip is legendary Boystown gay bar Little Jim’s Tavern.

The listing could signal yet another dramatic change for the eastern edge of Lake View, which has undergone a rapid transformation in the post-recession development boom.

Despite housing Little Jim’s and its neighboring bar, Big Jim’s, the property, which spans 3501 to 3519 North Halsted Street and listed on April 29, is being marketed as vacant land.

One of Chicago’s oldest gay bars, Little Jim’s originally opened in 1975, according to a 2014 report by the Windy City Times. Should the tavern shutter, it would be the latest in a string of neighborhood institutions to do so, including Spin Nightclub and Gay Mart in 2014, Halsted’s Bar & Grill in 2016, and Hollywood Mirror earlier this year.

Compass real estate agent Elizabeth Pyle declined to comment on the listing. Records show that the property is owned by Sherwood Investments and Trust Company in Philadelphia. Proprietor Tom Sherwood did not immediately return a request for comment, but a member of his staff did confirm the company’s ownership of the Halsted Street property. Jeff Shand, general manager of Little Jim’s, could not be immediately reached.

Should the property sell for a price tag in the millions, there’s reason to believe it could go the way of the Heartland Cafe in Rogers Park, which was demolished in April to make way for a six-story apartment development. But Tressa Feher, chief of staff for 46th Ward Alderman James Cappleman, says that any proposed zoning changes would go in front of residents before a decision is made.

“We have not been approached by anyone for this site,” Feher said. “If there’s a request for a zoning change, we take that request to the local community group, and if it’s a project that’s over $10 million, then that would go to our 46th Ward development and zoning committee.”

That committee, Feher added, comprises 40 different community groups, including the East Lake View Neighbors.

But Michael Zink, that community group’s president, said the site falls just outside of their jurisdiction, illustrating its complex location on the border of the 44th and 46th Wards.

In addition to their cultural value, the buildings also feature ornamental terracotta inlays, posing a question of historic preservation. Feher said that any conversation about redevelopment would take this into consideration; she highlighted recent preservation-minded developments in the area, including Sarah’s Circle women’s center on Sheridan Road and a new residential building at 3817 North Broadway, which restored and reused an ornamental facade with terracotta eagles.

“In our ward, we have a lot of landmarked and protected buildings, and that’s a huge part of what we do,” Feher said. “Even if the building itself is not eligible according to city rules, we try to work with the community to [repurpose them].”

Described as a “once in a lifetime opportunity” in its listing, the five-lot property could be a boon for a developer as much as it is a sign of the changing landscape in Boystown and East Lakeview.

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