The 1855 Home of a Legendary Chicago Journalist Sold in Winnetka for Almost $2 Million

The 16-room home of Henry Demarest Lloyd, a muckraking, socialist-leaning writer for the Tribune, closed at 99 percent of the asking price.

Outside the Winnetka home

Photography: Dennis Rodkin

List Price: $1,999,000
Sale Price: $1,982,000
The Property: You may not normally think of tony Winnetka as the cradle of socialists, but this 16-room home that sold last Monday has been the home of a prominent 19th-century muck-raking journalist who advocated for socialist reforms, and his son, a founder of the Communist Labor Party.

The house dates to 1855, when it was built next to a Winnetka shoreline inn, the Wayside; it was later moved twice, ending up on the inland side of what’s now Sheridan Road. In 1878, Chicago Tribune editorialist Henry Demarest Lloyd and his wife, Jessie Bross Lloyd (whose father, William Bross at the time was the Tribune’s major stockholder and publisher), bought the house, called Wayside.

Henry Lloyd, who never joined the socialist or communist parties although he once described himself as a “socialist-anachist-communist-individualist-collectivist-cooperative-aristocratic-democrat,” wrote many books and articles, including a pioneering look at the monopolistic ways of Standard Oil. Their son William Bross Lloyd was a founder of the Communist Labor Party. In 1920, he was one of 20 Communists that a Chicago criminal court found guilty of conspiring to overthrow the US government. (The New York Times story referred to him as “millionaire of Winnetka”). The Lloyd family has included pacifists and a founder of the Women’s International League for Peace and Freedom.

The streetside statue commemorating Henry Demarest Lloyd
The streetside statue commemorating Henry Demarest Lloyd

All of them lived in or passed through Wayside, which was in the Lloyd family until the 1960s. Visitors included the Tuskegee Institute’s Booker T. Washington and the feminist writer Charlotte Perkins Gilman, according to a history of the house.

Henry Lloyd is commemorated by a streetside statue on a corner of the property that depicts a huddled laborer above the inscription, “Society should give every man not his daily bread but a chance to earn his daily bread.”

An early-1980s nomination for the National Register of Historic Places said the 2/3-acre property still contained an 1896 barn outfitted as a children’s gym “with trapezes, slide, and seesaw,” and that Henry Lloyd’s writing room was intact as he had left it. I don’t know whether those two things are still true. The listing agent, Paige Dooley, did not return calls asking for comment, and I did not reach sellers Randall and Judith Larrimore. (According to the public records, they owned the house from at least 1996, but when they bought it and for how much isn’t indicated.)

The listing photos showed lots of historical details—check out the wood trim in the foyer and the various porches, covered and uncovered. Public records don’t yet indicate who bought the property.

Price Points: The house, which listing photos show was vacant at the time of the listing, went on the market April 22 and was under contract six weeks later; the deal closed July 22 at 99 percent of the asking price. That’s a much cheerier outcome than the one for another Lloyd family home in Winnetka. The endlessly quirky home of Henry and Jessie Lloyd’s ex-daughter-in-law Lola Maverick Lloyd—which I featured here and later here—sold in May after nearly six years of trying. The final sale price: $660,006, or 45.5 percent of the 2007 asking price.

Listing Agent: Paige Dooley of The Hudson Company, 847-446-9600; paige@thehusoncompany.com

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