Every city has history, but Chicago’s is richer than most, and learning about it is as easy as taking a stroll through the streets (or the real estate listings).

1407 N. Hoyne Ave., Chicago

$6.495 million

real estate: 1407 N. Hoyne Ave., Chicago

Photo courtesy of @properties.

Constructed in 1886, this brick Victorian abode on a large corner lot in Wicker Park recently underwent an extensive renovation that includes a custom kitchen outfitted in gleaming white stone by O’Brien Harris and luxe velvet-covered living room walls. And that’s all without sacrificing original details such as the “carpenter’s lace” in the beautiful turret. The icing on top is a third floor suite that includes a guest bedroom, an exercise room, and an east-facing terrace.

400 Forest Ave., Oak Park

$1.65 million

real estate: 400 Forest Ave., Oak Park

Photo courtesy of @properties.

Located smack dab in the center of the Frank Lloyd Wright Historic District, the enormous William H. Copeland House makes a grand first impression with its large veranda and geometric glass art entry. Original Arts & Crafts moldings, a brick fireplace, and a built-in cabinet with leaded glass windows reveal Wright’s influence. A one-bedroom detached coach house has the same vibe.

5026 S. Greenwood Ave., Chicago

$4.5 million

real estate: 5026 S. Greenwood Ave., Chicago

Photo courtesy of @properties.

Standing on .82 acres, the 17,000-square-foot Goodman Mansion in Chicago’s historic Kenwood neighborhood was designed by Treat & Foltz and built in 1892 by the Goodman family behind the much-heralded Chicago theatre. Undeniably spectacular, the home includes seven bedroom suites, 12 fireplaces, and a spacious ballroom. An extensive three-year renovation has resulted in restored plaster moldings, woodwork, and Jacobean ceilings and leaded glass windows. Less visible but still important, the house has all new mechanicals.

750 Hutchinson, Chicago

$3.995 million

real estate: 750 Hutchinson, Chicago

Photo courtesy of Berkshire Hathaway HomeServices KoenigRubloff.

Surrounded by lush gardens on nearly six city lots in the Hutchinson Historic District near the lake and park, this historic estate by George Maher kicks off the show with an elegant port-cochère. Inside, a large reception hall flanked by two sun rooms opens to the main living areas. The home also includes a high-end kitchen, eight wood-burning fireplaces with mahogany mantels, and glass mosaics.

269 Vine Ave., Lake Forest

$2.995 million

real estate: 269 Vine Ave., Lake Forest

Photo courtesy of EXIT Realty.

Constructed in 1905, this three-story estate is located on a beautiful street just minutes from downtown Lake Forest. Exuding historic character (think crystal chandeliers, crown moldings, and multiple fireplaces), the six-bedroom abode offers a large kitchen with teak countertops and top-of-the-line appliances, and two wine cellars. Not to mention a detached one-bedroom duplex coach house with its own fireplace and a sweet master bathroom.

480 Oak St., Winnetka

$5.195 million

real estate: 480 Oak St., Winnetka

Photo by VHT.

Designed by Chicago architect Benjamin Marshall and built in 1913, this 6,300 square foot French Regency style manse boasts an expansive multi-level patio with wide open views of Lake Michigan. Tons of windows, including a skylight over a long corridor, and a glass ceiling over the breakfast area, ensure that the elegant home is flooded with light all year round.

 

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Tate GunnersonTate Gunnerson is a Chicago-based freelance journalist with an equal appreciation for natural beauty and good design. He is a passionate supporter of St. Jude Children’s Research Hospital and the National Kidney Foundation.