“Bachelor pad” may be a common term, but bachelor pad style is a bit more complex: Every guy has different lifestyles, hobbies, and tastes—all of which can be reflected in their homes. So, while one guy’s perfect bachelor pad might be a penthouse with a killer view, another man might prefer a manse with an expansive yard and patio. Whatever your preference, there’s probably a space out there that suits it. Here are six options to start your search.
This condo building has an indoor pool, so you can keep your swimming and water skills strong through the cold winter months and be ready for boating, surfing, and beaching come summertime. Erin Mandel, @properties, 312-399-0848
Watch old classics on lazy Sundays, or invite friends over for viewings of new favorites. This home’s theater has plenty of big, comfy seats—and a serious screen—for either option. Kevin Wood, @properties, 773-472-0200
This expansive Lincoln Park home is LEED-certified—complete with geothermal HVAC, energy-saving Lutron windows and radiant floor heat, and a solar heated indoor pool, so you can relax and feel good about your energy savings at the same time. Joanne Nemerovski, Koenig Rubloff, 312-264-1100
Host mellow get-togethers or big parties in this West Town home. The basement is equipped with a full bar and wine racks perfect for any style or size gathering. Jennifer Ames, Coldwell Banker, 312-440-7525
Practice your jump shots, and challenge your buddies to some friendly (or not-so-friendly) tournaments with your very own sports court in the backyard of this historic Lakeview home. Julie Harron Real Estate Group, Barbara Steinhauser; Baird & Warner; 312-981-2303, 773-294-8984
A worldly, wine-drinking gentleman needs somewhere to store all of his wine—and the cellar in this massive home will certainly do the trick. Whether you share it with others or keep it to your bachelor self is up to you. Peter Tortorello and Eudice Fogel, Koenig Rubloff, 312-893-8136, 312-368-5342
PHOTOGRAPHY COURTESY @PROPERTIES (130 N. GARLAND); COPYRIGHT POSITIVE IMAGE (1503 N. PARK); COPYRIGHT JENNIFER AMES CHICAGO (1850 W. ERIE); COPYRIGHT VHT STUDIOS (1904 W. PATTERSON); COURTESY BERKSHIRE HATHAWAY HOMESERVICES (2015 N. CLEVELAND)