Getting your Trinity Audio player ready...

As summer comes to an end, I thought it would be nice to explore some properties on the other side of the lake in Harbor Country and the surrounding southwest Michigan area. These design-forward residences, all roughly an hour or two from Chicago, could serve as second homes, weekend getaways, or your everyday digs. We have a vintage but updated farmhouse, along with a midcentury modern design inspired by a developer who became known as the father of California ranch homes. We also have a modernist home that is part of a low-density, architect-designed residential enclave located on a former Boy Scout camp. It includes a private 60-acre lake, fruit orchards, a lodge, a beach, and three miles of hiking trails. We also have a newer home in the popular destination of Saugatuck, as well as a 19th-century schoolhouse-turned-residence in Michigan’s wine country.

41 Camp Madron Rd., Buchanan, Michigan, $849,000

Camp Madron is a former Boy Scout campground that was transformed by Wheeler Kearns Architects in the 1980s into a private community of about 50 custom homes spread across 360 acres. The architects designed this four-bedroom, two-bathroom residence, completed in 1997, with the surrounding landscape in mind. The main living space, with a free-floating partition wall, looks like a work of art that blends seamlessly with nature. The bedrooms make you feel like you’re in a treehouse. Speaking of the outdoors, you can relax on the large outdoor deck and enjoy the views of the trees and prairie grass landscaping. There is also a seven-person hot tub and a built-in fire pit. The property comes with $282 monthly HOAs.

15752 Locke Rd., Union Pier, Michigan, $995,000

Set on a picturesque acre of land near the Red Arrow Highway, this 2,300-square-foot farmhouse with a white picket fence is a true Harbor County retreat for those seeking to get away from it all. Originally constructed around 1920, the interior has been thoughtfully updated inside and features a two-story great room on the main level, along with four bedrooms and a versatile tandem area upstairs. That flexible space could be used as an office, reading nook, or whatever you wish. I love all the places to sit back and relax, from the screened porch to the expansive outdoor deck.

841 Holland St., Saugatuck, Michigan, $1,075,000

Overlooking Goshorn Creek, not far from downtown Saugatuck, this custom-built two-bedroom, two-bathroom home was completed just three years ago. Although its asking price was recently reduced, it is still the highest per-square-foot price among the five listings. At nearly 1,700 square feet, it is also the smallest. The low-maintenance exterior features clean architectural lines, wood siding, a metal roof, and a bright orange front door. The house has a completely open layout, ideal for a family vacation home. The balcony overlooks the creek, and more outdoor living can be enjoyed in the private hot tub or at the fire pit, which appears to be an essential feature with all our properties.

3206 W Valley View Dr., Saint Joseph, Michigan, $475,000

Inspired by architect Cliff May, the father of the modern ranch, this 2,524-square-foot mid-century modern home features four bedrooms, two bathrooms, and a three-season room. The walk-out lower level includes a recreation room with a wood-burning fireplace, additional bedrooms, and a full bathroom, which could easily be turned into a guest suite. I love the bamboo overlay cabinets in the kitchen! Located just south of downtown St. Joseph, the property spans a little less than an acre and backs up to a green space and Hickory Creek. It last sold in 2018 for $322,000, so the current asking price reflects a nearly 50% increase in less than a decade.

1055 Mount Tabor Rd., Buchanan, Michigan, $989,000

Nestled among the winding roads and various wineries that make up the Southwest Michigan Wine Trail is a charming 1870s schoolhouse. Since September 2024, this 2,520-square-foot building has been converted into a two-bedroom, two-bathroom residence officially operating as a short-term rental called District 5 Schoolhouse. This property offers many possibilities, whether you want to continue its business arrangement or use it as your own private retreat. But you certainly can’t beat its history and character, as well as its prime location close to the wineries, breweries, orchards, farmers markets, and the Fernwood Botanical Garden.

Rachel Freundt is a freelance writer for Chicago magazine.