While it is nice (if you can afford it) to have reliable passive income, it is also important to remember that maintenance and long periods of vacancy can possibly limit profitability. Our first property is located in a popular tourist destination, on Forest Avenue in the Frank Lloyd Wright Historic District in Oak Park, which attracts visitors from all over the world. So it makes sense that this historic home has a separate Airbnb-style rental unit on its lower level. We also pay a visit to Harbor Country in Michigan to explore what’s on the market, along with some other options in Chicago and Evanston.
204 Forest Ave, Oak Park, $800,000
According to the AIA Guide to Chicago, the Queen Anne-style Emerson Ingalls Row Houses were designed by local architect William J. Van Keuren in 1891-92. Located directly across from Austin Gardens, the nearly 3,200-square-foot residence, featuring seven bedrooms and four full bathrooms, was last listed for sale exactly 13 years ago when it was bought by only its third owner. There are some cool details here: exposed brick walls, an original wooden staircase, a built-in bench, original pocket doors, and a midcentury modern kitchen with Sears cabinets and Formica counters. The lower level, with its own private entrance, has operated as a successful Airbnb, generating over $30,000 annually, but could easily become an in-law suite or nanny’s quarters.
16153 Krob Rd, Union Pier, MI, $429,000
Known as Krob Cottage, this two-bedroom, one-bathroom home, spanning just over 1,000 square feet, has been successfully used as a vacation rental in the popular getaway destination of southwest Michigan. There is a lot to love about this property, not least its close proximity to Union Pier’s Town Line Beach. The three-season screened porch and patio overlook mature, lush landscaping that includes a koi pond and a fire pit. The large barn currently serves as a perfect hangout and storage space, but could potentially be converted into a guest house.
2108 Harrison St, Evanston, $1,399,000
In North Evanston, near the shops, eateries, and train station on Central Street, there is an almost 3,000-square-foot, three-bedroom residence currently on the market. It has been owned by the same family for multiple generations. The property also includes a rear coach house. This separate 1,824-square-foot residential space features two beds and two full baths, making it ideal for visiting guests, an office/studio, or generating rental income. The main house has been updated and includes a full basement and partially finished attic. This is our priciest property, but its value truly comes down to it being multi-family, and, of course, location.
6431 N Paulina St, Chicago, $925,000
Located on an extra-deep lot near Clark and Devon in Chicago’s Rogers Park, this 4,641-square-foot, five-bedroom residence comes with three levels of fully finished living spaces. The property has been renovated inside and out since it last sold two years ago for $576,300 (yes, the current asking price is a 50% increase). It features a trendy black facade and an open-concept interior with brand-new flooring. But what caught my attention is its lower level, which includes two additional bedrooms (three are upstairs), a full bath, a powder room, a large living space, and a designated space ready to become a kitchenette. With its private rear entrance, this space would be perfect to use as a short-term rental.
7 E Beech St, Three Oaks, MI, $620,000
Returning to Michigan to share an updated 1880s cottage nestled in the charming small town of Three Oaks. This 1,444-square-foot, three-bedroom home is an excellent option for individuals who want to be able to walk to nearby restaurants and shops while remaining close to the lakeshore. Since the property last sold six years ago for $85,5000 (that’s quite a jump in asking price), its transformation included a gourmet kitchen and a primary bedroom with an ensuite bathroom and walk-in rainfall shower. One can enjoy the outdoors from the covered front porch, the 750-square-foot back deck, or the backyard fire pit.