While hunting through current real estate listings, it’s always fun to come across a property that completely surprises you. These five homes are slightly deceptive at first glance. But once you go through the photos, you’ll be astounded by their interiors and other distinctive qualities. The first listing, for example, sits behind the facade of a converted horse barn in Chicago’s Old Town Triangle — and it’s not one, but two separate residential buildings on parallel lots with green space in the middle. Then there is an “old money” time capsule on Lake Shore Drive: A suburban residence with pieces of a historic church inside. The price point of the following properties might not be to everyone’s liking, but we can still enjoy looking through the photos of these five remarkable properties.

1721 N Fern Ct, Chicago, $3,750,000

On a narrow street near St. Michael’s Catholic Church is a single-family residence: an ivy-covered barn with exposed brick walls and a unique layout built in the early 20th century. There’s also an old Victorian structure, almost entirely hidden from view. Three buildings? Well, that explains the $3 million-plus price tag. According to Crain’s, the current owners pieced all the properties together through the years and rent two of them out with gross revenue of $73,000 a year. The additional structures could be used as an Airbnb or art studio. I’m guessing the old horse barn belonged to the home in the middle, but what really makes this listing shine is that amazing outdoor space.

1500 N Lake Shore Dr UNIT 10A, Chicago, $1,299,000

It’s not every day that you find a property on the open market for the first time in more than 75 years. That’s exactly what happened in 2022 when this five-bedroom, three-bathroom condo went up for sale for just under $1.3 million. It’s located inside the only Chicago work by architect Rosario Candela, best known for designing luxury New York City apartment buildings throughout the 1920s. Inside this unit you’ll find gorgeous views of the lake as well as an original floor plan with formal rooms and a vintage kitchen with built-in refrigerators and other elements. A reminder of the Prohibition days, there’s a bar concealed behind wood paneling where you can mix drinks for your friends. Part of a cooperative, the condo’s monthly $5,603 dues cover utilities, taxes, and other services.

518 Keystone Ave, River Forest, $1,475,000

Located a five-minute walk from the River Forest Metra station, this Second Empire-style home was built in 1874 by a descendent of the town’s founding family. With seven bedrooms and four full bathrooms, this single-family residence with a separate coach house in the back was featured on a housewalk last year. I attended that event and learned the home’s arched stained glass windows and bathroom partition were salvaged from an old church. Set back from the street, the villa’s original details include beautiful woodwork, pocket doors, and gas light sconces. What a great opportunity to own one of the oldest surviving houses in town.

745 W Buckingham Pl #1, $935,000

While this might look like your typical 19th century apartment building from the outside, prepare to be wowed once you step into this four-bedroom, three-bathroom condo that is spread over three floors. Located in East Lakeview, Buckingham Greenhouse is the last surviving building connected to George Wittbold, a German immigrant who became one of the city’s premiere flower sellers with nurseries, orchards, offices, and a block-long greenhouse. One of the units was occupied by a former Amlings flower store (the neighboring greenhouse was torn down in 1997 for parking when this condo conversion took place). Much of the original character remains intact from an ornate glass-and-wood boxed vestibule entry to ornate pillars and crown moldings.

217 W Eugenie St, Chicago, $1,825,000

We’re back in Old Town Triangle to share an 1870s brick-and-wood workers cottage that was completely renovated by local architects Wheeler Kearns in 2009. The three-bedroom, two-bathroom home is now an excellent combination of historic charm and sleek contemporary design. Because it’s located in the middle of a local historic district that restricts any exterior changes, the architects created “a historic ‘face’ to the street, and a contemporary interior and ‘face’ to the garden.” The wall of floor-to-ceiling glass in the rear of the house brings in a lot of natural light, making it feel bright and airy. It’s close to Lincoln Park and all that North and Wells has to offer.