There is nothing more Chicago than the classic courtyard apartment building. Popular between 1902 and 1929, thousands of these buildings are found in just about every neighborhood of the city. Coming in different shapes and sizes, the standard U-shape tends to be the most common. But Chicagoland also has numerous examples of L-shaped half courts, S-shaped modules, and multi-court structures that resemble the letter M. How did this unique building style take root in the city? A 1902 ordinance was passed to prevent the overcrowded and dangerous conditions of tenement housing that defined the 19th century. It required new multi-unit buildings to not only have windows in every room, but to take up no more than 65% of the lot. The result? Every apartment — usually no taller than three or four stories — was guaranteed light and ventilation, along with views of a shared central green space. Separate entrances also provided much needed privacy. Let’s take a look at this vernacular building type, many of which have now gone condo.

2424 W. Greenleaf Ave. No. 3, $170,000

You won’t find courtyards quite like the ones at Park Castle in West Ridge. Designed in 1925 by architect James Denson, the castle-like structure comes with turrets, battlement, crenellations, and gargoyles. Fountains with female figures grace the outdoor spaces. The sprawling double-courtyard complex turns its back to Western Avenue and instead opens up directly to Indian Boundary Park. The building originally had a moat filled with swans; the retaining walls and bridges still exist today. Inside you’ll find one of the city’s best-kept secrets: an extravagant mosaic pool with a tent ceiling that takes you right back to the Roaring Twenties. Talk about amenities! This corner unit currently for sale has been recently remodeled with a brand-new kitchen and bathroom. So you can think of this condo as medieval meets modern.

1526 E 59th St Unit 1C, $132,193

This 1,000-square-foot, one-bedroom, one-bathroom condo might be small, but its front yard is enormous. Not only does the Midway Apartment Building in Hyde Park have a beautifully landscaped courtyard, but the Midway Plaisance and Jackson Park are right across the street. It’s the perfect excuse to spend time outdoors. Built in 1924 by architect Paul Frederick Olsen, the architecture itself is a star attraction with an impressive limestone entrance gate and metalwork accents around the windows. Inside you’ll find an airy unit with east and west exposure that also has a heated sunroom that can be enjoyed year-round: Perfect for reading.

5547 S Kimbark Ave #1, $179,000

Staying in Hyde Park to share something that I didn’t think still existed in our culture of HGTV renovations: A 1923 courtyard apartment building with a historically intact first-floor unit. There is an abundance of character and charm here with the natural wood trim, vintage hardwood floors, and original windows and doors including a transom in the kitchen. South-facing windows bring in lots of light and air. And something you don’t see everyday: One of the closets has an original Murphy bed, which used to be a common feature in these kinds of apartments. It can accommodate overnight guests who can escape to the University of Chicago campus, just a few blocks away.

3133 W Palmer Blvd #1, $329,900

Not all courtyard buildings are architectural marvels with statues and manicured landscaping. Most people who have rented or bought real estate in the city probably lived in a design just like this condo located in Logan Square. Plain brick exterior with a gated entrance and simple lawn, nothing too elaborate. The 1920 building sits opposite Palmer Square, which provides nearly eight acres of additional green space and a direct connection to the historic boulevard system. The condo itself is a mix of old and new with two updated bathrooms. But the best part? Washer and dryer included in the unit!

1327 W Lunt Ave Unit 3B, $197,500

Originally constructed in 1917, this vintage Rogers Park condo building is right next to a Metra and Red Line stop, as well as a few blocks away from Loyola Beach. It has everything one would expect in a classic courtyard apartment with an interesting architectural design and attractive landscaped garden. The top-floor unit features tall ceilings, original hardwood floors and doors, a wood-burning fireplace with original mantle in the living room, and a master bedroom that opens up to a 16-foot balcony overlooking the beautiful courtyard and its central fountain.