A Renovated Townhome in Hyde Park

1168 E. 54th St.

Price: $499,000
Square feet: 2,000 (estimated)
Taxes: $5,650
Agent: Kathleen Malone, Compass

The square footage may not seem much different from that of a condo, but the three-floor setup of this townhome lets you separate living (cook while entertaining on the main floor), sleeping (retire to two bedrooms upstairs), and everything in between (turn the basement into another lounge or a place to let the kids run wild). The basement also has a room that could serve as a third bedroom or home office.

Everything feels almost brand new, too, thanks to a 2019 renovation that blew out an old wall between the kitchen and living room, gutted the kitchen and full bath, and installed new flooring. And when the weather complies, you can sip your morning coffee on the deck off the kitchen and enjoy happy hour on the balcony off the primary bedroom.

What’s Around: On a street of townhomes and apartment buildings, this place is a few blocks from Hyde Park’s commercial hub. Both Nichols Park and Hyde Park Produce Market are close by.

A Sleek Condo in a Converted Barracks

242 Leonard Wood S., Unit 211, Highland Park

Price: $449,900
Square feet: 1,577
Taxes: $11,565, plus $548 monthly HOA fee
Agent: Karen Chien-Rooney, Compass

If you are working with a half-million-dollar budget, you might be tempted to exclude the North Shore from your Zillow filter. But this two-bed, one-bath condo shows there are gems at that price among the eight-figure estates. It has a big footprint, and the 25-foot peaked ceilings make the space, which features a second-floor loft, feel even bigger. In the summer, a balcony off the kitchen gets plenty of sunshine, while in the winter you can relax by a gas fireplace in the living room. (Another cold season perk: A heated garage spot is covered by the HOA fees.)

The unit is part of the old Fort Sheridan, closed in 1993 and converted to residential and other uses. The army outpost was erected after the Haymarket riot of 1886. This unit is housed in the brick barracks that overlook the 50-acre parade ground where soldiers conducted drills in preparation for the two world wars and Desert Storm.

What’s Around: The old barracks are steps from the Fort Sheridan Forest Preserve, with its 3.65 miles of trails and views of Lake Michigan.

A Maher-Designed Mini Manse in East Garfield Park

3234 W. Washington Blvd.

Price: $485,000
Square feet: 5,832
Taxes: $5,540
Agent: Richard Lomax and Jennifer Bell, Fulton Grace

When famed Prairie school architect George Maher designed this three-story, six-bedroom greystone in 1901, it cost $80,000 — roughly $3 million today — to build. You’re getting a massive amount of space for your dollar, with one big caveat: The property is in need of some serious renovation, so you’ll end up spending a lot more than half a mil. There are a few touches from the previous owner worth keeping, among them a subway-tiled shower and well-maintained glass-mosaic and gold-enamel fireplaces.

Despite the need for work, landing this much square footage — plus a two-story coach house you could overhaul and turn into a rental — at this price point feels like hitting the jackpot, which is historically appropriate: The first owner, Patsy King, made much of his riches on fueling the popularity of policy, an illegal lottery-style game.

What’s Around: At the end of the block is Garfield Park, which stretches across 184 acres. The neighborhood is largely residential, with both single-family homes and multiunit buildings, though it is also dotted with overgrown, empty lots.

NOTE: Unless estimated, the annual tax amounts provided are for 2023.