Best Areas for Downsizers

The conventional image of downsizers is that of a retired empty-nest couple cashing out of the burbs and buying a condo downtown. The difference today, say many real estate experts, is that the Loop and its environs are just one option. Farther-out nabes offer great dining and shopping, and numerous suburbs have improved their walkable amenities and doubled down on condo construction. These three neighborhoods and three suburbs represent solid investments for those seeking condos in the $350,000 to $950,000 range.

Peter Litton and Sharon Parke
After their daughter started college last year, Peter Litton and Sharon Parke, both tech professionals, traded their 100-year-old house in Old Irving Park for a 1,700-square-foot two-bedroom condo with floor-to-ceiling windows in the Loop for $905,000. It’s a block from Millennium Park. Photo: Tim Klein

In the City

Hyde Park

Median condo sale price:$175,000
Change since 2006:–15%
Change since 2015:9%

With a rejuvenated main drag and a downtown-worthy array of cultural attractions—including the Smart Museum of Art, the Logan Center for the Arts, the Promontory, and the Court Theatre—this South Side neighborhood has much to offer downsizers. “Hyde Park just keeps getting better,” says KoenigRubloff’s Susan O’Connor Davis, who notes the recent arrival of Whole Foods and Target. A steady increase in home values shows no signs of flattening. You can buy a two-bedroom luxury condo with indoor parking for as little as $420,000.

Lake View

Median condo sale price:$350,000
Change since 2006:11%
Change since 2015:3%

Home prices in neighboring Lincoln Park seem to have plateaued, but real estate agents predict that prices in burgeoning Lake View will keep appreciating. A robust number of condos in handsome older buildings—many with door staff and, of course, a lake view—are attracting buyers looking for a downtown feel but wanting more space for their money. You can find a two-bedroom prewar co-op here for less than $600,000.

A four-bedroom condo in Hyde Park
A four-bedroom condo in Hyde Park: $495,000 Photo: Matt Driscoll/Courtesy of Susan O’Connor Davis/Berkshire Hathaway KoenigRubloff Realty Group


Median condo sale price:$349,500
Change since 2006:23%
Change since 2015:1%

The Loop might seem too hot to handle—it’s the only one of our picks where sale prices have dramatically exceeded peak—but a condo in the heart of downtown remains a great investment. Experts believe the appeal will only grow, especially with Millennium Park events and new dining and drinking options such as Revival Food Hall and the Chicago Athletic Association Hotel. Inventory gets scooped up fast, and condos consistently sell above list price, but new luxury units going up on the neighborhood’s southern and western fringes may soon ease the crunch, if only temporarily.


In the Suburbs


Median condo sale price:$223,250
Change since 2006:N/A
Change since 2015:–1%

Young families have flocked to the near northern burb for its lake access, shopping and dining, proximity to the city, and vibrant, engaged community. But one of its lesser known assets is a strong inventory of affordable condos, in both modern and prewar buildings. A three-bedroom unit in an LEED-certified building with a pool and a gym goes for around $625,000.

A three-bedroom condo in Lake View
A three-bedroom condo in Lake View: $715,000 Photo: Keller Williams Luxury Realty


Median condo sale price:$258,500
Change since 2006:N/A
Change since 2015:–2%

For empty nesters who are seeking the genteel suburban vibe of the North Shore but don’t want the hassle of a huge house and yard, Glenview has a lot going for it—including the likelihood of slow and steady price appreciation, thanks in part to an excellent school district. Metra access to downtown Chicago doesn’t hurt, either, and there are plenty of local amenities, including the Glen Town Center shopping mall and several golf courses, to keep retirees busy. “I think the empty nester does really well in Glenview,” says Danielson Connors. “It’s highly walkable and easy to get to the train.” For around $500,000, you can snag a three-bedroom condo that feels more like a house—with forest views and an attached garage.


Median condo sale price:$145,380
Change since 2006:N/A
Change since 2015:5%

A revamped downtown, a forest preserve, a farmers’ market, low crime: Palatine is an ideal downsizer town. This market still has room to grow, and the median house price is roughly half that of neighboring Barrington. A 2,000-square-foot condo with a backyard (and maintenance service available to take care of it) goes for around $400,000.

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