Downsizing in Chicago: Finding a Home That Fits Your Life Now
When I talk with longtime Chicago homeowners about downsizing, the conversation gets interesting once we move into the details. What would you happily stop maintaining? What do you love about your current home? What would make an ordinary Tuesday a little easier?
For clients thinking about retirement or planning ahead, the answers might include having everything on one floor, being able to leave town with fewer arrangements, or walking to the lakefront and a favorite neighborhood restaurant. Those preferences give us a useful starting point for finding the right home.
Two examples from my practice show how different that process can look.
Finding the Right Fit, Down to the Details
One search involved clients returning to Chicago from Aspen. Their budget was under $900,000, and they were considering the Gold Coast, Lincoln Park, and Streeterville. They wanted lake views, access to an indoor pool, and enough space to feel comfortable.
Then came the details that made the search distinctly theirs.
They wanted a proper dressing room. Most two-bedroom apartments did not offer enough closet space, so a three-bedroom home made sense: the third bedroom could become the dressing area they actually needed.
They also preferred a traditional or partially enclosed kitchen. An open floor plan would work only if a manageable renovation could screen the kitchen from the living room.
I think those are sensible things to know about yourself before you buy. If seeing the kitchen from your sofa will bother you every day, it deserves a place on the search criteria. If generous wardrobe space makes your home work better, a third bedroom may be a practical choice.
That is why I encourage clients to describe how they use their rooms. Bedroom counts and square footage give us a starting point; the way you live helps us judge whether a particular apartment will feel comfortable.
Understanding the Ongoing Costs
The financial details need the same attention.
A purchase budget under $900,000 tells me one part of the story. I also want to understand the monthly expenses a buyer will be comfortable carrying, especially when retirement is part of the planning.
An association assessment of $5,000 a month, for example, represents $60,000 a year before property taxes or any mortgage payments. A property tax bill of $35,000 a year is another figure that deserves careful consideration. A home can fit the purchase budget and still carry ongoing expenses that make the move less appealing.
When comparing condos, I want us to understand exactly what the assessment includes. Heat, utilities, parking, door staff, and amenities all affect the comparison. An indoor pool may be something you will enjoy several times a week, or something you will help maintain without ever using. That is a personal decision worth making consciously.
I also want to look closely at the building’s reserves, planned projects, association meeting minutes, and any discussion of special assessments. A renovated apartment can be lovely, while the building around it may have substantial work ahead. Understanding both helps my clients decide how much responsibility they are comfortable taking on.
Making the Move Work for You
Another client’s plan took the conversation in a different direction: selling a large Chicago condominium and moving into a rental apartment.
He intended to use some of the equity released by the sale to help cover rent. Money previously going toward property taxes and condominium assessments would also contribute to the rental budget.
For someone who has owned a home for many years, renting deserves a fair hearing. It can offer flexibility and fewer direct maintenance responsibilities. The decision still calls for a careful comparison of sale proceeds, moving expenses, rent, and possible future increases.
I would want a client considering that route to understand how the arrangement would work over time. The appeal of simplifying is real, and the numbers should support the plan.
These examples are useful because they show how individual a move can be. One search required a third bedroom and a kitchen that could be screened from view. Another involved considering an entirely different way of living, with equity from a condo helping support a rental.
Across the Gold Coast, Lincoln Park, River North, and Streeterville, I encourage clients to pay attention to the practical details of each property. Are there steps between the sidewalk and the elevator? How far is the parking space from the apartment? Does the bathroom layout work comfortably? Is the grocery store an easy walk with bags in hand?
Those details are worth noticing while we are looking, especially if the goal is a home that will continue to work well in the years ahead.
I also encourage people to begin the conversation early. There is value in seeing different buildings, understanding their costs, and deciding which belongings and routines you want to bring with you before setting a moving date.
My role is to help you connect those decisions: what your current home might sell for, what the next home would cost to buy or rent, and how the transition could come together at a comfortable pace.
If you are considering downsizing in Chicago, I would be happy to talk through the specifics with you. Tell me what you love about your home, what you are ready to hand off, and what you would like everyday life to feel like after the move.
