Quick question: How do you know when it’s the right time to downsize your home in downtown Chicago?
The short answer: If you’re living with unused rooms, worn down by constant upkeep, or sitting on equity you haven’t tapped, it might be time to start the conversation.
Why Downsizing Matters in Chicago
I’ve worked with so many homeowners across Chicago who tell me the same thing: the home that once fit their life perfectly now feels too big, too expensive, or just too much work.
Downsizing isn’t about “giving up.” It’s about creating space — both physically and financially — for the life you want to live now.
And here in Chicago, moving into a downtown condo can feel like a complete upgrade. Imagine stepping out your door to grab coffee in Streeterville, taking a morning walk along the Lakefront Trail, or catching a show in the Theatre District — without ever worrying about shoveling snow or replacing a roof.
Here are three clear signs you might be ready to make the move.
- Empty Rooms and Unused Space
The Sign
Walk through your home with fresh eyes. How many rooms do you actually use on a daily basis?
I can’t tell you how often I meet homeowners in Lakeview or Lincoln Park who are hanging on to homes with four or five bedrooms — even though they only use one or two. Spare bedrooms turn into storage zones, dining rooms collect dust, and finished basements sit quiet year-round.
Why It Matters
Even if no one is using those rooms, you’re still paying for them: property taxes, heating and cooling, cleaning, and ongoing maintenance. All of it adds up.
Downtown Chicago Advantage
When you downsize into a condo, you’re only paying for the space you actually live in and enjoy. Plus, many downtown buildings offer amenities that feel like a lifestyle upgrade — rooftop decks, fitness centers, club rooms, even dog runs for your furry family member.
I had one client move from a single-family home in Ravenswood into a two-bedroom condo in Lakeshore East. She told me, “Anne, I don’t miss the space. I feel like I gained more — community, security, and a place where every square foot matters.”
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Home Maintenance Feels Like a Burden
The Sign
What once felt manageable now feels overwhelming. I hear it all the time: “Anne, I just don’t have the energy to keep up with this house anymore.”
Whether it’s a leaky roof, weeding the yard, or keeping up with repairs, the never-ending to-do list can start to feel heavier than the benefits of homeownership.
Why It Matters
Time spent on upkeep is time you’re not spending on the things you love — whether that’s travel, visiting family, or exploring everything Chicago has to offer.
Downtown Chicago Advantage
This is where condos truly shine. In a professionally managed building, all the heavy lifting is handled: landscaping, snow removal, exterior maintenance, even trash and recycling.
You get to lock the door and head to Navy Pier, spend a weekend in Michigan, or visit grandkids out of state without worrying what’s happening back home. That kind of freedom is priceless.
One of my Gold Coast clients said the biggest surprise was how much mental energy she regained after her move. “I don’t spend Sunday afternoons thinking about gutters or my furnace anymore. I just go downstairs, grab a latte, and enjoy the neighborhood.”
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You’re Sitting on Untapped Equity
The Sign
If you’ve owned your home for 15, 20, or 30 years, chances are it’s worth a lot more today than when you bought it. That growth in value is equity — and it’s often sitting locked inside your property.
Why It Matters
That equity can be the key to living the retirement you’ve imagined — or just making daily life easier. For many of my clients, selling a larger home and buying a smaller condo frees up hundreds of thousands of dollars in cash. That money can support travel, hobbies, healthcare, or simply peace of mind.
A Chicago Example
One couple I worked with sold their Wicker Park three-flat (where they’d raised their kids) and moved into a two-bedroom condo in the West Loop. Not only did they cut their monthly expenses in half, but the sale also gave them enough to buy a condo outright — no mortgage. They told me, “We’re finally using our money instead of sitting on it.”
Downtown Chicago Advantage
By moving into a condo, you often free up equity and lower your monthly costs (property taxes, utilities, and maintenance). You also position yourself for a lifestyle that makes more sense long-term: fewer stairs, more convenience, and a location that puts everything at your fingertips.
A Quick Self-Check
Here are three simple questions to ask yourself:
- Do I really use every room in my home?
- Am I spending more time maintaining my home than enjoying it?
- Would unlocking my equity change the way I live today?
If you said yes to any of these, it might be time to think seriously about downsizing.
Why Downtown Chicago Works So Well for Downsizers
Chicago has some of the best neighborhoods for downsizers who want convenience, community, and culture. Here’s why:
- Walkability: From the Loop to River North to Lakeshore East, you’ll find everything you need — grocery stores, coffee shops, theaters — within a few blocks.
- Healthcare Access: World-class hospitals and clinics like Northwestern Memorial and Rush are nearby.
- Security & Community: Most downtown condos offer 24/7 door staff and active resident communities, giving you peace of mind and social opportunities.
- Lifestyle Upgrades: Want to swim indoors in January? Many buildings have pools, fitness centers, or spas. Want to host a family gathering without cleaning your whole house? Many offer reservable party rooms.
What to Do Next
If downsizing has been on your mind, here’s how to get started:
- Take stock of your space. Walk through your home and notice which rooms go unused.
- Compare your costs. Look at taxes, utilities, and upkeep versus what you’d pay in a condo.
- Explore neighborhoods. Tour buildings in areas you love — maybe you’ve always dreamed of being near the Art Institute or the Riverwalk.
- Know your numbers. Get a professional market analysis to understand your home’s current value and equity.
- Make a plan. Downsizing doesn’t have to be rushed. With the right guidance, it can be a smooth, empowering transition.
Final Thought: Less Space, More Life
For so many of my clients, downsizing into a downtown Chicago condo has been the key to a simpler, freer lifestyle. It’s not about losing space — it’s about gaining time, energy, and freedom.
If you’re starting to see the signs, let’s talk. I’d love to help you explore your options and make a plan that works for your next chapter.
Sources & Further Reading
- Dell’O Investments – Top 7 Signs It’s Time to Downsize Your Home
- Farm Bureau Financial Services – Signs You Should Downsize Your Home
- HomeLight – When to Downsize Your Home
- Investopedia – Downsides of Downsizing in Retirement
- Property People LLC – 5 Benefits of Downsizing Your House in Chicago
- 55places.com – The Active Adult Guide to Downsizing Homes
