Chicago Condo Regret: $193K Profit Lost

After seven months on the marketmy once-perfect suburban home had a new family.

I pictured them filled with hope, just as I had been. With the moving truck loaded, I burned sage in every corner of the empty house, wishing them the fortune I’d missed with my ex and his three kids.

That same day, in the fall of 2018, I headed to downtown Chicago to unload in my new condo.

I planned to build a new life for decades to come in an idyllic two-bedroom, two-bathroom walk-up on the tree-lined street.

I perched my desk in the bay window, overlooking Chestnut Street, adjacent to the perfect bookshelf with floor-to-ceiling storage space and an attached ladder.

I couldn’t imagine anything would ever take me away.

A series of unlucky events pulled me away

Then, 16 months later, in February of 2020, my cat died unexpectedly at only 9 years old from advanced kidney disease. Two weeks later, I was laid off from my job for the first time in my life.

In another few weeks, suddenly the world was talking about the coronavirusand I was stuck with a mortgage without promising prospects of a new job.

Further complicating my life, my boyfriend and I accidentally got pregnant. I was 40 years old and had been told during decades of fertility treatments with both of my ex-husbands that I didn’t ovulate and would never get pregnant.

Despite the surprise, we were elated at the prospect of welcoming a healthy baby into the world. So, when I lost the pregnancy eight weeks later, I fell into a deep depression.

I had no job, no pet, no baby.

Even though I enjoyed a sub-3% mortgage and had bought at a good price, I was paying over $11,000 annually in property taxes on top of my mortgage and a monthly HOA of $550 for a building with very few amenities.

My boyfriend and I amicably split, so I was on my own. I ultimately decided I needed to downsize so I could pause and figure out what to do next in life.

I rented a place in Bridgeport

I listed the unit in the summer of 2020. It sold quickly, and I happily broke even on the sale.

I moved to a new neighborhood on the south side of Chicago, Bridgeport, renting a small but renovated unit with 1,000 square feet.

Although my square footage was cut in half compared to my condo, so were my monthly expenses, so I figured it was a fair trade.

I’ve moved a couple of times over the last five years and have continued to rent. I’m ready to buy again, but it’s become significantly harder with higher interest rates and sparse inventory in Chicago.

I’ve made two offers on condos in downtown Chicago in the past 90 days, both over asking price, and was outbid. I am full of regrets for leaving my condo and having no home equity.

Now, with inflation and interest rates hovering near 7%, I couldn’t even afford the same condo I left if I wanted to. The current estimated value is $193,000 more than I paid for it in 2018.

I gambled and lost

Every time I see headlines about soaring home values, I can’t help but think about the equity I willingly walked away from.

My decision to sell under duress during a turbulent time in my life has locked me out of a booming market.

I often wonder what life would be like if I held onto that beautiful Chestnut Street condo, enjoying the security of a fixed-rate mortgage and the appreciation of a valuable asset.

Instead, I’m now navigating a competitive market with dwindling hope, trying to reclaim a piece of the stability I let slip away.