Sunday

07-06-2025 Vol 2013

Downsizing Dream: A Chicago Woman’s Journey Through Homeownership Challenges

After a serendipitous sale of her suburban home, a woman found herself shifting her dreams to downtown Chicago, envisioning a prosperous future in a cozy two-bedroom condo.

The sale marked a new beginning, as she prepared for a fresh chapter with her meticulously arranged furniture overlooking the vibrant Chestnut Street.

However, within just over a year, her aspirations began to unravel.

In February 2020, tragedy struck when her beloved cat passed away unexpectedly at the young age of nine due to advanced kidney disease.

Shortly after, the weight of job loss settled heavily on her shoulders, marking the first time in her life she faced unemployment.

As the world braced for the onset of the coronavirus pandemic, she found herself grappling with financial uncertainty without a clear path to employment.

The situation intensified when she learned she was unexpectedly pregnant at 40, an event long thought impossible due to previous fertility treatments.

While both she and her boyfriend felt joy about this surprise, they were heartbroken just weeks later when she experienced a miscarriage, deepening her struggle with depression.

Now, without a job, a pet, or a child, she confronted the stark reality of her life.

Despite securing a favorable mortgage rate of under 3%, the financial burdens piled up, including over $11,000 annually in property taxes and an HOA fee of $550 each month for her condo.

The amicable split with her boyfriend left her fully independently navigating her turbulent life, ultimately leading to the difficult decision to downsize to regain some semblance of stability.

In the summer of 2020, she placed her condo up for sale.

Fortunately, the property sold promptly, allowing her to break even and begin anew in a quiet neighborhood in Bridgeport.

She found a small, renovated unit with about 1,000 square feet—less than half the size of her previous condo—but embraced the changed circumstances considering the reduced monthly expenses a fair trade.

However, the past five years brought continual relocations, and she remained a renter, increasingly determined to transition back into homeownership.

Yet, the landscape had shifted drastically; rising interest rates and limited inventory posed formidable barriers.

In the past 90 days, she made two offers on downtown Chicago condos, going above the asking price, only to face rejection each time in a fiercely competitive market.

Regret loomed large as she reflected on the circumstances surrounding her decision to sell, especially in light of soaring home values.

What once seemed a pragmatic choice now felt like a gamble that turned against her in the wake of tumultuous life changes.

The current estimated value of her former condo eclipsed the price she paid by a staggering $193,000, rendering her dreams of reclaiming her lost equity a distant aspiration.

As inflation soars and interest rates hover near 7%, she acknowledges the irony of her situation—unable to afford a condo similar to the one she walked away from just a few years ago.

Each day, new headlines about skyrocketing home values remind her of her missed opportunity.

Navigating the challenges of a once-booming market, she grapples with both regret and resilience, determined to find her footing once more in the world of homeownership.

image source from:businessinsider

Charlotte Hayes