For many, the decision to move isn’t just about square footage or market trends—it’s about envisioning a future. That was exactly the case for this Chicago family, who found themselves at a crossroads between the practical need for space and the deeper pull toward planting roots.

Enjoy a photo tour of the families beautiful home. Photos by Meg Tange.

Here are a few of our favorite photos of Annie + Aaron’s forever home.

“When we first moved into our three-bedroom condo, it felt huge,” they recall. “But with two people working from home and a toddler running around, we quickly realized we needed more room—not just for work, but for life.” Beyond logistics, there was an emotional shift at play. “We wanted to truly commit to Chicago for the long haul, and for us, that meant finding a single-family home where we could put down roots and stay forever.”

But making that leap—selling one home while searching for another—came with its own challenges.

“Finding the perfect place was harder than finding a buyer,” they admit. “We had a clear list of must-haves, but every home required a compromise. Either we loved the house but not the neighborhood, or vice versa.”

Then, one day, they stepped inside the one. The charm was instant. Transom windows, mosaic tile, pocket doors—character that spoke to them in a way no modern new-build had. It was a home with history, but fully renovated for the future.

From there, the process moved fast. With their dream home secured, it was time to shift gears and list their condo. “Decluttering was a huge part of getting market-ready,” they explain. “Doing a walkthrough with Meg and her team before photos were taken was invaluable.”