ASK ANTHONY: Don’t “empty nest,” Re-nest!

Things I am considering as I downsize from a home to a condo

Spring has finally arrived here in Chicago, and I am happy to say that I am halfway finished with a major move… my personal version of a good spring cleaning! For years I have had far too much square footage and far too many things. I have long enjoyed the pleasures that a freestanding home provides, but lately I have had other interests occupying my time (like renovating a really big boat) and I decided that it might be time to free myself of some lifelong clutter and downsize to a condo lifestyle.

While I will admit there have been some strong emotions involved in saying goodbye to many of my favorite possessions and closing the door on this chapter, I will also admit that there is a great sense of fun and excitement in being my very own interior design client for the first time in years!

“There’s an axiom among some real estate agents that when it snows in March, it’s time to call ‘gently’ graying past clients and suggest that now is the time to buy a condominium.”


Condo living, or more broadly, downsizing and trading a single-family home for community living, is increasingly becoming an attractive option to baby boomers. With the kids out of the five-bedroom house with the sprawling lawn, many empty nesters admit they’re left with too much space and the home maintenance, aka ‘honey-do’ tasks that come with a big house.

Downsizing to a condo eliminates responsibilities like grass cutting, garden tending and snow shoveling, but there are trade-offs for the benefits. Most community associations require homeowners pay a monthly maintenance fee, which covers the preservation of those common area services—beyond lawns and roads, services like a doorman, the building elevators, a gym or a pool. The maintenance fee can be intimidating to prospective buyers in addition to the specter of the occasional assessment. Assessments require owners to pony up additional money for special projects. On average however, condo association fees are less when compared to the costs of homeownership.


Here are some due diligence tips if you’re considering down-sizing to a condo:

  • Review the association financials. They are arduous, but they showcase the financial health of a community. Make sure there is no pending litigation and that there is an ample reserve fund. A well-funded HOA sees neither special assessments nor frequent maintenances fee increase.
  • Read the last two years’ minutes. Find out what the residents have been talking or complaining about. You’ll see the issues, if any, and know whether you want to be part of a particular community.
  • Familiarize yourself with the association bylaws and the rules and regulations. This lets you know what you’re buying into. There’s nothing worse than being attached to your golden retriever and the condo bylaws limit dogs to 40 pounds or forbid pets.
  • Ask to see the community newsletter if a larger building – say 40 or more units. If there isn’t one, ask why. Community communication and transparency are absolutely essential. Homeowners whose boards don’t tell them what’s going on are unhappy, associations that have a newsletter seem to have the least amount of controversy.


Downsizing can be a big adjustment, especially for those who are “empty nesters” or recently widowed. While I am neither, I am seizing this opportunity as a “re-nester” and enjoying the creative process of fitting a selection of my favorite things from a 3600 sq.ft home, into a 1600 sq. ft. condo.

I am using an online auction service to assist in the packaging and sale of much of my furniture and 40+ years of collecting objects, aka clutter. This entire process has changed my focus, and given me energy towards this new urban lifestyle with all of its added amenities. While my dog Lola may not be as thrilled about the elevator ride when she wants to go outside, I am looking forward to some fun and sun while lounging by my new rooftop pool.

The latest trend is to go big by going small… and in my case going bold – just finished painting the entry foyer in big white and black horizontal stripes. Love the new look!


Live Brilliantly
Stay Positive
Be Happy,
Anthony Michael