Across the city I am seeing a clear strategy from many owners and listing agents: pricing slightly below what we believe to be fair market value to spark interest, drive showings, and encourage multiple offers. This is a tactic that has long been popular on the coasts, especially in California, and it has now become more common in Chicago as well.

Even in this fast paced environment, it is important not to lose sight of true value. Offering significantly over list price can sometimes make sense, but it can also turn into a stretch that does not align with your long term goals. This is where having a trusted realtor in your corner really matters. My job is to walk you through the numbers, show you the comps, outline different offer strategies, and help you decide when it is worth leaning in and when it is wiser to step back.

What are homes actually closing at?- Example time!

To make this feel more real, let us look at an example in Roscoe Village.

A recent condo sale in Roscoe Village was listed in March for $515,000. It is a solid second floor condo in a brick building built in 1997 with a low monthly HOA of $125. The location is excellent, just a few blocks from the L and close to the restaurants and boutiques that make Roscoe Village so charming. The seller purchased this condo in April of 2022 for $465,000.

From the listing photos and details, it does not appear there were significant updates between the 2022 purchase and the 2026 sale. I was not the listing broker on either transaction, but this example is helpful for illustrating what is happening in the market. Based on my experience and recent comparable sales, I would peg the fair value of this condo around $540,000. The sellers chose to list at $515,000 to build momentum and increase foot traffic. The strategy worked. The unit ultimately closed at $615,000. ($150k return on investment in 4 years, not bad for the seller right?!) 

Do I believe the “value” of this condo is $615,000 today? If an appraiser were sent out tomorrow, I would expect them to land closer to $565,000 in the current market. A little more than what I said was fair market value because appraisers are basing value on a wider radius vs next door comparables. So the buyer effectively paid a premium of around $50,000 to secure a home they really wanted in a neighborhood with strong demand and a history of appreciation.

Is that smart? That depends on your budget, your time horizon, and how much you value living in that specific pocket of Roscoe Village. If the new owners hold the property for the next five years, there is a real possibility that appreciation catches up, but as always, the market and time will tell.

Let us take the example one step further and compare it to the rental market. A nearby rental recently leased for about $4,000 per month. It has similar square footage and upgrades and is in the same general area.

Now let us look at what a mortgage payment might be on the condo sale at $615,000. Using my mortgage calculator on my website, and assuming for illustration that the buyers put 20 percent down, their estimated monthly payment for principal, interest, taxes, and insurance would land around $3,714.28 for a two bedroom, two bathroom, roughly 1,400 square foot home in Roscoe Village.

I do not know the exact details of the winning offer, but this gives you a sense of how buyers are thinking and what the trade offs look like. The key takeaway is that recent closed sales, not just eye catching list prices, tell the true story of value.

What this means if you are buying

The May market tends to reward buyers who are prepared and clear on their priorities.

• Stay ready. The right home can still go under contract quickly, so having your pre approval, down payment plan, and decision makers aligned is essential.
• Focus on value, not just price. A competitive list price can still be a good long term move if the home fits your lifestyle, location, and financial goals.
• Be strategic, not reactive. Not every listing deserves an aggressive offer. Knowing when to stretch and when to wait is where a good advisor earns their keep.

If you are feeling a mix of excitement and stress, you are not alone. That is exactly when it helps to have a plan and someone experienced to talk through the options with you.

Thinking of selling?

Late spring is often a sweet spot for sellers in Chicago. Buyers are serious, the city looks its best, and outdoor spaces start to shine in photos and in person. Longer daylight hours mean more showings after work, more foot traffic, and more people dreaming about where they want to live next.

If you are considering selling this year or next, this is a great time to start the conversation. We can review your home, your timeline, and whether a strategic pricing and prep plan could put you in a strong position.

As the weather warms up, buyers are paying closer attention to how a home lives both inside and out.

What is standing out right now:

• Easy access to outdoor areas like decks, patios, terraces, and balconies
• Simple but inviting setups, for example a small seating area, string lights, planters, and an herb garden
• Light and airy interiors that highlight natural light and greenery

Even a modest balcony or patio can become a major selling point when it is styled well. Thoughtful photos of these spaces absolutely help your listing stand out online.