Every summer, I notice the same thing.
The questions change.
Spring is full of excitement. Fall brings strategy. Winter is usually planning. But midsummer? That's when people start wondering if they've missed their window.
As someone who’s been doing this for decades, these are the questions I get asked every summer, along with a few new ones that have popped up this year.
Will Waiting Until Next Spring To Sell Make Me More Money?
This is probably the question I hear most once summer is in full swing.
The honest answer? Maybe… but probably not for the reason you think.
Many homeowners assume spring automatically means higher prices because it's considered the "busy season." While spring often brings more buyers, it also brings significantly more competition. If there are twice as many homes hitting the market, buyers have twice as many options.
Instead of trying to time the market, I encourage my clients to focus on timing their lives. If your home is ready and moving makes sense for your family, waiting for a different season isn't always the advantage people imagine.
Every market and every neighborhood is different. That's why looking at local data matters much more than following national headlines.
Why Did My Neighbor's House Sell for More Than Mine?
This is one of the hardest questions to answer because every home tells a different story.
Even homes on the same street can have dramatically different values depending on updates, layout, natural light, condition, outdoor space, floor plan, buyer demand, and presentation.
Price per square foot only tells part of the story.
Sometimes it's the renovated kitchen.
Sometimes it's the corner lot.
Sometimes it's simply that one home was marketed more effectively than another.
This is why pricing a home isn't about copying the house next door. It's about understanding what buyers value today.
Why Do Some Homes Receive Multiple Offers While Others Don't?
It's easy to assume multiple offers happen because of a hot market.
In reality, they're usually created by a combination of preparation, pricing, and presentation.
The homes that generate excitement are typically the ones that feel move-in ready, photograph beautifully, and are priced strategically to create a buyer frenzy from day one.
When buyers feel they're looking at a home that's been thoughtfully prepared and priced as a great value, they act quickly.
That's why I spend so much time helping sellers before their home ever reaches the market. The work you do before listing often determines what happens after the listing goes live.
Are Chicago Property Taxes Really That High?
It's one of the most searched questions about buying in Chicago right now… and one of the most misunderstood.
The short answer is: yes, property taxes can be higher here than in many parts of the country. But that's only one piece of the equation.
What many buyers are really asking is, "Am I paying more here than I would somewhere like Nashville, Dallas, or Miami?"
Maybe.
But those cities often come with different tradeoffs. Some have no state income tax but higher homeowners insurance. Others have lower property taxes but longer commutes, higher utility costs, or rapidly increasing home prices. Every market has its own version of "cost."
That's why I encourage buyers to stop looking at one line item in isolation.
Instead of asking, "What are the property taxes?" ask, "What will it actually cost me to own this home each month?"
That means looking at your mortgage, taxes, insurance, HOA assessments, maintenance, and utilities together, not separately.
Even within Chicago, two homes with nearly identical purchase prices can have very different tax bills depending on the neighborhood, exemptions, and how the property is assessed.
The goal isn't to find the lowest property taxes. It's to understand the complete financial picture.
How Do I Know if a Condo Building Is Financially Healthy?
Buying a condo isn't just about loving the unit; it's about understanding the building behind it.
Before my clients purchase a condo, I'm reviewing much more than finishes and floor plans.
I want to understand the association's reserve funds, upcoming capital improvements, potential special assessments, owner-occupancy rates, and the overall financial health of the building.
A beautiful condo inside a poorly managed building can become an expensive surprise.
Doing your homework before you buy can save you significant money and stress down the road. But it's not just about asking the right questions; it's about knowing who to ask. Over the years, the relationships I've built with property managers have uncovered information that isn't always obvious on paper, helping my clients avoid purchases that could have cost them hundreds of thousands of dollars.
What Should I Know Before Buying in a Historic Chicago Building?
Some of my favorite homes in Chicago are in historic buildings.
There's a reason so many buyers are drawn to them. Right now, I'm actually seeing a renewed appreciation for vintage homes and pre-war architecture. That charm is part of what makes Chicago such a special city.
But buying in a historic building also means looking beyond the beauty.
I always encourage my clients to understand not just the unit they're buying, but the building itself. Are there upcoming capital projects? Has the association been proactive about maintaining the roof, masonry, windows, elevators, or plumbing? Are there healthy reserve funds? Is the building well managed?
Historic buildings have often stood for nearly a century because they've been cared for. The key is making sure that care is continuing.
I've also found that buyers sometimes assume "older" means "more problems." That's not necessarily true. In fact, many vintage buildings have exceptional craftsmanship and have already undergone thoughtful updates over the years. On the other hand, I've seen newer buildings with maintenance issues simply because they weren't constructed to the same standard.
Every building has its own story.
Real estate is always changing, but one thing never does: every client deserves advice that's specific to their goals, their neighborhood, and their timing.
If you're wondering about buying, selling, or simply planning your next move, chances are someone else is asking the same question. The difference is having someone who can help you find the answer that's right for you.
