We Won the Home, Sold the Old One in 4 Days, and Got More Than He Asked For — Here's How It All Happened

Buying and selling at the same time is one of the most stressful things a person can do in real estate. The timing, the financing, the emotions — it's a lot to manage. But when it comes together the right way, with the right strategy and the right agent in your corner, it can look something like this.

Recently, I helped my client accomplish something that a lot of people in Chicago's competitive real estate market only dream about: we won his dream home before it ever hit the open market, and we sold his current condo — a place he'd called home for 20 years — above asking price, under contract in just 4 days.

Here's the full story.

Part 1: Winning 111 E. Chestnut St., Unit 37K in Streeterville

My client had his eye on a unit at 111 E. Chestnut Street in Chicago's prestigious Streeterville neighborhood — one of the most sought-after high-rise addresses on the Near North Side. Located steps from Michigan Avenue, Lake Shore Drive, Northwestern Memorial Hospital, and some of the best dining and shopping Chicago has to offer, it's the kind of address that doesn't stay available for long.

When the listing came to our attention, the listing agent had an open house scheduled and a full queue of tours lined up. In a market like Chicago's, that's a recipe for a multiple-offer situation — exactly the kind of competition that drives prices up and leaves buyers frustrated and empty-handed.

We didn't wait around to find out how that would play out.

We put together a strong, compelling offer designed to do one thing: make it easy for the seller to say yes — immediately. The offer was structured to stand on its own merits, and it did. The listing agent canceled the open house. The pending tours were called off. My client had a deal.

That's what it means to work with a top Chicago buyer's agent — not just someone who shows you homes, but someone who knows how to read a situation, move fast, and craft an offer that wins. If you're a first-time homebuyer in Chicago or an experienced buyer looking to compete in a hot neighborhood, strategy matters as much as the number on the page.

Part 2: Selling 3930 N. Pine Grove Ave., Unit 1211 — Above Asking, in 4 Days

The moment my client went under contract at 111 E. Chestnut, the clock started. He owned a condo at 3930 N. Pine Grove Avenue, Unit 1211 in Lakeview — a neighborhood that continues to be one of Chicago's most desirable places to live, work, and invest. He'd owned it for 20 years. It was a significant asset, and the sale needed to be handled with the same urgency and precision as the purchase.

We didn't waste a single day.

Within 72 hours of going under contract on the buy side, we had professional photography, video, and a full marketing plan live and ready to go. The listing hit the market sharp — priced right, presented beautifully, and backed by a targeted strategy to get maximum exposure to qualified buyers in the Chicago condo market.

The result? Under contract in 4 days. Above the price my client was hoping for.

This is what separates a great Chicago listing agent from one who simply puts your home on the MLS and waits. Marketing matters. Timing matters. Presentation matters. A great Chicago real estate agent treats every listing like it's the only one — because to your client, it is.

What This Means for You — Whether You're Buying, Selling, or Both

If you're a first-time homebuyer in Chicago trying to figure out how to compete in a market where the best properties are gone before the weekend open house — this story is for you. You don't have to lose. You just need a strategy and someone who knows how to execute it.

If you're a homeowner in Chicago thinking about selling — maybe you've been in your place for years and you're not sure what it's worth, what the timing looks like, or whether the market is right — this story is for you too. Your home can sell fast, above asking, with the right preparation and the right agent.

And if you're looking to buy and sell at the same time in Chicago — arguably the most logistically complex move in real estate — know that it can be done smoothly. It just takes coordination, hustle, and a trusted advisor who's done it before.

Whether you're searching for condos for sale in Streeterville, exploring homes for sale in Lakeview, or anywhere across Chicago's North Side and beyond, I'm ready to help you write your own story.

Let's Talk.

You don't have to figure this out alone. I work with buyers, sellers, and clients doing both — and I bring the same level of urgency and strategy to every single transaction.

📞 Reach out today. Let's get to work.

www.mattayorealtor.com

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