How a First-Time Buyer Secured a $650,000 Penthouse Condo in Old Town by Avoiding the Spring Market Rush

Buying a home in one of Chicago’s most desirable neighborhoods can feel intimidating — especially for first-time buyers competing against aggressive spring demand, multiple offers, and bidding wars.

Recently, I helped a client successfully close on his first home purchase in Old Town, securing a 3-bedroom, 2-bath penthouse condo with a private rooftop terrace for $650,000.

The key to this win? Timing, strategy, and leveraging slower seasonal market conditions.

Why Buying in Old Town Is Highly Competitive

Old Town Chicago remains one of the city’s most sought-after neighborhoods for condo buyers thanks to its walkability, historic charm, proximity to downtown, lakefront access, vibrant dining scene, and excellent transportation options. Inventory — especially for larger condos and penthouse units with outdoor space — is often limited.

During peak spring and summer months, buyers frequently encounter:

• Multiple-offer situations

• Escalation clauses and bidding wars

• Short showing windows

• Less negotiating leverage

• Higher final sale prices

For first-time buyers, this environment can be stressful and financially challenging without a strong strategy.

Using the Off-Season to Gain a Competitive Advantage

My client specifically wanted to avoid the intense spring buying rush, so we began searching in October, when buyer activity traditionally slows across the Chicago real estate market. Fewer active buyers often creates opportunities for stronger negotiation leverage, more flexible sellers, and smoother transaction timelines.

By entering the market in the fall and early winter, we were able to:

• Avoid bidding wars and multiple-offer competition

• Negotiate confidently without emotional pressure

• Take time to evaluate opportunities strategically

• Identify motivated sellers still active during slower months

This seasonal approach allowed us to move thoughtfully while still acting decisively when the right property became available.

Finding the Right Penthouse Condo in Old Town

After monitoring inventory carefully, we identified an exceptional opportunity: a penthouse 3-bedroom, 2-bath condo with a private rooftop terrace, offering both space and outdoor living — two features that are increasingly difficult to find in urban Chicago condos.

The property was well positioned within the market, and we acted quickly with a strong, clean offer. We were under contract by mid-December, just before the holidays — another period when competition is typically lighter and sellers may be more motivated to move forward.

Leveraging Agent Relationships for a Smooth Closing

One often overlooked advantage in competitive markets is the power of professional relationships. Through proactive communication and rapport-building with the listing agents, we were able to maintain transparency, alignment, and efficiency throughout the transaction.

This resulted in:

• Clear expectations between all parties

• Fast communication and problem-solving

• Minimal friction during inspections and negotiations

• A smooth closing timeline

Just 30 days later, my client officially closed and began setting up his first home — decorating, personalizing the space, and enjoying the benefits of homeownership in one of Chicago’s best neighborhoods.

Smart Timing Can Create Real Buying Power

This transaction highlights how strategic timing can dramatically impact outcomes for buyers. Entering the market during slower seasons can often unlock better pricing, reduced competition, and improved negotiating leverage — especially in high-demand areas like Old Town.

For buyers willing to plan ahead and stay disciplined, off-season opportunities can lead to exceptional results.

Thinking About Buying a Condo in Old Town or Chicago?

If you’re considering buying your first home in Old Town, searching for a penthouse condo in Chicago, or looking to avoid bidding wars in a competitive market, having a clear strategy makes all the difference.

I help buyers identify opportunities, navigate negotiations, and secure strong outcomes in any market cycle.

👉 Connect with Matt Ayo, Chicago Real Estate Broker at Compass
Visit mattayorealtor.com to explore neighborhood guides, buyer resources, and schedule a private consultation.