Lessons Learned Across Generations in Real Estate

2026 will be a year of perspective and momentum, and while the past few years have continued to test the real estate industry in ways few could have predicted, I look back with real pride and gratitude. Busby Group remains a team of strong, savvy, and deeply knowledgeable professionals who genuinely support one another, more importantly, work tirelessly to help our clients achieve their dreams of homeownership at every price point. Sometimes it truly does take a village.

As a Baby Boomer, I believe that looking ahead still requires vigilance and adaptability. Interest rates have normalized compared to the historic lows of the early 2020s, inventory continues to ebb and flow by neighborhood, and economic and political shifts, both locally and nationally, always warrant close attention. One thing that has not changed: real estate remains a long-term, relationship-driven business.

Much of our team is made up of Millennials, and that continues to be a tremendous advantage. Millennials are now firmly established as the largest segment of homebuyers, and they are increasingly joined by Gen Z entering the market for the first time. At the same time, the largest intergenerational transfer of wealth in history is well underway, with trillions of dollars expected to pass from Boomers to their children and grandchildren over the coming decades. Real estate remains one of the primary places families are choosing to build, protect, and grow that wealth. Whether you’re a Boomer, Gen X, Millennial, or Gen Z, there are constants in real estate that continue to hold true.

I still remember reading that Andrew Carnegie once said that the majority of millionaires built their wealth through real estate. I bought my first condo at age 25 in New York City, back when “Yuppie” was a common label. Like many young buyers, I sold it to move up to the next stage of life, and eventually to Chicago, a city I had never even visited before relocating. Mortgage rates at the time were in the double digits, and neighborhoods like Lincoln Park looked very different than they do today.

With no internet, no online listings, and no digital tools, we relied entirely on a seasoned Realtor recommended by my mother-in-law. It turned out to be some of the best advice I’ve ever received. She didn’t just help us find a home, she helped us find a neighborhood, a lifestyle, and a sense of belonging. That relationship extended far beyond a single transaction, and it shaped how I understand real estate to this day.

Years later, I know what I didn’t know then: what makes a good investment in Chicago, what tends to hold value, and what doesn’t. I also learned something just as important - the way a client feels after the transaction matters enormously. That philosophy is exactly why referral business continues to be the backbone of Busby Group.

I learn as much from the younger members of our team as they learn from me, and not just about real estate. My children are now well into adulthood, so I understand the mindset of today’s Millennial and Gen Z buyers. They come prepared, ask thoughtful questions, and are optimistic about building their future. In return, they keep me current on everything from new restaurants to wellness trends and technology. From my team, I’m constantly learning new strategies, new tools, and new ways to simplify and elevate the client experience.

The market will always evolve, but one thing never changes: real estate is about the experience. That experience begins with the very first conversation and continues well beyond the closing table. Making every step thoughtful, efficient, and genuinely enjoyable is what creates lifelong clients and lasting relationships.

We firmly believe that the experience Busby Group provides can never be replaced by an algorithm or a discounted service alone. Representation matters. I once worked for a destination club owned by a real estate development company, where every decision revolved around the client experience. Focusing on that experience didn’t just benefit the client - it made the work itself deeply rewarding. That lesson has stayed with me.

Having team members of different ages, backgrounds, and perspectives allows Busby Group to deliver well-rounded advice, nuanced market insight, and exceptional service, while having a lot of fun along the way. That’s how we continue to rank among the top 1% of Chicago real estate brokers. We love matching buyers with homes in every Chicago neighborhood. In many ways, we truly are matchmakers.

One of the most satisfying moments in this business is still saying, “We have a deal.” It marks the beginning of a new chapter. There may be nerves, excitement, and even a few bittersweet emotions along the way, but navigating those moments with knowledge, integrity, and discretion is exactly why having the right broker matters.

Here’s to moving forward in 2026 - using everything we’ve learned from the past to guide us confidently into the future.

 Contact us to discuss your real estate goals.

Ultra-Luxury Real Estate: Wealth, Movement, and What Comes Next

The 2025 Compass Ultra-Luxury Report offers a clear view into where wealth is forming, where it is moving, and how it is being deployed through real estate. At the highest end of the market, residential real estate continues to function as both a reflection of economic growth and a strategic store of value.

In 2025, national sales volume for homes priced at $10 million and above reached $38.63 billion, with 2,261 closed transactions nationwide. These figures reinforce an important distinction. Ultra-luxury housing is not a barometer of overall housing health. It is a barometer of wealth creation, capital migration, and long-term confidence.

As Compass Chief Economist Mike Simonsen explains, the data tells a straightforward story. Wealth continues to be created, and it wants to live somewhere. In 2025, that meant continued strength in established ultra-luxury markets such as Manhattan, Palm Beach, Aspen, and Silicon Valley. At the same time, emerging luxury hubs including Scottsdale, Dallas–Fort Worth, and Brooklyn gained momentum, signaling a broader shift in how affluent buyers are underwriting lifestyle, opportunity, and long-term value.

Chicago and the North Shore: Local Luxury Strength

Chicago’s luxury market showed notable strength in 2025, particularly at the upper end of the price spectrum. According to Crain’s Chicago Business, the number of homes selling at $4 million and above reached record levels, marking a meaningful milestone for high-end activity in the region. This performance underscores continued demand among affluent buyers despite broader market normalization.

Price trends further support this resilience. Case-Shiller data cited by Crain’s shows that Chicago-area home values continued to grow steadily year over year, placing the metro among stronger-performing large U.S. markets. While growth has moderated, pricing stability at the top end reflects confidence and disciplined demand.

Suburban luxury markets remain equally compelling. The North Shore, including Winnetka, Kenilworth, and Lake Forest, continues to attract buyers seeking space, privacy, and proximity to the city. Homes in these communities frequently establish regional benchmarks, while Hinsdale and surrounding affluent suburbs regularly see transactions well above $1 million, reinforcing sustained demand at higher price points.

Within the city, core luxury neighborhoods such as the Gold Coast, Lincoln Park, River North, and the Near North lakefront continue to appeal to buyers prioritizing architecture, views, and long-term livability. Limited inventory in these areas keeps well-positioned properties competitive, particularly those offering iconic design or premier locations.

Insight, Influence, and Impact in Today’s Luxury Market

Compass frames the ultra-luxury segment through three essential lenses: insight, influence, and impact. At this level of the market, data alone is not enough. What matters is how that data is interpreted and applied.

Ultra-luxury buyers in 2025 were not simply purchasing homes. They were making long-term decisions about lifestyle, capital allocation, and where they want to anchor wealth. Buyer psychology, design trends, technology adoption, privacy considerations, and global mobility all played a meaningful role in how decisions were made.

At Busby Group, our Luxury Collective mirrors this approach. We track not only national and local market data, but also top-tier sales activity and the qualitative signals that influence outcomes. Understanding how buyers think, what they prioritize, and how they evaluate value allows us to guide clients beyond the transaction and toward informed, strategic decisions.

From Resilience to Recalibration in 2026

If 2025 was defined by resilience, early indicators suggest that 2026 will be a year of recalibration and opportunity. The $10 million-plus segment is entering a more deliberate phase, marked less by urgency and more by discernment.

Buyers are taking additional time, underwriting decisions carefully, and prioritizing assets that align with long-term lifestyle, security, and value creation. This shift does not signal weakness. Instead, it reflects maturity and confidence in the market.

For sellers, this environment rewards thoughtful pricing, strong presentation, and strategic positioning. Well-prepared properties in premier neighborhoods continue to command attention and strong results. For buyers, moments of recalibration may create windows where quality, leverage, and timing intersect.

What This Means for Luxury Buyers and Sellers

For clients operating at the highest levels of the market, ultra-luxury real estate remains a powerful tool. It reflects confidence in long-term economic growth and serves as a tangible expression of wealth strategy.

Across Chicagoland, from the Gold Coast and Lincoln Park to the North Shore and Hinsdale, demand continues to be driven by location, quality, and long-term livability. Limited inventory in these markets reinforces the importance of informed strategy and experienced guidance.

At Busby Group, our Luxury Collective closely tracks national and local data, notable sales, and emerging trends to help clients navigate this evolving landscape with clarity. Whether buying, selling, or evaluating timing, informed strategy remains the defining advantage.

Contact us for a private consultation to review your real estate goals.

Read the full report here.