Surprise: Boomers are upsizing, not downsizing

What AI can’t touch

Everyone's bracing for AI to take their jobs. I think we should be doing the opposite.

Over 200 economists and tech leaders just warned about large-scale job displacement — but look at which jobs they're worried about. Software, customer service, entertainment. All work that lives on a screen.

This job needs a body in the room. You can't walk a property, read a seller, or earn trust through a chatbot. AI takes care of the busywork. We keep the part that actually closes deals: a personal touch and a steady hand.

There's never been a better time to be an agent.

To learn how the industry's thinking about this at scale, jump down to today's Foundation Plans, where I talk with Cynthia Taylor, Zillow’s SVP of Product, about AI and the future of real estate.

- James

Why the housing market is hurting this summer

Pending home sales in June, a measure of signed contracts on existing homes, fell 5.4% from May. And according to NAR's current market report, sales were down 0.3% from June 2025 and were well below expectations.

Here are the other key takeaways from the update:

• Mortgage rates are the highest in nearly a year — Rates hovered around 6.6% in June, and combined with record-high median home prices, are making things especially tough for first-time buyers.

• Builder confidence keeps sliding — Homebuilder sentiment fell to 34 in July, marking 15 straight months below 40, the longest such stretch since 2012.

• Builders are cutting prices and leaning on incentives — 37% of builders cut prices in July, up from 35% in June, while 63% are now offering sales incentives, the 16th consecutive month above 60%.

• Builders are getting squeezed too — Rising land costs, materials, and a persistent labor shortage are hitting builders just as hard as buyers, according to NAHB's chief economist.

My take

This is less a housing slump than a waiting game. Buyers are hoping for lower mortgage rates, builders are hoping affordability improves, and sellers are still adjusting to a market with fewer bidders. Until one of those shifts, expect sales to stay uneven. The opportunity for agents isn't to wait alongside them: it's to help clients see clearly what's actually possible in today's market and make decisions based on today's realities, not yesterday's expectations.

Boomers aren’t downsizing, they’re upsizing

Boomers were supposed to downsize in retirement. Instead, they’re buying bigger homes. About 7% of buyers ages 61 to 70 say that they chose their new home because they wanted more space, up from 4% for that age group in 2016. 

That’s according to NAR’s latest report via the Wall Street Journal. Here’s what else they report:

• Empty-nest boomers already own 28% of U.S. homes with three or more bedrooms, compared to just 16% for millennials with children.

• Boomers make up 42% of all home buyers — the largest share of any generation — and are often cash buyers, giving them an edge over younger, mortgage-dependent purchasers

• Boomers and older Americans hold an estimated $110 trillion in wealth, much of it from decades of home and stock appreciation, fueling the shift toward bigger homes rather than smaller ones

• The reasons behind the shift: more space to host family and grandkids, remote work letting adult kids stay longer, capital-gains taxes that make selling less appealing, and a thin, pricey market for smaller homes

My take

This is a wake-up call. Yesterday's assumptions don't always survive today's market. Retirement no longer means automatic downsizing. Many boomers have the equity, savings, and flexibility to buy larger homes that fit how they actually want to live—whether that's hosting family, housing adult children, or simply having more space. And with boomers now making up the largest share of home buyers, agents who still treat them as downsizers are leaving business on the table. Understanding how this generation shops today, not how it shopped a decade ago, is a competitive advantage.

Free market data you can drop right into your listing presentations

Want instant credibility with clients? Show up with current, local market data. Zillow’s free interactive research tools give you the insights you need. Bring those visuals directly into your presentations and buyer conversations. Whether you're advising a seller on pricing strategy or helping a buyer understand what's happening in their target neighborhood, having clean, up-to-date data at your fingertips makes a real difference. It's free, it's always current, and it takes the guesswork out of the conversation.

The biggest home sales of the year so far

The ultra-wealthy aren't just buying more — they're buying bigger, and the price tags prove it. Nine of the year's ten priciest sales cracked $55 million, with Florida dominating the list and one Indian Creek Island estate blowing past everything else at $170 million. 

Here are the biggest sales of the year so far, according to Redfin:

1. 7 Indian Creek Island Rd., Indian Creek, FL 33154: Sold for $170 million in March

2. 2500 E. Maya Palm Dr., Boca Raton, FL 33432: Sold for $75 million in May

3. 1660 S. Ocean Blvd., Manalapan, FL 33462: Sold for $70.9 million in June

4. 1940 S. Ocean Blvd., Manalapan, FL 33462: Sold for $68.3 million in February

5. 820 S Ocean Blvd., Manalapan, FL 33462: Sold for $62.5 million in May 

6. 2910 Sycamore Canyon Rd., Montecito, CA 93108: Sold for $59.9 million in April

7. 70 Vestry St Unit PHS, New York City, NY 10013: Sold for $57 million in February 

8. 1610 N. Ocean Blvd., Palm Beach, FL 33480: Sold for $55.2 million in April 

9. 8 E. 62nd St., New York City, NY 10065: Sold for $55 million in February

10. 4296 Cutlass Ln., Naples, FL 34102: Sold for $55 million in January

My take

Florida isn't just winning on volume — it's winning on price. Six of the ten biggest sales this year happened there, and Manalapan, a town of about 508 people, somehow landed three of them. That's tax policy, waterfront scarcity, and wealthy buyers relocating from high-tax states all doing exactly what you'd expect. New York held its ground with two sales north of $55 million, but this list is really a highlight reel of where the top 0.01% is choosing to park its money — coastal, tax-friendly, and increasingly concentrated in a handful of zip codes.

Schematics

The news that just missed the cut

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• Use this buyer system to close more deals

• The Chicago suburb where million-dollar homes sell in a week

• How team leaders scale without building a mega team

Foundation Plans

Advice from James to win the day

This week on Rise Above the Ranks, I talked with Cynthia Taylor, SVP of Product at Zillow, about what AI actually looks like for agents day-to-day — not the buzzwords, the real workflow.

We covered how top producers use data to know exactly who to reach out to and when, what Zillow's new "Likely to List" feature does, and why she still believes agents will be central to 90% of transactions five years from now. 

Definitely watch this if you want to know where this business is actually headed.

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Just in Case

Keep the latest industry data in your back pocket with today’s mortgage rates:

“Your time is limited, so don’t waste it living someone else’s life.” — Steve Jobs

Each day is a gift – a chance to live the life you want. Ruthlessly focus on your goals. Don’t let your past or the fear of being judged distract or paralyze you. Choose to live with an integrity that you can be proud of.

Have a wonderful weekend, and I’ll see you back here next Friday!

- James