If you're an estate planner, financial advisor, or CPA working with high-net-worth families, you've probably noticed something: land is different. It doesn't behave like a stock portfolio. It doesn't move like residential real estate. And it certainly doesn't feel like a bond. Yet most advisors treat it the same way they'd treat any other illiquid asset—with a referral to a generalist agent and a hope that things will work out. They usually don't.

Over my years working with families, advisors, and institutions across the St. Louis region, I've learned that land isn't just another asset class to liquidate. It's a category unto itself—one with unique risks, hidden complexities, and surprisingly high stakes. And if you're advising clients who hold significant land or farmland, you need to understand why treating it differently isn't optional. It's essential.

Why Land Is Fundamentally Different

Let me start with the obvious: land is illiquid.

You can't sell farmland the way you sell 1,000 shares of a mutual fund. There's no daily market price. There's no standardized product. Every parcel is unique—different soil quality, different drainage, different access, different market conditions based on what's around it. That alone changes everything about how you should advise your clients.

But illiquidity is just the beginning.

Emotional complexity is real. Many of our clients inherited land from parents or grandparents. There's history there. There's memory. I've had conversations with multi-million-dollar landowners who couldn't bring themselves to sell their family farm because of what it represented, even though holding it was draining their estate's cash flow and complicating their tax situation. As an advisor, you need to recognize this. Your clients won't tell you about the emotional weight in their first meeting with you—but they'll feel it acutely when it comes time to let go.

Valuation is complicated. A real estate agent might give you a price per acre based on comparable sales in the county. But that's rarely the whole story. Is the land tillable or pasture? What's the soil type? Is there access to water rights? Has it been farmed, or is it development land? What's the environmental history? A generalist agent might miss critical factors that could shift the value significantly in either direction. I've seen appraisals that missed major easements or mineral rights issues entirely.

Multi-heir situations amplify all of these challenges. When land is split between three siblings, or held in a trust with multiple beneficiaries, the politics become part of the transaction. One heir wants to keep it. Another wants to liquidate. A third is simply absent from the conversation. Timing becomes fraught. Fairness becomes contested. A broker who doesn't understand how to navigate family dynamics will make things worse, not better.

Where Generalist Agents Fall Short

Here's what typically happens: A family inherits land. They call a local real estate agent who primarily sells houses and small commercial properties. That agent lists the property at a price they think is fair, based on market comps and some quick research. The listing sits for six months. Or a year. Maybe they get an offer from a developer or another farmer at a discount. Or maybe it just never sells, and the family is stuck carrying the cost of taxes, insurance, and maintenance indefinitely.

The problem isn't that the agent is dishonest. The problem is that they don't specialize. They don't understand:

- The tax implications of a land sale (step-up in basis, 1031 exchanges, capital gains planning)

- How to market land to the right buyers (institutional investors, agricultural operators, conservation groups)

- The nuances of farm leases and tenant relationships

- How to structure a transaction so it closes faster and generates more interest

- The difference between a traditional listing and an auction, and when each makes sense

A generalist agent will show your client's land to local realtors and hope something sticks. A specialist will market it to a national pool of buyers, position it strategically, and execute a sale that maximizes value and minimizes timeline.

Why Advisors Need a Land Specialist in Their Network

You wouldn't refer a complex tax matter to an accountant who's never worked with trusts. You wouldn't refer a contentious family law issue to an attorney who handles divorces once a year. Land sales deserve the same principle.

When you have a land specialist in your professional network—someone who understands estate planning, trusts, valuation, marketing, and family dynamics—you become better at your job. You can confidently guide clients who are sitting on significant land holdings. You can recommend a sale or a strategic hold based on actual expertise rather than a guess. And most importantly, you can protect your client relationship by ensuring that the sale process runs smoothly, transparently, and with maximum value recovery.

The advisor who says, "I know someone who specializes in land sales—let me connect you," immediately positions themselves as the expert who thinks comprehensively about their client's entire portfolio. That's what builds trust.

The Hidden Costs of Getting It Wrong

What happens when you refer a land sale to someone who doesn't specialize?

The property sits on the market too long, carrying carrying costs all the while. The family becomes frustrated. They second-guess the asking price. They lower it, which signals weakness to buyers. They eventually sell at a discount to someone with leverage over them. Meanwhile, your client is paying property taxes, insurance, and possibly maintenance costs on land that's generating no revenue while it lingers on the market.

Or consider a multi-heir situation where the sale process becomes contentious. Without someone skilled at managing family dynamics and communicating clearly about the process, heirs get frustrated. They disagree about the timeline. They worry they're being cheated. They bring in outside advisors and create layers of complexity that slow everything down. Your client relationship frays because you referred them to someone who didn't handle the soft skills as well as the hard ones.

Or there's the tax angle: An advisor doesn't mention that a 1031 exchange might benefit their client, so the land is sold in a way that triggers maximum capital gains tax. That's the kind of costly mistake that happens when the specialist isn't part of the conversation.

What Your Clients Are Actually Facing

Let me paint a picture of a typical scenario I see:

A widow inherits 250 acres of farmland in Southern Missouri. It's worth roughly $2 million. Her late husband's estate planning attorney suggested she consult with her financial advisor about what to do with it. Her advisor—a competent professional who manages her investment portfolio—doesn't know much about farmland. The property is currently leased to a tenant farmer. It's generating maybe $6,000 a year in net income after taxes and insurance. The widow doesn't want to be a landlord. She has no children who want to farm. She needs liquidity for living expenses and estate planning.

She has three realistic paths:

1. Keep it and manage it as a rental (lowest liquidity, ongoing liability, diminishing returns)

2. List it with a traditional agent (better than option 1, but slow and uncertain)

3. Explore an auction or strategic sale with a specialist (faster, broader buyer pool, better transparency)

A generalist agent might present option 2 as the obvious choice. A specialist will analyze all three against her actual financial and personal goals.

The Board Connection: Why This Matters

I serve on the Board of the Estate Planning Council of St. Louis, and I see this issue come up constantly in our discussions. Estate planners and attorneys are encountering more and more land holdings among their clients—farmland, family acreage, investment properties held for decades. And they're recognizing that they need partners who understand the specialized issues involved in liquidating land, particularly in trust and estate contexts.

That's not a marketing claim. That's a professional need, validated by a peer organization of estate specialists.

What to Look for in a Land Specialist

If you're considering building a referral relationship around land sales, here are the traits that matter:

- Deep understanding of trusts and estates. Do they understand step-up in basis, multi-heir sales, fiduciary responsibilities?

- Multiple sale options. Can they offer traditional listing, auction, or hybrid approaches? Or do they have one hammer and treat every land sale like a nail?

- Transparent communication. Will they keep you informed throughout the process? Will they protect your client relationship?

- National reach. The best land sales involve buyers from beyond the immediate region. Can your specialist market nationally?

- Institutional credibility. Do they work with institutional investors, family offices, or sophisticated buyers? That's a sign of expertise.

Ready to Strengthen Your Land Sale Advisory Practice?

If you're an advisor or attorney who works with clients holding significant land or farmland, let's talk about how to position yourself as the expert who thinks comprehensively about every asset class—including land. I'm available for confidential consultations with professionals who want to build a deeper understanding of how land sales fit into estate planning.

Jake Brown

Legacy Land Specialist | Principal

Trophy Properties and Auction

jbrown@trophypa.com | 314-602-1116