Florida’s shortage of available land in key development corridors is not primarily due to limited geography or environmental regulation, according to Bill Eshenbaugh, founder of Eshenbaugh Land Company. Instead, he points to the decision-making of multigenerational landowners, who keep productive land off the market even as prices soften and development demand slows.
“Landowners today are probably debt-free,” Eshenbaugh says, referencing the aftermath of the 2008 financial crisis, when lenders largely stopped making land loans. “It’s also a generational experience. Big landowners have second – and third – generation heirs behind them. Why be in a hurry to sell?”
This reluctance creates a fundamental disconnect between institutional buyers, who expect market pricing to drive transactions, and Florida’s largest landholders, whose priorities are shaped by legacy, timing, and alternative income.
Multigenerational landowners do not respond to typical market incentives, Eshenbaugh explains. “If I take a 30 percent haircut today, how do they make up for that?” he asks, describing the seller’s perspective. “I’ve only got one chance to sell my ranch, or one chance to sell my citrus land, or whatever it is that they’re selling.”
This creates an asymmetry in expectations. Even if the market slows, Eshenbaugh notes, many landholders see Florida’s long-term appeal as unchanged: “So if we think this is just a temporary slowdown, and we think that Tampa is a pretty good place—we have evolved into a place that people want to be—the employers are coming here and bringing good jobs with them.”
Because these landowners have no debt and no forced timeline, they can wait. “If I’m a landowner, I can wait,” Eshenbaugh says.
Eshenbaugh recounts a recent transaction to illustrate how long-term thinking shapes decisions. “I had one family where I sold some land for them in 2021, and they’re my age, they’re in their 80s. They said, ‘Well, you know, Bill, we’ve been in this citrus business since the last century.’ I said, ‘Well, that’s only 20 years ago.’ He said, ‘No, no, the other last century, 1890.’”
With a 140-year operating history, these families view short-term market changes as irrelevant. “They don’t have any debt on it, and they’re willing to wait to get the right price for it, even though they’re in their 80s. They’re not going to spend the money. They’ve done all right. They’re going to put that money to the next generation or grandchildren or somewhere else,” Eshenbaugh explains.
While Florida’s citrus industry faces long-term decline, cattle ranching has experienced a resurgence, further reducing landowners’ motivation to sell. “Cattle prices are higher than they’ve been in maybe 50 years. When I was selling my stuff, it was a dollar or two a pound at auction, live weight. Today it’s four, five, six, seven, eight dollars a pound,” Eshenbaugh says.
This price surge creates a genuine decision point for ranchers: “If you have an 800-pound female heifer, do I keep her a couple more years and breed her and have calves, or do I sell her today for four dollars a pound? That’s $3,200 for an 800-pound calf. Maybe it’s time to put her on the truck and let her go.”
Despite these high prices, many ranchers continue to hold their land. “It’s the first time that cattlemen have felt good about their business in a long time.” Positive cash flow from ranching removes the pressure to sell land for development.
The most reliable trigger for land sales, Eshenbaugh says, is not market pricing but generational transition. “We have those generational tugs of war,” he explains. “Usually, the last generation is about ‘give me the money now.’”
He describes a typical scenario: “Are we dealing with grandfather, father, and son, and somebody in that group wants to keep the land? Usually grandfather and father say, ‘I’m tired. I’ve been doing this for 40 years.’ And grandson says, ‘I want to be a lawyer downtown. I don’t want to punch cattle, handle citrus, or handle tomatoes. That’s just too much hard work.’”
Even then, the family retains control over timing and terms, often waiting for more favorable market conditions before selling.
Citrus land carries unique development value, further supporting the hold strategy. “Citrus land is good for houses. It’s high, it’s dry, and it’s sandy, because orange trees don’t like wet feet. They won’t grow in wet soils. So they’re good, high sandy soils to begin with, ideal for development in the residential when the time comes,” Eshenbaugh says.
As a result, families with declining citrus operations are not forced to sell at distressed prices. They can hold land that is likely to appreciate further as development demand returns. “If you’re sitting there and you’ve been generationally into citrus, you can wait a little bit,” he notes.
Tax policy changes are one of the few factors that can create urgency for land sales. Eshenbaugh recalls a surge of transactions during the Biden administration, when proposed capital gains tax increases prompted sellers to act. “There was a big push that maybe they’re going to raise capital gains to normal income tax rates or higher. We conducted several transactions in the last quarter of that year. Sellers said, ‘I am not going to pay 40 or 50 percent taxes on this stuff. I’m selling today to make sure I get capital gains locked in on it.’”
When those tax changes did not pass, some sellers regretted moving too quickly. “Congress did not approve any new tax bills, and so those people are still probably going, ‘I panicked. I wish maybe I wish I hadn’t done that.’”
These combined dynamics create a supply constraint that cannot be resolved through pricing alone. Despite Tampa Bay’s population growth and economic expansion, little land comes to market because owners have no urgent reason to sell at current values.
“They’re not desperate. They’re not overleveraged. They’re not facing forced liquidations,” Eshenbaugh says. Landowners are waiting for conditions that justify the permanent decision to convert farmland into development sites.
Eshenbaugh’s firm now focuses on identifying the specific catalysts that might influence families to sell, such as changes in tax law, generational handoffs, or shifts in agricultural profitability.
For institutional buyers expecting more land to come to market as prices rise, Eshenbaugh’s experience suggests a more complex reality. Florida’s largest land parcels in prime growth areas remain in the hands of families operating on generational timelines, supported by alternative income and no leverage. This creates a structural supply constraint likely to persist, regardless of near-term market trends.
Explore similar articles from Our Team of Experts.
A new breed of mid-sized real estate operators is emerging, combining institutional-grade expertise with the agility to pursue opportunities across specialty housing sectors, according to on...
Amid growing market uncertainty, private lending expert Philip Bennett argues that experience in evaluating distressed commercial real estate assets has become more crucial than ever, partic...
