Knight Kiplinger sold his family’s media empire to a new British owner. Now he’s obsessed with a plan to build a town from scratch on the Florida coast. (Evelyn Hockstein/For The Washington Post)

Knight Kiplinger has lived a dual life for decades.

Kiplinger the journalist, in the past three decades, piloted his family’s century-old media empire through a tumultuous digital transformation before selling it to a London-based publisher earlier this year.

Then there’s Kiplinger the real estate visionary and historical architecture buff.

Kiplinger, 71, is inventing a city of 10,000 people that will rise out of 1,000 acres of Florida farmland — part of a 3,400-acre parcel that has been in his family for decades.

“It’s the big enchilada,” said the journalist/developer, liberated from the daily grind of a print media enterprise. He has found renewed purpose creating a small city called Pineland Prairie smack in the middle of one of the Sunshine State’s richest, most anti-development counties.

It’s a passion project that draws on his family’s long history of a classic buy-and-hold investment: real estate.

Talk about second acts.

“You can see him breathing more comfortably and easy,” said one Washington businessperson who spoke on the condition of anonymity to talk freely. “He is now free of the burden of running his family business in a stressed industry. The project has been on his mind for 20 years.”

Kiplinger’s devotion to Pineland Prairie has been tested.

“This county has been a graveyard of ambitious development projects,” said Kiplinger, clearly buoyant as he described it in his corner office in downtown Washington this year. “People said, ‘Knight, you’re going to get your head handed to you.’ ”

Pineland Prairie required local leaders to change the county’s official planning policy — a move opponents say could have far-reaching effects on its citizens’ way of life. And they did, approving it 4 to 1, to the chagrin of the anti-development crowd that includes Maggy Hurchalla, sister of the late Janet Reno, who served as U.S. attorney general under President Bill Clinton.

“He did a marvelous PR job telling everybody everything they wanted to hear,” said Hurchalla, adding that she did not play an active role in opposing Kiplinger’s project.

“The precedent they had to make to approve him will hurt the county in the future. It will open the floodgates for rural development. It’s going to make taxes higher. Make it a less pleasant place to live. Martin County is no longer anti-development.”

Kiplinger said he is out to change people’s lives.

“I went to the county and said, ‘Let’s work on creating a vision for a new kind of town,’ ” he said. “Seventy percent of this property will be left open forever. I am using the other 30 percent, 1,100 acres, to create a compact, new town by the best practices of modern planning. Compact, walkable, environmental.”

Kiplinger’s goal is to replicate a small-town vibe in golf-crazy southeast Florida, which is dominated by wealthy residents who live behind gated walls in big houses and drive big cars.

“Martin County is full of beautiful, gated, golf course communities for affluent seniors,” Kiplinger said. “It’s not an unmet need. I said, ‘Where are the young families going to live? The schoolteachers? Your children coming back from college who want to live in the same community? They can’t afford big houses on fairways.’ ”


Austin Kiplinger, publisher of Changing Times magazine, and son Knight Kiplinger in 1987, the magazine’s 40th anniversary. (Harry Naltchayan/The Washington Post)
A family affair

Real estate runs through Kiplinger veins.

“Kiplingers love the land,” said Knight, whose forebears included carpenters, carriage makers and home builders. “We were farmers in Ohio. Then they came to Pennsylvania in the 19th century in the great German migration.”

His grandfather, W.M. “Kip” Kiplinger, was an economics reporter who began the Kiplinger publishing company in the 1920s. It included the four-page weekly Kiplinger Letter, a biweekly tax letter and Kiplinger’s Personal Finance.

But always lurking in the background was a real estate gene that Knight Kiplinger inherited.

As the Kiplinger publishing business thrived, the family wisely used the money to seed investments in real estate, stocks and bonds — now held in a diversified holding company called Outlook Inc. Outlook was not part of the sale to the British publisher.

“We are very patient, long-term investors,” Kiplinger said.


Financial and political expert Willard M. Kiplinger. (Joseph Scherschel/The LIFE Picture Collection/Getty Images)

The Kiplingers built the company’s Washington headquarters for $1 million in 1949. It sold the building six years ago for $16.5 million (it is now a hotel) and used the money to buy two Walgreens stores and a Wawa convenience store. The company also owns an office building in Stuart, Fla., where SunTrust Bank is the lead tenant. The family personally owns a Montgomery County farm where it raises horses.

Knight Kiplinger’s first venture was partnering three decades ago with a major developer to build the Villages of Urbana, a community of 8,000, out of land he owned in the sleepy rural village in southern Frederick County, Md.

“In 1992, I went before the county council of Frederick County and I described my vision for Urbana,” Kiplinger said. “We restored several historic buildings and built the town around them. I’m really into historical preservation.”

They have helped develop successful projects in Prince George’s County, Md., including a just-completed development in Hyattsville called Editors Park that includes 86 townhouses, 40 condominiums and an apartment building with 352 units called the Edition.

A start at Bay Tree Lodge

So how did the Kiplinger family end up with 3,400 acres in Florida?

Kip Kiplinger arrived in Martin County in 1952, egged on by a friend who said the area “is Florida for people who think they don’t like Florida,” according to Pineland Prairie’s website.

Two weeks later, Kip had a contract to buy Bay Tree Lodge, a 20-acre estate that had been owned by the brother of legendary financier Bernard Baruch and later by the Cheek family of Nashville, who founded Maxwell House Coffee.

Century-old Bay Tree, with its five cottages, waterfront lodge, tennis court, pool and boats, for the past six decades has been free to Kiplinger employees for two weeks a year. The location has been so popular that when Knight announced the sale of the company last winter, one of the first questions from employees was whether Bay Tree would still be available to them.


Land in Martin County, Fla., where Knight Kiplinger wants to develop a community called Pineland Prairie. (Knight Kiplinger)

Kip Kiplinger acquired other parcels throughout that corner of Florida, then donated it in pieces over five decades to build churches, homes for civic organizations, hospitals and libraries.

That built up a lot of goodwill with the local decision-makers.

“His family for generations have contributed in multiple ways to our community, shaping what we are today,” said Doug Smith, a member of the Martin County Board of Commissioners. “When somebody needed to step forward, they were there to do so. They donated the land in the city of Stuart for our first library. They donated lots of other tracts of land for community parks and environmental facilities.”

One of the plots they bought in the 1980s, they held on to. That is the 3,400 acres that will make up Pineland Prairie. It’s mostly been used for farmland.

“For years, it was citrus,” Knight Kiplinger said. “The industry in Florida was decimated by a blight, a Mediterranean fruit fly and by hurricanes, freezes and thaws. We’d still be in the citrus business if Mother Nature had not put us out of business. So we went to tomatoes, potatoes and sweet corn.”

Years passed. Florida became one of the most populous and thriving states in the union, with many wealthy pockets of developments. Land values skyrocketed. As the state grew around Martin County, the 3,400 acres between the Florida Turnpike and Interstate 95 became a nugget of development gold — “if you could get the land use changed,” Hurchalla said. “And they did.”

Even with all Kiplinger’s goodwill, Martin County was known as a notoriously difficult place to build. Big projects such as Pineland Prairie are typically planned in secret, then sprung on the local community in an inches-thick application by a team of zoning lawyers, consultants and accountants.

“Nobody comes here,” said Jacqui Thurlow-Lippisch, a Martin County native and a community activist. “It’s like torture.”

Kiplinger, known for his discipline and attention to detail, took another route.

“I took out a full-page ad in the Stuart News,” he said. “I said in an open letter to the people of Martin County, ‘I am starting a process to work with the people of this county and your local government on envisioning a new kind of community unlike anything that’s here now.’ ”

Kiplinger envisions a community built around new urbanism on the order of Kentlands, in Gaithersburg, Md. New urbanism, founded in part by architect and urban planner Andrés Duany, promotes walkable neighborhoods built less around the automobile and emphasizing diverse housing and employment.

“This is very much part of his bloodstream,” one longtime friend said of Kiplinger. “He understands real estate. He has an intuitive feel toward it.”

Kiplinger flew between Washington and Florida like mad, attending more than 40 meetings to advocate for his development and to lobby officials and answer questions.

“I traveled around the county meeting with anybody,” Kiplinger said. “I’d show them photos of towns I like around America. Neighborhoods I like. Houses I like.”

At Smith’s suggestion, Kiplinger hired a team of experts and facilitators including Marcela Camblor, an urban planner who worked with a regional planning council in Florida before founding her own firm. “I told Knight, ‘I would certainly start with Marcela and go from there.’ ”

Smith, who calls Duany’s Seaside community on the Florida Panhandle “one of my favorite places,” said Pineland Prairie’s ambitions remind him of the close-knit towns where he grew up in New England, “where if you did get in trouble, your parents knew before you got home.”


Three decades ago, Knight Kiplinger partnered with a major developer to build the Villages of Urbana out of land he owned in Frederick County, Md. (Justin T. Gellerson/For The Washington Post)

Nathaniel Fenton, whose family owns a 10-acre organic farm in Martin County, sees Kiplinger’s Pineland Prairie as an opportunistic venture that will perpetuate the sprawl that is fast spreading through his state.

“He is an astute businessman making a calculated play on people’s desires for a more holistic life,” Fenton said. “But what he is providing is essentially no different from the standard model of development in the state of Florida for the last 80 to 100 years. He is going to make many millions.”

Smith believes Pineland Prairie will be a community that will last for decades, becoming a home where people of various income groups and ages are integrated with common spaces, retail stores, restaurants and a turn-of-the-20th-century vibe of friendliness.

Kiplinger, ever mindful that he is the guardian of a family reputation built over a century, said he chose quality over the quick buck.

Even in Martin County, Smith said, if you hire enough lawyers and are willing to wait out the approval process, you can get your project built.

“It’s important to his family name and dedication to Martin County that he didn’t surrender to mediocrity,” he said. “They could have done sprawl. They chose to be different.”

Thurlow-Lippisch sums it up this way:

“Development is reality,” she said. “This is the best of a difficult reality.”


“My grandfather was a journalist,” Knight Kiplinger said. “His hobby was buying land. For three generations, our company continued to invest in land. By my grandfather, my father, brother and me.” (Evelyn Hockstein/For The Washington Post)
'Immaculately preserved'

Nearly a thousand miles north of Martin County, in the rolling countryside north of Washington, lies a 200-year-old, 400-acre farm that may best explain the Kiplinger family’s love of the land.

Montevideo is a historic farm that Knight’s father, Austin, and his wife, Gogo, acquired in 1958. The farm was established by a great-grandson of Martha Washington.

Much of the property is still devoted to farming of corn, soybeans and wheat. The property, crossed with trails, barns and historical buildings, is also the permanent home of the Seneca Valley Pony Club and the Potomac Hunt Races held each May. The Potomac Hunt holds its annual fox hunt there each Thanksgiving.

“One of Knight’s great loves is Montevideo,” one friend said. “It is a beautiful old estate that has been immaculately preserved. Lovely grounds. That is where he goes.”

Kiplinger has hosted the Historical Society of Washington, D.C., at Montevideo, including tours of cemeteries, schoolhouses and the ruins of Seneca stone mill.

“My grandfather was a journalist,” said Kiplinger, sitting in his office, clad in a sweater and shirt, looking more like a landed squire than a hard-bitten journalist. “His hobby was buying land. For three generations, our company continued to invest in land. By my grandfather, my father, brother and me.”

Kiplinger estimates that they won’t break ground in Florida for at least two years. In the meantime, engineers are pricing out the cost of sewers, roads, water, electrical power and the million other pieces that go with building a new city.

He doesn’t know the cost but plans to partner with investors and developers and sell pieces of the land in phases, while retaining control over Pineland Prairie’s design.

Adhering to the original plans could be hard.

“The stand-alone city is hard to build,” Hurchalla said. “I don’t know what it will look like, but it will be what the market wants. Planners love new urbanism; the market doesn’t.”

Kiplinger estimates the city will realize a few hundred million dollars in revenue over the life of the project, in the sale of finished lots, retail sites and employment locations.

Now that Kiplinger is out of the grind of journalism and into his mode as a long-term investor, he is thinking in terms of decades. He estimates that Pineland Prairie will occupy the rest of his life.

“This is a 25-year building process,” he said. “In 20 years, I will only be 90.”