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Philip T. Cowherd lives in Winter Park, and grew up in College Park. But, says the life-long investor in local real estate, “my whole world is Parramore.”

Now 70, Cowherd has been accumulating properties in Downtown Orlando for 40 years, just like his father before him and just as his two sons, Bradley and Clay, do now. He started walking its streets at age 11 – back then the brick had yet to be covered with asphalt – collecting rent for his dad.

“In 1958, those houses rented for about $6 to $8 per week,” he said. “A lot of them are still there.”

And a few are part of Cowherd Realty and Development‘s substantial portfolio, one he’s now looking to sell off – if possible in one fell swoop.

The listing went live in December: 52 properties that include single-family residences, duplexes, triplexes, vacant lots and an eight-unit apartment building. Each sit within a mile of one another, each has tenants secured. As of last week the whole kit and caboodle was listed at just under $6.5 million.

Cowherd has spent 90 percent of his life in Parramore, he will tell you fondly, but as a young man fresh from the University of Georgia, that wasn’t the path he’d been planning.

“When I came back from college, my father wanted to give me the business that he’d developed over the years and I refused to have it because I didn’t want to do the same thing I’d been doing my whole life,” he said.

By then, Cowherd was a real estate broker in Winter Park – so instead of acquiring the family assets he helped his dad sell them off. But life, he’d find, has a funny way of circling you back to where you’re supposed to be.

Several years later, a friend who’d bought three of the elder Cowherd’s duplexes surfaced with a desperate need to sell. So Phil bought, and when the city approached him about property rehabs through a government program, he signed on. Before long, he was a town hero, working hard to turn the Parramore neighborhood around.

“Pretty soon,” he said, “I’d bought back everything my father tried to give me!”

More accurately, Cowherd owns four of the properties his dad once held, which amused the old man to a degree, but now Cowherd is the one laughing at his sons.

“They grew up laughing at me, saying, ‘Dad, why don’t you get out of Parramore?’ It used to make me nuts. And now they’re doing the same thing,” he laughed. “They’re buying up commercial and industrial and they have a bigger investment there than I ever did!”

Cowherd laughs quite a bit, in fact he’s jovial when speaking of his career and semi-accidental life spent in Parramore.

“I have far more friends in Parramore than I have anywhere else, people I’ve known all my life,” he said, acknowledging his ample portfolio grew in part due to the strategy of making up in volume what he was losing on units. “I couldn’t make it with five residential properties there, so I figured I’d spread the overhead.”

That volume approach kept spreading, and before long his list of properties numbered close to 100.

“And so the 10-year plan I started in 1958 turned into a 60-year plan that’s finally starting to pay off.”

Cowherd may be looking to divest, but he’s hardly looking to retire.

“I honestly believe that if you quit working, you rust up and you get old and you die,” he said. “You have to stay active. And luckily I’m doing something I’ve done my whole life and I actually enjoy it so I figure as long as I keep doing it, I’ll do it.”

And he’ll get to whatever he’s doing in the well-tooled seat of a Porsche Cayman. Cowherd has been a fan of auto racing, and sports cars in general, for decades. His first was an Austin Healey Sprite.

“My father told me that car’s only big enough to carry a message in,” he said. “But here I am, 50-something years later, and I’m still driving such automobiles.”

These days, it’s Porsches. Cowherd’s small collection includes models from the ’70s, ’80s and 2000s. While he’s never raced himself, he enjoys the sport immensely and frequents tracks in the Southeast, including those in Daytona and Sebring. He has a friend who races and enjoys an occasional role in the crew, changing tires and washing windshields when called upon.

“I’m a polisher and driver of pretty cars,” he said, admitting that while owning the older models is fun, driving them can leave much to be desired.

“The truth is that your recollection of how wonderful an old car was is not real,” he said. “You drive a 1970s car and you think, ‘What in the world did I drive this thing for?’ Once in a while, I’ll take one to a car show and get a ribbon or something, but mostly I drive the new ones.”

The Orlando native enjoys his status as a Princeton graduate, bragging often before admitting he’s speaking of the elementary school in College Park. Son Brad lives nearby, near property he owns and leases to popular haunts Infusion Tea and the Soda Fountain ice cream shop.

Even so, Cowherd’s sons, like their father and grandfather before, see the value in Parramore.

“My sons keep talking about Parramore becoming the warehouse district – and I think that they’re right,” he said. “It’s going to become that neighborhood that the young people start to move into, tenants are coming here now that I’d never believed would be here two or three years ago. We’ve got a brewery up the street that the kids own, and next to that there’s a gym that’s full of young people of all races and all sizes and shapes. The contractor for the soccer field is there. It’s a different world and it’s changing.”

He’s hoping to see that change come full circle.

“I believe that Moses lived to be 140,” he said. “I’m 70, so I’m about halfway through it. And Moses, if I remember, never got to go to the Promised Land. I’m figuring that Parramore will become the Promised Land at some point, so I’m going to stick it out as long as I can.”

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