Historic homes and proximity to downtown make Portland a candidate for NuLu-style gentrification.

(Editor’s note: This is the first in series of posts looking for the next NuLu, trying to spot the next Louisville neighborhood where housing stock and geography have the potential to start attracting people and investment.)

With a $5 million buyout of Wayside Christian Mission, a group of investors lead by Gill Holland transformed almost over night a five-block stretch of East Market Street  during the worst economic downturn since the Great Depression,

Once dominated by homeless shelters and vacant buildings, the area now is NuLu, Louisville’s trendiest restaurant and retail hub.

A list of restaurants, boutiques, art galleries and other businesses too long to detail here have opened since 2008. Which we think is nothing less than an organic, private-initiative miracle.

We’ve seen it before NuLu as Butchertown, Germantown and Clifton all went from dodgy and depressing to vibrant neighborhoods with buzz generating retail, restaurants, renovated homes and music venues.

So, where in Louisville could this sort of dramatic transformation happen next? How is a nationwide trend toward authentic neighborhoods and away from stifling, soulless subdivisions going to change Our Fair City?

To answer this question, we went back to Holland, who produces music and movies at his The Green Building headquarters, for his take on which area is rife for an influx of residents and investors.

His answer: Portland, just west of downtown. It’s the oldest part of Louisville, and long thought consigned to poverty and neglect.

The biggest thing the Portland neighborhood has going for the next “hot” Louisville neighborhood turns out to be … Gill Holland.

Now he has acquired a property on the five points of 15th, Bank and Rowan streets in what he calls “the gateway to Shippingport.”

Can he work his magic again?

Gill Holland purchased this building in Portland.

The property is an attention-getting ship-like building built in 1880. “They were going to tear it down,” Holland recalls. “I was able to buy it for less than the price of a car. It seemed a shame to lose such a cool building.”

A “cool building” doesn’t necessarily make a hot neighborhood. But Holland says he sees the potential. “It’s less than a mile from 21C,” he notes, “and downtown is booming. At some point, people will realize it’s crazy that we don’t go past West 9th Street.”

His vision for Portland isn’t necessarily of art galleries and trendy restaurants. Not yet, anyway.

First thing, he says, is to renovate the properties and make the neighborhood livable, a residential destination for young people priced out of the Highlands or Old Louisville.

“I really believe it’s easy enough to fix,” he told Insider Louisville. “Lots are valued at $10,000 and houses at about $25,000, so it would require far less up-front investment.”

One notion of his is to get some artists, who tend to have more adventure in their soul than coins in their pockets, and tell them, “We’ll give you free rent in this very cool shotgun bungalow area of town that’s less than a mile from downtown if you fix it up and live there for three years.”

Oh yeah. And you have to have a dog.

Why a dog? “Because then they’ll go out and walk their dogs,” Holland says, “and that begins to build the sense of neighborhood and community.”

Costly? Not necessarily. “If I could raise $40 million, I could buy some properties – the right 40 – and go block by block. Portland could be less than 10 years away from flipping.”

Private investment is critical. “I need to convince some civic-minded investors that while they might not make any money, they won’t lose any, either. Five years from now, they’d get their money back and they’d have done something amazing for the city.”

But Holland’s convinced the city government could play an active role in this, as well. It would be worth the city’s while.

“There are some city-owned properties there that the city spends money on to maintain, but they’re empty,” Holland says, “so the city loses potential tax revenue. The city ought to be giving them to anyone willing to improve them, pay taxes on them and pay maintenance on them. It would save the city a half-million dollars.”

Could it happen? Colombian architect Alejandro Echeverri, former director of urban projects in Medellín (and winner of the prestigious Curry Stone design prize) has said, “Put a beautiful building in an economically distressed area and watch the positive ripples.”

“You always hear about a crack den being a cancer in a neighborhood,” said Holland, “so why wouldn’t a nice building have the opposite effect?”

It appears to have worked in Medellin, once a city infested with the thriving Colombian drug trade. And it worked on East Market Street, too.

“I bought this building five years ago,” Holland said of his The Green Building at 732 E. Market St. in NuLu, which he and his wife Augusta Brown Holland turned into Louisville’s first LEED Platinum building. “Do you see what’s happened here in five years?”

He said the other day he saw a Ferrari parked in front of The Louisville Beer Store on East Market and North Shelby. “Would anyone have thought they’d see a Ferrari parked on Market Street five years ago?” Holland asks, rhetorically.

“I don’t think so!”