Winnipeg lawyer Howard Tennenhouse has been travelling to and from Israel for 31 years now, visiting relatives, seeing the sights and, more recently, dabbling in the real estate market.

Actually, it’s a little more than dabbling as the 54-year-old attorney has compiled an impressive roster of properties he has bought and sold across the country. He’s even contemplating turning it into a second career.

He recently sold one of the first units he acquired, a small apartment in Zichron Yaacov, just south of Haifa, for 425,000 shekels (US $116,000). In 2005, he paid $70,000 (all figures US) for it.

His first purchase, also in Zichron Yaacov, was his “dream home,” a 120-square-metre “penthouse” with a view of the southern end of the Carmel Mountain range. He recently sold that one as well, and in the period from his first purchase to today, he’s bought  – and sold – seven or eight other Zichron properties, four more in Ashdod and a couple of properties in Eilat. He’s also developing a “villa” (a semi-detached unit) in Ashkelon, a “tzimmer” (an upscale bed and breakfast) and a restaurant in Zichron Yaacov and a property in Atlit. One of his big projects is developing condominiums on a small irregularly shaped plot of land near the Old Port in Jaffa, Israel’s hottest market, that cost him $1.2 million. And there are others.

In Winnipeg, he owns a 2,200-square-foot bungalow – that’s it.

It took a while, but the real estate bug has bitten Tennenhouse in a big way. When he retires in three years, he plans on moving to Israel permanently and relying on real estate to keep him busy and provide an income.

So far, he’s made quite a success of it. The real estate market in Israel has been booming since he got involved six years ago, Tennenhouse said.

When he first got into the market, he wasn’t looking at making it a business. An ardent Zionist, he had dreamed of moving to the Holy Land and viewed Rishon as the ideal retirement venue – it was close to relatives who lived in Kibbutz Ma’anit, was alongside Highway 6 and the north/south train line. After doing his due diligence, he travelled to Israel and purchased his first property with that in mind.

Later, to raise capital, he invited seven or eight partners – Jewish guys he knew in Winnipeg – to put their money into Zichron real estate. “They were interested not just in money – they all had money – but in owning a piece of property in Israel. They didn’t do it for the cash, but they all made some money.”

Eventually, he bought out his partners. On one of his trips to Israel, on the night before he was to fly home to Winnipeg, he came across an ad by a real estate agent in Ashdod. He called him and the two developed a rapport. On a subsequent trip, Tennenhouse purchased his first Ashdod property for $92,000, “just to test the waters.” Today, it’s worth $170,000, he said. He acquired a 2,200-square-foot penthouse for $275,000 four years ago. It’s worth more than $500,000 today. Another of his properties earns $1,500 a month in rent from a cellular tower on top.

“Ashdod is red hot,” Tennenhouse said. “It’s developing as a city. It has a great beach, they’re developing the infrastructure, Russian and Ethiopian immigrants are moving there and they need homes.”

But isn’t Ashdod close to Gaza, he’s asked.

“What isn’t close to Gaza?” Tennenhouse replied. “If it’s not close to Gaza, then it’s close to Lebanon. If it’s not close to Lebanon, its next to the West Bank.”

Ashkelon, even closer to Gaza, is likewise developing a strong real estate market, he said. He’s building a semi-detached “flat” there, in effect riding the coattails of his real estate agent and friend, Roni Sharon, whose family is in the development business and is constructing the units.

In Israel, personal relationships are vital, Tennenhouse said. Not only do you have to know the market, you have to know the right people who in turn know other right people and are able to navigate the bureaucracy and obtain all necessary permits and financing.

After having a bad experience with one of the big name Israeli financial institutions, his lawyer connected him to the Bank of Jerusalem, which provided the funding for his forays into the market. In Israel,  you’re required to put down 30 per cent cash on residential properties and 40 per cent on commercial. “They didn’t restrict me in getting new properties,” he said.

All the properties are rented and that income pays the mortgages, he said. Ashdod is so hot, he added, “when a tenant leaves, I can rent it out within 24 hours.”

Recently, Tennenhouse teamed with Annabelle Almagor to establish Habitat, a boutique real estate company. In addition to employing a number of agents involved in buying and selling properties, the company is marketing his Jaffa project. It’s also involved in developing and marketing one particularly large deal, a $100-million luxury apartment project.

Almagor is well connected in Israel, he said. She once served as executive assistant to President Shimon Peres, her father was influential in the Labor party and security agencies, and she grew up knowing many prominent Israeli figures. Her father established a settlement in Sinai, where her brother was born – the first Jewish baby born there in 2,000 years.

Tennenhouse, who visits Israel three or four times a year but calls there every day or two, said the success of his law practice has given him the wherewithal to invest in Israeli real estate. A big part of his practice is representing First Nations clients who received compensation for the abuse they suffered in the residential schools scandal. His clients benefited from the $2.9 billion (Cdn) compensation fund set up for them and his fees have pretty much gone into real estate.

“The Natives have become the greatest Zionists in the world,” he quipped.

As for himself. “Once I retire, [real estate] will be my income-producing vehicle and more importantly, I love it. It’s fun,” he said.

“It’s fun to create something from nothing and to meet interesting people.”