Searching for a compelling new business venture, two semi-retired city businessmen broadened their real estate portfolios in a burgeoning town on the Pacific coast of Nicaragua.

The owner of the Amsterdam Billiards Club in the East Village, Greg Hunt, and the founder of the Jazz Standard in Murray Hill, James Polsky, scooped up four prime properties in the town of San Juan Del Sur, Nicaragua, including a large mountain.

While in the last five years a slew of Americans, Canadians, and Europeans have jumped to purchase real estate on about 40 miles of pristine Nicaraguan beachfront property that spans north of San Juan del Sur, Messrs. Hunt and Polsky believe they made a prescient investment.

They saw an opportunity in purchasing land on the main drag of San Juan Del Sur. As the only major town on the south Pacific coast of the country, it is a hub for international real estate investors who rely on the town for building materials and ease of transport. Along with a handful of city friends, they have purchased three main street properties that Mr. Hunt says have doubled in value since they were acquired in 2004.

The crown jewel of Mr. Hunt’s investment, however, is the 4-acre mountain property. Majestically jutting out into the pacific and in view of central San Juan Del Sur, Mr. Hunt thinks the pristine beachfront, only a short launch from town, is a prime resort location.

At first, Messrs. Hunt and Polsky were dead set on developing their properties, but in the last few years the reality of owning land about 4,000 miles from Manhattan has tempered their aspirations.

“We’d like to develop the mountain property, but we might be better off flipping it,” Mr. Hunt said.

For Messrs. Hunt and Polsky, the unusual road to the former Sandinista stronghold started in 2002 when they met at their children’s nursery school on the Upper West Side.

“At the time we were both semi-retired, and looking for something to do with our lives,” Mr. Hunt said.

The plan was hatched in 2003 when Mr. Hunt vacationed at a friend’s home in Tamarindo, Costa Rica. A former sleepy fishing village, Tamarindo has flourished into a bonified resort destination with properties selling for millions of dollars. While on the trip, and at the urging of a Costa Rican developer, Mr. Hunt cautiously crossed the border with his wife and two children into Nicaragua to find the same pristine land as in Costa Rica for about a fifth the price.

Mr. Hunt returned to New York, and sold his friend on the investment. “We’d go to each others’ parties and Greg would draw maps of the land we were going to buy on the back of cocktail napkins,” Mr. Polsky said.

It took about a year and six scouting trips to Nicaragua before they closed on more than $2 million in properties. While title issues were a major obstacle, they felt secure in the investment after obtaining title insurance from an American company with offices in Managua, the capital city. And unlike many properties in Costa Rica and Mexico that carry long-term leases, they bought the properties outright.

Although the recent election of the former Sandinista leader, Daniel Ortega, as president has international investors fearful of land reforms, Mr. Ortega has been outspoken about promoting foreign investment in the country.

For Mr. Polsky, a lifetime New Yorker and Yale graduate, the returns on Nicaraguan real estate run twofold. Along with doubling his investment in a few short years, he savors the adventurous aspect of owning land in a place with “seemingly no rules.”

“Coming from the structured world of the Upper West Side, Nicaragua offers something totally untamed,” Mr. Polsky said.