By now the contours of the affordable housing dilemma are painfully familiar — soaring real estate values have squeezed middle-class Islanders, forcing them to choose between a shaky rental market or relocating off-Island. In an attempt to move the debate beyond Darwinian free-market economics and glacially-paced town initiatives, Vineyard realtor Jim Feiner is attempting to forge a third path, blending private philanthropy and free-market economics to provide affordable homes for the Island community.

With his lean, tanned face and a trim build shaped by vigorous kayaking and windsurfing, Mr. Feiner, 45, buzzes with the energy that comes from a commitment to a mission. In recent years he has committed personal capital — intellectual, financial and emotional — to finding a way to put Islanders in their own homes. After years of struggle and setbacks, his efforts are beginning to bear fruit.

Mr. Feiner lives year-round in Chilmark with wife Deborah Dunn, an Island teacher, and their son Elijah. His parents, Fred and Carol Feiner, ran the Beach Plum Inn from 1969 to 1984, and as a child he helped out at the inn, doing everything from gardening to cooking. After graduating from New Hampshire College in Manchester (now University of Southern New Hampshire) in 1987 he entered the Vineyard real estate industry in the late 1980s, where he discovered he enjoyed working with clients.

“I really like people,” he says. “Having grown up in the hospitality industry, I think people are fun. It’s challenging, sometimes people are difficult, but overall working with people is a lot of fun.”

Through the real estate market, he got a firsthand glimpse at the impact rising home values were having on the middle class.

“I saw a lot of people who have been living here for a long time bouncing around from place to place, doing the Island shuffle,” he says. “A fair amount of people have left.”

In 2000 he joined Chilimark’s town advisory committee to explore the needs of the town and assess residents’ attitudes toward the issue. The committee worked to create bylaws that would allow owners of four-acre parcels to peel off a one-acre, deed-restricted lot. After sending query letters to every owner of a four-acre lot, the response was muted; there were no takers. This was the start of a familiar pattern — Islanders in favor of the concept of affordable housing, but unwilling to make the steps necessary to make it happen.

“It was interesting to see the lack of support for that program,” he says.

After years of slogging out affordable housing initiatives in Chilmark, Mr. Feiner was dismayed at the lack of concrete progress.

“We had one unit of affordable housing in seven years,” he recalls. “I thought, that’s a lot of work for very little return,”

As he began thinking about other housing options, he saw a three-acre parcel on Dr. Fisher Road in West Tisbury come on the market with a walking path to the school.

“I said, ‘This is a perfect place for families,’” he recalls. He and a future resident purchased the land and worked with a West Tisbury bylaw that allows three units of housing on a three-acre lot, with one house priced at market rate and two perpetually deed-restricted. In all, it took four years to get the necessary permits in place. Along the way Mr. Feiner faced stiff resistance from residents on the road who felt the extra population density would have a detrimental effect on the neighborhood.

“I got a first-hand taste of NIMBY [not in my back yard],” Mr. Feiner says.

When residents declared the property an environmentally sensitive frost bottom, Mr. Feiner was forced to go to the Massachusetts Environmental Protection Agency and pay to have the site surveyed and analyzed. Houses and septic tanks were resited to avoid violations. Despite the setbacks, he persisted with the project.

“My goal was always to try to get people land for the cheapest amount. This is not for profit. We’re not building houses. We’re just creating the opportunity for people.”

So far Mr. Feiner and the market-rate resident have purchased the land outright. The plan is to have the two affordable housing applicants buy their percentage of the property from Mr. Feiner. Mr. Feiner is hoping to subsidize the applicants’ land costs with a blend of private funding and affordable housing grants. Ideally he will see a neutral return on his equity.

“I’m hoping my money will come back,” he says. “I’m not in a financial position to donate money. If I lose a little bit, that’s life, but I would like to see my investment back.”

He brushes off suggestions that he’s put his money where his mouth is to a degree that few other Islanders have been willing to, saying: “I saw this as a very viable opportunity. Our goal was to bring the land cost down low enough so someone could add into it the cost of construction and be below the cap.”

One potential challenge is the difficulty of securing private donations to help get applicants into their new homes.

“A lot’s happened in three years, in terms of the economy and people’s extra cash flow,” he says.

In addition to getting Islanders into homes, Mr. Feiner wants to raise awareness of affordable housing as a critical issue that requires commitment across the Island community rather than lip service.

“Everyone knows we need affordable housing,” he says. “Probably it’s going to go to their friends, but nobody really wants it in their backyards because of some sort of perception of negativity, which I can’t understand.”

Regarding the recalcitrance of the residents on Dr. Fisher road, he muses, “We wouldn’t have had a problem if it was a 3,000, 4,000 square foot house. People would rather see a summer resident than their friends. That doesn’t make any sense to me.”

Despite the roadblocks, he remains undaunted. What keeps him going when frustrations and obstacles mount?

“I like challenges,” he says. “I’m a realist. I think it’s real that you can do these things. I’m not averse to a little bit of confrontation. I don’t think anyone’s going to brand me in a negative way for doing what I’m trying to do. I certainly know I’ve ruffled some feathers, but that’s life.”

Is it realistic to make headway on such a large-scale problem?

“I think it’s doable. I’m not trying to pull a fast punch, do a 40B, there’s no profit motive here. I try to make it as transparent as possible, and hope that people will see it as being a benefit to the community. When you create affordable housing, you’re creating assets for the town.”

By thinking outside the box and working to make affordable housing a reality, he hopes to show others who may have been discouraged by the dearth of past progress that solutions are indeed possible.

“I feel if we have tools out there we can use to create affordable housing, why not use them? By me doing it, I could potentially give hope to other people. It’s about hope. It’s not insurmountable.”

Even as he works to see the West Tisbury project to completion, Mr. Feiner is eyeing a second initiative in Chilmark, CAHO (Chilmark Affordable Housing Opportunity). In this project, donors would contribute funds to purchase the 12-acre Vincent property. After purchase, the property would be subdivided into five lots, three of which would be sold at market rates and two which would be sold at $40,000 as affordable lots. Donors would recoup their donation from the sale of the market-rate lots.

“This is benevolence for free,” Mr. Feiner says, as donors would see their donation returned upon the sale of the full-price properties. Mr. Feiner encourages interested parties to contact him for more information.

“For the Island to continue to be a healthy environment, we need to have a certain amount of security for a diverse population for our community,”