A smiling sandy-haired toddler hung from his mother’s hip as he dipped his hand into a colorfully decorated box to pull out a hot pink card. “This one,” he said cheerfully as he handed off his selection to Chilmarker Todd Christy.

Mr. Christy glanced at the card. “Four Beech Grove,” he said.

The boy’s was just one in a sea of smiling faces, but none were brighter than his mother, Jennifer Wlodyka’s, as she heard Mr. Christy call out her new address to the crowd.

Mrs. Wlodyka and her husband, Lev Wlodyka, were the lucky recipients of one of six resident home sites in the Middle Line Road affordable housing complex, in a lottery held during the Chilmark selectmen’s meeting Tuesday night. The journey has been long and winding for the first town-owned affordable housing project, but after years of roadblocks and speed bumps, success now seems close enough to touch.

“It’s been what, six years? Nine?” said selectman J.B. Riggs Parker. “I’m trying to remember when the first date was when we got into this. It started many, many years ago . . . Now I guess we get on with it,” said Mr. Parker.

Chilmark resident Cameron Parry was the first winner to be announced, qualifying automatically for a lot under conditions set by the Martha’s Vineyard Commission designating the first two sites for applicants with income levels of 100 per cent or less of the Dukes County median income, with preference given to Chilmark residents. Mr. Parry was followed by Jennifer Slossberg, who was the only other applicant whose income fell below the median income. This qualified her for a home despite the fact that she has not been an Island resident for five consecutive years in her life — the minimum to be considered as an Island preference.

The other winners, all with income levels of 150 per cent or less of the county median income, were the Wlodykas, Matthew Bradley, Jeff and Emily Day, and Michelle and Chip Leonardi. Alternates were also chosen in both income categories in case any of the lottery winners drop out.

Each winner will receive a long-term lease on a one-acre lot in the Middle Line Road complex, off Tabor House Road. They will pay $20,000 up front and be granted the right to build on the lot, though the land itself will be owned by the town.

“What they are is EMT paramedics, policemen, a town accountant, a couple of landscapers, a local fine woodworker, and then a builder,” said Mr. Christy, who works as the executive assistant for the Chilmark housing committee, of the lottery winners this week. He said the town had hoped that the project would come to benefit people who really represented the hard-working, local community. The turnout, he said, was better than they could have imagined.

Emily Day, Chilmark’s newly appointed town accountant, and her husband Jeff, a Chilmark police officer, have been trying for years to secure property on the Vineyard. Tuesday night marked their fourth official lottery. “We’re just happy and grateful and grateful some more,” said Mrs. Day yesterday.

Many of Mrs. Day’s happiest memories have taken place in Chilmark, including Jeff’s proposal and their wedding. They also started a family here — one that is growing out of its current home. “His toys are taking over the house!” she said of her two-year-old son. “We’re going to try to start [building] as soon as we can.”

At the meeting Tuesday, the selectmen also approved the names chosen for the roads in the Middle Line neighborhood. Molly’s Lane, the main road running through the development, will memorialize the late Molly Flender, who was a major player in the early planning for the project. She died in 2005. The other streets will be called Beech Grove, Holly Lane, and Oak Lane.

The project is far from finished — the town hasn’t yet broken ground on the rental-unit portion of the project that will be built alongside the resident home sites. But in another step forward, voters approved a Proposition 2 1/2 override on Tuesday for $2 million in loans and Community Preservation Act money that will fund the rental unit project. The selectmen said they expect to put that construction project out to bid by next month, and start building this spring.

“I never expected it would be this difficult to do an affordable housing project,” said selectman and board chairman Frank M. Fenner Jr. “It’s been a long process and I’m happy to be here tonight.”

In other business Tuesday, selectmen:

• Voted to make cemetery commission superintendent Coco Adams and police officer Sean Slavin permanent employees.

• Voted to bring parking ticket processing in-house rather than outsource it to Plymouth as has been done in the past, at the recommendation of the county parking clerk. Tickets will maintain the same fee structure.

• Agreed to put an article on the annual town meeting warrant to rescind the current compensation plan for seasonal town employees.

• Discussed but took no action on the possibility of requiring town-leased to lots have a liability policy that names the town additionally insured for a minimum of $1 million. Mr. Fenner said the additional cost to the leaseholder would likely be between $150 and $200 per year and would give added protection to all. But Mr. Doty wanted more information. “It hasn’t been explained enough to me,” he said. Selectmen will address the issue again at their Feb. 2 meeting.