New housing program rolls out for first Vineyard family

Madeline Conover and Frank Guido, a young couple with two children, visited Conover’s parents during the COVID pandemic and never left. They decided they wanted to settle on the Vineyard where Conover was born and raised instead of the northwest Massachusetts town they had been living in. 

Since 2020, the couple have started businesses, bought a local gym, and raised their kids.

But one thing they haven’t been able to find is housing of their own. For five years, the family lived in a cottage next to her parent’s house, until they heard about a rental opportunity through a budding program a few months ago. 

This fall, the Conover and Guido family became the first to receive a rental through the new Lease to Locals program in Chilmark, a housing initiative that offers cash incentives to seasonal residents who have a vacant home they’re willing to rent to year-round residents. 

The family moved into a five-bedroom home in Chilmark two weeks ago with all of their belongings, including a grey couch with wide cushions that their five-year-old daughter, Stellaluna and two-year-old son Giovanni lounged on a recent September afternoon. The couple, sitting on an opposite loveseat, described years of apartment searching on the Island that led to winter rental opportunities time and time again. 

“You can find a winter rental pretty easily, but a year-round affordable [one], not so much,” Conover, a clinician and gym owner, said. Their rent is just over $2,000, a far cry from the estimated average of $3,000 for a one-bedroom apartment on the Vineyard. And while it’s just a year for now, they are grateful for the new program.

Lease to Locals was brought to the Island this year by founders Colin Frolich and his wife, Kai. They’ve launched it through their company Placemate Inc. in fifteen other resort towns across the country, and Chilmark was the first on-Island to participate. As of their official start date this August, they’ve seen a wide range in interest — from homeowners to tenants — and Frolich said he’s taking it as a sign the program is working well. 

While not a silver bullet, Lease to Locals is seen by some as a tool that could help the Island with staggering housing inequalities, where more houses are vacant in the offseason than are lived in. 

Through the program, property owners looking to rent their space to a year-round resident for a year are given up to $12,000 as part of the program. For seasonal homeowners who are hesitant to open their space to families or individuals they don’t know well, the initiative helps to match tenants as well as motivates them to find families or individuals they’re comfortable with housing.

According to Frolich, the point of Lease to Locals is to find a creative solution for areas where short-term rentals and seasonal homes are a big part of the local economy. In Chilmark, the program was funded through the town, using money that was repurposed from the Molly Flender Affordable Housing Trust and excise tax. 

“We’ve had seven homeowners reach out so far, interested in the program,” Frolich said of the outreach since their inception in Chilmark. 

The interest in solutions like this one have grown, partly due to pushback against new development in the communities that are facing significant housing crises. 

“This is a housing program that doesn’t require a shovel to go in the ground,” Frolich said. 

As of last week, the town of West Tisbury announced it would be possibly joining Chilmark in initiating the program, though with a different funding model. The town’s affordable housing committee will be bringing the idea to their town meeting in the spring, where voters will decide whether to move forward with the idea. Frolich said he hopes the “Lease to Locals” program eventually becomes an Island-wide project. 

“This program is just getting started,” Frolich said. 

Frolich said banning short-term rentals in an area is a tough sell, but incentivizing year-round rentals is a bit easier for locals and town boards to navigate. The only catch: the financial incentive is for the first year only. After that, it’s up to the homeowner whether they want to continue renting to the year-rounder or stop their involvement altogether. According to Frolich, over half of participants in their programs off-Island usually stick with it. 

After this year, Conover and Guido, in their new, five-bedroom Chilmark rental, are not sure if they’ll be able to stay, so they said they’ll make the most of their time in the house together. The home they’re living in now is off of North Road, and their lease is up next fall. Stellaluna, their daughter, has her own bathroom and bedroom, their son Giovanni has a room of his own, and the parents are enjoying the extra space. 

“Now I have my own, own, own room,” Stellaluna exclaimed excitedly as she jumped up on the couch. 

Guido owns a painting company, called Stella Painting, and is a caretaker for houses across the Island. He and Conover said the amount of empty homes throughout the off-season is staggering, and is even more difficult to see during a struggle to find year-round accommodation. According to the Martha’s Vineyard Commission, more than 60 percent of houses are considered vacant, meaning they are lived in for two months or less out of the year. 

“It’s so sad these houses are just there and not being used,” said Conover. 

As a caretaker of seasonal homes on the Island, Guido cited some familiarity with this dynamic. One of his jobs revolves around him caring for vacant homes while owners are away, which he and Conover said can be difficult to see when they’ve been searching for a year-round rental for so long. Some of those feelings came full-circle when Guido found out about the Lease to Locals program through one of the homeowners he caretakes for. 

“It’s about finding the right people who want to help and work with locals,” Guido said. 

“Let’s do more of it,” Conover added as she smiled at her family.