Dylan Benson
Candidate for:
Ward 2 Councilor
What do you see as the biggest housing problems in Gloucester; whom do they affect; and what would you do to rectify these problems?
We also need to ensure that our older adult population can age in place with dignity, in housing that meets their needs and allows them to remain part of the community they helped build. At the same time, we must prioritize housing that supports our current workforce—and expands opportunities for new workers to live here as well.
This kind of workforce housing is essential not only for sustaining our local businesses on Main Street and beyond, but also for attracting new businesses that want to invest in Gloucester. If we want to grow our economy in a smart, sustainable, and inclusive way, we need housing policies that serve everyone—from lifelong residents to young families to potential newcomers.
Building a Gloucester that works for all of us means making thoughtful choices now, so the city remains vibrant, diverse, and economically resilient for generations to come.
How do you define affordable housing and workforce housing and whom do you see as needing them?
In the City of Gloucester, a worker must earn over $24 per hour, working full-time year-round, just to afford a modest two-bedroom rental without being cost-burdened. Affordable housing is generally defined as spending no more than 30% of one’s monthly income on housing costs, yet many working-class individuals in Gloucester are struggling to meet this standard. Too often, they face impossible choices—between paying rent and putting food on the table. These hardworking members of our community are frequently overlooked, and their needs urgently demand attention.
To tackle this challenge, Gloucester must pursue a collaborative, multi-faceted approach. This includes the development of mixed-income housing that serves a range of residents, partnerships with nonprofit organizations to expand rental assistance and supportive services, and strong advocacy for local and state policies that prioritize affordable housing.
By implementing these strategies, Gloucester can better support its workforce, preserve community diversity, and build a more inclusive city where everyone has the opportunity to thrive and call home.
What are you hearing from businesses and employers about their ability to hire or retain workers given the current housing situation?
What I’m hearing from both employers and employees is the same—and it’s worrying. Lots of local businesses tell me they can’t find or keep workers because so many people who work here don’t actually live here. The cost to own or rent, plus the lack of available housing, means workers are forced to live in other towns. That hurts not just our workforce, but the whole community.
I’ve also talked to parents worried about whether their kids will be able to build a life here, and seniors who want to age in place but aren’t sure they can afford to stay. I’ve heard from Ward 2 residents who say it’s really tough to both live and work in their own neighborhood because of housing problems. And young people keep telling me that owning a home in Gloucester feels like it’s slipping further away.
All of this tells me we have to step up and do everything we can to make affordable homeownership a reality. This isn’t just about housing—it’s about making sure families can thrive, businesses can grow, and Gloucester stays a place people want to call home for years to come.
Do you think new housing development is being shared fairly across all neighborhoods in Gloucester? If not, where is it lacking, and how can the City address this inequity?
No, from what I’m hearing from constituents, housing development isn’t being shared fairly across Gloucester. Right now, most new development is happening downtown, and that feels unfair to a lot of people. It’s important that we support housing growth beyond just the center of downtown.
I hope we can address this inequity by encouraging more housing in other neighborhoods and wards—not just concentrated in one area. That means supporting affordable homeownership and rental options citywide, so every part of Gloucester shares in this growth fairly. We need to make sure all neighborhoods have a fair chance to benefit from new housing opportunities.
What specific steps will you take to increase the supply of affordable and workforce housing in Gloucester, especially for local workers and young people and young families?
To increase affordable and workforce housing in Gloucester—especially for our local workers, young people, and families—I’ll push for clear, practical steps that actually get results. First, we need to expand mixed-income developments and support projects that include units affordable to people who work here but can’t afford to buy or rent in the current market.
I can support and encourage greater partnerships with nonprofits and housing advocates to increase rental assistance and create more pathways to homeownership. We also have to update and improve city policies to make it easier, not harder, to build affordable housing while protecting the character of our neighborhoods.
Most importantly, I’ll make sure the community’s voice is part of every step—from planning to construction—so the solutions we create truly fit Gloucester’s needs. This isn’t about empty promises; it’s about real action that keeps our city diverse, vibrant, and affordable for everyone who calls it home.
Now that Massachusetts has legalized Accessory Dwelling Units (ADUs) by right in all residential areas, what proactive or incentivizing steps can the City take to encourage their development as part of Gloucester’s broader housing strategy?
Now that Massachusetts has made Accessory Dwelling Units (ADUs) allowed by right in all residential areas, Gloucester should take steps to encourage people to build them as part of our overall housing plan. We need to keep letting folks know this is an option, and also take a close look at our local rules to see if we can make some changes that make building ADUs easier and more attractive.
ADUs are a great tool. I know a lot of families living in multigenerational homes who see ADUs as a way to help grandparents and parents age in place. They also help the “sandwich generation” manage the high costs of housing older family members while still caring for their kids. Plus, having grandparents close by helps with childcare, which is a big help for families.
Encouraging ADUs the right way gives us more affordable housing options while keeping families close and helping Gloucester stay a community where people can live through every stage of life.
Where do you stand on two or three family homes across all neighborhoods to meet the housing needs of the average Gloucester family and worker?
I’m all for allowing two- and three-family homes across all neighborhoods because it’s a practical way to help workers and families afford to live and thrive here in Gloucester. More housing options like these make a real difference for people trying to stay in the city.
That said, it has to be done in a way that respects the character of the neighborhoods.
Do you generally support building more modest size and clustered housing—such as duplexes, multi-family, townhouses etc.? If so, where in the city do you see opportunities for this kind of housing development?
Yes, I support building modest-sized, clustered housing—like duplexes, multi-family units, and townhouses—provided it fits the community’s needs and respects the character of the neighborhood. In Gloucester, there are a few spots in Ward 2 where this kind of development could be a good fit, but it has to be carefully planned.
Most importantly, any project like this must involve meaningful input from the neighborhood, including renters and abutters, throughout the entire process. It’s essential that the people who live nearby have a real say in what happens in their community, so we create housing solutions that work for everyone.
What specific zoning reforms or other modifications would you advocate to support more housing, including for example, multi-family, accessory dwelling units, and affordable homes? How could permitting and approvals be streamlined while preserving community input and environmental protections? Do you support eliminating or modifying practices like minimum lot sizes or parking requirements?
There are definitely zoning changes that could help support our housing needs here in Gloucester, but any changes need to happen with real neighborhood input. The people in the neighborhoods where these changes would take place must have a voice from start to finish in the process.
I’m open to looking at modifications like minimum lot sizes to allow for more flexible housing options. When it comes to parking requirements, we have to stay mindful of the parking challenges many neighborhoods already face, so any changes there need to be carefully balanced.
What role should the City play in encouraging the redevelopment of underutilized commercial or industrial sites, such as the Shaw’s properties, into housing or mixed-use developments? What incentives could the City offer to support this?
One area the City should definitely look at is underutilized lots—like the Shaw’s property. I’d support changing the zoning there to allow for mixed-use development that includes both commercial and housing.
If this means we can get a grocery store back on that site, it would be a huge win for a neighborhood dealing with a food desert—especially for seniors and folks without easy access to transportation. The City can play a key role by encouraging redevelopment through smart zoning changes and offering incentives that attract responsible developers who will meet community needs.
Would you support a “Tenant Opportunity to Purchase” ordinance, enabling tenants the first right to purchase a building if the owner decides to put it on the market?
Yes, I support a “Tenant Opportunity to Purchase” ordinance. It gives tenants a fair chance to buy their homes, helping protect long-term residents and making homeownership a dream that might otherwise be out of reach for many. This promotes stability and keeps families rooted in Gloucester.
What steps would you take to prevent the displacement of long-term residents and vulnerable populations as housing costs rise? Do you support the Rent Stabilization bill currently before the Legislature? Why or why not?
Yes, I support the Rent Stabilization bill as written because it lets local governments cap annual rent increases—more like limiting hikes to inflation rather than full rent control. This helps protect long-term residents from sudden, unaffordable rent spikes while keeping the market balanced.
Would you consider policies like Real Estate Transfer fees on high-end properties to increase funding for the Affordable Housing Trust? Would you support a Home Rule Petition to establish a small percentage Gloucester transfer fee on real estate transactions over $2 million?
Yes, I see a real estate transfer fee on high-end properties as one tool in the toolbox to help support the affordability crisis. I would support a Home Rule Petition to establish a small transfer fee on transactions over $2 million here in Gloucester to generate funding for our Affordable Housing Trust.
How will you work to keep Gloucester livable and affordable for fishermen, teachers, service workers, young people and families, and seniors—particularly when it comes to housing, transportation, and access to essential services?
To keep Gloucester livable and affordable for fishermen, teachers, service workers, young people, families, and seniors, I’ll focus on practical steps that make a real difference. That means supporting more affordable and workforce housing across all neighborhoods—not just downtown—while making sure new development fits the character of our city.
I’ll also back policies like encouraging accessory dwelling units and modest multi-family homes, so folks have more options to live close to where they work and grew up. At the same time, I want to make sure neighborhoods have a say in the process from start to finish.
When it comes to transportation and essential services, I’ll push for solutions that keep our community connected and make everyday life easier, especially for seniors and families without easy access to transportation. It’s about balancing growth with preserving what makes Gloucester special, so everyone can thrive here for years to come.
Earlier we asked about access to housing for seniors and young people. How will you work to reduce the shortage of affordable housing—particularly for other vulnerable households facing housing insecurity or homelessness? What steps would you take to expand access to supportive housing for people with disabilities, mental health needs, or substance use disorders?
To reduce the shortage of affordable housing for seniors, young people, and vulnerable households facing housing insecurity or homelessness, we need a multi-layered approach. That means backing policies and projects that create more affordable and workforce housing throughout Gloucester, making sure these developments have strong community input and fit the character of our neighborhoods.
At the same time, we must expand access to supportive housing for people with disabilities, mental health needs, or substance use disorders by partnering with nonprofits and service providers who specialize in these areas. The City should prioritize resources and build stronger public-private partnerships to support programs that combine stable housing with the services people need to succeed.
This isn’t just about building homes—it’s about building a community where everyone has a real chance to thrive and live with dignity.
Housing policy intersects with issues like transit, racial equity, climate resilience, and economic sustainability. How can Gloucester’s housing policies advance progress in these areas?
Housing policy connects with transit, racial equity, climate resilience, and economic sustainability in important ways. In Gloucester, we need to keep pushing for expanded CATA routes, especially to help seniors get to places like Market Basket, Shaw’s, and Stop & Shop in East Gloucester. Making it easier for seniors to carry their groceries on the bus is a simple but meaningful change.
We should also work with the MBTA and the state to increase train service, including more express trains to Boston, which would support both housing and economic development by improving access to jobs and opportunities.
On the climate front, our housing and development policies should focus on resilience—building smarter in lower-lying areas vulnerable to flooding and storms. At the same time, we must break down barriers that prevent equitable access to housing, making sure everyone in our community has a fair chance to live and thrive here.
How will you promote the development of energy-efficient, climate-resilient housing in Gloucester to address rising energy costs and climate risks? Do you support requiring all-electric systems in all new construction as part of that effort? Why or why not?
Yes, I support promoting energy-efficient, climate-resilient housing in Gloucester, including requiring all-electric systems in new construction. It’s a key step to address rising energy costs and climate risks.
However, we need to be careful that these requirements don’t unintentionally create barriers that slow or block smart development. Any new housing must also fit the character of our neighborhoods while keeping homes affordable and accessible.