Housing Trust helped orchestrate one family’s Salisbury homecoming

The Sherwood family, from left, Jase, Bill, Carter and Abby, at their new home in Salisbury. Photo by Debra A. Aleksinas

SALISBURY — The walls are bare and the rooms are not yet fully furnished, but the modest, gray house at 70 East Main Street is a happy home to Bill Sherwood and his three children, ages 4 to 17, thanks to assistance from the nonprofit Salisbury Housing Trust (SHT) and countless others who gave of their time and talent to help the young family return to the community where their ancestors go back generations.
“I always wanted to live in town and previous to this opportunity, I couldn’t afford to live in town,” said Sherwood on a recent Saturday morning two weeks after the housing trust transferred ownership of the renovated, 3-bedroom, two-story home to him for $250,000.
Just one week earlier, the family had spent their first night in their new home. It was SHT’s 16th house to be sold as affordable housing in Salisbury.
“Carter slept in his own room for the first time,” said Sherwood of his youngest child, who is 4. The youngster, taking a break from giving bear hugs to the family’s yellow Lab, Max, talked excitedly about dressing up as his favorite superhero, The Flash, for Halloween, “because he’s fast.”
“I’m having a sleepover tonight,” said Carter, naming all of his friends who would be arriving later that day. The youngster attends pre-school at Salisbury Central School.
“All the people that helped us out who were seen and unseen, it’s really a miracle,” noted Sherwood, who sold his house in North Canaan so that he and his children, Jase, 17, Abby, 15, and Carter, could move closer to his mother after the tragic loss of his wife, Katy, to cancer three years ago.
“It was a tough time. We also lost my dad Robert, who was known to everyone as Bullet, around that same time,” Sherwood recalled of the family’s trying times.
Leo Gafney, Trustee Emeritus of the housing trust, remembered Bullet Sherwood as being deeply committed to the community. He served the Lakeville Hose company for 48 years, was the “informal mayor” of Salisbury and “an amazing guy,” said Gafney.
“If there was anything going on, he was there. If there was an accident, he would direct traffic. If there was a fire, he would help with housing. He even played Santa Claus at the church during the holidays.”
Gafney noted that one of SHT’s main missions is to make affordable homes available to volunteers.
“Getting Bill back to Salisbury fits our model perfectly,” he said, noting that Sherwood has followed in his late father’s footsteps as a volunteer firefighter with the Lakeville Hose Company for 15 years.
In addition, Jase is a junior member of the hose company. The teen, a junior at Oliver Wolcott Technical School, has his sights set on a career as an HVAC technician. He said he wants to give back to the community in the same ways his grandfather and father have.
Abby, who will turn 16 in early February, is a sophomore at Housatonic Valley Regional High School and member of the girls’ volleyball team, which she revealed is enjoying a successful season.
As a bonus, said Gafney, the home is located across the street from a portion of the rail trail leading to the commercial area around LaBonne’s Market, providing easy access for the children to where Sherwood’s mother, Catherine, resides.
Paying it forward
At the same time Sherwood was purchasing the Salisbury home from the housing trust, he needed to find a buyer for his circa-1900, single-family house on Pease Street in North Canaan, which he had purchased in 2013.
That’s when John Harney, president of the Housing Trust and local real estate agent, contacted Melissa Gandolfo of Gandolfo Realty in North Canaan asking if she knew of buyers who would be interested in the property.
“We were searching in the community for a young family that needed an affordable home that was responsible, pre-qualified and ready to go, and we just worked together,” recalled Gandolfo.
She found a “lovely young couple to work with,” who was expecting their first child.
The couple had been renting in Torrington, and the husband was commuting daily to and from work at the White Hart Inn in Salisbury, said Harney.
“Here was another local kid who grew up, went off to college and came back,” only to find that he and his wife were priced out of the real estate market. “That’s where Melissa worked with him and suggested Bill Sherwood’s house,” said Harney.
Sherwood suggested a price of $150,000, which was accepted by the young couple. But to meet FHA loan requirements, the property had to pass a “strict appraisal,” Harney explained.
That meant all hands on deck, as family and friends, including Sherwood, spent several weeks in July and August making repairs and demolishing an old barn on the site.
“They were all over the house. There were people over people putting down floors, painting and spackling every room, installing a new deck,” recalled Harney, who compared it to an old-fashioned barn-raising.
Housing Trust board member Ryan Cooper, owner of Tri State Landscaping and Property Management LLC, lent Sherwood his excavator to tear down the barn and repair the grounds.
“When the FHA appraiser arrived, she must have thought she had the wrong address,” said Harney.
Referring to the $150,000 sales price on his North Canaan property, Sherwood said he could have upped the asking price a bit, but “I wasn’t trying to make a couple of bucks, I wanted to help the buyers out. That’s the kind of people we are.”
Sherwood noted that, coincidentally, the purchasers of North Canaan home are his late wife’s brother’s stepchildren, “so that house is kind of still in the family.”
The ties that bind them
The Housing Trust’s Cooper and his landscaping crew were among the dozen or so contractors and businesses who volunteered their time and resources to help with renovations on the home. Little did Cooper know at the time that his childhood friend would become its owner.
“Earlier this year when we began seeking applicants, I was excited to hear of Bill’s interest to come back to Salisbury,” Cooper explained. “I thought this would be a fresh start for Bill and family following the loss of his lovely wife, and great for our volunteer fire department, which Bill is very active on.”
“SHT couldn’t have selected a better family for this home,” said Cooper, “and I hope it brings Bill and his family some much needed positivity and new beginnings. It makes all the hard work my team and I put into it that much better knowing a lifelong friend has taken the keys.”
Sherwood had also been an employee of Cooper’s landscaping company before landing his current property management job at Harris Farm, a 1,000-acre, private estate on Smith Hill in Salisbury managed by Don Stevens, a well-known woodcarver.
The father of three pointed to a delicate, hand-carved wood duck which occupies a place of honor on the fireplace mantle along with his late grandfather’s military flag.
“Don also presented our family with a hand-carved cardinal when my wife passed away,” he noted.
Gandolfo said she was thrilled by the circle of friendships from both communities that helped two young families obtain affordable homes.
Housing Trust board member Judy Gafney asked that homeowners with smaller houses who are looking to sell contact the Salisbury Housing Trust before putting them on the market.
“Come and sit down and talk to us. We may be able to purchase them.”
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PUBLISHER’S NOTICE: Equal Housing Opportunity. All real estate advertised in this newspaper is subject to the Federal Fair Housing Act of 1966 revised March 12, 1989 which makes it illegal to advertise any preference, limitation, or discrimination based on race, color religion, sex, handicap or familial status or national origin or intention to make any such preference, limitation or discrimination. All residential property advertised in the State of Connecticut General Statutes 46a-64c which prohibit the making, printing or publishing or causing to be made, printed or published any notice, statement or advertisement with respect to the sale or rental of a dwelling that indicates any preference, limitation or discrimination based on race, creed, color, national origin, ancestry, sex, marital status, age, lawful source of income, familial status, physical or mental disability or an intention to make any such preference, limitation or discrimination.

Students dressed in neon lined the soccer field for senior night under the lights on Thursday, Oct. 16. The game against Lakeview was the last in a series of competitions Thursday night in celebration of Homecoming 2025.
As homecoming week reaches its end and fall sports finish out the season, an air of school spirit and student participation seems to be on the rise across Housatonic Valley Regional High School.
But what can be attributed to this sudden peak of student interest? That’s largely due to SGA. Also known as the Student Government Association, SGA has dedicated itself to creating events to bring the entire student body together. This year, they decided to change some traditions.
Spirit week from Oct. 14-17 was unlike those of the previous years. From wearing Housatonic merch to Boomer vs Baby day, this year’s spirit week held a little friendly competition to see which grade could participate the most.
“I think that students are bored of the same old activities and events, so it’s good to switch things up even slightly to incentivize interest within students,” said SGA president and senior Mollie Ford. “Plus the point system is super beneficial because it gives students a reason to participate.”
The school spirit sentiment can be seen outside of just the school. Senior Simon Markow is known for his photography throughout the community, and has dedicated time to help Housy sports teams’ social media posts.
“Since I’ve started photography, I think school attendance [at sports games] has gone up,” Markow said. “I feel this year, students will be more aware of games and are more likely to be at the games.”
Whether it’s a pink-out volleyball game or an under the lights soccer match, it’s likely you’ll see some familiar faces.
Social media has played a large role in this over the years. Almost every student organization at Housatonic has an Instagram account, and it’s helped reach students more efficiently than a poster or email would.
“The increase of social media use, with the help from me but as well as the teams themselves has definitely increased student interest,” Markow said. “With Housy teams posting more about their upcoming games, and my help showing the cool goals, spikes, or touchdowns, it’s enlightened students to watch the games themselves.”
In a small school, promoting pride has proven to be a challenge. But this year’s senior class has made some adjustments in the hopes to change that.
“The SGA community has spent the last few years really focusing on student participation, because we think it’s the students who contribute to a better climate,” Ford said. While Housatonic’s student body may be small in size, it seems they certainly aren’t small in spirit.
The weekend of Homecoming at HVRHS was packed with events including rival games under the lights, senior night, and a new take on Homecoming that moves it outside — and it wouldn’t have been possible without the students of Housatonic.
Orchestrating was no easy feat, especially considering much of the work was left up to the students.
Historically, HVRHS has hosted night games for boys and girls soccer and the GNH football team, but when members of the soccer team asked the athletic director, Anne MacNeil, she left it up to the students to acquire the lights necessary to host a night game.
“I said, ‘Hey, if you can find the lights, we can make it happen,’” MacNeil said. “I usually take control of it, but I really wanted to have the teams have the initiative and take responsibility for it. I think by having them do that, they have a lot more invested in it.”
Finding lights for the game was a challenge in and of itself, and it fell on the students, parents, and alumni to come together if there was to be a night game at all.
Luckily for the players, Patricia and Dino Labbadia, parents of senior Anthony Labaddia, were able to amass the support of the community and get all the necessary equipment donated for the night game.
“We’re fortunate with our communities. Our parents know people in communities and they were able to ask… [and] find the resources,” MacNeil said. “We’ve got a great senior group and senior parent group who have really taken charge … and really made the whole season possible.”
In the end, the night came together spectacularly, and the senior ceremonies, rivalry games, and nighttime fixtures made for a memorable night on the day before Homecoming.
The action began at 4 p.m. Thursday, when the JV Girls Volleyball team played rivals Lakeview High School at home.
At 4:30, the middle school boys soccer team as well as the cross country team faced Northwestern at Housatonic’s lower field and cross country course respectively. Also at 4:30, the JV boys soccer team took on rival Lakeview at Housatonic’s upper field.
At 5:15, the girls varsity volleyball team honored their seniors at Housatonic’s Senior Night ceremony, including captains Katie Crane and Victoria Brooks, before an intense match against Lakeview.
At 6:15, the boys varsity soccer team honored their seniors, including captains Everet Belancik and Abram Kirshner, before kicking off under the lights at Housatonic’s upper field against the Bobcats.
Friday night changes
Typically, Homecoming is hosted in the cafeteria with a DJ and the entire room open as a dance floor. Dancing is the main event, with a small photo op stationed next to one of the exits.
The typical formal dance filled with LED lights and glitter looked a bit different this year. For the HVRHS 2025 Homecoming, the activities all took place outside. There was a large bonfire for students to hang around, a tented area perfect for dancing, and lawn games to play.
The inspiration for this change comes from the Homecoming hosted during the COVID-19 social distancing restrictions put into place at the time. Senior class President Madison Graney said “Other years passed, graduating classes really enjoyed it and we wanted to give it a try.”
Although the theme of Homecoming remains the same, new tasks came in preparation for the event. Including the Bonfire “adds a whole new component,” Graney said. “[We] have to contact the fire department to ensure that the bonfire is being contained.” Hosting the dance outside also demanded “more preparation the day before … set up the tents and make sure it’s a safe and fun space for everyone to enjoy.”
Opinions about Homecoming’s new look vary amongst the student body, with some excited for change and others comfortable with the familiarity of an inside dance. Alexa Meach, an HVRHS senior, expressed that “Everyone that I’ve talked to’s plan is to get dressed up, take photos, and then change into more comfortable clothes because it’s going to be freezing. I feel like we could have had a different event for the bonfire. I think they could have been two separate events.”
Graney said the change is “A really great way to change up the tradition ... [and] another good way to get to know your peers and your teachers and interact with the student body all at once.”