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.”
Eddie Jacob was recently promoted to Assistant Brokerage Manager for four Litchfield Hills offices of William Pitt Sotheby’s International Realty.
William Pitt Sotheby’s International Realty has appointed Eddie Jacob as Assistant Brokerage Manager for its four Litchfield Hills offices, the company announced on Nov. 19.
In his new role, Jacob will support agents and help oversee operations in the firm’s Kent, Litchfield, Salisbury and Washington Depot brokerages.
He joined the company’s Litchfield office as a sales advisor in 2024 after more than a decade managing high-pressure workflows in the legal services and global translation industries.
Before moving into real estate, Jacob coordinated teams across New York, San Francisco, London and Hawaii, handling rapid-turnaround projects for law firms, federal agencies and international corporations.
“Real estate feels very similar,” said Jacob, who acted as the go-between for clients and linguists during eight deadlines and significant cases. “Buyers, sellers, attorneys and agents are often dealing with stressful situations, and my job is to keep things steady and moving forward.”
“The fast-paced environment I came from taught me how to stay calm, focused and organized—skills that will be instrumental in my new role.”
Jacob, who lives in Morris with his wife, Molly, said he was drawn to real estate as a way to more deeply engage with the Litchfield County community. The couple is expecting their first child this winter.
In Morris, Jacob serves as chairman of the town’s Ordinance Committee and has worked with regional partners, including South Farms, where he helped bring the brokerage on as a supporter of the venue’s summer music series.
He also previously co-managed a boutique entertainment company producing seasonal music events in New York City, an experience that further strengthened his ability to coordinate teams and community-facing programs.
Julie King, brokerage manager for William Pitt Sotheby’s, said Jacob’s promotion reflects his steady rise within the firm.
“Eddie has quickly distinguished himself as a thoughtful collaborator, a trusted resource for his peers and an engaged member of the community,” said King. “His professionalism, adaptability and commitment to supporting others have made him a natural fit for this leadership role.”
Jacob will assist in shaping strategy, strengthening office operations and supporting more than 100 agents across the Litchfield Hills region.
Founded in 1949, William Pitt Sotheby’s International Realty and Julia B. Fee Sotheby’s International Realty manages a $5.1 billion portfolio with more than 1,100 sales associates in 29 brokerages spanning Connecticut, Massachusetts and New York.
Mohawk Mountain was making snow the first week of December. The slopes host practices and meets for the HVRHS ski team.
FALLS VILLAGE — After concluding a successful autumn of athletics, Housatonic Valley Regional High School is set to field teams in five sports this winter.
Basketball
Berkshire League basketball tips off Tuesday, Dec. 14. HVRHS’s girls' and boys' squads will face Nonnewaug High School to start the season. The boys' varsity team is under new leadership this year with the addition of head coach Bobby Chatfield. The boys will be out for revenge in the season opener at Nonnewaug, which knocked HVRHS out of the BL postseason tournament last year.
The girls will be at home Dec. 14 for the first league game of the basketball season. Coach Jake Plitt returns for his fourth season at the helm. Last year, the HVRHS girls were eliminated in the semifinals of the BL tournament by Northwestern Regional High School on their way to repeating as champions.
Hockey
Ice hockey players have joined a co-op team this year with New Milford High School. Two HVRHS athletes will be on the team: Logan Miller and Melanie Rundall.
Games and practices will be held at Canterbury School’s O’Neil Arena. The first official hockey game of the 2025-26 season will be Dec. 17 at home against the Newtown-New Fairfield co-op.
The Housatonic co-op team that was previously led by coach Dean Diamond disbanded after last season due to a player shortage. The New Milford co-op is led by coach Hank Dietter.
Swimming
The HVRHS swim team will begin the season with a road stretch. The first meet will be held Dec. 18 at Shepaug Valley High School, followed by meets at Northwestern and then Lakeview High School. The first home meet for the swim team will be Jan. 14 against Nonnewaug, held at The Hotchkiss School’s pool.
New to the team this year is freshman Phoebe Conklin, who competed at the YMCA National Long Course Swimming Championships in Ocala, Florida, this past summer. Conklin qualified for nationals in the 50-meter freestyle, 100-meter freestyle and 100-meter butterfly. The HVRHS swim team is coached by Jaqueline Rice.
Skiing
The HVRHS ski team practices and competes at Mohawk Mountain ski area in Cornwall. Competition will hit the slopes beginning with a group meet at home Wednesday, Jan. 14.The HVRHS ski team is coached by Bill Gold.
Indoor track
The last winter sport to get underway will be indoor track. Silas Tripp was the lone Mountaineer to sign up for the sport. He will represent HVRHS in meets, but travel with Lakeview athletes to meets. The first scheduled event will be at Bethel the weekend of Feb. 6 to Feb. 8.
A mother bear and her cubs move through a backyard in northwest Connecticut, where residents told DEEP that bear litters are now appearing more frequently.
SHARON — About 40 people filled the Sharon Audubon Center on Wednesday, Dec. 3, to discuss black bears — and most attendees made clear that they welcome the animals’ presence. Even as they traded practical advice on how to keep bears out of garages, porches and trash cans, residents repeatedly emphasized that they want the bears to stay and that the real problem lies with people, not wildlife.
The Connecticut Department of Energy and Environmental Protection (DEEP) convened the meeting as the first in a series of regional Bear Management Listening Sessions, held at a time when Connecticut is increasingly divided over whether the state should authorize a limited bear hunt. Anticipating the potential for heated exchanges, DEEP opened the evening with strict ground rules designed to prevent confrontations: speakers were limited to three minutes, directed to address only the panel of DEEP officials, and warned that interruptions or personal attacks would not be tolerated.
“We really want to hear from you,” said Justin Davis, DEEP’s bureau chief for natural resources, at the meeting. He said that DEEP is preparing a bear management report in early 2026 that evaluates the challenges the state is facing and the strategies going forward dealing with them. He said the report will include feedback from the public generated at the listening sessions. He urged attendees, however, not to turn the meeting into a discussion about whether there should be a hunt or not.
Davis called the return of black bears to Connecticut a “conservation success story,” but one that now comes with challenges. "They're large animals, they're powerful and they can become comfortable being around people--and they're opportunistic, and they love to eat."
DEEP shared data showing that black bears have been reported in nearly every Connecticut town and that conflicts involving trash, bird feeders, livestock and home entries have increased sharply in recent years. The state’s bear population was last estimated at roughly 1,100 to 1,200 animals, a number that DEEP recognizes has grown since the study was conducted in 2012.
Eric Hammering, the office director of Environmental Review & Strategic Initiatives at DEEP, told the attendees that since 2020 there have been 264 reported home entries in 38 municipalities in northwest Connecticut, citing data from the state's State of the Bears report released in March.
A home entry, he said, is defined as an event when a bear actually goes inside a resident's living space.

DEEP officials stressed that bird feeders and unsecured household trash are the two biggest drivers of bear conflicts. They advise residents to remove feeders entirely and keep their garbage inside or in bear-resistant containers. DEEP representatives noted that once a bear discovers food, it is likely to develop habits and return.
Many attendees said they see widespread noncompliance in their neighborhoods — particularly among part-time residents and short-term rental guests who leave trash out for days. Several said they were frustrated that the people causing the problem are often not the ones who attend sessions like this.
As a result, a number of residents called for stronger statewide enforcement, including fines for leaving trash unsecured and penalties for repeated violations. Without consequences, they said, the same households will continue to attract bears and put neighbors at risk. Others described practical steps to reduce bear activity--including the use of secure dumpsters, food composting stations, and the placement of electric fencing around livestock and beehives.
Again and again, residents emphasized that the underlying issue is human behavior. One attendee summarized it succinctly: “There are 3.6 million people in Connecticut and far fewer bears. Human behavior is the problem.”
Lynn Levine, a Litchfield resident who enjoys seeing bears, said common sense steps are the answer. She said that when she first moved to the area, she mistakenly left her garage down open with a 15-pound bag of shelled peanuts inside. "A bear dragged the bag around the side of the garage, sat down and had a teddy bear picnic." She said she learned not to leave the garage door open, especially with food inside.
Not all the stories were lighthearted. An 82-year-old Sharon woman recounted repeated break-ins that left her shaken and facing thousands of dollars in repairs, including a bear walking into her kitchen while she was washing dishes. A veterinarian described livestock attacks, including an alpaca that was mauled and dragged. A farmer said bears caused about $160,000 in crop losses in one year and that cornfields across the region face similar damage.
Several speakers added that DEEP’s limited staffing means local police often end up responding when bears are struck by cars or behaving aggressively.

Cornwall First Selectman Gordon Ridgway, who attended the session, said afterward that he was troubled by how outdated the state’s population data is.
“My biggest personal take-away was surprise — that DEEP doesn’t have a handle on how many bears are here,” he said. “They said they haven’t surveyed them since 2012. How do you make a plan or policy without doing a survey?”
Ridgway said Cornwall has received about 40 bear-related reports this year, including home and vehicle entries and injuries to pets. “People are frightened by intrusions onto their property,” he said. “These are not happy stories.”
He noted that in 2012 -- when the state said it last did its population count -- “a bear was a novelty,” but sightings today are very common. “Today, most people see a bear every week. It’s no longer a novelty — it’s a real issue.”
Ridgway said he supports developing a statewide management plan and wants Connecticut to examine approaches used in other states, including reducing their numbers.
While most attendees at the Dec. 3 session indicated they opposed a hunt, Ridgway said that is not a true reflection of how his constituents in Cornwall view the issue. “If we had a vote, it would be close as to whether there should be a hunting season.”
Only one attendee — a longtime hunter from West Cornwall — advocated for a controlled bear hunt. He argued that the population is “exploding” and that education and bear-proof containers are “a band-aid.” In keeping with DEEP’s rules, other residents did not respond, and the session took place without conflict.
Much of the remaining discussion centered on unsecured trash, short-term rentals, and outdated dumpsters at state parks that residents say train bears to expect human food. Some questioned why the listening session was not better publicized, and Ridgway echoed that concern, saying it should have also been held at the high school to allow more residents to attend.
DEEP collected comment cards at the end of the session. Staff said all feedback will be reviewed as the agency drafts its statewide bear management report.
Rick Osborne, manager of the Kent Transfer Station, deposits the first bag of food scraps into a new organics “smart bin.” HRRA Executive Director Jennifer Heaton-Jones stands at right, with Transfer Station staff member Rob Hayes at left.
KENT — Residents now have access to around-the-clock food-scrap composting thanks to two newly installed organics “smart bins,” unveiled during a ribbon-cutting ceremony Monday morning, Dec. 1.
Rick Osborne, manager of the Kent Transfer Station, placed the first bag of food scraps into the smart bin located at 3 Railroad St. A second bin has been installed outside the Transfer Station gate, allowing 24/7 public access even when the facility is closed.
The initiative is part of a regional effort to expand composting opportunities and reduce the amount of waste sent to state trash facilities. Housatonic Resources Recovery Authority Executive Director Jennifer Heaton-Jones, who attended the ceremony, said the bins demonstrate what small towns can achieve in addressing Connecticut’s broader waste challenges.
“This is proof that even our smallest towns can make a big difference in tackling the waste crisis in our state,” Heaton-Jones said.
Also present at the event was Transfer Station staff member Rob Hayes.