DELIVERING OUR

MISSION

Windham & Windsor Housing Trust

2025 Annual Report

Delivering Our Mission - Cover

DELIVERING OUR

MISSION

Delivering Our Mission - Cover

CONTENTS

A NOTE FROM OUR DIRECTORS
‣ Delivering Our Mission
 
SUZANNE’S STORY
‣ A Fresh Start,
A Growing Community
CANDACE’S STORY
‣ Repairing Home,
Restoring Independence
RUSSELL & SCOTT’S STORY
‣ Finding a Home at
Central and Main

A NOTE FROM OUR DIRECTORS

Another year, another annual report.
What is special, what is fresh, about Windham Windsor Housing Trust?

Dear Housing Trust Friends,

As national priorities ignore the lived realities of rural communities, WWHT continues to meet the moment in very tangible ways. For us, affordability is not just a buzzword. It is at the very core of our work to address the cost-of-living crisis experienced by so many families today.

First and foremost, we are steadfast in our commitment to create permanently affordable homes throughout southeastern Vermont. In 2025, we completed construction on Central & Main in Windsor and welcomed 25 households to their new energy efficient, modern rental homes in the Upper Valley. We also broke ground for the Alice Holway Drive project in Putney. Now 25 households are excited to move into a newly constructed building in the heart of Putney Village. Finally, we successfully permitted and funded Phase I of the Chalet Redevelopment in West Brattleboro which will feature a newly constructed building with 31 rental homes. When all phases are complete, this revitalized parcel will include a total of 70 new homes including 8 affordable homeownership opportunities.

What makes these new communities special is that they will be affordable and well-managed in perpetuity and these homes will not fall prey to the speculative nature of the housing market. They will provide homes for middle- and low-income households with long term affordability protections, laying the groundwork for a stable and thriving life.

Elizabeth Bridgewater, Executive Director
Leo Schiff, Board President

Homes Repaired

WWHT Houses Icon White

%

WWHT is also a key player in addressing the crisis of unsheltered people. In 2025, over 40% of our rental units were leased up to community members who have previous experiences of homelessness.

Our work also addresses the affordability challenge of our aging housing stock. Through our Green Mountain Home Repair Program, Vermonters have access to low-cost loans and grants to complete health and safety upgrades to their homes, repairs that they otherwise could not afford. And through our continued administration of the Vermont Home Improvement Program, we are helping private property owners bring rental homes back online, many of which were in significant disrepair and not fit for occupancy. Fixing up homes, whether owner occupied or to prepare them for a renter, is a win for everyone involved because it is a cost-effective way to preserve existing homes in our community and improves the quality of life for those who live in them.

The cost-of-living crisis isn’t exclusively about housing costs. Vermont and the nation suffer from income inequality, under-investment in public resources, a confusing and hard-to-access health care system and a frayed social safety net. All of these variables can affect affordability in other areas of one’s life. To help address this, WWHT provides services through our SASH and SASH for All Programs and our in-house staff support our residents in gaining access to community resources that will allow for successful tenancy and improved health outcomes. 

We are proud of the work of our team to create permanently affordable homes and to support the residents who live in them. Read more about the direct impact of these programs in this report. We couldn’t do this work without the support of institutional and individual donors in our community supporters.  Thank you for your partnership in helping Southeastern Vermont thrive!

 

With gratitude,

Elizabeth Bridgewater
Executive Director

Leo Schiff
Board President

A NOTE FROM OUR DIRECTORS

Another year, another annual report.
What is special, what is fresh, about Windham Windsor Housing Trust?

Dear Housing Trust Friends,

As national priorities ignore the lived realities of rural communities, WWHT continues to meet the moment in very tangible ways. For us, affordability is not just a buzzword. It is at the very core of our work to address the cost-of-living crisis experienced by so many families today.

First and foremost, we are steadfast in our commitment to create permanently affordable homes throughout southeastern Vermont. In 2025, we completed construction on Central & Main in Windsor and welcomed 25 households to their new energy efficient, modern rental homes in the Upper Valley. We also broke ground for the Alice Holway Drive project in Putney. Now 25 households are excited to move into a newly constructed building in the heart of Putney Village. Finally, we successfully permitted and funded Phase I of the Chalet Redevelopment in West Brattleboro which will feature a newly constructed building with 31 rental homes. When all phases are complete, this revitalized parcel will include a total of 70 new homes including 8 affordable homeownership opportunities.

What makes these new communities special is that they will be affordable and well-managed in perpetuity and these homes will not fall prey to the speculative nature of the housing market. They will provide homes for middle- and low-income households with long term affordability protections, laying the groundwork for a stable and thriving life.

Our work also addresses the affordability challenge of our aging housing stock. Through our Green Mountain Home Repair Program, Vermonters have access to low-cost loans and grants to complete health and safety upgrades to their homes, repairs that they otherwise could not afford. And through our continued administration of the Vermont Home Improvement Program, we are helping private property owners bring rental homes back online, many of which were in significant disrepair and not fit for occupancy. Fixing up homes, whether owner occupied or to prepare them for a renter, is a win for everyone involved because it is a cost-effective way to preserve existing homes in our community and improves the quality of life for those who live in them.

The cost-of-living crisis isn’t exclusively about housing costs. Vermont and the nation suffer from income inequality, under-investment in public resources, a confusing and hard-to-access health care system and a frayed social safety net. All of these variables can affect affordability in other areas of one’s life. To help address this, WWHT provides services through our SASH and SASH for All Programs and our in-house staff support our residents in gaining access to community resources that will allow for successful tenancy and improved health outcomes. 

We are proud of the work of our team to create permanently affordable homes and to support the residents who live in them. Read more about the direct impact of these programs in this report. We couldn’t do this work without the support of institutional and individual donors in our community supporters.  Thank you for your partnership in helping Southeastern Vermont thrive!

 

With gratitude,

Elizabeth Bridgewater
Executive Director

Leo Schiff
Board President

Elizabeth Bridgewater, Executive Director
Leo Schiff, Board President

Homes Repaired

WWHT Houses Icon White

%

WWHT is also a key player in addressing the crisis of unsheltered people. In 2025, over 40% of our rental units were leased up to community members who have previous experiences of homelessness.

SUZANNE’S STORY:

A Fresh Start, A Growing Community

SUZANNE’S STORY:

A Fresh Start,
A Growing Community

Community leader at Windham & Windsor Housing Trust smiling indoors, showcasing engagement in affordable housing initiatives and community development efforts.

Ayear ago, when Suzanne first moved into the Snow Block, it marked the beginning of a hard-earned reset. After decades spent living in a 5-bedroom house on three acres of land in Massachusetts, followed by three years in rural New Hampshire, she arrived in Brattleboro carrying the weight of a deeply personal upheaval. The transition from rural quiet to a downtown apartment was jarring. 

“It was a big, big adjustment,” she admits. “To be honest, I was scared to death. Part of it was coming from a domestic violence situation, but I also wasn’t used to living in a downtown environment.”

Suzanne found support immediately, from both inside and outside her building. “I did express the situation I had just come from,” she says. “There were people on my floor who reached out to me and really went out of their way to help me. And when I mentioned my concerns to the police, I really felt like they kept an eye on me. That really made me feel a lot safer.”

A retired social worker, Suzanne spent her career bringing people together, and it didn’t take long for that instinct to resurface. When the idea of a resident game night surfaced during one of the early Circle meetings, she stepped forward. With support from Joyce on the Housing Trust staff, Suzanne worked through the logistics of building participation: finding a time, encouraging neighbors and keeping things welcoming. Residents from multiple floors began to show up for a variety of games — dice games, dominoes, Uno — with each gathering helping to build community and strengthen connections.

Even as participation dropped off over the winter months, as the spring approaches, Suzanne looks forward to reviving it. “I have hope,”  she says. “It’s still a good idea.”

Suzanne with her ‘guard dog’ — a gift from her kids to help her feel safe.
Suzanne’s optimism extends beyond game night, to the Restorative Justice Circles put on by Interaction, where she has been an enthusiastic participant.

“I love to go,” she says. “And Rachel (the facilitator) is amazing.” She recalls one particularly impactful session that brought together residents, Housing Trust staff, Brattleboro police and community representatives. “Just having that conversation — where tenants could share concerns directly with people who could respond — that was really effective.”

At the same time, she understands why some residents remain skeptical. Trust, she notes, builds slowly, especially in a community that has faced real challenges. “People want to see that something comes out of those meetings,” she says. “Something concrete. And that takes time — but I have faith.”

Suzanne creates miniatures:
this particularly meaningful creation includes
tiny heirlooms worked into the details.

That sense of realism, balanced with optimism, defines Suzanne’s view of Snow Block today. When she first arrived, the environment felt overwhelming and, at times, unsafe. But over the past year, she has seen meaningful change — both in building and in relationships among residents.

“It feels much safer now,” she says. “And what I’ve noticed is that people are starting to know each other. There are little pockets of community forming.”

Looking ahead, Suzanne’s hopes for the Snow Block are straightforward. “I want people to feel safe,” she says. “And I want us to keep building on this idea that we’re all in this together.”

CANDACE’S STORY:

Repairing Home, Restoring Independence

Candace has lived in her modest, two-story Guilford home since 1998. She bought it during a challenging period in her life, when stability and a sense of place mattered most. What she found was a sweet little house full of possibility.

Over the years, that possibility has been realized through persistence, care and the resources of Windham & Windsor Housing Trust — particularly the Green Mountain Home Repair Program. Now 79, Candace reflects on a long journey of maintaining and adapting her home — one that took on new urgency after she experienced a stroke.

“I had to move downstairs,” she explains. “There wasn’t a bedroom, but I did have a half bath.”

Through the Green Mountain Home Repair program, Candace was able to renovate her home for safety and independence. The project transformed her first floor, adding a walk-in shower with grab bars, accessible fixtures, and a washer and dryer — critical upgrades that allow her to live comfortably on one level. Additional work, including insulation improvements and basement upgrades, made the home safer and more energy efficient.

The project was also a testament to collaboration. Program staff helped coordinate funding and logistics, while Candace’s ex-husband, a finish carpenter, and his wife contributed significant labor and materials. “They did an immense amount of work,” says Candace. “And they bought me the washer and dryer. It’s much more accessible now, and is also very pretty. It’s made such a difference.”

For Candace, the impact of the Housing Trust goes far beyond the physical improvements. Having worked with the organization over many years – through homeownership education, earlier repairs, and now this latest renovation – she describes a deep sense of trust and gratitude.

“I got to work with Jerry again, and that was such a blessing, I can’t tell you,” she says. “He is so steadfast, clear, prompt, professional and empathetic. He is a gem. And I’ve worked closely with Tara, too — she is another jewel. They helped find the funds, fulfill the grants, and give me options that would best serve me.”

Candace says the importance of clarity is essential for a process that can be complex and overwhelming for a homeowner.  “There’s just a lot to manage, especially at my age,” she says. “They took the time to explain everything and gave me the courage to move forward.”

Today, Candace’s home stands as a powerful example of what’s possible when thoughtful investment meets personal resilience. More than a repaired house, it is a place where she can continue to live safely and independently.

“This program is allowing me to stay here, in my home, and age in place,” she says. “I feel very fortunate.”

RUSSELL & SCOTT’S STORY:

Finding a Home at Central and Main

Russell and Scott's Story

For Russell and Scott, home is no longer a place of uncertainty — it’s a place of ease, connection and quiet gratitude.

After years in a remote and increasingly unaffordable farmhouse in South Royalton, the two knew they needed a change. At 90, Russell continues his work as a translator and editor, while Scott, 72, lives with lasting complications from a serious back injury that ended his teaching career.

The opportunity to move to Central & Main in Windsor came through Russell’s daughter, who lived across the river in Cornish, and encouraged them to explore the new development. From their first conversations with Stacy at Stewart Property Management, the process was seamless.

“From there, it was smooth sailing,” Russell says. “We’ve been here nine months now, and we are very content.”

Their apartment offers both comfort and functionality, including a small extra room that Russell uses as an office, allowing him to continue a decades-long career translating books on art and working with publishers around the world. Daily life has become much easier. Living in town means close access to shopping, services and healthcare, and even small conveniences, like covered parking in the winter, have made a difference.

“I don’t have to shovel snow anymore,” says Russell. “That is very nice.”

Just as meaningful for them is the sense of community they have found. While residents bring a range of personalities and backgrounds, Russell and Scott have made several good friends in the building.

“We made instantly good friends with the people across the hall. It has been
very helpful.”

Russell says he is especially grateful for the affordability. “I think the mission is wonderful. To have such a lovely apartment at a very reasonable rent — it means everything. My income is quite modest, and I’m very grateful to be here.”

He is equally appreciative of the people who helped make their move possible.

“They’ve been very good to us,” he says of the Housing Trust and property management staff. “It’s been a very positive experience.”

Russell and Scott’s story is a simple one: a move from hardship to comfort, from isolation to connection. At Central & Main, they have found all of that and more — peace of mind, and a place to call home.

Delivering Our Mission - Central and Main
Delivering Our Mission - Central and Main

Delivering Our Mission

The MISSION of Windham & Windsor Housing Trust is to STRENGTHEN the communities of Southeastern Vermont through the DEVELOPMENT and STEWARDSHIP of permanently AFFORDABLE housing, and through ongoing SUPPORT and ADVOCACY for its residents.

Delivering Our Mission

The MISSION of Windham & Windsor Housing Trust is to STRENGTHEN the communities of Southeastern Vermont through the DEVELOPMENT and STEWARDSHIP of permanently AFFORDABLE housing, and through ongoing SUPPORT and ADVOCACY for its residents.

What does it mean to be a mission-driven organization? For Windham & Windsor Housing Trust, it means integrating our mission into every decision, every strategy and every operation. It means measuring success not only in homes built, but in the strength and stability of the communities those homes support. Every project, partnership and program is grounded in a clear purpose: to ensure that people across southeastern Vermont have access to safe, permanently affordable housing. In 2025, that commitment was put into action in significant ways — through new construction, preservation, resident services and advocacy — demonstrating what it means to truly deliver on the mission.

A major milestone came with the opening of Central & Main Apartments in Windsor, adding 25 permanently affordable homes in a walkable downtown neighborhood. The development represents years of planning and partnership, and today provides energy-efficient apartments where residents can live close to jobs, services and community life. For Windsor, the project reflects more than new construction; it represents an investment in the long-term vitality of the town and the people who call it home.

In Putney, the organization broke ground and made significant progress on constructing Alice Holway Drive, a new neighborhood that will bring another 25 homes to the village center. This development will help expand housing choices in a community where affordability challenges have made it increasingly difficult for working families and older residents to remain.

In West Brattleboro, plans for the transformative Chalet Redevelopment advanced significantly during the year as WWHT received key funding and permits to move forward. The project design includes 8 single family homes for homeownership, townhouses for rental opportunities, new multi-family rental buildings and a community space in the iconic chalet building. In all, the Chalet Redevelopment will preserve, retain and create a total of 70 affordable new homes to the region in the multi-phased development.

In Brattleboro, the organization also secured funding to redevelop the historic Holton Home, adaptively repurposing the building into 21 permanently affordable apartments. Chartered in 1892, the Holton Home served generations of older Vermonters as an assisted living residence until a few years ago when the program restructured. WWHT is happy to return this building to permanent housing in the community. The redevelopment will preserve the building’s historic exterior while transforming the interior from 36 small bedrooms into a mix of studios, one-, two- and three-bedroom apartments.

What makes the Holton Home project especially meaningful is its commitment to inclusive housing. Through a partnership with Black Mountain Assisted Family Living, up to five apartments will be set aside for individuals living with developmental disabilities, providing supportive housing within a walkable neighborhood that keeps residents connected to community life. The project has also been recognized as a state priority under Vermont’s Act 186 initiative, which supports community-based housing options for people with intellectual and developmental disabilities.

Arrow right
Alice Holway Drive, Putney
Shared Equity Homeownership Program

WWHT’s work in 2025 also demonstrated the power of reclaiming and repurposing underutilized spaces. In Springfield, a once burned and blighted lot was transformed into a beautiful, energy-efficient Shared Equity home for a local family. Supported by funding from the Vermont Housing and Conservation Board and the Vermont Housing Finance Agency’s Middle-Income Homeownership Development Program, the project resulted in a Zero Energy modular home within walking distance of the high school and downtown amenities. More than a single home, this effort served as a successful pilot—bringing together WWHT’s strengths in new home development, homebuyer support, and stewardship of the Shared Equity program, with additional projects already in the pipeline.

And through its Shared Equity Homeownership Program, WWHT continued helping households achieve stable, affordable homeownership while ensuring these homes remain affordable for generations to come. In addition to the Springfield home that was built, several homes within the program changed hands during the year, creating opportunities for new buyers while preserving long-term affordability. Currently, the program stewards 152 homes across the region. 

Beyond development, WWHT continued to provide critical support to current and prospective homeowners. The Green Mountain Home Repair Program assisted 24 households with low-cost loans for essential repairs, helping residents remain safely in their homes. 93 participants completed the Homebuyer Educational Workshop, and one-to-one counseling supported 32 households in successfully navigating the path to first time homeownership. Through the Vermont Housing Improvement Program (VHIP), 53 units were completed across Windham and Windsor Counties, created in partnership with private property owners to expand the region’s rental housing supply. In 2025, WWHT also launched a new partnership with HomeShare Vermont, further expanding creative housing solutions.

Supporting residents across WWHT’s housing portfolio remained equally central to the mission. While the Windsor SASH program has continued to operate at full capacity, SASH-for-All services in the Brattleboro area – operated in partnership with Brattleboro Housing Partnership — saw notable growth in 2025, reflecting both increased demand and the program’s expanding reach. Like the traditional SASH model that links affordable housing with health services for older adults and people with disabilities, SASH-For-All brings health services and resources to low-income residents of all ages and abilities. By focusing on prevention and early intervention, the program helps residents address health, financial and social challenges before they escalate — strengthening housing stability over the long term.

Arrow right

(Clockwise) Christa tends to her plot at the Putney Landing Gardens, WWHT Staff lends a hand to Green Up Day, Elena and Ellen celebrate NeighborWorks Week, Residents chat with Resident Support Staff at shared meal in Windsor Village, HomeShare VT launches Partnership with WWHT.

(Photos 1–4) Christa tends to her plot at the Putney Landing Gardens, WWHT Staff lends a hand to Green Up Day, Elena and Ellen celebrate NeighborWorks Week, Residents chat with Resident Support Staff at shared meal in Windsor Village, HomeShare VT launches Partnership with WWHT.

In 2025, the program served 188 actively engaged participants — adults and children — by year’s end. A core component of the model is the development of individualized Healthy Living Plans, created in partnership with residents to identify personal goals and improve overall wellbeing. Participation in these plans grew significantly, with 94% of full-benefit participants completing a plan by the end of the year — reflecting deeper engagement and more personalized support. 

Access to care and community resources also expanded meaningfully. Over the course of the year, 75 referrals connected residents to healthcare providers, mental health services, food access programs and legal assistance. Mental health support, identified as one of the most significant needs among participants, became an increasing focus, with on-site services reducing barriers to care and encouraging sustained engagement.

Beyond individual services, SASH-For-All fostered a strong sense of community. The program coordinated more than 157 events and activities, including wellness clinics, resource workshops, and community gatherings that reduced isolation and strengthened connections among residents. Partnerships with local organizations also expanded access to food, healthcare and other essential supports. 

Across WWHT’s self-managed properties, the impact of this work is reflected in the lives being reached. In 2025, 41% of new leases were made to individuals exiting homelessness — demonstrating the organization’s critical role in providing not just housing, but pathways to stability.

Listening to residents also shaped the organization’s work throughout the year. Through ongoing conversations and advocacy, WWHT responded to concerns about safety, wellbeing and community stability. These insights helped guide both operational decisions and broader advocacy efforts.

This work took place during a period of uncertainty surrounding federal housing resources and potential funding reductions. By maintaining strong partnerships and staying focused on its mission, WWHT continued advancing projects and protecting the housing stability of the communities it serves.

From opening new homes to advancing future developments and strengthening resident supports, the work of 2025 reflects a sustained commitment to building stronger communities. Every home created, every resident supported, and every partnership strengthened moves southeastern Vermont closer to a future where everyone has access to a safe, stable and permanently affordable place to live.

Our Donors

Your gift matters for so many reasons.

Ongoing support helps us engage with a broad range of community connection efforts.

Through placemaking work with our new developments, we seek direction from the local community to put shape around functional art that creates a sense of unique place and which encourages connection in our new developments.

In Putney at Alice Holway Drive, we’re rooting these elements directly to this place by gathering stories from community members about Alice Holway, Carol Brown, Eva Mondon, and the Aiken Wildflower Nursery. With the guidance from our community art advisory team, a public facing place-based mural is being crafted. This will tie thematically to the Gathering Table planned for back yard.

These pieces of art are an act of community making and build a sense of belonging. Community matters and your support makes this work possible.

(Left) Concept Sketch Proposal for
Place-Based Art at Alice Holway Drive
by Briony Morrow-Cribbs

Our Donors

Your gift matters for so many reasons.

Ongoing support helps us engage with a broad range of community connection efforts.

(Above) Concept Sketch Proposal for
Place-Based Art at Alice Holway Drive
by Briony Morrow-Cribbs

Through placemaking work with our new developments, we seek direction from the local community to put shape around functional art that creates a sense of unique place and which encourages connection in our new developments.

In Putney at Alice Holway Drive, we’re rooting these elements directly to this place by gathering stories from community members about Alice Holway, Carol Brown, Eva Mondon, and the Aiken Wildflower Nursery. With the guidance from our community art advisory team, a public facing place-based mural is being crafted. This will tie thematically to the Gathering Table planned for back yard.

These pieces of art are an act of community making and build a sense of belonging. Community matters and your support makes this work possible.

Financials

Statement of Activities

REVENUES

WWHT Revenues 2025
EXPENSES

Donations

Individual Donations

Sponsors

For more information, click here to read the complete financial report for the year 2025.

OUR STAFF

Delivering Our Mission

Jennifer Anderson, SASH Nurse
Kenneth Bagster, Maintenance Technician
Molly Bennett, SASH Coordinator
Kayla Bernier-Wright, Homeownership Specialist
Elizabeth Bridgewater, Executive Director
Tara Brown, Lending Manager
Kathryn (Kat) Bushey, Work Order Coordinator
Kim Chewning, Director Property & Asset Management
Jennifer Cravinho, VHIP Administrator
Jeremy (Jerry) Freeman, Jr, Rehab Specialist
Katherine Freyenhagen, HR & Operations Manager
Sandra Garland, Director of Finance
Morgan Gero, Leasing & Revenue Manager
John Green, Maintenance Technician
David Grobe, Rehab Specialist
Tim Herzig, Staff Accountant
Robert Hoffman, Facilities Manager
Dallas Kadlik, Assistant Leasing Agent

Lisa Kuneman, Associate Developer
Elizabeth Lachapelle, Property Manager
Elena Luring, SFA Coordinator
Michael Lynch, Maintenance Supervisor
Marion Major, Outreach & Marketing Coordinator
Ana Mejia, Homeownership Specialist
Peter Paggi, Director Housing Development
Jeremy Paquette, Homeownership Program Coordinator
Susan Rousse, Compliance & Tenant Relations Manager
Kevin Roy, Maintenance Technician
Joyce St Jean, Supportive Services Manager
Zan Sykes, Maintenance Technician
Robert Tormaschy, Front Desk Coordinator
Peter Virchick, VHIP Coordinator
Bruce Whitney, Director Homeownership
Katrina Willette, Accounting & IT Specialist
Kristina Willette, Admin Assistant

OUR BOARD

Leadership Community

Resident Members
Anne Chapman, TREASURER
Samba Diallo
Jean Risman
Ellen Snyder
Dora Urujeni
David Vandervert

Public Service Directors
Carol Buchdahl
Chuck Collins
Patricia Eisenhaur
Cynthia Gubb
Leo Schiff, PRESIDENT
Kayenta Sylvain

General Community Members
Debbie Boyle, SECRETARY
Danny Frehsee
Prudence MacKinney, VICE PRESIDENT
Victor Morrison
Joan Weir

OUR BOARD

Housing Locations and Services

Areas We Serve

Areas We Serve 2025 map

Design: lmwdesign.com | Photography: justinaltman.com and the Windham & Windsor Housing Trust

Design: lmwdesign.com
Photography: justinaltman.com and the Windham & Windsor Housing Trust

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