Anna Womack considers her Woodstock housing story a “Cinderella story.” She and her roommate, Kam DelMonte, share a 550-square-foot apartment along with two cats. Though it’s a tight fit, it’s conveniently downtown, walkable to shops and restaurants.

To make the space livable, they’ve creatively designed the interior: a living room reading nook anchored by bookshelves, a cat tree, and Womack’s expansive record and CD collection. Portable shelves cleverly maximize kitchen storage.

“I was a measuring fiend for a while,” laughs Womack, 32.

Womack and DelMonte’s housing journey highlights a larger crisis unfolding across Woodstock and Ulster County, where rents and home prices have soared while wages stagnate. The surge in second-home buyers and short-term rentals has intensified the problem, prompting local officials and nonprofits to pursue new policies, shared-living programs, and community land trusts. At stake is whether workers and long-term residents like Womack and DelMonte can afford to stay in the community. Recently, Ulster County Executive Jen Metzger signed a law offering property tax breaks for homeowners who construct Accessory Dwelling Units (ADUs)—small backyard homes or apartment conversions—provided they’re used for permanent housing instead of vacation rentals. Yet, with pressures intensifying, the community faces an urgent question: Can workers and long-term residents still afford to stay?

Womack and DelMonte describe their apartment as “cozy and comfortable.” Their monthly rent is $1,800, plus utilities, pushing the total beyond $2,000—not including a separate storage unit. Splitting this expense consumes about 30 percent of their respective $50,000 salaries. Womack is an HR manager at Sunflower Market in Woodstock, and DelMonte, 28, is a grocery assistant manager at Adams Fairacre Farms in Kingston. They share subscriptions and meal-prep to manage costs.

“It makes it hard to put things into savings,” Womack said.

“It’s more than one paycheck,” DelMonte said of the monthly rent. 

Despite these challenges, they consider themselves fortunate. Median rent in Woodstock nears $1,700, and the median home value nears $550,000, according to the U.S. Census Bureau. Realtor Sharon Breslau notes one-bedrooms average $1,600–$1,800, while houses on modest lots range between $400,000–$600,000. 

Still, because of the area’s popularity, modestly priced homes are often sold fast. A search for 1 bedroom apartments in Woodstock on the Internet yielded a price range closer to $2,000 per month. And, the trendiness of the area on social media can sometimes make a modest “Catskills” home turn into a viral sensation. 

According to the U.S. Department of Housing and Urban Development, affordable housing should cost no more than 30 percent of a person’s household income. In Ulster County, where the median income is $63,306, that equates to roughly $1,583 per month, according to data from the Ulster County Housing Smart Communities Initiative. Many residents, however, have to exceed this threshold.

For Womack and DelMonte, the search for affordable housing was difficult until they found their current apartment on Zillow and Facebook Marketplace.

“It was a godsend,” Womack said. 

Motivated by her experiences, Womack joined the Woodstock Housing Committee earlier this year and has become an outspoken advocate for finding housing solutions for working folks. The Woodstock Housing Committee was established in 2019 to help align with the goals outlined in the town’s 2018 Comprehensive Plan, in order to focus on community inclusivity, sustainable growth, and environmental stewardship. 

Across Ulster County, residents face similar struggles, juggling roommates, multiple jobs, or leaving the area entirely. With a minimum wage of $15.50 per hour, modest rentals and homeownership remain largely unattainable.

A Hudson Valley Pattern for Progress report found the median price of home sales in Ulster County at $440,000 in 2024, creating a significant gap for families earning the county’s median income. Nearly half of county residents spend over 30 percent of their income on housing. 

In Woodstock, housing pressures intensified during COVID-19, driven by investors and second-home buyers. Local tourism growth further strained housing availability.

“Affordable housing is one of the most critical topics,” said Town Supervisor Bill McKenna. “Our town needs diversity. We need places where everyone can afford the rent or the bills, and without that, a community dies.” Since McKenna came into office in 2017 he said he’s been exploring potential parcels for affordable housing with the idea this was a long-term challenge. “This problem is not going to go away, we’re not going to build something and all of a sudden not have a problem.” 

“Employees of Woodstock cannot afford to live where they work,” added Katherine Tegen, co-chair of the Woodstock Housing Committee.

The committee evaluates and proposes viable and affordable housing solutions for recommendation to the Town Board. Meetings occur monthly on the fourth Wednesday at 5:15 p.m., conducted virtually via Zoom from January through April and in-person at the Great Room, 45 Comeau Drive, during the remaining months.

Currently, Woodstock Commons, a 53-unit complex managed by RUPCO, is the primary affordable housing development. Recognizing the need for additional solutions, the Woodstock Housing Committee hired Fisher Associates in 2024 to study potential affordable-housing sites. A decision is expected by year’s end.

Ulster County Executive Jen Metzger recently signed legislation offering property tax exemptions for homeowners constructing Accessory Dwelling Units (ADUs), provided they’re not short-term rentals. ADUs, or Accessory Dwelling Units, are living units located on the same property as the main house, which can be either attached or detached from the main house. 

“ADUs are a really fantastic way to add housing pretty quickly, it’s probably the quickest way that you can build a house at affordable housing, if the local zoning in the community supports it,” Metzger told The Overlook. Other affordable housing initiatives include the county’s Housing Action Fund, which also includes seed grants for early-stage housing ideas from individuals and organizations.

“We are really trying to address the full gamut of creativity when it comes to housing,” Metzger said. 

Tegen fully supports ADUs, noting they will “increase the community’s housing stock” and doesn’t agree with short-term rentals as a housing solution. 

“Short-term rentals have negatively impacted some neighborhoods with an influx of temporary visitors who do not participate in the Woodstock community and who strain the town’s services,” Tegen said.

Kirk Ritchey, former co-chair of the Woodstock Housing Committee, believes deeper issues have long contributed to the crisis.

“Reasons for the current housing shortage have been occurring for many years,”  Ritchey said. “Some of those causes can be explained and understood, but the cultural resistance to building more homes for year-round residents is not as straightforward and is often misunderstood. Yet the conversation is just now beginning to occur at the leadership level of our state, regional, and local governments. It will take time to produce results.”

Local nonprofits, like RUPCO, offer initiatives to help landlords refurbish units and create new affordable housing opportunities. Additionally, Ritchey founded the Woodstock Housing Alliance, a community land trust initiative designed to secure land for moderate-income housing, insulating it from market pressures.

HomeShare Ulster County, run by the nonprofit Family of Woodstock, is another innovative solution, pairing people needing housing with homeowners offering spare rooms. The program, launched in 2019 and serves the northern part of the county. It has grown increasingly popular, resulting in a growing waiting list.

Janice LaMotta, who manages HomeShare, has her own experience with the local housing crisis. In 2015, she relocated to Woodstock from West Hartford, Connecticut, to accept a position at the Woodstock Artists Association and Museum (WAAM). Through a realtor, she found a cottage in the hamlet of Willow.

She described the home as “idyllic” and “perfect,” with an affordable rent of $1,450 per month. But during the height of the pandemic, LaMotta received a 30-day notice from her landlord, who intended to upgrade the cottage and increase the rent significantly. That summer, she had to move back to Connecticut and live with her daughter. When she returned to the Hudson Valley in the summer of 2021, she rented a cottage in Olivebridge, New York, and later moved to Cold Spring. She briefly considered returning to Woodstock in 2023 but was deterred by the challenging housing market.

“Rents went crazy, and properties were up two to three times, the rental stock was minimal,” she said. 

Now leading HomeShare, LaMotta believes her experience helps her understand and support others facing similar difficulties.

“Even though my background isn’t in housing, I felt I was a victim of the housing crisis and that really sensitized me to the applicants that came into the program,” she said.

HomeShare matches individuals seeking housing with those who have extra space, often facilitating a mutually beneficial exchange of housing for practical assistance or services. Among the program’s 10 active matches, participants range from their 30s to their 80s and come from diverse personal and professional backgrounds—all sharing the urgent need for affordable housing. 

HomeShare’s success includes partnerships like Susan Robertson, 78, and Donna Salvadore, 63, a licensed practical nurse. Robertson offers space in her Mount Tremper cottage, while Salvadore covers utilities and provides companionship. It’s a symbiotic and mutually beneficial living arrangement, that also offers a solution to the housing crisis. 

“It’s a hybrid of caretaking and oversight,” Salvadore said of her responsibilities. “It’s [HomeShare program] so greatly needed, a service like this…nobody’s doing anybody a favor, we’re just bartering.”

For Womack and DelMonte, the fear of rent increases looms large. They’re planning to invest in their apartment with small improvements—paint touch-ups and decorative windchimes. 

“If the rent gets raised, then we’re just going to have to reassess,” Womack said. “I would be back to square one…potentially having to move out of town, which again, I really would rather not do. I really love our apartment and I’m really grateful for it.”

Homeownership remains distant. DelMonte dreams of “a bigger space which is reasonably priced.”

“I don’t think about buying a house because I don’t make enough money,” DelMonte said.

Womack imagines owning a cottage, where she can write poetry and play music. But even then, financial concerns linger:

“Can I afford taxes on that property?” she wondered.

For now, Woodstock’s residents and community leaders continue to innovate, searching for sustainable solutions—bartering, policy changes, nonprofits, and shared-living models—to keep their town vibrant and livable.

Amy Wu is a reporter covering Woodstock and Saugerties. Send correspondence to amy@theoverlooknews.com.