Waterbury Turns Historic School into Housing with Help from State Grants

In the heart of Waterbury, a long-closed Catholic grammar school is poised for a second lifem as housing for working families and hospital staff. The transformation of St. Mary’s School into 80 modern apartments is more than a local real estate story. It’s a case study in how historic preservation, public-private collaboration, and targeted state housing grants can align to revitalize communities across Connecticut.

A Second Life for a Storied Site

St. Mary’s Catholic Grammar School, shuttered in 2018, has sat quietly on its 2.2-acre lot, until now. In 2023, the city acquired the property using federal pandemic relief funds, and now plans to sell it to Kaybar Development Corp. for $1.6 million. The New York–based firm, with deep ties to Waterbury, intends to invest up to $20 million to create 80 apartments, blending adaptive reuse of historic buildings with new construction.

The development plan includes converting the school, convent, and gym into housing while adding green space, a playground, and off-street parking. The units will be a mix of one- to three-bedroom apartments, with the proportion of income-restricted housing tied directly to how much the project receives from a new state housing initiative.

How State Housing Grants Are Driving Innovation

This redevelopment is one of the first major attempts to tap into Connecticut’s new $20 million program to support housing for health-care workers. The grant program offers flexible funding to communities that can demonstrate both housing need and shovel-ready opportunities.

In Waterbury, the proximity of St. Mary’s to St. Mary’s Hospital makes this project a natural fit. According to the developer, both St. Mary’s and Waterbury Hospital confirmed the need for local housing to support staffing retention and recruitment. Depending on how much the state contributes, ranging from $6 million to $16 million, between 50% and 100% of the units could be income-restricted to keep housing affordable.

This model demonstrates how thoughtful planning can turn targeted grants into tangible housing outcomes.

Connecticut’s School-to-Housing Movement

The St. Mary’s project is part of a larger trend: reimagining old schools as new homes. Historic schools offer strong architectural bones, central locations, and deep community roots, making them ideal candidates for adaptive reuse.

Manchester’s former Nathan Hale School is undergoing a similar transformation. In Waterbury itself, the historic Webster School was converted into apartments, showing that this model is not only feasible but desirable. These projects strike a balance between preserving the past and building for the future.

Urban Renewal with Long-Term Benefits

Turning a dormant property into active housing offers cascading benefits. Neighborhood safety and aesthetics improve almost overnight when neglected buildings are restored. Local economies benefit from construction jobs and increased population density that supports small businesses. Most importantly, residents, including essential health-care workers, gain access to stable, nearby housing.

By reducing commute times and housing stress for hospital employees, the city is also improving health care outcomes indirectly, a compelling, if often overlooked, side effect.

A Trusted Developer with Local Roots

Kaybar Development Corp. isn’t new to Waterbury. Its renovation of the historic Brown Building and Odd Fellows Hall helped redefine parts of downtown. That experience, and local credibility, will be critical in turning the St. Mary’s vision into a vibrant residential community.

The company plans to apply for state funding this August, with hopes to close on the property by December. A public hearing is scheduled for August 11, after which the Board of Aldermen will vote on the sale.

A Model for Communities Across Connecticut

The St. Mary’s redevelopment is more than a local success, it’s a template. With the right incentives, partners, and vision, Connecticut’s towns and cities can repurpose dormant landmarks into community assets.

If you're a homeowner, investor, developer, or policymaker wondering how these kinds of projects might work in your neighborhood, this is the moment to act.

Contact us below to explore how you can be part of Connecticut’s next chapter of revitalization, whether it’s buying, selling, investing, or leading community-driven development.

Governor Lamont Veto on Housing Bill Puts CT’s Housing Crisis Back in Local Hands

Connecticut is in the midst of a housing supply crisis, with a shortfall estimated at over 99,000 units statewide. This gap has contributed to rising prices, constrained availability, and growing frustration among renters, buyers, and developers. A recent legislative effort, House Bill 5002, aimed to address these issues by mandating that every town contribute a "fair share" of affordable housing and easing zoning restrictions for multi-family developments. However, the bill was vetoed by Governor Ned Lamont, setting off renewed debate over how the state should tackle its housing challenges.

The Supply Crunch

The numbers tell a clear story: while the national housing supply grew by 9.4% over the last decade, Connecticut saw only a 3.9% increase. The pace of residential building has slowed, with a 10% decline in permit issuance compared to the previous year. This lack of new construction has strained the market, pushing home prices higher and reducing rental availability. These trends impact not only first-time homebuyers and renters but also the broader economic health of the state, as employers struggle to attract and retain workers due to limited housing options.

Why the Bill Was Controversial

House Bill 5002 sought to accelerate housing development by standardizing zoning expectations across municipalities. It proposed minimum thresholds for affordable housing units in each town and reduced requirements for parking and density that often hinder the construction of smaller-scale multi-family homes.

Supporters of the bill argued that it would help break down barriers to housing development and promote more inclusive, transit-accessible communities. Critics, however, viewed the bill as an overreach into local governance. Municipal leaders expressed concern that the mandates could undermine thoughtful community planning and burden towns with one-size-fits-all policies.

Governor Lamont acknowledged the state's housing needs but emphasized the importance of local control, suggesting that towns should lead housing efforts with support and incentives from the state, rather than under strict legislative mandates.

Policy Path Forward

Despite the veto, the conversation around housing reform is far from over. Governor Lamont indicated he is open to a revised version of the bill that balances the need for housing with respect for local autonomy. This opens the door to a potential compromise that may include regional planning frameworks, targeted incentives for compliance, or a phased approach to housing targets.

Stakeholders across the real estate spectrum, developers, municipal officials, housing advocates, and legislators—are likely to be deeply involved in shaping the next proposal. The debate is expected to continue into the next legislative session, as the state grapples with how to align long-term housing goals with community needs.

Implications for Real Estate Stakeholders

For developers and investors, the veto introduces a degree of uncertainty. While some may view the delay in reform as a setback, others might see an opportunity to engage in shaping a more collaborative policy that offers clarity and support for responsible growth.

Homeowners and neighborhood groups may welcome the preservation of local decision-making, but without broader action, affordability challenges may persist. Buyers and renters will continue to feel the squeeze unless the housing supply meaningfully expands.

Connecticut's housing supply crisis remains a pressing issue. Addressing it will require not only bold policy but also careful collaboration among all levels of government and the real estate community. As the state considers its next steps, the focus must remain on solutions that are equitable, effective, and adaptable to the diverse character of its towns and cities.

Need help navigating the shifting real estate landscape? Whether you’re buying, selling, investing, or managing property, contact us below for expert local insight and strategic support.

The Connecticut Bills That Didn’t Make It in 2025

The Connecticut State Capitol in Hartford, where key housing reform bills stalled during the 2025 legislative session.

As Connecticut’s housing crisis deepens, several high-profile efforts to expand tenant protections and reform local zoning laws failed to gain traction during the 2025 legislative session. Despite widespread recognition of the state’s growing housing shortfall—estimated at over 110,000 units—key bills that aimed to address affordability, stability, and accountability ultimately stalled.

Here’s a closer look at the most significant housing-related proposals that didn’t pass, how far they advanced, and the political dynamics that blocked them.

Just-Cause Eviction Protections

At the top of many tenant advocacy agendas was a bill to establish just-cause eviction protections, which would have prohibited landlords from removing tenants without a valid legal reason—such as nonpayment of rent or lease violations.

Progress: The measure was introduced and discussed in both chambers but never advanced to a full vote. Despite strong support from housing advocates, it encountered unified opposition from landlord groups who argued it infringed on property rights and could deter investment in rental housing.

Why it failed: Legislative leaders cited concerns about the bill’s potential to create legal ambiguity and unintended financial consequences. Without a compromise between landlord and tenant stakeholders, the proposal remained stuck in political limbo.

Fair Rent Commissions & Rental Assistance Expansion

Another proposal aimed to boost housing equity by mandating fair rent commissions in every municipality—building on a law that previously required them only in towns with populations over 25,000. The bill also included provisions to expand rental assistance and even pilot mortgage relief for student loan borrowers.

Progress: The bill cleared the Housing Committee but failed to gain further momentum.

Why it failed: Budgetary constraints and concerns about imposing state mandates on small towns without sufficient funding contributed to its downfall. Legislators also faced pushback from municipalities worried about administrative burdens and perceived loss of autonomy.

Affordable Housing Appeals Penalty (HB 6126)

This bill would have added enforcement teeth to the state's long-standing Affordable Housing Appeals Procedure (8-30g) by penalizing municipalities that repeatedly failed to meet housing development benchmarks.

Progress: Though discussed during early session debates, HB 6126 never advanced past the initial committee stage.

Why it failed: The proposal met fierce resistance from local governments and home-rule defenders who argued that state-imposed penalties would be punitive and counterproductive. There were also concerns about how such penalties would be implemented and adjudicated.

Multi-Family Zoning Protection

This bill sought to prevent municipalities from enacting blanket bans on multi-family housing developments, a key strategy to increase housing density and affordability.

Progress: The bill passed the House with a 94–54 vote but was never taken up in the Senate.

Why it failed: Intense pressure from local officials and homeowner groups, combined with legislative caution around zoning mandates, led to its quiet demise.

Mobile Home Resident Protections (HB 5428)

Targeted specifically at mobile home communities, HB 5428 aimed to enhance protections for residents by increasing relocation payments and requiring clearer disclosure of fees.

Progress: The House approved the bill after removing caps on miscellaneous fees, but the Senate did not act on it.

Why it failed: The bill’s scaled-down scope and lack of high-profile sponsorship likely contributed to its low priority in the Senate’s final agenda.

“Towns Take the Lead” Zoning Reform

This comprehensive zoning reform bill would have offered financial incentives to towns that pursued local housing reforms, including allowing mixed-use developments, removing minimum parking mandates, and promoting transit-oriented housing.

Progress: Despite support from housing advocates, the bill was delayed due to a threatened Republican filibuster and ultimately expired before a vote could be held.

Why it failed: The bill’s sweeping nature, combined with political friction and a crowded legislative calendar, made it too heavy a lift for 2025.

What These Failures Reveal

While each of these bills addressed different facets of Connecticut’s housing problem, they shared common obstacles:

• Strong resistance from local governments.

• Legislative reluctance to enforce mandates.

• Political fragmentation between House and Senate leaders.

Notably, many of the bills that failed had substantial public backing and the support of housing experts. Yet, in nearly every case, local control advocates prevailed.

Looking Ahead to 2026

Several of these measures are expected to return next year—possibly with revisions to ease political concerns. Rising public frustration, coupled with stagnant housing growth and affordability challenges, may drive a shift in legislative willingness to tackle structural reforms.

Conclusion

Connecticut’s 2025 legislative session offered no shortage of bold ideas to fix the housing crisis—but most of them never made it to law. As renters struggle, housing advocates regroup, and towns resist change, the battle for affordable, accessible housing is far from over.

Need help navigating Connecticut’s complex housing market? Whether you're renting, buying, selling, or investing, contact us below for expert assistance in finding your next home—or your next opportunity.