A Long Island-based family investment group that has invested heavily in downtown Waterbury over the past four years is putting five redevelopment properties on the market as it looks to raise capital for larger acquisitions.
The Mariolis family, which has purchased at least 10 properties in and around downtown Waterbury since 2021, has listed four of those buildings for sale, along with another redevelopment property in Manchester.
John Mariolis said the sales are intended to generate cash as the family shifts its investment strategy.
“These are a little smaller among our asset class, we are trying to consolidate to invest in a bigger property,” Mariolis said.
Natalie Zoef, of New Haven-based Vanguard Private Client Group, is representing the family in the sales.
The Waterbury properties now on the market include:
- 111 Bank St. — The former Tony’s Men’s Shop, a four-story, 11,040-square-foot brick building dating to 1900. The family purchased the property for $190,000 in late 2021 and has since converted the upper floors into eight apartments. It is listed for $1.19 million.
- 158 Grand St. — The former John Bale Bookstore, an 11,592-square-foot, four-story brick building dating to 1900. Purchased for $325,000 in mid-2023, the property has been approved for conversion into 10 apartments above ground-floor retail space. Light demolition and apartment framing have begun. The asking price is $825,000.
- 68 Center St. — A four-story, 14,496-square-foot office-over-retail building purchased for $535,000 in mid-2023. The property is being marketed as an apartment conversion opportunity with an asking price of $850,000.
- 140 Grand St. — A 6,596-square-foot, four-story brick building dating to 1895 with nine apartments above the Grand St. Tavern. The family acquired the property for $350,000 in mid-2023 and is seeking $1.39 million.
The family is also selling the 137-year-old Apel’s Opera House building at 35 Oakland St. in Manchester. The Mariolis family paid $770,000 for the 27,548-square-foot building late last year and announced plans to convert it into 26 apartments.
The five-story brick building originally housed a theater, undertaking parlor and retail showroom. Most recently, it was occupied by a variety of commercial tenants, including a wood pellet supplier.
At the time of the purchase, John Mariolis said he hoped to launch a renovation of up to $3 million this February.
Zoef said the property has full approvals for 22 one-bedroom apartments and four two-bedroom units. The interior has already been demolished and is ready for construction, she said. It is listed for $1.45 million.
Despite the sales, the Mariolis family continues to pursue redevelopment projects in downtown Waterbury.
Working with a partner, the family paid $585,000 in late 2025 for the 23,000-square-foot Exchange Courtyard building at 24-30 Bank St., where plans call for up to 25 apartments. Mariolis said in a recent interview that detailed architectural drawings are now being prepared.
