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Developer in Conn. Dreams of Bridge Over Long Island Sound, More Affordable Housing

Connecticut developer Stephen Shapiro dreams of a bridge over Long Island Sound, connecting Conn. to N.Y. for economic benefits. He also focuses on creating more affordable housing options in the state.

September 22, 2025 - Northeast Edition
CT Insider

Penfield Reef Lighthouse on the Long Island Sound at sunset Fairfield, Conn.
Shutterstock photo
Penfield Reef Lighthouse on the Long Island Sound at sunset Fairfield, Conn.

Stephen Shapiro's name has become synonymous with housing in Connecticut, with around 20 either under development or completed throughout the greater Bridgeport area.

But the Easton developer has a grander vision — one that calls for the creation of a 14-mi.-long bridge spanning Long Island Sound, connecting Connecticut to New York's Long Island. He sees it going from Bridgeport across the water to Sunken Meadow State Parkway just north of Kings Park, N.Y.

"That's my dream," said Shapiro, who has housing projects throughout the area, including Fairfield, Easton, Bristol, Trumbull, Milford and Shelton. "Imagine getting to Ocean Beach [in New York] from here in 45 minutes."

Shapiro is not the first to envision just such a bridge — with a lower level for train service connecting Metro-North to the Long Island Railroad — traversing the Sound. New York officials have commissioned such studies in the past, but Shapiro hopes to spur interest in Connecticut for the project, CT Insider reported Sept. 21.

"It would bring in $8 to $10 billion a year in revenue [and] yes, the initial construction would cause some issues, but the final result would be an economic boon," Shapiro said. "This is not my idea. It is something that should have been done that has never gotten done."

He said such a bridge, with its connection in Bridgeport, would help to revitalize the Park City and bring financial benefit to the Naugatuck Valley and state while alleviating traffic in lower Fairfield County, Conn.

And Shapiro's idea has caught the attention of some Connecticut lawmakers as well.

"A project that can bring in revenue and that will lower taxes, bring jobs and economic growth as well as protect American lives in the event of a natural disaster should be welcomed with open arms," said state Rep. Joe Hoxha, who represents Bristol and Plymouth and is a member of the Naugatuck Valley Council of Governments.

The next step, he told CT Insider, is to make the public aware that such a bridge is possible, followed by bringing in the federal government, which could provide millions in grant dollars to offset costs.

Shapiro said the greatest benefit would be cutting traffic bottlenecks in New York City and Connecticut, specifically Interstate 95 and the Merritt Parkway in Fairfield County, Conn., two of the most congested highway stretches in the country.

In addition, he noted that a $39 bridge toll — less than the cost of the ferry while providing one-fifth the travel time — would pay for construction in 48 years, and this does not consider any other economic benefits.

It also would add a safety component in case Long Island was hit with a hurricane like the Long Island Clipper, a devastating Category 3 storm that slammed the region in 1938 causing widespread damage and deaths.

Shapiro said a Long Island Sound bridge would be a key evacuation route for 8 million people if needed.

"I am always thinking about what's next ... where can I help make this a better place," said Shapiro, who was born in Bridgeport and grew up in Fairfield. "This would be it."

Shapiro Also Wants More Affordable Housing in State

The veteran developer spends the majority of his time creating housing projects throughout the greater Bridgeport area.

Connecticut is in desperate need of accessible, affordable housing, and he said he is answering the call.

Shapiro began his real estate career a couple years after dropping out of Fairfield University when he was 19. He bought his first house at 22 and did his first of more than 100 house flips at 23 before shifting to larger housing developments.

"I kept growing, learning and doing," he said. "I was building new houses, dealing with zoning already. I lived here my whole life. I know the place like the back of my hand. I figured if I am already working with zoning just building a house, why not go for something bigger."

Shapiro currently has 20 developments — either in the building process or completed — in municipalities from Bristol to Fairfield to Milford, and several other towns in between.

According to CT Insider, Shapiro has been most vocal about "middle housing," or multifamily residential developments more moderate in size and scale than towering apartment buildings. His goal is to create more homes like this — sometimes called "workforce housing" — that allows town employees and seniors to have an affordable option.

Shapiro has approved plans in Fairfield (19 units on Stillson Road and 39 units on Congress Street); Bristol (28 units of hospital workforce housing); Monroe (a five-unit single family subdivision); Newtown (an eight-unit single family subdivision); and Stratford (14 units of workforce housing and a five-unit single family subdivision).

In addition, he has pending applications in Fairfield (108 units on Biro Street); Trumbull (48 units on Reservoir Avenue); Shelton (separate plans for Shelton Avenue and Armstrong Road); Milford; and the Easton/Trumbull line on Plum Tree Road.

By teaming up with former Connecticut Speaker of the House Jim Amann, Shapiro has begun to lobby state lawmakers for middle housing incentives at the local level.

This workforce component would allow for town employees, including teachers, police, fire personnel and senior citizens to have first crack at renting units during the first 30 days the development is taking applications.

Shapiro wants middle housing developments to get the same exemptions from local zoning regulations as affordable housing projects under Connecticut's 8-30g, a state statute designed to increase low-cost housing by enacting long-term affordability protections.

The state legislature is considering a bill that would offer grants to public housing authorities for middle housing developments.

"This is not a partisan issue, it's a fact," Shapiro said. "Everyone knows Connecticut is short on housing, and we need to work together for reasonable density developments in reasonably placed areas."

In most cases, the housing he proposes sits near public transportation. Affordable housing also allows people to live where they work.

"The benefits to society are so common sense, I don't get the opposition," he said. "I want to serve the need based on what the climate is, based on what the needs are for society, the economy. But I want to do more than just housing — I want to do what is best for society."

And that next project may be a bridge over the Long Island Sound.


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