STAMFORD — Gov. Dannel P. Malloy is pulling up stakes in Stamford, placing his Shippan home on the market for $1.5 million, and raising questions about what he has planned in the coming years.

Malloy and his wife Cathy first purchased the structure in 1998, moving it about 100 feet to a half-acre lot at 277 Ocean Drive East and transforming the building from a historic carriage barn into a luxury four-bedroom home where they raised their three sons. While the Malloys vacated the house in 2011 after the governor’s inauguration, filling the space with a renter who paid $8,000 a month, the house has always loomed large in their life.

Reconstructing it back in 1998 and 1999 was a labor of love for the Malloys, who are known as dedicated preservationists. When they purchased the barn, it was still attached to a gardener’s cottage by a second-story breezeway, according to Chuck Jepsen, the neighbor from whom the Malloys purchased the property. Jepsen lives in the nearby “Holiday House,” a Queen-Anne style home built in 1887 by Colonel Woolsley Hopkins, a descendant of Shippan’s forefather Moses Rogers.

“We had always had very formal shingle Colonials,” Cathy Malloy told The Advocate in 1999. “This time we wanted something different.”

And with all the attention paid to the minute details of the home — all the stones from the original foundation pepper the walls and the wainscoting in the great room was preserved from the barn’s original lining — the house came to represent more than just a place to live for the Stamford family. And it has cost the governor much more than the $550,000 mortgage he took out on it.

In 2004, investigators from the chief state’s attorney’s office questioned whether contractors Malloy hired to renovate the barn received preferential treatment in the bidding process for city contracts — a scandal that cost him a gubernatorial nomination for the 2006 election. In August of this year, the property again found itself in the middle of an inquiry into Malloy’s perceived improprieties when it was discovered that a city worker, driving a city truck, was trimming the hedges on the governor’s private property. That incident launched a citywide investigation, and left mud on Malloy’s face.

The home was also the scene of a police search in 2007, where officers found drugs, including cocaine residue, in the governor’s son Ben Malloy’s bedroom.

But despite the skeletons tucked away in the closets — which include an actual skeleton found in the attic of the home when the Malloys first purchased the barn — the home has remained a cherished spot for the family.

In 2011, when the governor and his wife first moved to Hartford, the pair put the home on the market for $1.8 million, while noting that even if the house sold, they planned to keep some kind of residence in Stamford. Unsuccessful, they lowered the price to $1.6 million, but it still didn’t sell.

“Our kids have friends in Stamford and I’m going to be working in Stamford,” Cathy Malloy told The Advocate at the time. “We’re definitely going to keep something in Stamford, but we’re moving because we really think it’s important to be residents of Hartford.”

But she later left her job in Stamford, announcing she was no longer sure whether she and her husband would purchase another house in Stamford if their carriage barn sold. But two years later, with only 14 months left in the governor’s term, and uncertainty about whether he could possibly win a second shot at the state’s highest office, the question arises: Why would the family choose now to shuffle out of Shippan?

“The Malloy luster has worn out, I think,” said Joe Tarzia, who is Malloy’s former nemesis in Stamford politics. “Obviously Tong didn’t do well in his mayoral campaign, and he was Malloy’s chosen person.”

But it could just be a good time to re-enter the real estate market with a prize property that flopped when conditions were less than stellar. And the market in the seaside neighborhood is picking up, according to June Rosenthal, a real estate agent with William Pitt Sotheby’s International, who has listed countless houses on the point in her career. The market in the area has not been as strong as usual, she said, likely due to concerns about waterfront or near-water properties in the wake of Superstorm Sandy. But she sees the area bouncing back.

“I think things are getting certainly stronger in Shippan,” she said. “With one house, I went from having no showings for a long time to having three in nine days, and I think the market is certainly gaining ground.”

maggie.gordon@scni.com; 203-964-2229; http://twitter.com/MagEGordon