Apr. 6, 2010--STAMFORD -- The Chesterfield Inn, the last remnant of Stamford's heyday as a resort destination, is up for sale at $2.75 million.

Located at 1404 Shippan Ave., the nine-room hotel is considered the city's only operating historic inn and one of the architectural centerpieces in the quiet enclave of Shippan.

Owned and operated by developer Thomas Rich, the property has been on the market for a little more than a month.

Rich, who also owns the Courtyard by Marriott on Summer Street, declined to comment on the sale. He is also one of the developers of Trump Parc, a luxury condominium tower that opened on Washington Boulevard last year.

In 2008, Rich bought the historic seaside property for $2.34 million after its previous owner, John Ruddy, spent almost three years restoring it.

"I think it's kind of sad," Ruddy said. "I know Tom did a lot of work to try to get the place running as a high-end hotel. But unfortunately, with the economy, he had a tough battle."

At one point, Rich had discussed with city officials the possibility of putting a restaurant inside the inn, according to Robin Stein, Stamford's Land Use Bureau chief. But the plan, which had received opposition from neighbors, was never officially submitted.

The house was originally built in the early 1860s for Benjamin Scofield as part of a 30-acre estate overlooking Long Island Sound.

During the early 1900s, the property was remodeled into a colonial-revival style and served as one of several beach resorts in Shippan. Ruddy's grandmother, Stella Ruddy, ran the inn from 1953 to 2002. In later years, it became a dilapidated boarding house.

Upon taking it over around 2002, Ruddy, who works as a contractor and lives next door, spent $2 million in renovations, installing bathrooms for each room and combining antique furnishings with modern amenities such as wireless Internet access and flat-screen televisions.

After running the Chesterfield as an inn for eight months, Ruddy put it on the market and eventually sold it to Rich, saying he wanted to dedicate his time to home restoration and building.

The renovated nine-room inn has been marketed as an accommodation for business travelers and as a setting for weddings or other special occasions. Rates run from $239 to $259 a night.

On Monday, the rooms were empty. Fay Cortez, a front-desk clerk, said there was an event scheduled that evening and there were several bookings in the coming months. She said spring was a busy season for the inn.

The picturesque sunlit rooms featured paintings and photographs that evoked the area's history. Hanging in the lobby was an early 20th century advertisement for the inn that read, "Every day is Sunday at the Chesterfield."

Despite its history, Martin Nirschel, a real estate agent with Sotheby's International Realty, said the property would be a tough sell.

"The market for quaint New England inns is not all that hot right now, especially in that location," he said.

Although the real estate listing notes the possibility of converting the inn back into a residence, Nirschel said its opulent style does not easily lend itself to being used as a single-family home.

Nonetheless, Nirschel said that its price fared well compared with waterfront properties in Greenwich or Westport.

"It's a very specific buyer that would buy it, but it's a gorgeous place," he said.

Last December, Ruddy was recognized for his work on the Chesterfield with an award from the Home Builders Association of Connecticut.

He said he hopes that the new owner will maintain and keep the building intact.

"It's an amazing piece of architecture for the neighborhood and the city of Stamford," he said.

Staff writer Elizabeth Kim can be reached at [email protected] or 203-964-2265.

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