Tag Archives: Hillandale Road

Early last century, Michael Calise’s grandparents came to New York from Ischia, a small island near Naples.  They spent summers in Westport, and liked the town so much that in the 1920s they bought a 10-acre farm on Hillandale Road.  The land extended from what is now Cumberland Farms, down to Torno Lumber, and out to what is now the center median of the Post Road.

The cost was $25,000.  The mortgage was 100 percent.

Calise’s grandfather — also named Michael — grew vegetables in an enormous garden, and raised pheasants.  He loved his beautiful trees, and great hedges.

But when the Depression hit, he went back to work.  He opened Westport Fish and Poultry Market across the Saugatuck River, near National Hall.  Later — when Prohibition ended — he added a liquor store.

The bank called the mortgage on the 10-acre farm.  But the highest bid was only $11,000.  He kept the property, and eventually paid off the mortgage.

In the 1950s he sold the corner of his property, on Hillspoint Road, to Gulf, which built a gas station.  He then built a small shopping center, and moved his grocery and liquor stores there — much closer to home.

Michael and his wife, Caterina, maintained the farm until the early 1980s.  They added a barn, but made no changes to the house.   After they died, relatives lived there for more than a decade.  Eventually they died, and the Calise family heirs planned to sell the property.

But they did not want to lose its historic nature.  They searched for a builder who would restore it.  They found Anthony Ialeggio.  He’d done a lot of restorations in town — including the original Masiello homestead on Cross Highway.

The Calises formed a partnership with Ialeggio.  He designed 2 homes, on either side of the original.  One was Italianate; the other a Federal- style Colonial, with a barn and garage.

“He could have divided the property into 4 lots, but then he’d have had to demolish my grandparents’ house,” Calise said.  “He kept them, and now there’s a wonderful streetscape.”

13 Hillandale Road -- the original Calise farmhouse. (Photo by Dave Matlow/WestportNow.com)

The home Ialeggio restored retains the original porches, roof line, even window placements.  Most trees were saved too, including 2 magnificent magnolias.  The current owners — Peter and Stephanie Durette — received a Westport Historic District Preservation Award last fall.

“By restoring the farmhouse, and building 2 new ones in the older vernacular alongside it, it looks like they’ve all been there 100 years,” Calise said.  “It’s not a subdivision street; it’s a period street.”  Other homes on the road — including A.E. Hotchner’s nearby — date from the early 1900s too.

Calise called the project “a lesson for what builders can do.  This could have turned into an 8000-square foot monster, totally out of character for the area.  Instead the houses are attractive, and nicely proportioned.”

Calise — who owns Settlers & Traders Real Estate — knows that bigger homes mean bigger bucks for builders.  Buyers want big homes too — these days, in these parts, 4000 square feet is considered small.  With most buyers paying $280 to $300 per square foot, many builders build big to amortize the cost of land.

But 1 of the 2 new Hillandale homes sold quickly.  The other lagged a bit, because of the overall market.

Calise is delighted that his grandparents’ house has been so handsomely restored — and that now it’s surrounded by equally attractive, and well-proportioned, homes.

“People always stop and stare,” he said.  “They like what they see where my grandparents lived, and up and down the road.”