Tag Archives: Westport Historic District

50-Year History Of Historic District

Bill Ryan moved to Westport 50 years ago this month. Except for 3 years in Paris, he has been here ever since. He and his wife Catherine’s 3 daughters went through the Westport public schools. Two grandsons are in Staples now; 2 small granddaughters enter the school system soon.

Bill spent much of his career with IBM, in corporate finance. He was  also VP of internal audit with AmeriCares, then returned to IBM to run a leadership development program for nearly a decade.

Locally he coached softball, and has been active in the Kings Highway North/Wright Street neighborhood association. (“Blame me for the speed humps or stop signs,” he says.)

Bill is also a member of the Historic District Committee. It’s a natural fit: His first home was in what is now the Gorham Historic District. He’s spent 40 years in the Kings Highway North Historic District — which is celebrating its 50th anniversary.

Bill writes:

“Westport is losing its New England charm. Too many houses are being torn down!”

Sound familiar?

While that refrain has been heard a lot over the past few years, it’s not new. It can be traced back at least to the early 1970s.

But back then a group of Westporters decided to do something about it. They formed a committee to explore establishing a local historic district. They hoped that by doing so, one of Westport’s oldest neighborhoods and many of its older structures could be preserved.

The result of their efforts was the Kings Highway North Historic District, created by an RTM ordinance in 1973. Coincident with the creation of the District, per state law, Westport’s Historic District Commission was established. It too has been functioning for 50 years.

Among the homes in the Kings Highway North Historic District: 104 Kings Highway North …

The committee was headed by the late Sylvia Milberg. It included Jacqueline Heneage who shortly after was elected Westport’s first female 1st Selectman.

Also on the committee was local architect Bob Gault, a scion of the long-time Westport family.

He now lives in Maine. But he remembers well the work the committee put in to see the District come to fruition.

“People were getting tired of seeing so many homes falling to the wrecking ball. Many of us were concerned there would be little of Westport’s history retained. The Kings Highway North area was a natural place to focus.” Gault recalls.

The committee zeroed in on Kings Highwa North and Wright Street. Property on Edge Hill Road, two parcels on Wilton Road and one on Old Hill Road were included, totaling 71 properties in all.

… 45 Kings Highway North …

To be approved, at least 75% of the property owners had to agree. While the measure passed handily, Gault recalls it was not without some cajoling. “Nobody in Town Hall is going to be telling you what color to paint your house!” members said.

As part of the process to justify the area as historic, the committee spent nearly 2 years gathering information and filing reports, before culminating in RTM approval.

This researched events that would fortify the position that the District was of historic significance. For example, many of Westport first settlers owned homes within the District, most of which still stand.

While George Washington may never have slept or dined along Kings Highway North, records show that he traveled along the road more than once. So did other historical figures, such as Lafayette.

The road was the prime east-west route before a bridge was established (where the Ruth Steinkraus Cohen Bridge is now located). The road curved to the north, where fording the river was enabled at the current location of the Kings Highway North Bridge.

In addition, the triangle green at the intersection with Old Hill Road was a military drill ground during the French and Indian War.

… and 6 Edge Hill Road.

In 1998 the Kings Highway North Historic District received the added distinction of being included in the National Register of Historic Homes.

In contrast to other neighborhoods, the streetscape in the District is pretty much what it was like 50 years ago. Trees and shrubs come and go, but structures have endured or been enhanced.

Property improvements and alterations do take place, as is very much in evidence on several properties.

But for changes affecting direct sightline from the street, a Certificate of Appropriateness must be presented to and approved by the HDC. The commission and its administrator work closely with property owners to ensure an efficient and effective resolution, in keeping with the history of the property.

A drive through the District today shows that changes do take place, but with an eye on history.

Even better: a walk through the area.

Kings Highway North Historic District walking tour.

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Historic District Honors Non-Teardowns Of The Day

Westport is a town filled with — and known for — teardowns. Thankfully, some building owners invest time, energy, care, concern — and money — to preserve our history.

Last night at Town Hall, the Westport Historic District Commission honored the men and women who persevere, to preserve.

WHD Preservation Awards went to the owners of 6 private homes, 2 neighborhood restaurants, an office and a church.

Kudos to:

8 Mayflower parkway

Built in 1926, and distinguished by a classically inspired portico, 8 Mayflower Parkway (off Compo Road South) was saved from demolition by David Vynerib, founder and principal of CCO Habitats. His extensive renovation restored the home to its prior glory.

19 SOUNDVIEW DRIVE

The “Stevens Cottage” was built in 1920, and is part of the Compo-Owenoke Historic District. Blanca and Sunil Hirani purchased it in 2020 — just before it was torn down — and then enhanced the entire streetscape of the beach exit road.

21 danbury avenue

Another home in the Compo-Owenoke Historic District, this bungalow was built in 1922 by Gertrude May Allen. It was bought in 2019 by Julie and John Headland, who preserved it in the midst of other teardowns in the area.

35 POST ROAD WEST

Built in 1825, the Davis Taylor House was a single-family residence that evolved into a multi-family dwelling from the 1920s through ’60s. Today the Federal style structure is home to Peter Cadoux Architects, who faithfully restored it as their office.

39 CROSS HIGHWAY

The original house was built in 1772 by Phineas Chapman, a Connecticut Militia lieutenant. It burned in 1877 and was rebuilt by his grandson, Charles Chapman. It remained in the family until 1927, when his last descendant died. It later served as a nursery school. Designated as a local historic property by Deborah Howland and her son Galen Murray in 2018, new owners Amy Gay and Matthew Burrows recently completed an extensive renovation of the property on a very visible road.

71 HILLANDALE ROAD

Green’s Farms Congregational Church was established in 1711, when Westport was part of Fairfield. A meetinghouse was raised near what is now the Sherwood Island Connector commuter parking lot. The church’s 3rd building was constructed in 1853, on Hillandale. It expanded in phases. In 2019 — with the structure needing major renovation — the congregation quickly raised funds to repair the original foundation, restore the steeple and overhaul the organ. Click here for a full story.

161 cross highway

The Masiello family opened Christie’s Country Store in 1926, to sell produce grown on their nearby farm. They gave up farming in the late 1940s, but continued the business and added a gazebo moved from Redding Road. In 1958 the market was enlarged. It has gone through various incarnations — including, briefly, a dry cleaner’s — but longtime owner Tim Purcell renovated it. It now houses the popular Porch @ Christie’s restaurant.

163 CROSS HIGHWAY

This property, built by James Masiello in 1922 for his wife Mary, has been in the family for over 100 years. The Colonia Revival home has been lovingly conserved by Jean Masiello.

222 HILLSPOINT ROAD

Built in 1919, this is the oldest continually operating retail and food store in Westport. Designed as a small market to serve the area around Old Mill Beach, it was known variously as “Old Mill Grocery,” “Kenny’s,” “Elvira’s” and “Joey’s by the Shore.” A year ago, when sale to a residential developer seemed imminent, a group of residents formed the Soundview Empowerment Alliance. They saved it from destruction, renovated it, and turned it once again into a beloved “Old Mill Grocery & Deli.” Click here for a full story.

276 MAIN STREET

The Patrick Rice House (aka the Gray-Coley House and the Lamar Webb House) is one of the finest examples of Italianate style in Westport. Believed to be built in 1869, it is part of the Gorham Avenue Historic District. It has been lovingly maintained by a long history of owners. Current stewards Kristin Schneeman and Ezra Greenberg have meticulously maintained the property since buying it in 2011.

The Historic District Commission is chaired by Grayson Braun. She and Donna Douglass wrote all the narratives for the awards. Bill Harris donated the printing of the programs for the ceremony through his organization, the Army Aviation Associated of America.

The awards were organized by coordinator Donna Douglass; former member and house researcher Bob Weingarten; former chair and current member Bill Harris, who donated the printing of the programs through his Army Aviation Association of America, and HDC members Scott Springer, Wendy Van Wie, Martha Eidman and Elizabeth  Bolognino. 

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Over Hillandale

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.”