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Over the years, I’ve written dozens of stories about teardowns. I’ve warned of the impending demolition of historic homes. I’ve lamented the loss of our classic streetscapes. Just this past Monday, I remembered a visit to a special house on Compo Cove.

But as much as I loved those houses, and mourned their passing, it was always about someone else’s property.

Today I’m writing about mine.

At least, it was mine from the time I was 3 years old, through college. It stayed “mine,” in the sense that my parents continued to own it, for decades after that. My sisters and I continued to visit, for holidays and special occasions (Sue’s wedding! My 50th birthday party!). And of course, to use the pool.

My mother died there — in the bedroom she’d lived in since 1956 — in 2016.

It was not a special house: 2,400 square feet, 4 bedrooms, 3 bathrooms, a basement and patio. It was the 5th house built on High Point Road during the post-war baby boom. Although each home on Westport’s longest cul-de-sac was different, it was just another suburban home.

34 High Point Road

Except, of course, every house is special to those who grew up there.

Like any home, this one has stories. My parents told us their move in. A St. Patrick’s Day blizzard buried the driveway. So my mother and father spent their first night in Westport sleeping not in the bedroom of the first home they owned, but in the back of the moving van.

A neighbor down the street was Rod Serling. He’d been a friend of my father’s at Antioch College (and helped persuade my parents to move not just to Westport, but High Point specifically).

Whenever his in-laws showed up, Rod “escaped” to my parents’ house. Who knows which “Twilight Zone” or “Playhouse 90” shows were written downstairs?

When my youngest sister Laurie was born, my parents turned the attic into my room. It was big, and on its own floor. Years later my mother asked, “Did you feel bad you weren’t near the rest of us?”

“Are you kidding?” I said. “It was right by the front door. I could sneak out at night!”

“You snuck out once?” she wondered, surprised.

“Um — more than once,” I said.

High Point Road was a great place to grow up. Nearly all 70 houses were filled with kids around my age. We rode bikes, wandered into each other’s houses at will, and played soccer, touch football and baseball at Staples High School, which was in the backyards of the homes across the street.

Our house sat on an acre of hilly land. My mother had a hand in much of the gorgeous landscaping. (I never forgave her for taking down my favorite apple tree.)

Beautiful back yard landscaping.

Perhaps the most unique feature of the house was a large window. I’ve never seen a larger window in any home. It faced east, framing beautiful sunrises, spectacular autumn leaves in the dozens of trees filling the yard, and animal tracks in newly fallen snow.

The view from the large window in fall …

… and winter.

Several months after my mother’s death, my sisters and I sold the house. We thought it would be a teardown then. But the new owner decided to renovate it himself.

It was a good idea. The kitchen needed updating; removing a few walls would create the open floor plan craved by owners today.

For whatever reason, it didn’t work. For 4 years, the house was in a constant state of disrepair. He took down dozens of trees; the lumber sat on the ground.

I drove by every so often, just to look. One day, a former neighbor flagged me down.

“What’s your mother doing to her house?” she asked.

“Well, she died,” I said. “It’s not hers anymore.”

“Oh, thank god,” the woman said. “It looks awful.”

It did.

Last spring, the house was sold again. The new owner — only the 3rd in its history — is a builder.

He had no intention of finishing the renovation. He would build a new house on the property.

Demolition permit

After watching our old home “ruined,” I was ready for the decision.

I knew that teardowns are part of the Westport real estate lifecycle. I’ve heard about so many, and written about plenty.

But I wasn’t quite ready for my house to be demolished.

I hadn’t realized how many machines would be involved.

I hadn’t thought about how quickly they would reduce wood, concrete and plaster — or, more personally, a roof, walls, floors, rooms, and (more romantically) memories — to (literally) dust.

I hadn’t imagined seeing only the foundation remaining. Then the next day, it too was gone.

After the first day, only the foundation remained.

I did not know that the swimming pool would be filled with detritus. Or that even more trees would be pulverized, exposing the home behind that had been shielded for so long. Or that the topography would be altered so much, so quickly, that I could barely recognize the land.

The front yard.

I did not think that things would change so dramatically — in less than a week — that the only thing left was the mailbox, and an outside light fixture.

(All photos/Dan Woog)

Yet that’s what happened. It’s the same thing that’s happened to countless Westporters. This time though, it happened to me.

34 High Point Road has joined the long list of local teardowns. Soon — within weeks, maybe — a new home will rise somewhere on the newly leveled land.

It will be bigger than “my” house. In many ways, it may be “nicer.”

I’ll try to refrain from making a value judgment. I probably won’t succeed.

I am sure of this: I hope the new residents will love it, like my family did. I hope they live there — like my mother did — for 60 wonderful years.

But I won’t hold my breath.