Remembering 34 High Point Road

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.

40 responses to “Remembering 34 High Point Road

  1. I’m so sorry, Dan. I know all these feelings.

  2. Claire Shumofsky

    You write eloquently about feelings I share with you about the first house I lived in in Fairfeild. When it was sold it was totally neglected and then torn down. The replacement to our modest “starter” house looms like a strange on a block filled with other modest homes. These are strange times in so many ways!

  3. the heart break is real – beautifully expressed -so many of us feel this too when we see the demolition of such natural beauty all around us for the sake of the insanity of newer, bigger, better – i think this should be an ongoing subject- remembering who the tear downs were – it is town history – our history XO

  4. Davidson, Jo Ann

    Dan, A sad story, familiar to many of us, and so well written. But the happy memories live on. Thank you.

    • Claire Shumofsky

      Hi Jo Ann,
      Dan’s memories resonated with me as well. Our first house was only a short walk from the second one and it was painful to pass it . Best regards to you from Maryland!
      Claire Shumofsky

  5. I feel ya. Deeply….My parents bought our house in ’61, the year I was born, we bought it in ’98, and I literally think I stay here out of an excess of nostalgia. I am pretty sure it will be a teardown (regardless of provenance(!) We are now one of the smallest houses on the block, (still, way more than we ever needed)… When we go, we’ll have to make sure we never drive down this street again!

  6. Great story! Great memories!

  7. Such a great visual piece Dan, I bet the next family will feel the vibes of the previously happy family that you were as they run around the yard and finger crossed, get the same many years of joy that you and your family did.

  8. Great post Dan! The first house we lived in in Westport – 260 Hillspoint Rd. – was torn down about 40 years ago to make way for the McMansions that are now strung along that section of the road. I hope the current residents, and their kids, have experienced some degree of the pleasure I had growing up in that neighborhood.

  9. You and your sister loved the house and treasured it. But a consolation: you can only truly appreciate something (or someone) when they’re taken away.

  10. Thanks for sharing the story of your family home….’sounds like a great place (and time) to have grown up here in town. While the house at 34 High
    Point will be different, the wonderful memories of your home and childhood shall be yours for time eternal.
    (N.B.: from someone who has been there, twice)

  11. Lynda Bluestein

    Thank you so much for writing this story! Rod Serling your neighbor and family friend? Your post reminded me how sad I was to try to go back to the house of my earliest memories find nothing but a weedy lot.

  12. As you say (very eloquently, of course) “It was not a special house . . it was just another suburban home . . . Except, of course, every house is special to those who grew up there.” So true, it’s not the house itself but rather the memories we associate with it. My childhood home at the end of Woody Lane is a short walk away from yours – using one of the famous cut-through paths in Town – and it too was nothing special, just a builder’s center hall colonial. While it has not been torn down, it’s been substantially improved and both a tennis court and pool has been added; I must say it looks lovely from the google satellite view.

    But it isn’t the house I grew up in; that “not at all special” but special to me house is pretty much gone, physically. But that doesn’t mean my cherished childhood memories from Westport have been harmed or diminished – including trick or treating all of the houses on High Point Rd!

  13. We were looking for a home in Westport a few years before that and didn’t find one. I wish I’d known you then – maybe we could have saved you some heartache as well as your home.

  14. Dan — This post struck a chord for all of us who were so lucky to grow up in Westport, thanks for sharing your story. Lone Pine Lane was our first Westport home. We lived in a 50’s Cape, nothing special, but what I remember best was a warm, tight-knit neighborhood, a huge group of friends and our endless summer adventures. Sports, sleep outs, playing in the woods, wading through Deadman’s Brook. Houses change, are remodeled and expanded, sadly even leveled. Thankfully the life memories they provide can’t be bulldozed. Thanks again for bringing it all back.

  15. Dan, Well said. Your dad was more that my broker, he was a close friend. I remember the many hours we spent talking in his downstairs office and the countless quick visits to straighten out his fax machine problems. Houses, like people, need to be lucky and your house was a lucky and happy one. Mike Turin

  16. Celeste Champagne

    As always, a wonderful tribute to your family beautifully expressed. Change is always difficult and in this case sad. Can’t wait for your memoire, Dan. There is so much to express you need a book!

  17. I’m always unsettled by the speed with which a house can disappear. Every house has a story, and most have many stories that have accumulated over years and decades, sometimes even centuries. The people who have lived their lives there leave parts of themselves behind, and these gathered traces are what gives an old house its character. But when the big machines show up one day in the yard, most of this is substantially gone in a matter of hours. It can feel almost like a murder.

    I realize that some old houses are too decrepit to be worth saving and that some of them were ugly even when they were new. But I can’t help but feel that Westport could be developing in a more organic fashion than it is right now.

    We need our builders, but maybe we’ve allowed them a little too much power?

  18. Nice column, Dan, and touching.

  19. Beautifully written as always. It’s so interesting that as Westport’s houses keep getting bigger, the town’s population has remained virtually the same for 60 years. There must be a LOT of spare bedrooms around town.

  20. Dan,

    Your poignant post reminded me of another house on Highpoint Lane, now lost to all but memories. My very dear friend and mentor Ann Gill and her family, lived at 53 Highpoint Road from the time it was built in the 1950’s until her death a few years ago. It was a classic midcentury gem, unchanged until the day it was demolished. Every detail was an homage to 1950 — design, decor and furnishings. On the many occasions I was a guest at dinner, I could look forward to Ann’s special Waldorf salad — another vestige of days gone by. Now I make it for myself in her memory.
    Sadly, five of the homes that provided a framework to my life —- four here in Westport —- have been plowed under in the name of progress. Those experiences have influenced my commitment to preserve as many of Westport’s historic homes for posterity with preservation easements, thanks to a visionary group of residents, the Planning & Zoning Commission and the Historic District Commission.
    We can’t save every memorable home, nor should we. By preserving what we can, we can save the essence of our history, like the whisper of fragrance that remains in a perfume bottle long after the contents is gone.

    • Hi Gloria. My grandfather, Victor Civkin was the architect for Ann Gill’s house. He designed several houses on High Point including the one I grew up in, also demolished. Dan was not a fan of the design and criticized it publicly on his blog back in 2010. It was a great street to grow up on and trick or treating was always an adventure because of so many home styles.

  21. I loved this story, Dan! Your childhood home may have been razed, but you continue to be a town treasure!

  22. Besides your beautiful story, Dan, the demo pictures bring up the point: Why do all builders destroy all the trees on a new site? Why aren’t even the ones within the setback spared? There oughta be a law.

    • Charlotte Thomas Ciardi

      I remember playing at your house many times with Susie and other Highpoint friends. We used to play school in your basement. Good times. What a great childhood we all had!

      • susan woog wagner

        Hey Charlotte..
        We did have some great times there. Remembering you, Lisa Klein and Heather Fernie!

  23. Tom Duquette, SHS '75

    Dan, you really captured the feelings associated with a Westport “tear down” that you used to know. I spent my first 18 years of life growing up in the same house on Valley Road and long after I moved away on every Westport visit driving by for that bit of nostalgia was a must; so many memories.

    At first witnessing friend’s homes get demolished was depressing enough but nothing really prepares you for the emotional gut punch of seeing your childhood home bulldozed. It’s progress I guess although I still have to drive by and look at the foreign invader now occupying our old lot and reminisce.

  24. Dan, so sorry about your house being “the teardown of the day” because it affects you personally. Your parents were so very kind to let the Barnett family use the pool. The backyard was beautiful and your mom did a great job nurturing the plantings behind the house. Thanks for the memories 34 Highpoint Rd😥

  25. I agree with everyone that you captured the feelings of having you childhood home torn down. My parents were the first owners of our house on Bermuda Rd. It was an “upside down “ house, with the living room and kitchen upstairs in order to see the water. They sold it in 1992, but I drove by every time I returned to Westport. It wasn’t just a house, it was “home.”
    In November of 2009, I made my usual visit. All that was left was the slab it was built on. The equipment and dumpster were still there. I think it would have been easier to see the new house (yet another McMansion on too small a lot), than to arrive just as it had been demolished.
    I felt like I’d been punched in the stomach. And I cried, of course. I don’t make it back to Westport very often anymore. However, I sure do miss the Westport I grew up in! And I still miss driving by “my” home.


    Our beloved home was bulldozed as well. It’s a life changing experience. My heart goes out to you.

  27. Dear Dan,
    When you move and leave a house, bulldozed or not it leaves many wonderful memories behind. It feels sad but the positive side of this is that you were lucky to have had such a positive time there. Keep the memories alive within you! Thanks for sharing.
    Pam Kesselman

  28. Beautifully said, Dan. I am so sorry-I’m sure it is very painful and emotional indeed.

  29. It does sting, doesn’t it Dan?! We all loved our individual High Point Rd childhood homes. The variety of styles and landscaping was a lovely feature of our street.

  30. Oh my! That is so sad Dan! It just breaks my heart!💔💔💔

  31. That is so sad. I cry inside every time I see a story like this about a tear down. I wish I could have afforded to buy this house and renovate it.

  32. Wendy Goldwyn Batteau

    Yes, Dan, and thanks for this! I sold my mom’s (our family’s) home 5 years ago but it was just the other day that I could bring myself to even look at a photo of the house that stands in its place. “Homeward bound” certainly has a new meaning these day.

  33. My family home on North maple met the same fate. Gone the beautiful dogwood trees, the blueberry patch, the apple trees the garden. When I drive by now it is totally unrecognizable! The entire topography has been changed, the towering maple trees all died and were cut down. I rarely drive by, I just remember how beautiful the yard was and imagine it is all still there.

    • Jalna, I can picture Andre’s house on North Maple Avenue exactly the way it was in the 1950s and 1960s. As a matter of fact, I can picture every house on the entire street from the 1950s and name the families who lived in those houses.

  34. Dan, I’m so sorry to hear this. Sorry for you and your sisters. As always, eloquently put.

  35. Thanks for writing about this, Dan. While the demolition is physical, seeing one’s own or even a familiar house torn down is a psychic demolition as well. More so when the land, as you say, is leveled.

    Having recently sold a family home (in Stamford), I am struck by the swift and irrevocable doom the trees on developer-bought properties suffer. The clear-cutting developer seeks expeditious solutions with little care for neighbors’ privacy, stewardship of aged trees, the place of the land in the familiar landscape.

    There oughta be a law.

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