“Then & Now”: #16

This week, Dave Matlow’s photographic chronicle of Westport’s homes — those that were demolished, and the ones that replaced them — takes him to what was once called “Westfair Village.”

One of the town’s earliest post-war developments, off Bulkley Avenue North and behind Westfair Shopping Center, it’s a tight-knit neighborhood with smaller-than-Westport-average lots.

During its near-80-year history, it’s seen many generational turnovers. Today — once again — it’s filled with families with young children.

Three homes from that neighborhood are featured today. The fourth — Blue Coat Lane — is off North Avenue, near Bedford Middle School.

Hunting Lane, April 2017 …

… and June 2026.

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Westfair Drive, December 2012 …

… and June 2026.

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Dexter Road, January 2005 …

… and June 2026.

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Blue Coat Lane, February 2014 …

… and June 2026.

(“06880” regularly covers Westport real estate, history … and much more. If you enjoy features like this, please click here to support our work.)

24 responses to ““Then & Now”: #16

  1. The Blue Coat Lane updated house is horrible and ugly!!

    • So rude. One of your neighbors lives there. I personally like it. If you don’t have anything nice to say, then don’t say anything at all.

  2. Matt, Way, way before you most likely lived in town, 50 years ago I was complaining about houses being torn down and replaced with new ones that weren’t very appealing.Matt, that house is garbage in my personal view! You couldn’t give me the house!

  3. Tracy MacMath

    Adorable capes replaced by ugly monstrosities. Just awful.

  4. Matt, Let’s try this again.I do not like the Blue Coat Lane house.Now, Dan Woog can take down my previous comment, if that makes you happy.

    • Jack,
      Here’s what I think (I think). They still don’t care what you think. It’s not because of the content of what you think it’s because you think. They think that you shouldn’t think. They think that only current Westporters should be allowed to think. Dan (Katz, not Woog) told me to tell you that he thinks you think too much. He cares what you think he just would like less of it. I think he’s thinking about imposing a one reply think limit for you and a no reply think limit for me. I think your next post should be about the thinking of the Titanic.

  5. I didn’t comment on the other houses because they looked like houses! Blue Coat doesn’t even look like a house.

  6. No more comments between Jack and others, please. If you have a new comment to make on the story itself, go ahead. Otherwise, that’s enough.

    • Dan,
      Thanks, (I think the “others” needed that).
      For what it’s worth, I’m vacationing in LA this week and everything that’s being said about Westport is true here. Just more so.

      • No, I didn’t “need” that. Your comment is rude and condescending as well. I do want you and others to ‘think’, but when someone’s opinion is outright disrespectful, it deserves to be called out. Stop making this into something larger and more important than it is. This is not an attack on one’s freedom to think and speak but to accept the criticism that comes along with it. I don’t care how old someone is or how long they’ve been living in Westport either – these are irrelevant.

  7. Tom Duquette, SHS '75

    This “Then & Now” feature has been interesting. While it makes me sad to see a lot of legacy Westport homes torn down (especially my old house or my friends) I have to admit I don’t hate all of the new builds replacing them.

    One thing I keep noticing from these photos is that the bay window trend that was popular back in the 70’s seems to be out of fashion. I don’t see them on any of the new houses pictured that I can recall. We had some remodeling done on our old Valley Road house around 1971 and had a bay window put in and it was a big deal to my parents.

  8. Beauty is in the eye of the beholder. We are all entitled to our view and our aesthetic, for some it is an old cape, for others it maybe a large modern town house. Jack thank you for your views as above you clearly have a view on what you like, it’s probably diametrically different from me.

  9. Aw, that Hunting Lane house was adorable!

  10. Julian, Thank you for your comment. I will provide a general comment about houses. Some houses, when they go on the market for a sale, realtors hear this from prospective buyers, “ No thanks. Can you show me something more traditional.” There are some homes that get bidding wars, and some that sit for a long time. We’re definitely moving into a buyer’s market, even in desirable Westport. I was in a situation once whereby a house I owned appreciated 95% in one day!! A friend of mine had 2 acres worth $250,000 and in one day, he turned down 15 million. Figure it out!

  11. I tend to like modernist homes, but Blue Coat isn’t really that… it’s just weird. No real cohesion to the design. And the block-y varying colors (even though they are all kind of bland colors) are a little dizzying.

    Dexter Road has all the charm of a hotel in a Monopoly set.

    I wouldn’t take a second glance at the others, which look pretty nice. Though a few minutes staring at the Hunting Lane house picture has me confused by the contrasting roof angles.

    (People are free to come scrutinize my 70-year-old house, which had some goofy design elements. Mainly on the interior – like entryways that seemed designed to discourage bringing in furniture!)

  12. Let’s not forget that each one of these houses is someone’s home. The houses were built to satisfy their needs and taste. Whether someone else likes them or not is irrelevant. If you were looking to buy a house, you would only choose to see those that meet your needs and taste. Times moves forward. Trends come and go (remember avocado green refrigerators and orange shag rugs?). Anyway, I enjoy this series on 06880 but would never think to make a negative comment about someone’s prize possession.

  13. Jack, we’ve been in Westport for a good 150 years, so like you and others here, the family has seen house styles come and go. And as a Boomer, for nostalgia’s sake, I suspect we would both have preferred all of Westport to have been frozen on the day the Beatles were first on Sullivan. Yes, the town looks more like Scarsdale every day, and yes, there is a special place in heaven for those who buy and preserve the remaining capes in town. But as to the new designs – and there are several like this now, including on our street where one replaced a Frazier Peters- they are designed and colored for sustainability, and yet they also have some very interesting interiors. Since you were around, you’ll remember the hue and cry over all the Larry Michaels contemporaries in the late 60’s and 70’s. Now they are much appreciated town classics. The new designs can be shocking for sure, but I have a sneaking feeling that like us, some generation will someday look back fondly on a Westport that included that house on Blue Coat Lane.

  14. Sam, Two other people besides me spoke negatively about the house on Blue Coat Lane. One even described it as “weird.” I seem to be talking the brunt of the complaints, even though Dan asked not to comment about me and other people.He wrote, “ No more comments between Jack and others, please.”

  15. Jack, I only addressed to you because I wondered why I was at first read so sympathetic to your view, and because I know you to have a long and very much valued legacy knowledge of the town and its history.

  16. Westporters making snarky comments about other people’s houses. As Greta Thunberg would say: “How DARE you!!!”

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