[OPINION] The Cape Cods Of Westport

From time to time, Scott Smith turns his eye on the Westport that most of us see every day, but seldom think about.

Recently, he’s written about culverts and concrete. Today, it’s Cape Cods. Scott says:

Having lived in Westport for 25 years, I’ve heard plenty about teardowns, and the McMansions that relentlessly rise in their place.

I prize the sheer variety of architectural styles still found throughout 06880, from the Revolutionary-era Colonials, the gingerbread Victorians and Frazier Peters stone homes, to the ’60s-era contemporaries and more uniquely modern one-offs.

What I haven’t heard much about is the history of Westport’s more modest houses.

I’m familiar with the ubiquitous Cape style (having lived in one), and know there are several neighborhoods in town filled with Capes — Washington Avenue near downtown and Fairport Road on the other end of town, to name two.

The streetscape of Washington Avenue, a relatively unscathed neighborhood near downtown.

I’m curious about not just these suburban standbys but, to be frank, the tract houses built a la Levittown, by a developer who used the same basic template to fill a street — even whole neighborhoods — with similar houses.

Most of these developments likely date from the 1950s. That is probably the case with Guyer Road, a nearby street I jog along, marveling at the vintage style of the homes.

Homes on Guyer Road, off Valley Road near Hillspoint. (

They look like a variation of a California ranch, with canted rooflines to handle the New England snow. Many have been remodeled of course, but with some you can still see the stamp of the founding design. Do the homeowners swap tales, tips and gripes, or know the history of the original builder?

I’m sure there are other such enclaves. I recall Saugatuck Shores having more cookie-cutter homes, before floods and the real estate market transformed the area into something else.

I imagine there are even older developments, from the pre-war era. I figure that one of the later “planned communities” — the Gault neighborhood off Imperial — doesn’t quite qualify, as they seem to be a related mix of custom homes. Same with the recently built Hales Court development, which is a different matter altogether.

I’d be intrigued to hear from residents of some of these old-school neighborhoods. I’d like to get the back story of who built them, perhaps what these homes first sold for, and if any untouched versions still exist. I bet not. Just the same, they are a part of 06880’s continuing history.

Fairport Drive, in the neighborhood once called Westfair Village. (Photos courtesy of Google Street View)

29 responses to “[OPINION] The Cape Cods Of Westport

  1. Susan Iseman

    Raising my hand from Watch Hill. We have some beauties here, as do the folks on Hickory Hill, next door. The town website used a photo I took of our 1910 cottage during the Summer Solstice in the “new residents” section.

  2. Excellent…thanks Scott! I’m amazed at the homes my grandfather built in the 40’s and 50’s that have been remodeled….it’s sad the “numbers game” and demand of today’s buyer has brought us to the huge home…looking forward to seeing what tomorrow’s “down sizer” is going to look like!!

    • Fillow Street, Sniffen Riad and Loren Lane off Clinton Avenue are all versions of the same 2 house styles, a front to back split, which looks like a cape from the front, and a traditional side split level. Most of the houses are still the originals, although since the sewer line just came through, that is beginning to change. We do swap stories about the original developers, as there are still some original owners and families! The most irritating uniqueness of our neighborhood construction is that all the original window frames were made of metal framing with hollow cores. Not good for cold and heat exchange, and also very difficult to install blinds and shades. 😞But otherwise, small but cozy homes in a real old-fashioned neighborhood where people walk dogs, jog with strollers and wave hello to neighbors.

      • Mary Schmerker

        My parents and grandparents built on Calumet Road in 1948. The houses on the streets off Clinton Avenue you mention as built in the 1950’s were also built on Calumet Rd, across from us, Googling our street address, 12 Calumet, our house has much the same look, just nicley updated. My Grandparents house,. their number might have been number 8, looks totally different. When I visit I always dive by and the neighborhood always looks welcoming. I do miss the “old days” when Fillow Florist was there with all their green houses, I used to love to go to the shop and watch Betty Mills make flower arrangements and courasages.

  3. Fred Cantor

    Here you go: https://06880danwoog.com/2012/01/30/1-road-3-neighbors-50-years-photos-tk/?noamp=mobile

    Our longtime home, which we sold to a friend four years ago, is the exact same size/footprint as the original. A couple of windows were enlarged in the front but otherwise the house looks the way it did in the 1950s.

  4. Happy to tell you story sbout house my parents built in “Gault Park” in 1954 Apparently it is on a unique plot that I was told growing up was owned by a botonist The pine trees are unique to the area Inordinently tall and what i was told each one different. sold in the later 80s changes made but the structure basically remains

  5. I haven’t been there for a while, but for a long time Warnock Drive was a total time warp…most houses a single style and if you parked 50’s or early 60’s cars in front would have been a total Mad Men set.

  6. Jack Backiel

    I used to know a lot of people from Westfair Village. Bauer Place and Bauer Place Extension have the same type of homes that sold for $3,000 dollars when built.

  7. I live in a farm house with a big red barn circa 1870, I love it.

  8. Barbara Sherburne '67

    I haven’t got much to add because my memory is fuzzy. Louise James Gerry’s father, something James, built some houses in the ’40s or ’50s, perhaps in the vicinity of Morningside Drive.

  9. The Oak Street neighborhood would be an interesting study of the same. Upper Oak Street is lined with capes from I believe the early 1900s, while the bottom of Oak and Lees Lane are filled with 1970-1971 colonials, I believe built at the the same. And as you turn the corner onto Richmondville and Millbank, there is a strip of mid century homes that all seem to be of the same mold. I do believe there are some original owners, at least along Oak.

  10. Julie Phillips O'Grady

    I grew up in the 70’s in the green house on the right of the awashingron Ave photo! Houses on Wasnigton Ave., Gorham and Evergreen were nicely ‘rightsized’ for the relatively small lots. I am greatly saddeded by the very oversized new houses being built on these and other Westport streets. I do not understand how the coverage regulations work these days.

    • Julie Phillips O'Grady

      Sorry for the typos!!!!

    • John D McCarthy

      Thanks to the formation of the Gorham Avenue and Evergreen Avenue local historic districts, sections of those streets will remain as they were when they were 1st laid out back in the 1910s and 1920s

  11. Some beach houses on Rowland Court are quite nice to look at.

  12. Bobbie Herman

    When I moved to Westport in 1983, the house I purchased was a 1949 Cape Cod at 52 Maple Avenue South. It was built at the direction of Rose Pritchard, who bought the one-acre lot and eight adjoining acres for $5000. She had eight more modest-sized houses built, A Cape next door at #54, and seven others on a new street around the corner — Pritchard Lane.

    In 1983, there were nine modest houses. Through the years, all but one have been replaced with McMansions. The one remaining Cape is the one I lived in for thirteen years — 52 Maple Avenue South. It is still standing, and I always drive by it if I’m in the neighborhood. I dread the day when all I’ll see is an empty lot.

    • Jack Backiel

      Bobbie, My sister was friends with the two sisters that lived in the first house on the right when you turned into the street. Maybe one was named Donna Royak? I probably spelled it wrong. They were a real nice family.

      • Bobbie Herman

        Jack — the family that lived there in 1983 was named McGrath. The wife’s name was Carol. I believe she inherited (or bought) the house from her father. They sold it in 1998 to a builder.

        • Jack Backiel

          Bobbie.. You’re right. I think everyone else died, including her sister, so she would have inherited the house, and McGrath was probably her married name. Her maiden name was Royak.

        • Jack Backiel

          Bobbie, Donna died and Carol was the last survivor in the family.

  13. Bobbie Herman

    My error — I should have checked more carefully. Ms. Pritchard had a total of seven houses built, not nine. She lived in 52 Maple, then moved around the corner to Pritchard Lane. TMI?

  14. Pam Barkentin

    How wonderful to take a look at the idea and celebrate the variety of older houses in Westport! After moving away for many years, I came “home” to raise my twins in 1995. I bought a 1920 Dutch Colonial on Richmondville Avenue that is a cookie cutter version of several other that still exist on the street. The builder was Clark Miller, and from town records I see he actually lived in my house. Sears catalog of the era also offered this mail order home. Over many years of restoration, I have peeled back the layers of previous renovations to let it shine almost as if in it’s original state. I feel very strongly that older houses should be preserved if possible. They are a part of Westport’s history, after all!

  15. Scott Smith

    Great stories! Thanks for posting, Dan —

  16. Cathy Barnett

    The Guyer Rd neighborhood I grew up in was mainly split level homes built during the 50s. A few of the houses were one story ranches. Further down Valley Road near Greens Farms Road are several one story cape style homes mentioned in this post. A few of these capes extend back into the small backyards like trailers. However they have been very well kept up throughout the decades, with well manicured landscaping. Valley Road is a narrow road that meanders from Greens Farms to Hillspoint Road with a variety of charming architecture.

  17. An excellent example of a sea of Cape Cod style houses that were owned by blue collar families would the ones that existed on Vani Court (originally designated as veteran’s housing in the 40’s).

    Around 2013, a developer discovered the street as a place to perform their magic to eliminate affordable housing and replace with McMansions. We spent 4 glorious years on the VC, but the change was quick and not the same as when we arrived in 2015.

    This is a small harbinger of the lack of affordable housing in Fairfield County, which will not be corrected by apartments or other multi developments being built. Westport (and other towns) should do more to protect blue collar housing and not sign off on every single knockdown that is sent to P&Z.

  18. Scott Brodie

    The northern end of Burr Farms Road (where I grew up) was developed by Norman Shapiro in the early 1950s. He built about a dozen identical split level houses on the street, though they were differentiated by being placed at different orientations on the lots. Only one or two remain in essentially the original configuration, but at least five of them survive in highly modified form. With a keen eye, one can still pick out the basic split level “bones”, and, often the original garage. A nearly original example was razed for a new McMansion behind my mother’s house just this past year.

  19. Jack Backiel

    Scott, I went to school with an Ann Shapiro. I wonder if he was her father. Sometimes you hear last names and make connections.

  20. Trudy Horan

    We bought the cape that was built in 1962 on 9 Covlee Drive. We bought in 1973. For 90k. It is on Bermuda Lagoon . We added 2 br, 2 ba, but maintained the charm. Stupidly, we sold in 1980, for $ 289k. To a rock star who still lives there.

  21. Cathy Barnett

    Scott Smith, if only my mom were still alive she could tell you the whole history of the Guyer Road neighborhood. Yes it was one of the housing developments built in the 50s. We moved to 2 Guyer in 1956 and we sold my mom’s house in 2018, the year she passed away. My mom had the distinction of being the last original Guyer Rd “homesteader” living there. There was a time we knew every family on the road. And my mom seemed to know the latest gossip. Years passed, my dad died in the 80s, I and my two sisters married and moved on. During those years the neighbors moved or passed away and my mom began to worry about who was living nearby. She really missed the old neighborhood and the friendships she made during those years.