These REALLY Old Houses

Recently, we announced the end of our “This Old House” series. The Westport Historical Society had run through the dozen or so homes they hoped to identify, prior to next fall’s exhibit of photos taken as part of a 1930s WPA project.

But you can’t keep a good house hunter down. WHS historian Bob Weingarten has sent along a few more photos from the archives. These too are unidentified.

Even more, they don’t have any labels. They could be anywhere in town. And — because they’re from the late 1800s — most are probably long gone.

Yet “06880” readers are an intrepid bunch. You’ve got an eye for architecture and history — and you remember a lot.

So here goes. Each house is numbered. If you recognize any — or just want to chime in on the subject of really old houses — click “Comments” below. (As always, you can click or hover over any photo to enlarge it.)

And if you know any of the people in the photos, I’ll be truly impressed.







Old house 6


old house 7






Old House 5




Old house 9



40 responses to “These REALLY Old Houses

  1. Jeff Porter

    What a wonderful peek into Westport’s past. Thanks for sharing these Dan.

  2. #1 looks like Riverside and #2 Bridge St

  3. Jack Whittle

    #10 reminds me of the Post Road / Compo Road intersection, facing east along the Post Road – misaligned then, misaligned now ; )

  4. Mary Ruggiero

    Great houses! 1 looks like it would be on main st on the way up to compo/ Clinton near where Bogeys was.

  5. Bob Weingarten

    I’ve had these photos for a few years and have been unable to identify them. Since the “Old House” series was so successful I decided to ask Dan to post these. Hopefully with the help of the 06880 readers we can identify them so that the WHS can file them in the appropriate archive files for future use by residents.

  6. James weisz

    #2 looks like a home on wright st

  7. David Squires

    Kool Old Pix! That was really “Back in the Day”!!!

  8. Don’t know where any of these houses were/are, but every one of them, even the more modest ones, are beautiful.

  9. OMG! Looking at these pics made my heart race!

    Sadly, I’m not kidding nor barely exaggerating. Look at them! I can imagine them (or at least perhaps, some of them) in today’s world, with BMWs parked in front on a paved driveway and a soccer net in the yard and maybe even a satellite dish on the roof ;( But at least, still loved, still a part of a thoughtful community and still “home.” I love it. I say it all the time — that’s what brought us here: the antiquity, the sense of history …and particularly, Banks Tavern, circa 1730…still standing proudly…thank God.

    Thanks for sharing this marvelous collection of Westport’s homes. Just lovely.

  10. I wonder how many of them went down for the Turnpike.

  11. Wow, kind of makes your heart hurt…
    BTW, that windmill (#7) may still be above ground – or it’s a kissing cousin of the small Bedford one that is/was midway up the hill above the intersection of Greens Farms Road and Beachside – not to be confused with the monster windmill that’s all the way at the top of the hill.

  12. Great Pictures. # 2 has the same windows at the top that the Wheeler House has and there is another one on Riverside Ave.

  13. Wendy Cusick

    #7 Clapboard Hill Rd on the Right hand side Take a left off the Greens Farms Rd Address I believe is No. 8 Clapboard It has a caretaker Chevy Silverado Pickup at Caretaker Garage at front of property. There is a special black fence around the whole property.The Windmill in the back of the property on the highest peak.
    #4 Looks really familiar just put bushes and large trees around some of these houses. Just can’t remember where I saw it.
    #2 Definitley Bridge St near Imperial Drive.
    #1 could be Bridge St too???. It looks like water behind it.
    #10 is near a cemetry right side of picture. Possibly Corner of Hillandale Rd and Church St South or around that area because the roads are “hill and dale” like there name
    Hint look deeper into the photo see what’s behind and around them.

    • Morley Boyd

      The romantically styled small windmill featured in image #7 does appear to still exist, but it has been highly altered. One can still clearly see the distinctive tower, though. The driveway for this structure is on Greens Farms Road (on the left just past where Beachside intersects). It’s sited about halfway up Clapboard Hill (the geological feature, not the road). At the very top of Clapboard Hill is a larger windmill associated with a residence whose driveway exits on Clapboard Hill Road. At least that’s what I think seems to be the case based upon memory – and Google Earth.

      • You’re right Morley, that’s it. It was part of the Bedford Estate at one time. Bedford sold his land to the State to put the Thruway in. It had extended past number 7 and included all of the land down to the water. Imagine!!

  14. Liz Doyle Boyd

    #1 Post Road east of Buckley Ave?

  15. Wendy Cusick

    Mrs. Hunter roll up your sleeves earlier than usual and break out your history books. You to Mrs. Paulsen!

    • Sorry, Wendy, I’m no use without hints! But boy, I’d sure like to move into #6 — not just for the architecture, but for those Longshore — type trees.
      (Plus, I’m still rather embarrassed about not recognizing the Lions Club plaque immediately… must have been cavorting down at Compo during the commemoration!!).

      Your knowledge above, though, is amazing!

  16. Morley Boyd

    Image #6 may be of that white house on the left hand side of Greens Farms Road if you are coming from the Sherwood Island Connector just before, I think, Wake Robin. As I recall, it’s an 18th century structure that was later remodeled in the Eastlake style – I think the evidence of that (including the cool stick work on gable end and elegant wraparound porch) has been lost but the flush boards on lower half of the front elevation still remain. Could be wrong but that stick work on the gables was really, really distinctive…I’m guessing this picture was taken around 1898 following the Eastlake remodel.

  17. Ellen Naftalin

    #9 looks like the last house on Turkey Hill, on the right, before Greens Farms Road. It has been added onto with a barn like structure after the time I knew her. Very tastefully done.
    My girlfriend Evelyn Munves used used to live there when we were Greens Farms Elementary School kids/friends.

  18. Ellen Naftalin

    #1 looks to be along the river or wet land by looking at the background.

  19. Wendy Cusick

    Mrs. Hunter and Mr. Boyd I like to take back roads not the highway. So I see these houses and interesting properties. #4 with the stone foundation and car port driving me crazy that I see it but not the street. We have similar stone house in Cranbury section of Norwalk (2 streets over from the White Barn/New development battle on Norwalk/Westport border)

    • Gosh Wendy, now you’ve got me pulling out my books on Arts & Crafts gardens, old “American Bungalow” magazines, and even the remarkable architectural illustrations by children’s book author/illustrator Barbara Cooney! Never a dull moment on 06880!

      p.s. I, too, always take the back roads… although (as we all know) it can be heartbreaking to see some of the changes.

      p.s #4 looks like a really strange mishmash of colonial/shingle style (without the shingles!) Creepy.

  20. looking at #1 again with the water in the background my first thought was Riverside but the drop to the water and the height of the house suggests steeper banks. Anyone? Was Ferry Lane around in the day?

    • I think it must have been on 33… Wilton Road. Look at how low the outbuilding is in the back. It’s quite a steep slope just before the intersection of Kings Highway North. Not quite understanding the path in front. It’s as though it were part of a little community of homes, perhaps on the north side of Riverside where the commercial buildings that front on the Post Road are? I don’t think it was one of the homes that were just knocked down by the Synagogue? But maybe it was knocked down to accommodate those commercial buildings. Best Guess for me.. route 33. Could this been part of the School complex where Fort Apache is now?

  21. or Stony Point….

  22. Wendy Cusick

    I can’t remember the number on Riverside Ave it’s a park now. 2 doors down from American Legion of Foreign Wars. It was demolished and the fire department practiced on it before it came down. Possibly one these houses. ( It was demolished because of water damage, I think it floods there)

  23. Wendy Cusick

    #5 Corner of Compo Rd and Bridge St #6 Farther down on Compo Rd near the Gault barn. Thought–maybe these most of these houses are that close together?? Riverside Ave, Bridge St, Compo Rd N and S, maybe Clapboard Hill, Turkey Hill Rd, Wright St, Corner of Greens Farms and Wake Robin etc…. all seem to have a common thread.

  24. Bob Weingarten

    I’ve been reading all the comments and will try to determine the locations of each house from them. Keep them coming. Today on focused on house #2, the Italianate house. I have determined, but could be wrong, that the closest house to the photo is the one at 68 Riverside Avenue. The Bradley-Wheeler House, the WHS house, is not the house since the second story has 5 windows instead of 3 and is not as wide as indicated on the photo. The Italianate houses on Bridge and Greens Farms Road don’t have round windows in the frieze at the roof level and again the second story wides look to large. The Riverside house may not be the same either but it is the closest. Note that the frieze at Riverside is set with octagonal-ended windows instead of rounded. Above the windows are no brackets but according to the history of this house, they may have deteriorated and not been replaced. The second story does have three windows but the placement is not symmetrical but this may have changed over time. The verandah is set with chamfard posts on pedestals, the same design as portrayed in the 1880s photo but there are less at Riverside Avenue then in the 1800s photo. Some may have been removed over time.

    GIven the similarities and no other Italianate house that I’ve seen in Westport, I believe that the house at 68 Riverside Avenue may be the same as the late 1880s photo and will place the late 1800s photo into the file of 68 Riverside Avenue. If you think I’m wrong in this assumption please continue to comment.

    • Jon McClure

      #10 to my eyes is definitely the intersection of the Post Rd and Compo Rd. The tree, is still standing at the location of the newly restored Compo Acres palette sign, with the same familiar “bump” you can see on the right side of the trunk. The house would have been where the People’s United Bank building now stands.

      • I believe Jack and Jon have it with image #10 – it seems to be the intersection of the Post Road and Compo – with Compo North coming in on the left. Jon, I think you are exactly right about the house on the left that was once where People’s Bank now rests. I’ve seen other images of that house that give the same location and I recall it had a stunning spider web sash in its gable. That same detail is visible in image #10 as well.

        Also those graceful Norway Spruces show up, I think, in other historic images of the inn (was it the Hawthorne?) that stood on the other side of the Post Road (where Compo Acres is now).

        On an unrelated note, I love the elegant cobblestone drain visible at the far right. This was when it was still considered prestigious to have a residence on the Post Road.

        • I don’t know about this. If the house where People’s Bank is now, the background would have a huge hill where Park and Spruce are now. I think it might be Evergreen and Evergreen there is no hill there and there’s a cemetery close by.

    • Behind 68 Riverside is a considerable Hill not visible in this shot. That’s the only problem. It’s the perfect Topography for The Bradley Wheeler House but it looks very different from it. Do we have any old pictures of the Bradley Wheeler House?

      • I also think 4 is a Bedford House on beachside. The sitation looks like one at a beach front and all the land around it looks flat which also suggests beach. ..was probably built the same time as number 7. It’s a guess of course..but they both look like good professional shots by the same photographer with similar materials at the building site. They look like they match. The transformations of mansions to bigger mansions happened a lot during through our history. The owner or architect is at the edge of the shot. It’s a fabulous house! Bedford is so prominent there are probably records to prove it one way or the other.

  25. Britt Anderson

    It’s a shame they are gone – these are beautiful homes. I MUST get to the Historical Society the next time I’m in town.

  26. Wendy Cusick

    We have to remember what Westport looked like before the trees got bigger. Farm land was sold and developed into streets, housing and cul de sacs. The Gault Stone Quarry was still in operation until the 1980’s. Some of these houses could be along Compo Rd, the property behind dips also no trees back then so you can see the River. Thomas and Baker Roads are steep hills. We have to look at the Geography of that time period.

  27. Maura Keenan

    #3 is definitely 21 Wright Street – the back of the house.

  28. #7 was on the Bedford Estate originally. It’s now privately owned off Greens Farms Road.

  29. #9 Looks to me like the intersection of EverGreen Parkway and Evergreen Avenue with the Old Cemetery fence on the extreme left.