This Old House #6

Last week’s house — labeled “Cross Highway — near Bayberry or Great Hill Rd. Westport” — has been positively identified as 167 Cross Highway. Click here for that photo, and comments.

This week — in our continuing quest to help the Westport Historical Society identify 1930s-era WPA photos, prior to an exhibition on old houses — we present the Osborn House.

Actually, an Osborn House.

There are 2 by that name in Westport. One — from around 1683-87 — is the oldest surviving house in Westport. Located at 187 Long Lots Road, today it’s the Wynkoop house. (Fittingly, the late Susan Wynkoop was a WHS president.)

The other  house — the one “06880” readers are asked to help identify — could be anywhere in town. The inscription on the back says simply “Osborn Ho. Westport.” Here it is:

This Old House - April 8, 2015

So put on your thinking caps. Click comments if you think you know where it is (or was — it may have been torn down in the decades since the WPA photo was taken).

PS: “Osborn” might also have been spelled “Osborne.” Does that help?

15 responses to “This Old House #6

  1. There apparently is a famous “John Osborn” house in Westport, see: No, it does not look like the one pictured above, but I include it just in case the one above is mislabeled and nearby.

  2. Is or was this house located on Evergreen Avenue? It looks like some of the residences that had back yards adjacent to the softball fields behind Town Hall

  3. To further confuse things, the Wikipedia entry for the “John Osborne” house (note the added “e” at the end) is for 909 Kings Hwy W in Southport (right over the Westport line); see: A picture of the house in an article about it (it’s apparently the oldest house in Fairfield), looked different than the one allegedly in Westport that I just mentioned in a previous comment, hence I assumed they were two different houses, hence worth mentioning. But… the National Historic Registry also lists the John Osborn house at 909 Kings Hwy W in Southport, with pictures identical to the one allegedly in Westport; see: So either I’m totally confused by seeing the same house at a different angle (and the blogger is wrong about the house being in Westport), someone drastically altered the original house, or they are indeed two different houses in two different towns… albeit perhaps still no relation to the one we are searching for (lol)… but just wanted to clear that up to avoid further confusion.

  4. Jack Whittle

    Assuming these are still taken from the batch of c. 1930 photos, the 1931 Westport directory shows just one Osborn(e): Mary Osborne (widow) living with son on E. Ferry Lane. However, the 1925 Town directory lists quite a few Osborns and Osbornes: John Osborn, a farmer on Buckley (yes, Buckley) Rd; William E. Osborn, apparently Westport’s Town Treasurer at the time, living on Imperial Ave; William F. Osborn, treasurer of Charles Kemper, living on Owenoke Park; and Walter Osborne, a barber, living and working on Taylor Ave.

    That should give us a few addresses to think about

  5. Sharon Paulsen

    For some reason, my memory sees this style of home in the North Main St., Clinton Avenue area.
    No rhyme or reason to it otherwise. Just an architectural style that I’d recalled, once having lived nearby, on North Compo.

    Also seems like it could have easily been in the Old Hill/Stonybrook area of town. There were a few oldies-but-goodies still around there back in the 1970’s, when I lived on East Meadow.

    Lastly, Red Coat Road seemed to have some structures like this, even recently.

    But ah, these are just my off the cuff thoughts – maybe to stir the pot a bit.

  6. Jack Whittle

    I’m thinking Imperial Ave, the portion closer to Bridge Street, and that’s where a well-known Osborne was living around this time.

  7. There’s an “Osborn House” at 31 Imperial Ave, but it does not appear to be the one above:

  8. Don’t forget, house numbers have, in many cases, changed substantially since the 30’s.

  9. Why not publish a “before and after” book of these old houses?

  10. My Osborn line never wrote an “e” on the end of their name. They were in Connecticut for over 300 years. Some cousins are still there, along with Hickok, Sturges, and Jelliffe family members. Hubby and I were in New Canaan several years ago and tried to find the old family (Hickok) house there, but we never did find it.

  11. Bob Weingarten

    Nancy great idea of a book but actually there will be a WHS exhibit later this year which will feature the WPA 1930s photos of houses and how they currently appear. The reason for this series is to identify the ones that have not been yet discovered. The exhibit will also include historic information and human interest articles on several of the houses. I will be the curator of the exhibit.