The Real Sears Modern Homes of Ossining, New York

Image courtesy of CBS

I don't recall when Ossining, New York first got on my radar as a place that potentially had a lot of Sears Roebuck houses. But in December 2016, I was focused on finding Sears houses in Westchester County, New York, where the Town and Village of Ossining are located. That was when I came across what looked to be, on first appearance, a treasure trove of Sears houses. In the spring of 2010, the Village had put out a document called the "Significant Sites and Structures Guide" of homes and buildings in the Village. That guide included an entire section dedicated to Sears Modern Homes. The guide noted that there were 102 Sears houses located in the village and even better, provided a list of addresses for all the homes. As I had been working through mortgages to identify Sears houses in Ossining, I was excited to see what I had matched and what I had missed. But the more I read through the guide and reviewed addresses, the more questions I had. It was clear that something was very off. 

My first clue that something wasn't right were the examples of "Sears" houses that were part of the narrative in the guide. In 2016, I didn't have the expert eye for Sears houses that I have today. But even then, I could see that a number of the examples that they showed were either not Sears houses at all or were not the models that they claimed them to be. Of the 14 examples shared, only 4 were clearly identifiable as Sears houses. Of the remaining 10, a few were possibly from Sears but most were definitely not houses from Sears. That many incorrect identifications just in the examples gave me a sinking feeling that the list of addresses was going to be equally off. 

A properly identified Sears "Garfield" at 17 Liberty Street, Ossining, NY
Image courtesy of Village of Ossining

Unfortunately, encountering list of houses incorrectly identified as Sears houses is nothing new for Sears kit house researchers. Rose Thornton has recounted the problems she encountered in Hopewell, Virginia when she discovered that a number of "Sears" houses shared in a brochure about Sears homes were anything but. Lara Solonickne had the unpleasant task of revealing the truth about the exaggerated claims of the number of Sears houses in Downers Grove, Illinois. As I started looking up the addresses of "Sears" houses in Ossining, I found myself encountering the same result - houses that claimed to be from Sears but that didn't match any of the models offered by Sears. After reviewing the 97 addresses (not 102, as stated in the narrative), I only could find 9 that matched models offered by Sears. A 10th house matched a model offered by Montgomery Ward. The rest? A collection of houses from various eras, some of which looked similar to models from Sears but were different enough that I was confident that they were not from Sears. Nine Sears houses out of 97 is a lot of misses. 

But here's where the story takes an unexpected turn. You see, Ossining has a lot of Sears houses. Besides the 9 houses that are on their list, there are almost 50 houses from Sears (over 60 as of 2023) that are not. I've been able to authenticate many of these houses through mortgage and deed records. Several of them are also testimonial houses that were referenced in the "Modern Homes" catalogs and related promotional material. 

Testimonial for Sears No. 111 (later known as the "Chelsea") at 33 Sherwood Ave

I have no doubt that there are probably more out there waiting to be found. By any count, almost 50 Sears houses in a single community is a pretty significant number. It's not 97 or 102 but it's still a noteworthy number. 

So how did Ossining end up with so many houses that were supposed to be from Sears but are not? I don't know the particulars of how Ossining came up with their list but I suspect it suffers from some of the same problems that plagued the inventories in Downers Grove and Hopewell. It's likely that the person or people who tried to identify houses as being from Sears relied on the general look and feel of the houses versus looking closely at the various elements of the house. I see this a lot in Facebook discussions of possible houses where many people assume that because a house looks similar to a model like the "Alhambra", that it is one. 

The Sears "Alhambra" as it appeared in the "Modern Homes" catalog

Listed as a Sears "Alhambra" at 15 Brookville Road

But that's not how it works. In the context of the millions of houses that were sold between 1908 and 1942, Sears houses make up a tiny fraction of that total. If a house is identified as being from Sears, it should match the catalog image or be pretty darn close. Yes, we know that houses have changed over time and that even when built, not every Sears house matched the image in the catalog. But far too often, the house that someone claims matches a particular Sears model isn't even close. 

Having looked in person and online at thousands of Sears houses and many times that number of houses that are not from Sears, it's pretty easy for me to pick out the real deals from the imposters. But for someone who hasn't had that level of experience identifying houses from Sears, you really need to scrutinize your possibilities and see how well they match the models from Sears. In the case of Ossining, too often, the answer to that last point was "not very well" or "not at all". 

As I reviewed the list of addresses, it was clear that houses that looked similar to the "Cedars" or the "Chelsea" or were of a Dutch Colonial design caught the eye of whomever was making the list. Houses similar in design to those models made up the bulk of the houses on the list. I could see the similarities each time I looked up a house. 

The Sears "Cedars" as it appeared in the "Modern Homes" catalog

Listed as a Sears "Cedars" at 9 Mohegan Road

But it was also clear that there hadn't been an effort to really match up the houses to the models in the catalog. Otherwise, it would have been readily apparent that the houses often weren't very good matches for the models from Sears (or didn't match anything that Sears sold). This isn't unique to Ossining. The same thing had happened in Downers Grove and Hopewell too. 

At the same time, it was clear that whomever was looking for Sears houses wasn't familiar with the catalog of models offered by Sears. It wasn't unusual for me to find actual Sears houses that were not on the list next door to wannabes that were on the list. Likewise, I found streets with multiple actual Sears houses yet those streets, like Acker Avenue and Ferris Place, didn't even make it into the guide. 

Authenticated Sears "Somerset" at 55 Ferris Place
There are 5 Sears houses located on Ferris Place

That reinforced my belief that the inventory relied on matching up possible houses to a handful of designs versus assessing them against the entire catalog of homes. It's not surprising that a first time seeker of Sears houses would miss some of these houses. 

Sears houses came in hundreds of different designs and even if you limit your search to the most popular designs, there's easily 50 different house designs that you would have to know well to consistently spot examples from Sears. There are some exterior elements, like porch columns, that can help you pick out candidates for further review. But at the end of the day, you really have to study the catalogs (or "Houses by Mail"), and - in my experience - visually see example after example, to really learn those models. It's not realistic to expect someone looking for Sears houses for the first time to be able to consistently recognize, much less accurately identify a wide range of Sears models. In the case of Ossining, there's close to 40 different models identified to date and it's clear that many of those simply didn't catch the eye of those doing the inventorying. 

One way that the inventory of Sears houses could have been done more accurately is through researching mortgage and deed records. It's clear that approach was not pursued in Ossining. Otherwise, the many examples I was able to locate and/or authenticate through mortgage research would have made it to the list. 

Knowing if and when a house was financed through Sears Roebuck helps immeasurably in the research process. For example, the house at 28 Hudson Street was correctly identified as being from Sears Roebuck but incorrectly listed as a "Carlin". The "Carlin" was only offered in 1918. But the almost identical "Windsor" was in the 1929 "Modern Homes" catalog, the same year this house was financed with a pair of mortgages from Sears. 

Sears "Windsor" at 28 Hudson Street that was identified as a "Carlin"

Likewise, knowing that a house was financed through Montgomery Ward, as the house at 20 Belleview Avenue was, would have avoided misidentifying the house as being from Sears.

Wardway Mount Vernon (Plan A) at 20 Belleview Avenue

In fact, there are several examples of Montgomery Ward houses in Ossining that I was able to authenticate through mortgage information. While not every Sears house identified in Ossining was financed through Sears, the majority of them were and that kind of research would have gone a long way towards building a more accurate list of houses. 

The good news, as I shared earlier, is that Ossining has almost 60 documented houses from Sears (over 60 as of 2023), many of them authenticated. With further research, I wouldn't be surprised to see more Sears houses identified. Ossining has a significant number of Sears houses and that's worth noting. But I hope the Village updates their list to reflect the houses that actually match models sold by Sears, especially the ones that have been authenticated.  I've included that list of a separate page that I will keep updated as new information comes to light. 

View the list of documented kit houses in the Village of Ossining, New York