Ossining, NY

Yesterday afternoon I walked around Main Street in Ossining and then explored that area north of Main and west of Broadway. There are a lot of great old brick buildings and small wooden houses of diverse architectural styles. Many of these homes are occupied but a few appear to be in various states of repair (or disrepair). Some old houses are abandoned, along with a few buildings in the Main Street area. Many of these buildings likely date from the mid-to-late 1800s.

All of these pictures are cell-phone photos, as this was an unplanned excursion and I did not have an actual camera with me.

My first target was 65 Main Street, recently on the market for around $100,000 and advertised as “tear down or renovate.” I’ve had a bit of fantasy lately about buying an old house and doing the restoration work myself, but haven’t got the resources to back it up. This would be an amazing project. The listings stated that the house was built in 1855, and there is good Hudson River brick under that cheap aluminum siding.

How about that amazing Hudson River view. Wow.

Nice doorframe details are intact too.

Further up Main Street I found this interesting door underneath a sign that said “Furnished Rooms.” I wondered if that sign was a leftover movie prop, as some movie scenes have been filmed in the area in recent years, including scenes from Bill Murray’s “Broken Flowers.”

This one belongs in Preservation Magazine’s “Yikes!” column, if they are still doing it. The fake pediment has nothing whatsoever to do with the original architectural trim around this storefront and it is made from the same cheap particle board that you might find in a bookshelf or TV stand from Home Depot.

Main Street looks good these days, but this building (above and two images below) was recently declared unfit for human habitation.

This door is at the back of the formerly abandoned, now renovated Ossining National Bank.

I found this awesome sign behind the Monitor Hose Company’s firehouse.

Foundation of a condemned building on Central Avenue.

Driving around aimlessly is a good way to find cool stuff. This previously-unknown-to-me industrial building appeared to me while driving through an otherwise residential area on the heights above the Hudson. Some kids playing in their driveway while their tennis ball-chewing dogs barked at me came over and said “No one ever goes in there. Only every two months you see someone.”

Heading back towards Broadway I found the buildings of Victoria Home, a skilled nursing facility in a shingle-style mansion with a 20th-century brick institutional addition.

Sadly the old gate pillars to the estate on North Malcolm Street have been toppled.

Lastly I show one of the fantastic arched underpasses of the Old Croton Aqueduct. This one is on Aqueduct Street.

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16 Responses to Ossining, NY

  1. Rebecca Elise says:

    This was great to see Rob. I haven’t had the chance to walk around Ossining lately, but I always appreciated the older buildings and remnants of former workers’ housing or industrial bldgs near Sing Sing. I enjoyed the red shingled house pic, and the last shot of the Old Croton Aqueduct. Funny, it looks so timeless – easily could be circa 1985 or 2005! (or 2012)

    • HV-Rob says:

      Thank you Rebecca. Yes, there really are a lot of great old buildings in Ossining. For the sake of historical record keeping I don’t usually post photos as black and white, although I love the “timeless effect” too, and that is how I really started photography, but my cheap phone has some color aberration going on, and not in a good way, so I converted most of the photos.

  2. Richard Cunningham says:

    Great stuff, Rob

  3. Eric says:

    I’m a member of Monitor Hose #4. I really liked that photo of the wall in our parking lot. All the photos are really great. There’s always something interesting to see when walking around Ossining. Too bad more people don’t take the time to appreciate it like you did.

    Also, if you get the chance, head north on Water St to look for the old Brandeth Pill Factory. No treaspassing, of course, but a neat old building.

    • HV-Rob says:

      Hi Eric,

      thank you for your note, I’m glad you liked the photos. Kudos to whomever painted that cool sign behind your firehouse.

      I am familiar with the Brandreth site. It appears in our Hudson Valley Ruins book. I might still post some photos to the web, but this blog already has a comprehensive post about the site.

      Thanks again,


  4. harry marcus says:

    my great grandfather founded monitor hose co. 4 he was harry macy. I have photos from your historical society, but I cant pick him out of the croud of 34 . if you pass by monitor hose co. 4 please walk in and speak to whoever is in charge and get a contact name and phone or e mail address . I don’t know if they have an archive with his signature or possible photos other than the historical societies one photo my address is 831 Cumberland terrace davie, fl. 33325 thank you for any help you can give me

  5. harry marcus says:

    my great grandfather was a founder of the dock rats, monitor hose co. 4 he was harry macy I have a granny photo from your historical society,but I cant pick him out of the croud of34. if you happen to pass by monitor hose co. 4. please walk in and ask to speak to whoever is in charge and get a contact name , phone and or mailing address. I don’t know if they have an archieve with his signature or possible photos other than what the historical society gave me. my name is harry marcus of 831 Cumberland terr. davie, fl 33325 phone 954 4528754 thank you for any help you can give me.

  6. Robert Brady says:

    The pic of Kil brook going under the arches is where we as kids fished for big eels.I wonder after 55 years are their still some around?At that time I lived on Independence PL. The best was the view over looking the Hudson river.Wow the memories.
    Thanks Rob

  7. Robert Brady says:

    Just found out from Cathy Murphy that Crawbucky beach is off limits private no trespassing?? is that true Rob? That was our old fishing grounds.If it is can you find out why for us? Thanks in advance Rob.

    PS; can you email me info and I’ll post it on FaceBook

  8. Kevin McDermott says:

    Dear Rob: re: “Further up Main Street I found this interesting door underneath a sign that said “Furnished Rooms.” I wondered if that sign was a leftover movie prop…” If — as I remember it — that sign was a small board, hanging from a mass-produced aluminum bracket…then no, it was no movie prop: it has been there as long as I remember, first noting it in the early 1960s. My parents moved to Ossining in 1957 (I was 4) and I moved away in 1978; I returned for the four years I was needed to look after my father intermittently until his death in 2011 (RIP). The sign was still there then…

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