Six Properties on One Rochester Street: How Gregory Street Started It All

Six Properties on One Rochester Street: How Gregory Street Started It All

Mark UpdegraffBusiness Member
Real Estate Broker · Rochester, NY · Member since 2010 · 1k+ posts · 685 votes

After reading Rich Dad Poor Dad—the book that seems to lead every young investor into real estate—I decided to take a leap of faith when everyone else said I was crazy.

I bought a house on Gregory Street in Rochester's South Wedge. The neighborhood was not like it is today. Blight and crime were pretty common. In fact, the little old lady I bought the house from had knives stashed in every corner of the house, sticking out where she could grab them. I imagined she did not want to get cornered during a break-in and wanted a weapon handy. By the time I finished collecting them, I had a whole bucket of knives!

Anyway, I did all the rehab myself and got the place ready to rock and roll. Then I was bored. What was I going to do with my time? I know—buy more!

I kept hustling and saving and bought another property, although it was not on Gregory Street. That was my second flag in the ground. It was not as good a performer, but now I had benchmarks. I still loved Gregory Street.

Lucky for me, as I was finishing the renovation on my first purchase, Tap and Mallet moved in two doors down. It became a popular bar and pub, and that was when I really saw the opportunity to focus my efforts on Gregory Street's blighted housing stock.

Along the way, I met another investor—an old-timer—and bought one of his dumpers on Gregory. We are still good friends today, and I am helping him unwind some of his holdings. I bought another property as a foreclosure. Then there was another one that was a TOTAL WRECK. We called it the Troll House for years because I could not afford to fix it. It stayed on the back burner. One year, before we finally renovated it and put it into service, we turned it into an incredible haunted house and opened it to the public.

It has been a wild ride. The best part was becoming part of the community and watching other property owners see our work and start improving their houses too. We helped lift that street up, and today it looks crisp.

For those of you who invested in a rough neighborhood before it turned around: what first made you believe in it?

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Harry B.Pro Member
Lender · New York, NY · Member since 2026 · 48 posts · 15 votes
1w

I bought my first flip in 2004. School district is a key indicator for staying on target for your exit strategy.

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  • Harry B.Pro Member
    Lender · New York, NY · Member since 2026 · 48 posts · 15 votes
    1w

    I bought my first flip in 2004. School district is a key indicator for staying on target for your exit strategy.

  • MD/DC · Member since 2024 · 1k+ posts · 1k+ votes
    1w

    I didn’t ever trailblaze but instead followed in the footsteps of folks like you and invested in fringe properties a few blocks from the upcoming inner city neighborhoods that were gentrifying. It worked well and your post brings back fond memories of a few builders and realtors who essentially changed the course of some blocks. They all moved on to larger suburban subdivision type deals but we were a scrappy bunch back in our youth lol.

  • Nicholas FloydBusiness Member
    NY · Member since 2026 · 166 posts · 56 votes
    1w

    I am from Rochester as wel, I actually just left that area about 30 mins ago now watching the bills game on east ave. Hey I would love to connect with you and if there's any value we could possibly add to each other

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