Westchester, NY or Fairfield, CT

I have been learning so much here and want to get some area specific advice.

My husband and I live in one of the most expensive areas in the US, and while our area is not as prone to the many issues in the market that some of the major “boom” areas are facing, we feel there are some definate good buys out there. We both work in real estate, and really want to figure out where to hone in for some good flips or rentals.

Interestingly, in this area the price of 2-3 family homes has been dropping (same w/ co-ops) with SFR, and Condos increasing (last report said condos are up in Westchester 14%). So, while i know everyone has predictions about the market “crashing” and gloom and doom, we, as do our friends and family in the area feel we are somewhat (not completely) provided with a buffer from ever turning upside down on a house, or actually not making a profit, as long as the purchases are WISE obviously.

So… we are ready to get in. We have 2 pptys (one is a rental/house that we renovated, one a condo where we reside). Now the question is-- What areas of Westchester and Fairfield have the best potential for what we have in mind? Also, my husband is a mortgage consultant, but how do most of you get financing on your flips/purchases/rehabs? Do you go to loan officers? Or do you do hard money loans?

Thanks for any help or insight.

Oh, also if anyone knows of good REI clubs in the area, or where to look-- my husband is interested in joining.

And, since both our jobs are commission based- and this is a risky business as well, how many of you are in this for life? What is the quality of life when you are constantly worrying about flips, or construction etc?


I heard that Bridgeport, CT. is supposed to have big upside potential.

we are somewhat (not completely) provided with a buffer from ever turning upside down on a house, or actually not making a profit, as long as the purchases are WISE obviously

Good luck with that! Ironically, that’s what they say at the top of every market. It’s kind of funny, but I heard an “analyst” say the other day that the stock market is bound to keep skyrocketing because we are living in a new paradigm! Seems to me that I heard that just before the dot-com bust!

I get almost all my financing from small local banks (portfolio lenders). I have bought the majority of my properties with 100% financing, but a maximum of 70% LTV from these small local banks. I have not found any mortgage brokers who can do that. Hard money could be an option of last resort for flips, but is normally out of the question for rentals. You don’t want to pay Uncle Guido’s extortion rates unless you have to.

Life is a long time, but I am in it for the long term and do this full time. Since I’m in the rental business, I’m not constantly (or ever) worrying about flips or construction. In fact, I’ve taken almost all of this month off and the money will still come in on the 1st! That’s what I like about rentals.


Thanks. Yes, i heard that the foreclosure rates are high there. It is a questionable area, but if there is potential, its worth lookint at.

I am a new investor, been looking in the TriState NY area. I have been finding some potential deals in Orange county. Supposidly one of the fasted growing counties in the region. I am looking mainly at rehabs.

I don’t like Bridgeport, CT.

The housing stock is largely comprised of old, poorly constructed properties.

Unless there is some motivation by the city to bring in business - worthwhile business - it is a long drive on I-95 to other cities that have garnered business. The city has a long long history of political corruption, a former mayor is in jail; the current mayor allegedly was caught doing cocaine!

Back to the interstate - 25 miles at 5 miles an hour makes for a long long commute.

Living next door in Fairfield -
Vicky S.