Analyzing deals in Westchester County, NY

28 Replies

Hi all,

I'm starting out by looking for a triplex to house hack in Westchester County, NY. The housing market here is expensive and all over the place - high price, high taxes; high price, low taxes; and even low price, high taxes. The lower price, low taxes tend to be ones I wouldn't feel comfortable in location-wise - most of these areas just don't make me feel safe.

There are homes in these areas are high price, low taxes. I can move a little farther south (which I know is getting into New York City), but even in the areas of the Bronx where I wouldn't feel comfortable for example, I'm priced out of my comfort zone. 

I'll be going with an FHA loan, so putting little down would still be possible on these more expensive homes, but how do other investors in Westchester (or in other similar markets) know when they're getting into that "danger zone."

For example, should I go for a higher priced house with lower taxes?

@Stephanie Minor I'm new to investing myself and am interested in the same area you are. My search radius is 50 miles and as Im currently in the Bronx, Westchester falls within the search radius. And WHO you telling that these homes are priced extremly high, I am on a 3 to 4 year plan just to save for the down payment even with a FHA loan. The strategy that im looking to apply is similar to yours #househack!

The best way to learn the area is to network with people who are in your local market, which may begin simply by finding a local REI club (go to, you may find something here) setting up keyword alerts here that may let you know when people post about Westchester and you may connect with people in your local area.

My initial analysis as to where to buy usually begins with the # of schools are in the area and how they are rated.

Good luck with your investing, I wish you a great deal of fortune!

@Stephanie Minor I started looking in Westchester too about 4 months ago.  I have finally narrowed down my search to Ossining where there is a diverse group, decent schools, and reasonalble taxes and home prices.  With the new Avalon housing and a new luxury housing builidng under contstruction near the train, I am thinking Ossining will see appreciation in the near future.  

My advice to you is to be patient,continue saving, and always look.  There will be a deal in whatever market you choose--you just need to be ready for it.

Wish you the best of luck!

Sounds like a smart plan - house hacking is a great first step.

I'm in a similar situation, looking for investment properties relatively near home in Westchester, but prices are crazy - also looking at Ossining, it seems to have potential with convenient access to NYC and a good bit of development going on. One wildcard is the prison, which I think will continue to be a drag on property values long-term, but as southern Westchester keeps getting more expensive, the population will likely continue to migrate north. I'm also looking at Yonkers, which is similarly developing although some areas are pretty rough. Finally there's Peekskill, which is also affordable but I'm not so sure about the schools or crime rates. 

I'm also intrigued by some areas in Connecticut, specifically Norwalk. 

Thanks for all your input guys! It's nice to hear the names of familiar places and listen to what other people in this strange place are thinking and doing. 

@Angel Rosado I did go to a meet up in the city, which was amazing! @Brandon Turner spoke! Keep up the hard work, and we'll get there!

@Justin Wright I love Ossining. I think it's a wonderful hidden gem. I have found that many of the readily available properties are two-unit homes, when I'm looking to start off with a 3-unit. I wouldn't mind moving there someday though :)

@John Merryman it's hard to know how much a prison will (or will not) affect home values. I grew up in Connecticut with a prison in town, but home values (and taxes) stayed strong because the school system was so good. Ossining is not a shining star when it comes to schools, but you never know what may happen as things develop. 

I also like Peekskill and would totally be willing to move there myself one day. I would look to invest there now if it were just a litttttle farther south. Since I will be living in my investment and have a job in the city, I think the commute would push me to the breaking point. The prices are very appealing though, and I would look into it more if I were you. 

I live in peekskiil and the prices up here make sense for those who are looking for investment. I myself am looking into purchasing more around here and around this area. Im also a real estate agent so i have a little better understanding of the areas around here. hit me up and lets talk if you're interested in looking around certain areas in westchester county

Hi @Christopher Oliver,

Thank you! I may get in touch. How far south from Peekskill are you familiar with/do you prefer to use your skills mainly in that area?

I too have been looking for an entry point into the buy and hold rental market in Westchester.  I grew up 5 minutes from Peekskill and strongly want to see this market explode the way it deserves to.  Peekskill has seen some great changes over the past few years with a number of restaurants setting up by the waterfront and downtown division st strip.  Having said that, the school system is still not very good which makes me weary of jumping in here.  Do you see the school system improving as new businesses move in and residential properties are improved upon?

I have looked at Ossining as well, and know some people who are invested there and really like the area.  I am open to different areas but want to feel fully confident when in the market I choose. Ultimately, the schools in these two locations are not the greatest, with Peekskill being slightly worse.

Any thoughts on school districts improving?

Hi all,

It has been a few months since this thread has been active but felt it was an appropriate place to mention that I have decided to make my first investment in Peekskill.  Contracts were signed last week on a 3-family and I am anxiously awaiting closing.

@Stephanie Minor , I hope everything is working out well in your endeavors!  If you have any updates and want to share, please do.

Hi all, 

@Andrew Pandolfino congrats on your 1st purchase. I just came across this post. I have a multifamily in the Bronx and am planning for the next. If you don't mind me asking, what do the numbers look like for that 3 family in Peekskill?  


I live in Yorktown heights and I would never invest in rentals reason being is 

•very high taxes around 7-9% property value Which does not give you a very high cash flow . 

 Westchester is very hot in flipping I have flipped 2 properties and no more then a month on the market. I really approve in this type of investment for the westchester area. 

@Christopher Oliver , @Ceasar Rosas , @Justin Wright  

Hi, to you or anyone else who can offer some insight or referrals.  I've been thinking of investing outside of bronx now.  I have been by some of these places but know very little of Ossining or Peekskill etc. My interest is large multi-families.  What do you guys think of these areas for those types of investments.  I am considering Jersey also because the eviction laws in NYC are too lenient.  So please offer experiences on eviction as well, if possible.   Thanks

@giovanni sotto. I recommend in areas like ossening Peekskill even tarrytown as good places to start. Or if your looking for a summer place to rent during winter time a property by the lakes are also good. If you are highly interested you can contact me so we can meet up and go over what your looking for. I have access to mls from the Bronx up to pougkeepsie. But I can still show anything even in Manhattan queens or Brooklyn. 

I've had the same issues with investing in the lower westchester area. The only way I've found to know if it's what you call a "Danger Zone" is by finding the properties that fit my criteria, then driving to them and assessing the area. Yonkers has a ton of multi family properties, most of them are in depressed areas but the few that aren't would most likely have lower taxes than other westchester towns and it's closer to Manhattan.

I live in Tarrytown but have found it almost impossible to find a listed multi family that would cash flow well there- if there is one, you have to bid aggressively as I've lost a few properties by trying to get them for below asking. Most of the deals I analyze in these areas are barely breaking 5% Cash on Cash return.

Hey everyone!

Just one question.... Is zillow a good place to find deals? I am interested in residential multi-family properties  because I hear mixed reviews about it. What about Realtor, truly and redfin?


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@Omar Sanchez redfin, realtor, trulia and zillow are cool. I am an agent in Westchester and would be available to help if possible with multis. I will tell you now that Yonkers and Mt. Vernon have the cheapest properties due to the crime and such. 

@Michael Lane Fleetwood is a section of Mount Vernon that is not in the crime. It's on the north side of town. Vastly different area. Yonkers near Bronx River Road and Cross County mall also doesn't have the crime issue. I actually live in Fleetwood. My issues there are taxes which are pretty high.

@Omar Sanchez I look at Zillow/trulia listing because the app looks good on an iPhone. But if your looking for deals I would use an agent. I have noticed a few times that Zillow was a few days behind the MLS on a listing. So I would be looking at the house through an agent and would pull up Zillow and it says off market.

Thanks for the info!Account Closed Yea because I have been getting confused lately and Ive noticed that sometimes the listings of the property(s) is not true.


@Jacqueline Pelter I totally agree with you about areas having better neighborhoods. Also some of those areas are starting to be cleaned up.

Thanks and no problem @Michael Lane . I don't know if you know but I am a newbie lol. I I have been to Westchester County, specifically Mount Vernon, and Yonkers.  From my experience they look like pretty nice and safe areas ( please correct me if I am wrong lol ). So you are telling me when it comes to prices and crime rates, its a good place to invest in Residential Multi-Family (1-4 units) properties? Ive heard that there are a lot of Duplexes, Triplexes, and Quads over there. One more thing.. I am also interested in these types of properties in The Bronx, specifically SoundView, since I am from there and currently live there, but I am still a little confused.  Yes I would love to contact you definitely!


Those places are very good to invest as a lot of people are relocating to lower Westchester from the city. I am looking to invest myself in Yonkers, Mt. Vernon and White Plains in Westchester specifically. I was just talking to agent who owns properties in the Bronx. Pm me and hopefully we can partner on a deal.

Hi everyone I'm an investor from the Bronx . Currently working on something if all goes well I will be looking for another multi ( hopefully 4 Fa. ). I would like it in the Bronx but if that doesn't come into play I would look at those areas mentioned so with that said I hope you guys don't mind me reaching out to you .

@Stephanie Minor  @Michael Lane @Sal Mazzone @Christopher Oliver @Account Closed I have a broker that send me a list of off market deals periodically.  I got one today there are a few in Yonkers and the Bronx as well. Actually there are a bunch, even Staten Island and Long Island too.  I'm not endorsing the list(or the broker)but a quick look tells me they are either short sales, or distressed.  If anyone.....(yes anyone)wants the list just PM and I'll pass it along.  I went into contract last week on something so I'll be out of the market for a good while.  

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