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Unfortunately, and I really wish it weren't so, the overwhelming majority of real estate agents are geographic illiterates and do not understand the difference between the borders of a community and the borders of the same-named ZIP Code postal zone.
Are you pre qualified for $400k or is this something that you and your Fiance figured out on your own?
First thing to do is to get pre qualified and then when you get the amount from the broker that you are qualified for, I would subtract $20k off the amount. That is what my wife and I did and we live very comfortable.
You will need money for the closing - at least $10k.
You will need money for renovations or repairs, at least $10k. Something will always need to be fixed.
Also keep in mind that Utilities need to be paid, like oil, electric, and water. Right now the oil prices are really good, but in a few weeks or months when you lock in, who knows. You have to make sure you have money on the side for those bills and all the other bills you may have in the future.
Massapequa is a really nice area, but there are also a lot of other affordable areas around it like seaford, bellmore, wantagh, bethpage, and Levittown. You can find a home in Levittown now for $280k plus. Maybe you can find a more affordable home that may need some updating and do the work as you live there.
For $440k....I would want a house that is already done. Especially in todays market. I dont think offering $40k under asking is a bad idea. Be prepared because the seller will come back with a counter offer, or they may not do anything. There are tons of homes on the market now. You will find yours.
I'd like to add that on Long Island, not only the purchase price should be considered but the RE taxes for the property as well. Taxes can vary from $5,000 to $10,000 for similar houses with the same price - but different monthly payments!
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