On March 13, 2017, I entered the next stage of adulthood by buying a house in New Haven.

People love to ask me questions about it, so rather than risk further interactions with live human beings, I’ve decided to share my experience with you, Dear Reader. And must I say you look quite fetching today. Blue really brings out your eyes.

Hot Flash

First things first.

Where should I buy a house?

In New Haven, duh.

But more specifically, you’ll be weighing various factors:

  • Price
  • Location
  • Incentives (like Yale Homebuying)
  • How “up and coming” of a neighborhood am I really willing to live with?

I work for Yale, so I’m going to take advantage of the Yale Homebuying Program, which means I have to buy a house somewhere in here:

Yale Homebuying Map
Available here:

I’m not sure what sort of dark ritual magicks are used to determine neighborhood eligibility. Sure, I get incentivizing purchases in the Hill and Fair Haven. (We’re not gentrifying, I swear!)

But why Wooster Square and half of East Rock? But not Fair Haven Heights or City Point? Maybe City Point is full of Harvard grads.

I don’t make East Rock/Wooster Square Money, and I’m not Hill Tough, so for me, the compromise was Edgewood. Westville Lite, if you will.

If you really know your neighborhoods well, by all means, give Hill/Newhalville/Fair Haven a fair shot, there are some great deals and great folks in those neighborhoods. Maybe you don’t care about Yale Homebuying. Then go for Westville or Fair Haven Heights.

If you have Fuck You Money, buy a house in East Rock and please invite me to your parties.

So now you’ve figured out where to buy a house… what next?

Hire a Realtor or Four

I worked with several realtors almost entirely at random. Trust me, if you hit “I’m interested” on a house on or, you’re gonna make a lot of new friends.

Some of them will bring you to weird neighborhoods you don’t like. Some of them will lackadaisically show you the houses they like and ask, “So are you gonna make an offer or what?”

I recommend asking your friends who they know, cause having a realtor you trust makes a huge difference. My realtor explained the kind of renovation loans available to me, knowing damn well I wasn’t gonna buy a house with all that fancy stuff like working plumbing and heat.

You’ll want to see a bunch of houses, just so you get an idea of what sort of house you can get for the money. You may also want to visit the properties at night. You know, just to get an idea of if they have friendly ghosts or mean ghosts.

Scary Ghost
This is actually a Cool Ghost, he just dresses like a badass to impress his ghost friends.

Next, you fall in love with a place and make an offer. Which gets rejected because the bank really just wants someone to flip the house. So you find somewhere else, buy that instead, cause you’ve learned at your age to settle, you know?

LIving Room
Hmmm, it already COMES with chandeliers?!
…. AND fake bricks in the kitchen?!
Pink Bathroom
… AND a disgusting pink and blue bathroom?!


Be Aware of Any Free Monies

If you work for Yale, fill out your Yale Homebuying Application and get up to $30k over 10 years.If you’re eligible for Re: New Haven based on income levels, you can get assistance for your down payment, energy saving renovations, and even college tuition if you’re about to get someone pregnant.

The SmartMove Homeownership fund helps people of low- and moderate-income buyers get a cheap second mortgage. Live Where You Work lets you borrow up to 20K at 0% if you are buying a home where you work. The Landlord Entrepreneurship Affordability Program (LEAP) helps you buy a 2- to 4-family house and renovate it to make that sweet sweet money.

So go out there and get your money.

Free Money Guy
Free Money Guy is so proud of you.

Getting a Mortgage is… Unpleasant.

Once you offer has been accepted, you start filling out all kinds of documents about your credit, finances, salary, blood type, Godfather I/II preference, and whether you saw blue or white in that dress.

The Dress

You also have to do all kinds of other crap. Like buy Homeowner’s Insurance. You know offhand the Replacement Cost if your house were to burn to the ground had to be built from the ground up in your particular location with modern day materials, right?

If you’re like me, and do a 203K or HomePath Renovation loan, you’ll need to get bids from contractors on all the work you wanna do. And you don’t know anything about contracting. Just nod your head and smile.

The appraisal might come in too low and then the mortgage company is like “dude we’re not giving you money for that crap house.” But rest assured, at least they aren’t trying to give you money for something that isn’t worth it. They’re protecting themselves and you. Well mostly them.

Then you get closing documents and you’re like wait wtf that’s like all my money. But that’s what you were saving it for, right? That whole “you should have three months worth of salary just in case” thing is just a suggestion, right? Right… ?

Great, now you own a house. Now what.

Nothing, just leave it abandoned indefinitely! What could go wrong?

Oh, did you know there’s a gas leak? No worries, the gas company will come over in a timely manner, sometime in the next eight to 40 weeks.

Water? Oh, sure, you’ll have to replace a valve or two and.. uh… that’s not supposed to be coming out of there, is it? Well, at least… water is coming out of… almost everywhere it should… ?

If you bought one of those fancy “ready to live in” houses, by all means, move in!

You also might want to clean up the two years’ worth of leaves on your yard. You know what’s under that first year? Grossness. That’s what.

Behold! Leaves.

Meanwhile, renovations are a fun time.

Torn down kitchen
This is what a kitchen is supposed to look like, right?
Torn up bathroom
At least I can sleep in the tub.

Wait, I need to buy a rake?

You’re very quickly going to realize you own literally none of the things you need to buy a house. Rakes? Hoses? Painting equipment?


How do you even get a ladder. When I was buying a car, I didn’t really consider ladder capabilities. Damnit.

But don’t worry. That weird feeling that you have no idea what you’re doing? Everyone has that. It’ll pass in thirty or forty years when you die.

If you have any specific questions, by all means, email me at I promise to give you my wildly uninformed opinion anytime.

Two polls this week:

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  1. As a long-time NH homeowner, I very much enjoyed this as well as the earlier version you presented at the Bradley Street Bicycle Co-op.

    I would add a screen to the four factors you list at the top of the blog – what is important to you. I live in SoHu, on a lot that is a bit more than .1 acre. If you like a decent-sized yard, you probably want to look elsewhere. On the other hand, my Walkscore is comparable to what you would find in Brooklyn.

    As small as New Haven’s neighborhoods are, there is a good deal of internal variation. In East Rock, SoHu is very different from the St. Ronan street area and Cedar Hill. Chatham Square is noticeably better off than the rest of Fair Haven.

  2. I live in the Annex which seems to not be apart of that homebuyer program but nonetheless, love my multifamily in New Haven! And I look forward to buying again in New Haven as well. This city is great to live in if you just dive in with confidence. Kudos for this article!

  3. As someone who tried to make a smart purchase in New Haven and after months going through the process failed miserably, I wish I could say I got to the fixer-upping part. Booooo to the mortgage companies.

    Congratulations on your homeownership, Josh!

  4. I may be moving to NH next year (job relocation), and I’m completely alien to the house market over there. My cousin is the only person I know over there and his experience with realtors while acquiring a home was not the greatest. Any tips were to start looking and get a more in depth view on the market?

    1. Hey Darryl,

      That’s a great question and one that’s difficult to answer. My experience with a realtor was pretty good, but I also went through 2-3 realtors. My advice is to learn about the homebuying process itself, perhaps by taking a course with your local bank/credit union, and once you feel comfortable with that, find a realtor and try them out. See if they feel like a good fit. If not, there’s no shame in finding someone else. Not everyone is a great for everyone else. Fundamentally, it’s about what YOU want. And only you know what you want.


  5. Price and location is definitely an important factor when buying a house. Also when looking for a house you really have to make a list of things you want to check in the house making sure it is the perfect house for you. Great blog by the way and thanks for sharing this information.

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