Chapter 5: Finding land

In which we clock many miles trying to find the perfect patch of greenery

Where we left off: After reaching out to our dream architect and finding that it wouldn’t break the bank to work with them, we needed to find a place to build.

This post is written by Ben with editing by Mindy.

Buying an imaginary home

Purchasing a piece of land is like creating an imaginary friend: it’s heavily determined by your mental capacity to envision things that don’t actually exist.

And while we may have had imaginary friends in our past, neither of us have owned an imaginary home.

So we needed to answer a few questions:

  • What do we want in a plot of land?

  • How do we find a plot of land?

  • How do we vet a plot of land?

Over the course of looking at houses, we had built some intuition about what we like and don’t like in a plot of land. The main criteria break down into internal and external characteristics.

External to the site, we wanted to be relatively close to a train station that would take us to NYC or (more realistically) could bring friends to our future home to visit for a weekend without requiring them to rent/own a car. I love the Western parts of the States, but we couldn’t fully give up the cultural beacon that is NYC. In addition, Mindy wants to be within non-airplane distance of her mother.

Next, we needed practical things like a reasonable drive to a (real) grocery store. We’re a number of years away from school-aged kids so good schools weren’t a major factor (but would be an added bonus).

Finally, we wanted homes around ours that were comparable in value. It feels dirty to say this out loud, but we didn’t want to invest a large chunk of our net worth in a house that might never sell (without a 50% price cut) due to its location.

Internal to the site, we wanted privacy and minimal noise from traffic.

If we were going to build a house with a lot of glass, we didn’t want to be right up against the road.

We preferred to have a view, although we weren’t willing to sacrifice everything for it. And I personally wanted a few acres of cleared land, so that I could re-enact that scene from the Lion King where Mufasa says “everything the light touches is our kingdom.”

Missing the land for the bushes

With a vague idea of what we wanted, we then had to find candidates. While real-estate listings for houses are reasonably representative, listings for land are next to useless. They are often like “here is a photo of a bush, imagine your dream home here!”

Here’s an example photo of a plot of land that I took. I have no memory of where this is or what I found remarkable about it.

I spent some time reading a book about buying rural land. The smart (but slow) way to do it is to look at county/local land records for unused plots and send out snail mail to people who pay property taxes from far away addresses.

Alternatively you can go to tax auctions— kind of like foreclosure auctions but for unpaid property tax. But these have been on hold since the pandemic.

We wanted to move faster, so we reached out to realtors referred by our architect to help us accelerate the search. They ran some searches on their MLS databases (these are the regional real-estate databases that Zillow and others scrape) and gave us a number of options. We combined this list with a bunch of other self-sourced listings from Zillow.

As an aside: I highly recommend getting familiar with the municipal records web portal for wherever you are looking. It’s much easier to find a plot of land if you have an accurate map of it and the surrounding properties. Some of these portals (like the amazing one for Dutchess County) will even call out flood zones (where you don’t want to build) and wetlands (where you legally can’t build even if you own the property).

It was completely unclear to us whether or not we were supposed to schedule formal “showings” for land like we would for an actual house. We could easily see 3-5x the number of land plots on our own schedule than if we were coordinating between a ton of different realtors.

So for the next couple weekends, we spent around 30 hours on the road racking up hypothetical trespassing violations.

Please don’t tell anyone.

The archetypes of land plots

The Suburb

This is a plot with a demolished house in an otherwise quiet neighborhood. The benefits are that you get the guarantee of buildability and possibly even a water and sewer connection, since there was previously a viable house on the property.

We only looked at one of these and decided that the area was too dense. By going rural we could get better views and more acreage.

The Jungle

This is a raw plot that’s entirely overgrown with stabby plants that violently poke you no matter how thick your pants are. A refined connoisseur of land might be able to evaluate the potential better than we could. But even with a drone to help us investigate, we failed to be particularly inspired by any of these.

The Price Gap

This is a plot bordered by housing that costs less than the raw land next to it. As an example, we found this property with cleared grounds and beautiful views:

Unfortunately, an online search indicated that in the past few years of available real-estate history, no house within 15 miles had sold for anywhere near the value of our future home. It’d be a non-issue if we never intended to sell. But since we didn’t know what the future held, it wasn’t a risk worth taking.

The Shitty One

Not really an archetype, but one plot we visited had beyond beautiful views of rolling Berkshire hills. The problem was: it was downwind from an industrial cow farm and reeked of cow shit.

The Logger’s Wake

We found a couple plots that had been cleared by a local logger. The result of this logging was sweeping views. Unfortunately, the most attractive of these lots was over 35 acres and 3x our land budget. Since it was all cleared, there wasn’t a way to subdivide it without risking someone buying the remaining chunk and eliminating the privacy we yearned for.

But the real problem was that the logger had left thousands of tree stumps. In the book I read about buying land, the primary takeaway was to run away from land with a lot of stumps.


Stumps are a huge pain to remove since you have to slowly grind them up or wait for them to rot (a process which takes many years).

The right way to clear land is to push trees over with heavy machinery—this way the roots come up as well. We could clear a little bit to build on and then wait 10 years for the rest to rot—but it wouldn’t look very nice in the meantime.

All in all, it sounded like an expensive logistics nightmare we weren’t excited to take on.

The Flag

This is a plot that’s behind another lot and connects to the road via a long private driveway. The benefits are that you get much more privacy at the cost of additional infrastructure costs to bring utilities (namely electricity and cable) up to the site.

Moving our goalposts

Along the way, we realized that land closer NYC didn’t strike the right chord with us. They were suburbs, not the lush greenery we were envisioning.

Extending our search to 2 hours to 2.5 hours outside the city led to some stunning drives, to the tune of:

There was a clear tradeoff between proximity to the city and sweeping, natural beauty. This is what we were looking for and why we were willing to move out of NYC in the first place.

After looking closely at various train lines, we found that the last stop on the Harlem Commuter line takes you all the way up to a town called Wassaic, which is right along the border between New York and Connecticut.

A number of land plots that we liked in that area were within a 15-20 minute drive to this train station (and a 2 hour drive direct to NYC). It seemed like we had found a sweet spot.

Coming to a decision

After our traumatic bid to buy a house, we felt the pressure to move quickly — both so we didn’t lose our opportunity and so that we could break ground before winter hit and the ground froze.

After a couple days of debate, we decided on Butter Hill, the 5 acre flag lot pictured above (and also below) because:

  • It had decent views and the potential for much more if we cleared trees.

  • It had a well, electric to the site and a (janky) driveway already in place (not cheap when the building site is 1/3rd of a mile a way from the road).

  • It was relatively close to a commuter train station.

  • It was 6 minutes away from a real grocery store.

  • It was on the cheaper end of plots we considered and seemed like a good value.

Next up: We make an offer and furiously investigate what building a house on this lot actually entails (spoiler: there’s a lot we wish we knew beforehand).