Serious News

Chris Duff

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85 Acres, 4 Parcels, Endless Challenges: Cracking the Code on Complex Land Deals | Ep. 19

This episode dissects an 85-acre Tennessee property split across four non-contiguous parcels with varying improvements—a 7,000-square-foot foundation with utilities, a standing barn, a subdivided home parcel, and vacant land. The complexity multiplies with recent seller purchases (2019-2022), active mortgages on multiple parcels, and the challenge of determining whether to sell as a package or separate listings.

Key Takeaways:

  • Recent Seller Purchases Signal Caution Properties bought within five years rarely yield good deals unless clear value-add opportunities exist—investigate why sellers with significant improvements (foundations, utilities) are exiting before anticipated completion.
  • Multi-Parcel Deals Require Separate Valuations Complex assemblages demand individual comping for each exit scenario (85-acre package, five-acre vacant, 60-acre with foundation, barn parcel separately) to determine accurate price per acre across different buyer pools.
  • Engage Experienced Realtors Early Properties with multiple exit strategies and unclear motivations require local expertise from agents who’ve moved larger acreage quickly—lean on their market knowledge before deep due diligence.

Listen to the complete breakdown of multi-parcel analysis, seller motivation assessment, and when to deploy local expertise versus internal analysis.

(Podcast transcript below)

Hey, Chris Duff over at Serious Land Capital, vacant land funding partner. So today I was just going through a whole bunch of properties on our land daily diligence Facebook group channel. just reviewing, various land deals around the country. definitely some unique ones today. And there was one in particular that,

Yeah, it was, very high, high degree of difficulty and, yeah, nearly stumped me on, on a couple of, of avenues in terms of trying to price it out properly. So some of the unique aspects was first it was four separate, APNs. They were all contiguous, meaning they shared boundaries with each other. but pretty wildly different.

acreages. So there was in total about 85 acres and some had improvements. Actually all four had some type of improvements on it, but they were different setups. So, you know, the largest acreage, which might’ve been 50 some odd of the 85 acres.

had a foundation placed for a 7,000 square foot house on it, septic and well already installed, but no further development on it. Pretty nice terrain overall, where the improvements were, was pretty flat land overall. There was some, a bit of a dip past the main road frontage area where

most of the building would occur. But overall pretty solid terrain that could be buildable for most areas of this full acreage. And then the second largest piece, again maybe roughly another 20, 20-ish plus acres had a standing barn much deeper into the property. And that seemed to be in good shape.

unclear if it was actually housing any personal property or anything. That’s a bit hard to tell from Ariel’s, but perhaps. And then there were two smaller properties. One was roughly four acres, though the current sellers wanted to subdivide off roughly an acre and a half of that property that has a standing home on it.

And so then they would just sell the landlocked portion. Well, landlocked just for that unique property, but it, it’s contiguous with the remainder of the parcels, it would have road access, so long as it’s sold with the one next to it. So then you’re looking at another two acres there. And then there was a, another smaller acreage piece, I think again, sub five acres, roughly on.

on that parcel that that one was, purely vacant land. and so when I’m assessing something like that, you know, there’s so many different variables to consider there. and also a little bit more background knowledge is that the current sellers and I don’t know what price they were asking for on this, but the current sellers had

recently bought all of the parcels but not all at once. So some were bought as recently as 2019, some even as recent as 2022. So usually if something is being sold or a seller has acquired something within the last five years, I’m generally quite skeptical about their level of motivation and whether I might be…

being sold like a false bill of goods here, a lemon that is just unexpected. Are they truly motivated because they gave up on their initial plans for the property, ran into money issues or figured out something out about the property that indicated it is not possible to actually complete their plans or it ended up being much more expensive than they anticipated halfway through. I don’t know, but…

Those are always open questions whenever I see situations like that. And in my experience, very, very rarely, you’re going to get a good deal from a seller who’s purchased within the last five years. There can be exceptions if you see a value add opportunity, like a possible subdivide, or you’re really looking to develop.

a property even further horizontally or vertically or both. That could be more viable where you could just buy off market, for instance, for somebody who had just purchased a larger parcel previously without planning to improve it. So those are avenues that are going to be exceptions to what I just mentioned.

but, know, nevertheless, you’d still want to be careful and understand again, the seller’s motivation. And maybe they did explore some of those value and opportunities just didn’t work out, for whatever reason. So always just want to try to glean more info there. So like, for example, this 85 acre piece that we were looking at, I mean, the fact that they had bought within the last five years had a full foundation laid out for a 7,000 plus square foot house with utilities already installed there.

something tells me that something must have significantly changed within their financial wherewithal or maybe some family dynamic there. Some would be really cautious about, what exactly happened? Because yeah, that’s obvious value add if you can purchase it at the right price. And…

you know, account for the premium that they might be looking to get on the property. But if, if, if, you know, the comps are supporting, there’s, there’s room here, especially maybe you could get a wholesale agreement if you can’t get a full flip equity type percentage on the deal. That is going to be something to actively consider.

as well there. Plus on those properties to make it even more complicated was at least two of them had what appeared to be an active mortgage on the property, at least per land ID. You’re never positive whether those mortgages are still present. It’s possible they paid them off early and the official records just wasn’t updated as was getting pulled from county related records into land ID or they might be

willing to pay off the mortgage with the price that you’re paying them and pay out of their proceeds. That’s always going to be best case, assuming you can still get a good deal inclusive of the mortgage within proceeds. But I’ve seen some sellers where it’s like, no, I want this price plus you need to pay off my mortgage, which virtually never works in terms of

of making the deal attractive enough. So that was yet another complication regarding that. But in terms of actually comping out the property, it gets tricky because my initial thought would be probably consider all 85 acres as a sole exit.

because it has the foundation work for a house, it has an existing barn, and then otherwise it’s still vacant land. Especially since they’re subdividing off an existing house on the property to be retained by the sellers. Which again, is another red flag because anytime sellers are living basically right next door, it’s very rare that you’re going to get a more attractive terms from a sales price.

from those sellers. Or the option is to utilize the existing parcel delineations and do we try to sell a five acre piece that’s purely vacant and then a 60 plus acre that has the foundation for the house and then a separate acreage with a barn on it. That’s another avenue as well. And so when you’re trying to set up your acreage filters within Redfin,

get very difficult to suss out what’s truly accurate price per acre. So then, you probably want to dive deeper and consider all those various scenarios. Okay, what if I just did the full 85 acres by itself, accounting for the various improvements on it as a sole parcel, or then I’m just going to suss out the roughly five acre piece by itself, comp everything out from there.

Comp out, you know, maybe another combination, the house foundation larger lot plus the barn together as a single parcel and then do another separate valuation for the larger parcel with just the house foundation and then the separate acreage parcel for the property with the barn on it.

And then you can start arriving at, what is a correct price per acre and status of the market for each of those different exit pathways and different acreages to allow you to come to a more accurate designation. But it’s especially complexities like that. When I’m doing the live Facebook review, that gets pretty time consuming quickly when I’m trying to.

a lot of other people’s deals there. So I just wanted to kind of follow up with my deeper thought process would be. But honestly, I probably wouldn’t spend that much time initially reviewing all that until I actually know, hey, what are the sellers looking for here? And is there existing mortgages? And then we could dive a bit deeper and I’d probably engage a realtor, probably one that was more recent on the larger acreage size. Usually those are going to be a bit tougher.

to sell there compared to more standard infill lots. I want to know somebody who’s moved larger acreage in the area quickly. And then they can usually scale down to take into account, okay, yeah, we can split up these parcels or list them all separately, but look for one buyer to take the whole thing down and just consider those various scenarios because the market’s going to be different for each of those property types. yeah, that’s a situation that I would really…

look to lean on a local realtor earlier on in the process than otherwise. But yeah, first and foremost, yeah, look at initially take back a lot of questions to the sellers and figure out, what are you guys looking for? What happened with the development in this house? is really sort out why they’re looking at accident. What is their motivation here? That’s something that should be tackled very early on.

before you actually get into, okay, figuring out these numbers. So then you can try to meet the sellers for what they’re looking for and a structure that makes it higher likelihood you can come to some type of arrangement that can work for both parties. So just wanted to share some thoughts about that. Again, if you’re looking for funding, seriousland.capital, landpricer.ai for the simple and accurate way to price US land.

just chalked with my engineering team this morning. They are going to be wrapped up building out the MVP by Wednesday of next week. That is January 30th, finally. So we are set to start testing in a real world environment right after that. And like I mentioned, the Facebook land daily, the diligence group, which has been growing steadily since the start of the year, like and subscribe this podcast, share it with anybody who you think might get value out of it.

and looking forward to the next one. Take care.

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