How To Lose A Fortune In Greenwich Real Estate


Gold diggers (now available in all genders) are one sure way to lose a fortune, but this site is about real estate! Photo used with permission of listing broker.

Maybe “lose a fortune” is a slight exaggeration.  Though we’re talking about hundreds of thousands, even millions of dollars here, this is Greenwich, after all, so the losses probably weren’t devastating to the people who suffered them, but they had to hurt.

And standing by to make matters worse, CT’s fun-loving Governor Malloy and his Hartford cronies were only to happy to collect multi-thousand dollar CONVEYANCE taxes on these sales, despite the sellers’ huge losses. So that just makes it perfect, doesn’t it.

Below, some of the more egregious recent examples of the difference between selling then and selling now…

Click on the link to see the property listing before & after, sales date and price revealed at bottom of each listing.

78 Doubling Road, before/after ($8.6M…5.6M)

26 Mohawk Lane, before/after ($7.5M…5.2M)

101 Brookside Drive, before/after ($5.995M…4.475M)

15 North Street, before/after ($4.550M…3.9M)

2 Parsonage Road, before/after ($3.684M…3.450M)

23 Chieftans Road, before/after ($3.050M…2.4M)

96 Riversville Road, now/then ($2.550M…2.399M)

82 Glenville Road, now/then ($3.00M…2.350M)

17 Sherwood Avenue, now/then ($3.150M…1.680M)

And there are many, many more like this, in every town in Connecticut and beyond.  There’s an economic “recovery” going on, but it’s a weak and pathetic one.

16 thoughts on “How To Lose A Fortune In Greenwich Real Estate

  1. Any way of knowing what the lucky fat-wallet first sellers did with their loot? Did they upgrade and buy larger themselves, downsize maybe, go to jail, stash their money under the mattress, or move to Cyprus? I am sure there isn’t one answer that fits all, but I’d be curious to see if there’s a trend.

    • Earth:
      Your question implies that these sellers knew, or suspected, they were selling at the top of the market. My experience has shown this not to be the case. I do recall some clients saying they thought the market was topping in 2003-2004, but they turned out to be off by 3 or 4 years. I’d guess the sellers in the examples cited probably over-paid for their next places, but who knows?

  2. Gideon, great post.

    I dont get it. I can remember when 26 Mohawk sold in 2008 for 7.5MM and at the time I thought it was a foolish price given its not a very special road or area of the backcountry.

    • Cos:
      I’ll admit that there is a perception that some streets in town are “first-tier”, while others are second-tier, and lower. But a few years ago, Riverside’s Winthrop Drive would certainly have been labeled second or third-tier. And if you’d predicted people would be paying $4M+ over there, in the year 2013, you’d have gotten a skeptical reaction. Yet, here we are. Streets can change, and usually do.

  3. Btw, Looking at that Chieftains sale, the price basically says that the association/gated community has negative value. Otherwise, dont you think this house would have commanded a few more dollars or the same exact price had it sat outside the gate on Sherwood Ave?

    Plop this house down in Riverside on a .35 acres and it sells for $1MM more. Stunning.

  4. The other interesting stat within your double listings is the Days on Market: I won’t bother to mention them all, but this one stood out in particular:

    Mohawk: 2008=394; 2013=1241 (!!)
    Does this mean Mohawk went back on sale right after it was bought in 2008??

    Doubling took longer to sell in ’07 than it did in ’13. 519 DOM v. 394.

    Brookside also took longer the first time around – 2008=381 days v. 2013=150.

    Of course, caveat numbers, even those of us who aren’t agents know that those numbers get, how shall I say this nicely, changed to protect the guilty?!

    • Earth:
      26 Mohawk sold in March, 2008 and was put back on the market about a year and a half later, in July 24, 2009. And yes, things often took a very long time to sell even way back when. No matter how good the market is, you can still be guaranteed to sit dead on that market if you are severely over-priced. As for numbers (DaysOnMarket) being “changed to protect the guilty”, it doesn’t happen. The only way to re-set the DaysOnMarket “clock” is to take the property completely off the market for 3 months.

      • The three month rule must be either Connecticut or Greenwich specific because where I am (Nashville) a house can be taken off the market for three DAYS and be put back on as new.

      • Jack:
        The rule’s entirely arbitrary and up to the local Board of Realtors. But it’s very much in the interest of individual brokers to have HONEST statics. For instance, if your competitor tells a potential listing customer, “My listings sell in 60 days”, when in fact, the broker’s listings routinely sit there month after painful month, it’s important to be able to show the customer the REAL numbers.

  5. Please fix your brother, he has an image in his head that he is too (let’s say late) to achieve, but let’s be gentle, Dear Gideon, please find a less cross eyed mate that has all the anatomical requirements and a brain (as you have demonstrated you have) and likes dogs, and don’t be too critical and you may get lucky and have a nice happy (ending) life with maybe some kids if you want to and quit the hair product because it’s obvious but keep up the exercise because there is always hope but look over 30 — I love the girls under 30 they still have “POWer” but there is alot to be said for the ones who are smart and have something going on in your generation and are over 30. And maybe she can make a mean shake….and make you laugh for goodness sake…..
    good luck.

  6. Reminds me of the left coast rule:
    How to make a small fortune in California?
    Start with a large fortune and buy a Winery!

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