Did I say “never”? Ok, I’ll admit to one teensy-weensy exception; every once in a blue moon, a property comes on the market that seems slightly over-priced ( I said slightly), but it nevertheless gets a deal in the first week or so. That’s your exception. And note that phrase “in the first week or so”.
Yup, if “magic” is going to happen, it’s going to happen quickly or not at all. In 25 years of observing the Greenwich market, I have never, ever seen someone rewarded for hanging in there, “waiting for their price”, not one time. That means, if you’ve had 20 showings and a month or so on the market and no offers? It’s not going to improve, I promise you.
14 Maher Avenue: Asked $1.495M Sold: $1,065,000.
I took a look at sales in the last 12 months priced $1,000,000 to 2,000,000. There were 170 properties sold in that price-range, in that time period. Most sold fairly quickly, a few months at most. But 21 of them (around 12%) were properties that took years and years.
(Note: The listings on this link for the most part do not show the real, actual original asking price or first listing date. That coveted, hard-to-cobble-together information is listed below.)
1. 14 Lake Drive…. Asked $1,249,000. Sold $955,000. Started 5/2010
2. 9 Greenwich Cove Drive… Asked $2,150,000. Sold $1,167,000. Started 9/2009
3. 30 Byram Shore Road… Asked $2,150,000. Sold $995,500. Started 4/2008
4. 28 Hendrie Drive… Asked $1,495,000. Sold $1,205,000. Started 5/2010
5. 14 Maher Avenue… Asked $1,495,000. Sold $1,065,000. Started 10/2009
6. 73 Dearfield Drive… Asked $2,295,000. Sold $1,250,000. Started 6/2005
7. 210 Weaver Street… Asked $1,700,000. Sold $1,205,000. Started 10/2003
8. 12 Perryridge Rd… Asked $1,775,000. Sold $1,100,000. Started 9/2008
9. 34 Crescent Rd… Asked $1,535,000. Sold $1,150,000. Started 5/2010
10. 63 Winthrop Dr… Asked $1,649,000. Sold $1,296,000. Started 10/2010
11. 30 Carrington Dr… Asked $2,550,000. Sold $1,500,000. Started 4/2003
12. 400 North Maple Ave… Asked $1,950,000. Sold $1,450,000. Started 11/2009
13. 1 Stallion Trail… Asked: $2,499,995. Sold $1,150,000. Started 9/2001
14. 357 Stanwich Rd… Asked $2,850,000. Sold 1,550,000. Started 8/2008
15. 18 Ferncliff Rd… Asked $1,995,000. Sold $1,550,000. Started: 6/2008
16. 93 Hillcrest Park Rd… Asked $2,195,000. Sold $1,542,000. Started 9/2009
17. 200 Lake Avenue… Asked $2,850,000. Sold $1,500,000. Started 9/2006
18. 27 Grove Street… Asked $1,999,000. Sold $1,639,000. Started 7/2007
19. 409 Round Hill Rd… Asked $2,195,000. Sold $1,300,000. Started 8/2002
20. 303 Shore Rd… Asked $2,375,000. Sold $1,740,000. Started 10/2009
21. 23 Baliwick Rd… Asked $2,995,000. Sold $1,750,000. Started 3/2008
Grossly over-priced properties do not “get their price”, and the more valuable properties are frequently over-priced by even larger percentages than shown above. The really big boys sometimes sell for as little as 50-40% of the original ask.
Greenwich Bored And Razed 
Thanks for this analysis. Greenwich is the weirdest real estate market I have ever encountered; it really seems to be a hobby for some of the residents to put their house on the market for years at a time at unrealistic prices. I like your idea of an auction type bidding process, putting a $1.6M house on the market for $1M and then let people bid it up (if they want to). Instead the trend seems to be to put a $1.6M house on the market for $2.3M and let it sit for months.