Who are the best real estate agents on the Upper West Side?
We've asked ChatGPT this 3 times over the past 3 days. It doesn't give the same answer twice, so instead of one day's list, here's how often it named each person. Ann Cutbill Lenane came up most — 3 times out of 3.
Named most often
ACROSS 3 ASKS
01Ann Cutbill LenaneDouglas Ellimannamed 3 of 3 times (100%)
02Dylan HoffmanCompassnamed 2 of 3 times (67%)
03Michael J. CarrollBrown Harris Stevensnamed 2 of 3 times (67%)
04Deanna KoryCorcorannamed 1 of 3 times (33%)
05Lawrence SchierCorcorannamed 1 of 3 times (33%)
06Lisa K. LippmanBrown Harris Stevensnamed 1 of 3 times (33%)
07Friedman Rosenthal TeamBrown Harris Stevensnamed 1 of 3 times (33%)
08The Kerins TeamBrown Harris Stevensnamed 1 of 3 times (33%)
09Anna KahnBrown Harris Stevensnamed 1 of 3 times (33%)
10Alyse KennySERHANT.named 1 of 3 times (33%)
11Larry SchierCorcorannamed 1 of 3 times (33%)
The most recent answer, in full
ASKED OCTOBER 30, 2026
01Ann Cutbill LenaneDouglas EllimanLongtime UWS specialist; top Elliman producer
02Lisa K. LippmanBrown Harris StevensTop Brown Harris Stevens West Side broker
03The Kerins TeamBrown Harris StevensHigh-volume UWS team with building expertise
04Dylan HoffmanThe Hoffman Team / CompassHigh-transaction team; strong Upper West Side presence
05Michael J. CarrollBrown Harris StevensThirty-year Upper West Side local expert
Shortlist of top-recommended real estate agents and teams for Manhattan's Upper West Side market.
Why two lists? Because ChatGPT rarely says the same thing twice. Ask it this question on two different days and most of the names change — across every question we track, only about one name in five survives to the next day. So the list at the top, counting how often each person comes up, is the more honest answer. The one below it is simply the most recent time we asked.
All of these names are ChatGPT's, not ours. We didn't pick them, we can't change them, and nobody paid to be here. How we do this.