I think they probably are both way overpriced now. Also how far are you willing to travel, how much traffic can you stand, how much property tax etc etc? Litchfield is a schlep and Hamptons is lots of traffic. It sounds like money is no object for you thought.
We have a home in Litchfield and love it. In non Covid times I think we used it more than our friends with Hamptons homes because we used it all four seasons. It’s more low key than the Hamptons. They are very different communities. I think most people would naturally gravitate towards one or the other, instead of liking both equally.
Most Hamptons owners use their homes all four seasons. Maybe not the super-wealthy, who also have Palm Beach and Aspen homes to visit.
@anonymous we are in our Litchfield home every weekend in the winter because we ski. My friends with Hamptons homes occasionally would use their home in the winter, like maybe once a month...and they don’t have third homes
Do you need the ocean? I think that is the main question.
Must it be Litchfield? We have a second home in Fairfield County on the water and absolutely love it (and it’s just an hour away). We like the more relaxed vibe and down to earth feeling there, but we are definitely not Hamptons people.
We are not really Hamptons people either but we did end up buying a house in Water Mill and I love it. I love being near the beach in the summer and I would 100% disagree about people not using their homes here all 4 seasons. Hank's Pumpkin Town is a fall necessity!
Agree which is why we bought in Westchester. Can get there more easily and in summer could commute to work.
Hamptons has more to do if you want to be around other people - nice restaurants, shopping, walkable downtowns, beach. Litchfield is more woodsy/rural - better if you want privacy, hiking, skiing, hanging out at your own house without seeing other people.