I think I'd like a summer home and a winter home

Love the concept, OP, although I've never been to either spot so can't comment on that specifically. If funds were of no consequence I'd take a flat in London for winter and one a renovated country house somewhere near Wiltshire or the Cotswolds for the summer months. Ah, dreams.

Upstate would be boring. If we’re fantasizing, I understand the place below The Evening Punctuationist on Park Avenue is available. $32 million, but it’s a duplex. Does not come with its own Randolf. Do you play Whist? Well, you can learn.

Just buy one home in St Louis instead.

Palm Springs, January to March Cape Cod/Ptown July to September Rest of the time right where I am now.

Westchester is not "upstate"

R5, If you live on Park Avenue, Yonkers is upstate.

It's hard enough to keep up with dealing with the issues of owning one house let alone two.

My winter home will be in the Antarctica and my summer home will be underwater.

Summer Wisconsin, winter Charleston.

Westchester is not really considered upstate.

I think I'd like a cricket or a beetle for summer and winter.

All the Australians/Brits I've met over the last month rent or sublet their homes while traveling two months a year. I don't know their finances, but they seem to be able to go wherever they please.

For me it would be Mercer Island and Panama City.

Summer in Nantucket and winter in Key West. I like islands.

I'd want a home I could use for both seasons, preferably something in the mountains...Catskills, Poconos, Adirondacks, the Berkshires.

Puerto Vallarta in Winter, a small island off the coast of maine in summer. Already doing it. I’ve given up a few things to be able to afford it but I’m very happy.

Winter in a city like NYC or London; summer in the French countryside somewhere.

A floor in NYC, weekends out Long Island, Amagansett.

we are going to be doing the Palm Springs/Traverse City circuit.

I love Westchester County but it’s $$$ and taxes are ridiculous and nearly everyone has kids, or they’d live in the city and avoid $30-$40K a year in local taxes. Def not upstate by any means.

I'd have to have three: Wilton Manors, Palm Springs and either P-town or Fire Island. Plus I'd do a couple gay cruises each year.

Bainbridge Island/Maui

R18, Traverse City in the summer and Fall is awesome! Winter, not so much.

We are wintering in Palm Springs this year. We go somewhere different every year. The last two years were Australia the year before was a four month road trip through the Southern U.S. Then through the North in late Spring.

Live up in the mountains during the summer. High elevation where it's cooler.

Westchester gets hot and humid in the summer. Maybe Maine instead.

While I could afford to do it, I just think it would be a hassle to maintain two houses and always be worrying about what was going on in the empty one. Are you planning to drive between the two locations (a looooong trip, obviously.) Because if you fly, there's only so much you can bring with you, so you'd have to have duplicates of many items.

I've had a winter/summer home OP (Chicago/Phoenix), and ... I really can't recommend it. If you are rich, sure, knock yourself out, but otherwise ....

Who is going to take care of the place 6 months out of the year? Check pipes? A/C? Yard?

Owning a second home is not cheap and (even more so now) the tax deduction isn't what it was. Long term, you may make money on the property, but you have to factor in what you put in.

When I finally sold my 2nd home, I did make a fair amount of money. I doubt I really came out ahead in the long (13 years) run though. Just do AirBNB,

Can be done, especially if winter home is main-home and summer home is a holiday/weekend one. Do no more than a 2.5-3 hour drive. Or train trip. Like LIRR out to Hamptons. 4:19 east, arrival 7:10. Quicker on summer trains. Or do any drive down to Jersey Shore or up to Connecticut or upstate NY. Don't know other areas, but an apartment in Chicago, say, and a weekend house elsewhere one'd want to go to, well, life can be fun.

Westchester is nice only if it have a family. The taxes are insanely high and most of it goes to the schools, which are generally excellent.

NYC base with a cheap weekend house upstate or Berkshires for spring, summer fall. 3 month rental somewhere warm Jan-Mar. - Tampa, South Texas or Tucson.

We have an apartment in Manhattan and a home on the Big Island in Hawaii. We spend May/June and November/December in NYC and the rest of the time in Hawaii. When we're not in NY, we Airbnb the apartment. In both cases, we use a maintenance company to manage the properties when we're not there.

It may sound expensive, but it's actually quite manageable. We don't have a mortgage, and no credit card balances. Also, I have lots of frequent flyer miles to get us back and forth. We both are in good health, and so far, it's worked well.

Nice life R30. Congrats.