I lived in the Northeast specifically Rochester New York for 55 years, And have never nor known anyone else to ever shovel a roof.

Be careful on the advice you give and pretending that it applies to everyone.

Good ideas here!
 

I like your post. Lots to consider. I personally am interested in the Wyoming ranches. Thanks

Dude you are so wrong. Don't paint everything with the same brush. You scaring the heck out of her you heck you scare the people out that live there and no better... 10-ft rule, training the septic tank, trying to put paranoia in someone. These are all optional depending on where you buy and not a requirement so don't scare everybody

Toms river NJ has many Senior communities .

P.s. taxes ...sorry .

We have neighbors who own there for years .

If you have an open mind, you might consider Sunny Rest Resort, near Palmerton, Pennsylvania. A number of Villagers have been there and loved it. It’s in beautiful mountains a half hour from Allentown and ninety minutes from Philadelphia. While it’s not a retirement community, a lot of people there are retired. It’s gated and fenced. While some people live there year round, the resort is mostly open summers. Weekdays are quiet, weekends buzzing. Most permanent residents own cabins or single-wide permanent trailers fixed up however they like. One comes up for sale now and then. Some are there every day in the summer and others on weekends. Lots of people rent camping sites and bring in an RV or trailer. Most people have golf carts for getting around. There’s one pool, big hot tubs, a small restaurant and a snack bar, volleyball, pool tables, a bar, a nightclub. It’s super friendly, especially if you are there all summer, as so many people hang out on their decks and invite you over. There are hiking trails in the woods. No golf course or club meetings to choose from, but there is still plenty to do, and there is so much community. If you buy a small used trailer, you can rent a nice site for under $5,000 for the summer, then store the trailer there for the winter. Buy a cheap used golf cart and you are all set.
Sunny Rest

This is not what you asked, but I agree with the gentleman who recommended an RV. Consider buying an RV and explore ALL the North. I liked the Poconos, but I hear some of the mountain and lake views in the North are a spectacular sight. There are women’s groups of ladies that camp/RV recreationally and full-time. You can find them on FB groups! Happy Retirement!!!

Try Pinehills in Plymouth Massachusetts. https://www.pinehills.com/
 

Pinehills in Plymouth MA is very similar to The Villages.

Any place in New York along Lake Champlain is beautiful. Adirondack Mountains are nearby too. Great beaches, fishing, golf, etc. Montreal to the north, Burlington Vt right across the lake, and Maine and New Hampshire make great day trips.

My son lives in Cape Cod. Lots of water sports. Buzzard's Bay area is good. Stay away from the Atlantic - sharks. Cooler than Boston in the summer with nice breezes. He lives a block from a swimming pond, has a small stream behind his house, and is close to the Bay. There are condos in the area (not huge developments) which would be nice for a part timer.

Not in Connecticut. Taxes!

Ohhhh. NYC! All the things to do! Gets my vote😄

As others stated, there's nothing like The Villages anywhere. However, a cool place for the summer is Frye Island on Sebago Lake in Raymond, ME. It's not a retirement community, but most everyone rides golf carts to get around. (approx. 475 houses) The only access from the mainland is by Ferry. It has a 9-hole championship golf course, but only one store/restaurant on the island. They also have entertainment various nights at the clubhouse and restaurant near the ferry. There are plenty of other stores/restaurants off the island when desired.

Rent in various areas
 

Every place has it's up and downs. Personally, I would rent in various parts of the country for 1-4 months depending on the area and your want for adventure. Switching starting locations each year. My husband and I traveled for a year and a half renting at places for a month using AirBnB or similar services. One of the things I use the most in these services is skimming through the reviews. This gives you a good idea of what to expect in the area and the rental. I always look for at least some negatives - more believable. I also prefer ones being rented by a nearby person. I have always found them much more helpful than any agency. Once there for a month you will make contacts if you want to have a return visit. Spring and fall are very different even in the same spot. Cottages along lakes or rivers are a personal favorite. Downtown's often have some great vibes. We traveled with our computer bag, 1 suitcase and an overnight bag each - these days you can buy what ever you may run out of our forgot just about anywhere.
Have a wonderful time !

Maine, Vermont, New Hampshire, Upper Michigan , Montana, or North Dakota. Maybe Wyoming.....If it was me......

How far north? Lakes, shore? Poconos PA, Hamptons NY,SIC NJ, Delaware? Best of luck!

Summers up North
 

I'm a Villager 7 months a year and go North for the summer to Cape Cod. I have a small 2 b/r condo in a mini Village atmosphere. 750 units, pickleball, tennis, par 28 golf, rec center with indoor/outdoor pool, fitness center, woodworking, pool tables, bocce, shuffleboard, and many more activities. 13 minutes to the beach. Great restaurants in the area. Lots of lobster. Also many 18 hole golf courses nearby.

It' an over 55 community called Southport in Mashpee, MA.

Beautiful Summers on Lake Michigan!
 

Door County Wisconsin!!
You would love love love it!!

we intend to be reverse snowbirds at some point too

55 Plus communities
 

Try Search 55places.com

The Poconos in PA
Mount Desert Island Maine
Bristol, RI
Vancouver, BC

Nothing like TV. You will have to find your own activity but enjoy the weather and beautiful country

I’m so glad that you set it straight on your finances not being anyone’s concern. I have seen so many snarky comments on these posts since I’ve been in tv….if you don’t have kind words for people keep them to yourself. Aren’t we the friendliest hometown??
Good luck on your search in the northeast and congrats on your lifelong journey to success

Go to Retirement Communities | 55+ Communities | 55places
Also , Ideal Living. I once went to an expo in Long Island about 9 years ago and I still am receiving their magazines.

North Conway, NH. Has everything. Maine, Vermont and Massachusetts easy drives away.

If you like your privacy, I would "Duck Duck Go" Dell Webb Community. Google permanently saves all of your search history. Why would anyone want to use google, when Duck Duck Go is such a great alternative. Privacy Simplified, it's another search engine. Just a suggestion.

Retirement Community in Plymouth MA.
 

You might check out the many retirement communities in the Plymouth MA (55places.com)

I have lived in Maine my entire life so far. My husband and I bought in the Villages in February and will become FL residents in November. We will still come home to Maine for part of the summer. Lots of people buy park models or campers and keep them seasonally in campgrounds for the summer months. That too is what we will be doing. We currently own a class A motor home which we have been living in since April and sold our home here in May. Recently bought a 31 ft camper already set up in a campground and will sell the motor home. We will come back to Maine to stay in that 2 or 3 months in the summer. It's the least expensive way to have the best of both worlds. And yes.... people ride around in golf carts here too just not anywhere near the extent of what TV has to offer.

You would probably love Point Sebago in Maine. Check it out!

Holiday City retirement community in Ocean County NJ.

I totally understand....I think a nice "villages" type of place up in the Adirondacks, Old Forge area would be fun. Golf Carts, the whole works. Of course the activities would be different swimming...in the lake, hiking..on the mountains, boating and fishing. Rent a small lodge from May thru Oct.
Now this isn't build yet... but what an adventure and investment.
I am currently in upstate NY for the summer and actually heading to "the forge" in a few weeks to stay at a very rustic condo...on the outside, updated on inside. So close to the senerio, but obviously needs more fun added.

Ps I would suggest some kind of fence around the whole perimeter... those damn bears scare me.

Lake George in upstate NY is nice.

As a person who did that it’s very expensive 4000-/ mo it’s hotel living and within weeks you’ll want to leave

I like the idea of renting in a variety of places, too. Starts with the letter V and ends with the letter O, RB are in the middle, makes this so easy.
In answer to your question, two ideas. Landsdowne Woods in Landsdowne, VA. It's the Old Leisure World. Both homes and condos with all the social programs of the Villages. I have friends who live there. Great retirement community. Located on the Potomac. The views are beautiful. Shut the door when you ready to leave. Convenient to Dulles Airport and the Appalachian Trail. Beautiful part of the country.
Second idea, Cashiers, The Highlands or Asheville, NC. I've spent some great summers in all those locations. Higher altitude and wonder summer temperatures with Southern ambiance. This is where Atlantans go to escape the heat. Why go to New England when you can stay in the South? The good season will be longer.

I would suggest that you rent 1 to 2 months in one place and go to various areas. The northeast is a large area and the range of options is endless. If you decide to purchase a home, look for a home in a retirement community that takes care of the outside property -- lawn mowing, snow removal, etc. Even if you have the money, it is often hard to find people willing to do snow removal for residential customers. Also, there are areas that have sump pumps in the basement -- you should avoid those areas because even with a battery back-up, the pump will continue to remove the water for only a short period of time. The cost of normal household maintenance is higher in the northeast than The Villages. Good luck with your search.

There is a sleepy town on Lake Erie, golf cart town, low taxes called Fairport Harbor. Fishing, golfing, lake activity, great senior center.

Look at the Fingerlakes in upstate NY. They are a series of lakes in beautiful rolling hills that offer many amenities in the summertime. We are snowbirds staying 3-4 months @Canandaigua Lake. The area “wakes up” in the summer with festivals, wine trails, & art.

Vermont
 

Burlington Vermont is a nice town. Lake Champlain is pretty! But you might run into Bernie Sanders there though. LoL

We traveled full-time in our motorhome prior to purchasing a winter home in TV. In the summer, we chase 70 degrees, ending up in Breckenridge, Colorado this year for the summer. Next year, we are going to try Nova Scotia and Prince Edward Island if the border is open. Owning a RV gives you flexibility to try other places.

Utopia - That's Easy!
 

I have a summer home on/near the Chesapeake Bay. I have a boat and travel to various locations around the Bay for long weekends. I love Annapolis, MD, St. Michaels, MD (at one point voted Top Retirement Location), Oxford, MD (a little more low key but beautiful).

There you have it or should I say, there you have my picks. :)