What makes more sense as to where to retire considering taxes, etc? Massachusetts, New York, or Connecticut?

[MrBojangles]

Specifically, Berkshire County Massachusetts, Litchfield or Fairfield Counties in Connecticut, or Dutchess or Westchester Counties in New York? Yes, all not great choices, but which areas are the best and the worst?

I should come to my senses and consider West Virginia, but DW and I like visiting these areas.

I don’t even know what state income taxes are in these areas. Other than Connecticut used to not have a state income tax and created one a bit over 30 years ago now and it cost them a lot more in the long run than not having one at all.

It would be nice if these three states would do something to stop the drain of folks out of there, especially when they retire, but they don’t “get it”.

 

[USGrant1962]

Here's a calculator where you can plug in your own numbers and see.

Best States to Retire for Taxes (2025) - Tax-Friendly States for Retirees

Some states have taxes that are friendlier to retirees' financial needs than others. Use SmartAsset's set of calculators to find out the taxes in your state.

smartasset.com

In the Northeast, PA and NH are generally considered tax-friendly for retirees.

 

[MrBojangles]

Here's a calculator where you can plug in your own numbers and see.

Best States to Retire for Taxes (2025) - Tax-Friendly States for Retirees

Some states have taxes that are friendlier to retirees' financial needs than others. Use SmartAsset's set of calculators to find out the taxes in your state.

smartasset.com

In the Northeast, PA and NH are generally considered tax-friendly for retirees.

I’m in Pennsylvania now and it isn’t nearly as beautiful as the areas outlined in the title of this thread. I like Virginia a lot as well and lived there before and feel like I paid more in income taxes there than in Pennsylvania, otherwise I might strongly consider Virginia as well.

I’m all for states rights but this is ridiculous having to pick where to retire and play this “game”. Realistically, there should be state income taxes or Federsl income taxes, but NOT BOTH.

General Grant is my 5th cousin.

 

[Dash man]

Pennsylvania has a flat 3.07% tax and doesn’t tax SS, pensions or 401k/IRA withdrawals.

 

[Diogenes]

Why not New Hampshire, just across the border from Massachusetts?

 

[MrBojangles]

Why not New Hampshire, just across the border from Massachusetts?

Haven’t been there but briefly 40 years ago.

Hadn’t considered it.

Let’s also throw Delaware in the mix, no sales tax.

Does Pennsylvania make sense? I feel like it’s expensive for what you get, especially the school tax, which is outrageous when you don’t have kids.

 

[MrBojangles]

I also sort of feel that you may not be seeing the trees through the forest when deciding on a state for reasons other than you like it when the elephant in the room is outrageous Federal income taxes? How much should a middle class couple be required to bear? A five figure number every year starting with a 5 is a tough pill to swallow.

 

[Al18]

I assume middle-class couple means 12% tax bracket. At the top of the 12% tax bracket, you’re talking 10K federal taxes per year. I don’t know how you’re paying 50K federal taxes.

 

[Gumby]

You could consider places other than Connecticut, but why? It is, by far, the best place to live in the USA.

 

[RetiredHappy]

I assume middle-class couple means 12% tax bracket. At the top of the 12% tax bracket, you’re talking 10K federal taxes per year. I don’t know how you’re paying 50K federal taxes.

It depends on whether you are still working or not. We were paying six figures in Fed taxes for a couple of decades while we were working. Now we are in the beginning of 24% tax bracket and consider ourselves middle class.

 

[MrBojangles]

You could consider places other than Connecticut, but why? It is, by far, the best place to live in the USA.

Where in Connecticut and please explain this further.

 

[Koolau]

Your individual mix of income is critical to consider. Most states exempt "something" and that may make them a "bargain" in your particular situation. We found our state to be very low tax for US but it's one of the "just moderately" good tax states (according to the site above).

As to "why" states have different tax rates (and tax consequences to their "subjects"), well, that can become political. IOW "fair share" may be defined differently in each state so YMMV.

 

[ncbill]

Pennsylvania has a flat 3.07% tax and doesn’t tax SS, pensions or 401k/IRA withdrawals.

But it does have an inheritance tax:

"4.5 percent on transfers to direct descendants and lineal heirs;

12 percent on transfers to siblings;

and 15 percent on transfers to other heirs."

 

[Dash man]

But it does have an inheritance tax:

"4.5 percent on transfers to direct descendants and lineal heirs;

12 percent on transfers to siblings;

and 15 percent on transfers to other heirs."

Yes it does. Two of our properties are in other states, so fortunately will not be taxed. But considering what the boys will get, the tax won’t sting too much.

 

[Gumby]

I did not and would not choose a place to live based on the tax rates. I try to keep in mind that in most cases things are cheap for a reason. Just for example, where do you usually find the cheapest houses? In the most run down neighborhoods full of drug dealers and other ne'er-do-wells.

 

[pb4uski]

In addition to taxes, consider health insurance costs.

 

[Aerides]

I would never decide on where to live because of taxes. I would live where I want to: Family, friends, activities, weather, and then make the finances work.

Moving is expensive. Moving for lower taxes may take many years to break even.

 

[Sojourner]

I also sort of feel that you may not be seeing the trees through the forest when deciding on a state for reasons other than you like it when the elephant in the room is outrageous Federal income taxes? How much should a middle class couple be required to bear? A five figure number every year starting with a 5 is a tough pill to swallow.

What does federal income tax have to do with deciding which state to live in? Also, while you and I might agree that federal income taxes are absolutely no fun to pay and can be quite burdensome, I don't think they can be characterized as "outrageous" when compared to many other first-world countries. Here is a list of OECD countries with higher rates than the U.S. (which has a top rate of 37%):

• Japan: Around 55.9% (national)
• Denmark: Around 55.9% (national and municipal combined)
• France: Around 55.6% (national, plus surcharges)
• Austria: Around 55.0%
• Sweden: Around 52.2% (national and municipal combined)
• Italy: Around 52.8%
• Ireland: Around 52.0%
• Belgium: Around 60.2% (can be higher with surcharges)
• Portugal: Around 58.2%
• Netherlands: Around 51.5%
• Germany: Around 47.5% (plus solidarity surcharge and church tax if applicable)
• Australia: Around 47.0%
• United Kingdom: Around 47.0% (includes 45% income tax + 2% National Insurance)
• Canada: Around 53.5% (federal + highest provincial rate)
• Norway: Around 47.4%
• Finland: Around 58.0% (national and municipal combined)
• Greece: Around 53.5%
• Israel: Around 50.0%
• Luxembourg: Around 47.2%
• Iceland: Around 44.4%
• Spain: Around 45.0%
• Chile: Around 40.0%
• Colombia: Around 39.0%
• Korea: Around 48.0%
• New Zealand: 39.0%

 

[SnowballCamper]

I certainly considered income taxes as the army moved me around the country for 20+ years. But it's just one part of a holistic decision. I'm glad there is no income tax here in WA, but I did pay almost 10% sales tax on the purchase of a new home. Whenever I look into the taxes in another location, I end up being happy with being here. It's not the cheapest, but has other benefits.

 

[braumeister]

I would never decide on where to live because of taxes.

+1
Things tend to even out when you look at the whole picture. Somewhere with low income tax may have high property tax or sales tax. You have to consider it all, and looking at averages published in someone's list doesn't help. You have to do the calculations based on your own individual situation, and then decide if any difference is really worth it to you.

 

[aja8888]

I certainly considered income taxes as the army moved me around the country for 20+ years. But it's just one part of a holistic decision. I'm glad there is no income tax here in WA, but I did pay almost 10% sales tax on the purchase of a new home. Whenever I look into the taxes in another location, I end up being happy with being here. It's not the cheapest, but has other benefits.

I've never heard of sales tax on the purchase of a new home! Wow!

 

[Walt34]

I should come to my senses and consider West Virginia, but DW and I like visiting these areas.

West Virginia can be nice but as with any state one has to do the homework first. There are spots in WV you couldn't pay me to live in but that's true of any state.

But we do like living in the eastern panhandle of WV, which is the "wealthy" part of the state, even more so than the capital. Housing prices range from several million to mid five figures for a house that is actually habitable. In looking for a five-figure house in many places you drive by to see if it's still standing. But realistically, around here a nice but not luxurious house will be $300k to $500k. Most of those will come with two to five acres.

There is a hospital fifteen minutes away, and two more 30 minutes away. Johns Hopkins is just over an hour away. This matters when you develop health issues. And of high importance to us, one does not have to plan daily life around rush hours and traffic.

 

[Flyfish1]

My vote is Litchfield Cty #1, Berkshire Cty #2, although I could easily switch that around.
They are both beautiful with lovely areas to live. I've lived in Westchester Cty NY - big NO on that one for me. I've lived in NJ right beside PA as well as NYC and currently reside in CT.

 

[Flyfish1]

You could consider places other than Connecticut, but why? It is, by far, the best place to live in the USA.

Gumby knows best!

 

[Graybeard]

I live in Litchfield County. You couldn't pick 3 worse states to live in unless you looked at California. All 3 have high taxes but it seems all you care about is taxes? All 3 states usurp your rights and highly tax everything but the air you breath, and I am sure they are working on how to do that. [mod edit]