What Retirees Wish They Knew Before Moving to Delaware

Living In America Homes
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Jun 17, 2026
Thinking about retiring to Delaware?
Most people start their Delaware research focused on taxes, cost of living, and home prices. But after helping countless retirees relocate, I’ve noticed something surprising:
The things retirees worry about most before moving are often NOT the things they talk about afterward.
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A lot of retirees move to Delaware expecting one thing and then six months later they're
talking about something completely different because they really truly thought that the
big story would be taxes.
Instead they're talking about health care or community or how often their family comes
to visit.
Then on the other hand they're talking about if where they chose to live they actually
enjoy their daily life or how different Delaware feels when that vacation lifestyle starts
to wear off and you actually live here.
And after helping countless retirees retire to Delaware I've noticed a handful of surprises
that keep coming up over and over again.
So if Delaware is on your short list for retirement let's go over some things that retirees wish
they would have known before packing up their house and moving to Delaware.
All right so before we get started there is something that I would like to acknowledge.
If you are figuring out where you want to retire to Delaware oftentimes it is very overwhelming
because you're not only thinking about your current life you are also thinking about your
future life.
Will my family come to visit?
How long does it take to get to the grocery store?
Where are my doctor's appointments going to be?
Maybe I don't have a doctor right now and maybe I don't need a specialist right now
but what does that look like in the future?
Do I want a ranch style home?
Am I okay with a two story home?
Maybe I don't want stairs later in life.
Will we make friends?
I want to be around people my own age but I'm really not sure if I'm looking for the
55 plus lifestyle.
And when it is a decision that is this important it is very easy to start researching everything.
You Google everything.
You're all over YouTube looking for different videos about the area about the health care
everything that there is about the particular spot that you would like to retire in.
And oftentimes by researching so much there are so many more questions that just keep
popping up and it can feel so overwhelming.
So today I want to go over a few things that I've heard retirees say I wish I would have
spent just a little bit more time talking about this.
Okay so let's start off with number one which is I really thought that taxes were going
to be way more important.
Now listen do not get me wrong.
Delaware's tax advantages are one of the number one reasons why people start looking at Delaware
for retirement whether that be property taxes our exemption taxes for retirement income
or the fact that we have no sales tax.
That's usually the number one reason why a retiree even considers Delaware to retire
here.
And listen they absolutely matter.
But something that is super interesting is once they actually move here the conversation
starts to really shift because they start thinking about how often is my family going
to visit me.
Maybe you have friends that are in Lewis and you chose to live somewhere inland because
the taxes were slightly cheaper so you have more money in your pocket but you don't really
enjoy your daily life as much as you thought you would because going to the grocery store
takes a little bit more time.
You're not so happy with your routine.
You don't feel connected into the community.
On the other hand you might be totally happy with the fact that you chose somewhere that
has slightly less taxes and is fitting the lifestyle that you have been looking for your
entire life.
The point I'm trying to make is that yes taxes get the attraction but your daily life is
what's going to give you the satisfaction in where you choose to live.
Number two on things I wish I would have known I didn't realize how important health care
would be.
Oftentimes when I have retirees moving here they are not at that stage where they have
a lot of specialists.
They're not going to doctor's appointments very often or they don't even want to think
about it at all and listen I do the same thing.
I don't want to think about getting to that point where I need doctors every single day
but it is something to consider and Delaware knows that we are a retirement state which
means they are dumping millions of dollars into our health care systems.
We have satellite locations popping up all across Delaware whether that be Sussex County,
Kent County or even Newcastle County.
But it is known that a lot of our specialists are in Newcastle County.
So while you may not want to think about the future and all of the doctor's appointments
that you may have it is important to take that into consideration because depending
on where you live in Delaware will determine your access to specialist appointment availability
travel time because if you are someone that lives in Sussex County and say you have a
specialist that you can only see at Christiana Hospital that is going to be a drive depending
on how many times you need to see that doctor.
One of the things you need to ask yourself is does the health care availability take
care of me now and what does that look like in the future.
Are there things that run in your family that you think you may have in the future.
It's important to look at those things before making the decision to move and what area
actually works for you long term.
Number three things I wish I would have known would be retirement happens on ordinary Tuesdays.
It is so easy to get caught up in the moment especially with the excitement of retirement.
If you're looking at the beaches and all the restaurants and the fact that you can go golfing
and you can take day trips and you want to look at beautiful model homes and you're looking
at the tax benefits and then you actually move in and you realize that you got caught
up in the excitement and it's not actually what you were looking for because retirement
is not lived in highlights.
It is lived in your daily life which is why I will ask you when you wake up in the morning
what does your ideal day look like.
I have heard time and time again people say I wanted to live in Lewis.
I wanted to be near the restaurants.
I was so excited.
It was like the number one thing on my list and then I realized I didn't really like my
daily life.
I didn't really like the beach traffic.
I realized that I wasn't going to a restaurant every single day and that wasn't my daily
life.
It's nice to go to a restaurant and have that availability but maybe I would have purchased
in Milton or Georgetown or even Ellendale where it was slightly cheaper and I could
have gotten a little bit more bang for my buck and still been able to go to the restaurants
the beach within 15 to 20 minutes.
Also it's important to look at the amenities of the community that you are choosing.
If you are someone that knows that you're going to spend all summer at the pool maybe
having an outdoor pool and a clubhouse is super important to you.
Even if that HOA is slightly more expensive than you were looking for and if you're someone
that honestly doesn't need all of that even if the community does have an HOA and it does
have a small pool maybe you choose that because the option is there.
It really depends on what you're looking for in retirement but make sure you're not just
focusing on just the highlights.
Look at what does your ordinary routine look like.
If you are someone that goes to the gym and you need to get to the YMCA or you need to
get to Planet Fitness or Club Fitness or you would like to use the fitness center in your
clubhouse think about those things before choosing where you want to live.
Number four on things I wish I would have known.
I underestimated how much community matters.
I hear this all the time especially from my retirees that are moving out of state.
I would like to be with people my own age in the same phase of life because honestly
I'm moving and I don't know if I'm going to make friends or I want to make friends or
I haven't had the biggest social group and that's the person that I would like to be
in retirement.
Also here's another important aspect that I hear often.
Because you are moving from out of state oftentimes your family is not moving with you so you
rely heavily on your community.
So for example maybe you have surgery and your family cannot come stay with you to help
you.
This is where I see people rely on their community whether someone brings over a dinner for you
or someone helps you around the house or maybe you take a bus trip together or maybe you're
looking for someone to play cards with you every Tuesday.
This is important even if you think you may not want to be part of the community.
Think about long term what are you actually looking for and what brings you joy in life.
Number five on things I wish I would have known.
I thought moving would end the uncertainty.
This one actually feels super important because many retirees think that if they research
everything and they find the perfect state the perfect community the perfect area the
perfect house the place with the cheapest taxes that they absolutely make the perfect
decision.
They still discover things that they couldn't have known beforehand.
What is your daily routine going to look like.
How am I going to feel about the fact that I don't really know anyone and I have to make
new friends or the fact that I need to use a GPS just to get to the grocery store because
I don't know where I am going.
This is totally not a failure.
This is just how transitions work and yes it will take some time to get used to your
new area whether that be you need to figure out that little hole in the wall restaurant
that everyone goes to for pasta on Tuesday nights or maybe you're looking for the best
ice cream place in the area or maybe you would like the best bookstore or you're looking
for a club to join or you really wanted to get into gardening and you don't really know
you join a club at the clubhouse.
My happiest retirees are the ones that are OK with the uncertainty and OK with being
uncomfortable for just a little bit in order to really get acclimated to the area and really
get the most out of retirement.
So the pattern behind all of these surprises that I keep seeing is my happiest retirees
are not the ones that just made the decision on financials.
They really truly thought about everything.
They thought about what is their health care going to look like.
Is the area that they want to be in suitable for them long term.
Is the house that they're choosing suitable for them long term.
Are they close enough and are they being realistic that their family will come visit them or
that they can go visit their family.
Do you really not want neighbors or are you just saying you don't want neighbors because
you're scared of the possibility that you may need to make new friends.
The ones that really truly look inside they feel the excitement.
They are looking for a change.
They are looking to get out of their comfort zone.
Those are my retirees that seem the absolute happiest when choosing Delaware for retirement.
And if you are still deciding on whether Delaware is the right fit for you for retirement.
I do have a Delaware fit guide where it covers all the things that we just talked about.
Whether you are looking for the lifestyle or you're looking for the health care or you
are looking for the right area for you.
It's packed full of information and that is down below in the description.
I really hope that this video helped.
If it did be sure to give me a thumbs up.
Be sure to subscribe to the channel.
If you are still early in your research I want to leave you with one final thought.
You do not need perfect certainty.
You do not need to answer every single one of your questions immediately.
And you do not need to eliminate every single risk before moving forward.
Most retirees gain clarity one layer at a time.
And listen I would absolutely love to help you in making that decision on deciding whether
Delaware is right for you for retirement.
My information is below in the description.
Don't forget to subscribe and hit that like button and hit that hype button and I will
see you on next week's video.
Thank you so much for making it this far into the video.
If you are interested in more Delaware retirement content check out this video right here.
And if you would love to tour Delaware 55 plus homes with me check out this playlist
right here.
And don't forget to subscribe to my channel.
