Westport CT Pros and Cons (2026)

So, you're probably doing research on Westport. Maybe you've even seen our 2021 pros and cons video. A lot has changed since then, and I bet you're wondering, is Westport the slam dunk that you hope it is, or are there some hidden things maybe you should know?

Hi, my name's Charlie Vincy. I've been helping hundreds of families relocate to the area for over a decade. And we're going to jump right into it.

Higher Prices Since 2021

All right, let's just start with the most glaring con. Since I did my last pros and cons video in 2021, prices are significantly higher. The reality is you're paying a lot more for a home today than you did just 5 years ago.

The good news is the market is also much better. I think that if you were to purchase a house, let's say back in 2018, 2019 before our big market shift that happened from COVID, you probably would have been less certain about the market. All these years of great appreciation certainly changed the optimistic outlook of buyers in town.

And well, frankly, you're benefiting from that trend of great market and people are also seeing the properties as a good value means that your investment is probably more secure than it would have been say if you bought before COVID. So the price increases do come with some upside.

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More Traffic Since 2021

Something I would say that really has significantly changed since 2021 is a little more traffic. We've had some reports I95 is more congested. We have people moving to the area. We probably have a higher population. So there's more people actually physically here.

We're also working from home more. So it means a little more local congestion. I can see it, sort of sense it, on the middle of the day, let's say Saturday near the village centers. But 95 is probably where it has been most obvious for most of us. Congestion building along I95 and it's something you'll want to take into account if you're going into the city.

The Commute

If you're not traveling by car, the train is consistent and continues to be really good. Depending on which station you leave, you're probably around 70 minutes to Grand Central. You're on the main line. There are no transfers in Westport.

And consider that you're up the line a bit from other major stations like South Norwalk and Stamford, which means you're likely to get a seat. You can sit down and get work done. So maybe rather than getting in as fast as possible, you can switch the approach as getting work done while you're getting in and getting out of New York City, which will just make you a whole lot more productive.

The Arts Scene

All right, let's talk about something that I didn't think of considering in the original pros and cons video that I created, the arts scene in Westport. The town is really focused on being an arts town. So, if that's important to you, if you feel that you're the type of person that gravitates in that direction, you should know one, that Westport has a long heritage as being an arts town, and two, it tweaks the town's focus on just about everything.

They really try to emphasize that fact in all of their marketing and even events that happen around town. So if you find yourself being more artsy or perhaps your spouse is, you feel like is in that realm, I think Westport's definitely a place to consider.

The Mill Rate Myth

Another thing that I find being reported as a pro, which I will tell you probably is less of a pro than maybe it appears, some sources are reporting a decrease in the mill rate, which is the calculating factor for your home taxes in Westport, as going down and this being a good thing.

Well, let me shed a little reality on that light. The mill rate is a multiplying factor. They take the value of the real estate in town, they multiply it by the mill rate, and roughly that's going to equal the town budget.

So the mill rate going down in this case is really a reflection of the value of the real estate going up. So the multiplying factor, you don't need as much money because the value of the real estate's gone up. They're going to use a multiplying factor to determine your taxes.

They can't double your taxes. They don't need that much money in town. People would get very upset about that. And so the mill rate or the multiplying factor goes down. This isn't necessarily a bonus. I think taxes are still increasing on a dollar amount for that particular home over time.

So you're paying a little more. A little more percentage of the value of the home is going down, but the number is still creeping up.

Suburban Living vs City Life

All right, let's talk about some of the cons of Westport compared to city life. I think one of the most obvious things that you're probably already thinking is that life is going to be a little simpler. There aren't as many entertainment opportunities in town, although there are plenty, especially when you consider adjacent towns like Fairfield or Norwalk, potentially even Stamford, where you would go for comedy shows and other things.

The reality of this is that you need a car to do all this. Westport's a lot less walkable than city situations that you may be used to. And so when you move here, it's more of a car life rather than getting up and walking anywhere.

Now you can walk in the town center. That area is highly walkable. Some of the area near the Saugatuck train station may be considered walkable as well. However, most of town is really typical suburban feeling and so the houses are spread farther apart and so walkability just becomes sort of nonexistent at some point when you get outside of the in town area.

Diversity Concerns

All right, let's talk about this sensitive subject, diversity. Please don't kill the messenger. I'm doing my best here to address a common issue that gets brought up to me on the phone over and over again when people call in and talk to me about different areas.

Diversity in Westport is relatively low and the concern for some people is, am I going to fit in?

Let me answer the question this way. I think that I have never had a personal experience in Westport that's made me feel like anyone of any race, color, or preference wouldn't fit in in Westport.

So, here's what I suggest. Come here, spend the day, live your life like you normally would live it, and see if you feel like you don't fit in. My hunch is you're actually going to really enjoy your time.

Come here. Go to the Black Duck. Have a really great greasy cheeseburger if that's what you're into. Go down to the waterfront shopping area and get some gifts perhaps for birthdays that are coming up.

If it's the right time of year, you can go over to Levit Pavilion, maybe the Westport Country Playhouse, see a show.

My point is spend a day here like you might normally spend a day bouncing around doing things and see if you really sense a feeling that you don't fit in. And if you don't, then you have your answer.

Dining Scene

One real pro for Westport is, and to be fair, a lot of the other towns can match this, but hey, you're living in town and you're going to want to go out for dinner occasionally and have a really nice meal. You probably would like to stay close to home.

And Westport has a really amazing dining scene. In fact, if you really want to focus on an area while you're here, place to get lunch is right by the Saugatuck train station. There's just a cluster of restaurants. Pull out your phone. They're all probably around four and a half stars, overwhelming majority of them.

So, the options are pretty much endless and they're all great choices. Westport's dining scene is really, really great.

Historic District

Another thing to love about Westport has a very large historic district. If you love historic homes and preservation, Westport has a larger area than many of the other towns and might be worth an exploration if you lean towards the older homes.

Reputation for Snoodiness

Another thing that I see online as a potential con for you, this is certainly not coming from me, but is a quote unquote snoody culture.

I think if you were to come, as I recommended you to visit the area, you'll be able to assess it. Then it might just be that I've lived here all my life and I just don't feel the snoodiness. But I think if you come to Westport, spend some time here, I don't believe that you'll see that.

One thing I should point out. You're coming from a different part of the world and you're coming into Westport. This is New York City. We are geared to be a little on the ready for people coming up to us and sort of pitching things to us.

And so if you walk up to someone here and you try to start a conversation like you might do in the South, let's say, you're going to get a different reception. That's not snoody. That's how we're built. We're New York City.

Just understand that we sort of are on the ready for someone coming up. What do you want from us is our general subconscious. And so just be aware of that.

I don't think that that means that people are any more difficult. I've actually spent a considerable amount of time in the Carolinas and I think I can compare pretty well.

I think when you break through the surface, people are just as friendly here as they are anywhere else. It's just that sort of shell that we have here in New York City. So keep that in mind. That's not snoody. That's sort of self protectionism.

Pros That Have Not Changed Since 2021

Lower Taxes Than Comparable Towns

All right, let's talk about some pros that haven't changed since 2021 and really keep Westport as a great option.

So, taxes. Relatively speaking, for the price that you're spending for a home, if you take that amount of money and you move it over into some of the adjacent towns or definitely over into Westchester County, you are going to pay more in taxes for the home.

So from that perspective, if you are spending say two, three, four million dollars on a home, maybe more, the amount of money you will pay in taxes is lower in Westport. So it's a great place to buy a more expensive home because, relatively speaking, you're going to pay less tax.

Low Crime

If you've done some research online, you can see that Westport relative to other towns on sites like Neighborhood Scout have relatively low crime ratings. That stayed the same.

Strong Schools

If you've gone and researched the schools, you can see that the schools have relatively high ratings as well. That stayed the same.

This is important. These are the things that are deal killers for people. If they were to change, then the value of the real estate potentially over time would go down. And so these have stayed consistent.

Excellent Amenities

And another thing that stayed the same is the amazing amenities in Westport. We have tons of videos on this, so I'm not going to elaborate too much here, but Westport's got a lot to offer.

Diverse Housing Options

Another great thing about Westport are all of the different options in living.

If you want to live in, say, something like a condo near town, you can do that. And if you want to live on a larger lot out of town, something more like an estate, something private, something somewhat secluded, you can do that.

If you want to live in a small community where the houses are closer together, I often call that the ultimate trick-or-treating location, you can do that.

So, Westport has a diversity of different types of real estate, suburban real estate, that fit into the overwhelming majority of people's requirements or what they're looking for.

Your Next Step

So, what's your next step? Beyond looking for properties, get out and explore Westport. See if it's a fit for you.

But first, give me a call. Get all your questions answered and let me know if you're planning to visit so I can show you where you're most likely to find what you're looking for. That way, you won't waste time or miss anything important.

And finally, bookmark my buyer guide for the towns you're interested in. It's where I keep all my maps, videos, and organized town info. It'll give you the tools to make a great choice.