Greenwich CT Pros and Cons: What Changed Since 2021

What happened in 2021 shocked even me. Today, you'd be hard pressed to find a home under a million bucks, and home prices have shot up about 70 percent since then. Before you fall in love with Greenwich, this is what you need to know.

Hi, my name is Charlie. Over the last decade I’ve helped hundreds of families relocate here from all over the world. Let’s find out if Greenwich is a fit for you.

Since I did my last 2021 pros and cons video, a lot has changed in Greenwich. I think one of the biggest and most obvious changes are prices. Clearly they’re up significantly. Depending on the data that you look at, you're up roughly 60, 65, maybe 70 percent depending on the neighborhood.

However, if you were back in the market before the big covid shift which happened in late 2020, you would have felt a little differently about the market. And so this stronger market, all of these price increases do have a sort of a pro in that you can be more confident in the housing market and the strength of the housing market. And that certainly is keeping a lot of pressure in demand on the market.

Inventory and How You Shop for Homes

Another big shift in the market is a significant reduction in inventory. Quite frankly, you shop differently for a home today. I’m not sure if this is a pro or con, but I definitely think it’s something that everybody needs to be aware of.

Prior to covid, you would quite frankly probably come and see, call it five houses. Maybe you come on another next weekend and see another five. Today, there just isn’t that much inventory.

So you may come and see a few houses and then see one at a time as the weeks go on, again depending on the time of year and how much new inventory is coming out. Perhaps a little more, a little less, but just to give you an idea, that’s a big shift. It’s a shift in the way that you shop for a home.

I used to come out and just see a bunch of homes, pick one. Today you sort of have to wait or know what you want, be really clear about it, and be ready to pull the trigger so when the right one does come, you’re ready to get it.

Bidding Wars

So the bidding wars are probably a con for some people. I think this is manageable with the right agent, the right person guiding you. They can show you how to get through it. However, it's something to be aware of. For new listings that are well priced in good homes with attributes that most people appreciate and are looking for, you're probably unfortunately going to be in a multiple offer situation, especially as we roll into the spring of 2026, seeing the low inventory rolling into the years and some of the other things going on right now.

Traffic and Congestion

Another big shift locally is the traffic. So we pulled a few more people into the area with the housing boom and unfortunately it seems as though that’s created a little bit more congestion. You may see it on Route 1 in Greenwich. You may see it on Greenwich Avenue.

I think where you're going to see it most is probably on I 95, likely the stretch even after Greenwich into Stamford is one of the problem spots. But since it backs up in Stamford, sometimes that causes some issues in Greenwich as well. But the traffic congestion is a little worse than it was 4 or 5 years ago.

The Commute

The nice thing is that if you're not traveling to work by car, which quite frankly most people going to New York City don’t do, they're going to take the train. The train has remained incredibly consistent. Times are pretty much the same now as they were pre covid and you can still get into Grand Central in about 45 minutes.

The train is consistent compared to a more stressful commute where the traffic’s up and down and you sort of don’t know exactly how much time it's going to take.

Remote Work and Internet Speed

You know another great thing about Greenwich, we’ve got a lot of people that talk to me about remote work and quite frankly, the questions around internet are quite common. Is it good enough for that type of living? Definitely. Quite frankly, not only in Greenwich but in all the surrounding towns, your internet speed is excellent. So working from home and making calls over Wi-Fi no matter where you are is just not a problem here.

Healthcare Access

Another real pro and a question I commonly get is around healthcare. What's the quality of healthcare in the area? If you need something, where do you go?

If you live in the city, you probably already know there’s a lot of great doctors in the city. When we're out here, we all have the city for doctor access, but we also have Yale New Haven sort of in the middle of the two. To be completely frank with you, between those two and many of the other hospitals that are in the area that have specialists and specialties, you really aren’t at any shortage for doctors in this particular location.

Low Taxes, Strong Schools, Strong Safety Ratings

Okay, so let’s talk about some of the things that haven’t changed but are still really good attributes for Greenwich. One is the relatively low taxes. Low compared to Westchester and low also compared to Connecticut, which is much lower typically than New York State. That persists.

You want to check into the school ratings, but many people are happy with what they see there. And that’s a really important attribute for people who are buying in this town because that’s a big reason why the prices have stayed so high over the years.

I think if you look into the crime ratings, you’ll see that they’re relatively low compared to the nation as a whole and even compared to the rest of the state. That’s another attribute keeping prices strong.

The “Snooty Resident” Myth

Alright, let me address another one that I see a lot more online. I’ll be frank. I don't think anyone has ever called me and asked this question, maybe not directly, but the quote unquote snooty nature of a Greenwich resident.

Here’s what I think people misunderstand. Greenwich is part of the New York City metro. We are New York City. When you are in New York, you tend to put a shell on you, protect yourself. There’s people coming up to you asking you, trying to sell you stuff, right?

So I think naturally that transcends into our personality. And what you're seeing is a person who has a little bit of a shell, who is protecting themselves. They don’t know what you're coming up to them for.

I think what you find is once you get past that shell and past that point, you're going to find that people here are just as friendly as everywhere else. It’s just that outer shell that's throwing some people off who aren't used to it.

Beaches

And if you're a beach person, there are a lot of really great beaches in the Gold Coast. However, Greenwich Point has got to be number one in my opinion. It is 143 acres with a beach with walking trails. I’ve never taken anyone there and not have them just totally wowed.

If you live in Greenwich or are a Greenwich resident you get access. There is a pass available for non residents. It's a little tricky to get. You go to the town website, find out more about that if you'd like. But the park itself is absolutely stunning and amazing.

Diversity Concerns

Okay, let me talk about a sensitive subject. Please don’t kill the messenger. This is a really common thing that I get a call about quite often. People talk to me about diversity. Diversity in Greenwich is relatively low if you compare it to a neighboring town like Stamford. And you look at the demographics of the two, it's obvious.

What I will say is I have not experienced anything that looks like racism or sounds like somebody’s being racist. That could just be maybe my position, the people I associate with, I'm not really sure.

But what I would recommend you do is come here, explore the area, live a day here like you normally would. Come here and do some shopping on Greenwich Avenue, have a really great lunch over at Little Pub, go to Bruce Park and bring the kids to the playground.

My point to you is spend a day here like you normally would and just see if you feel like you don’t fit in. And if you feel that, you have your answer.

Walkability

Another thing that people often ask me about is walkability. Some parts of Greenwich are highly walkable. Old Greenwich in particular, downtown, even parts of Cos Cob. Highly, highly walkable.

Now, there are always places to go for a casual walk with a stroller, for a run, for a bike ride. You’ll see people doing this all over Greenwich. But when people talk about walkability, generally they’re looking for more of an urban type environment. And you’ll find that throughout different areas in Greenwich are definitely a lot of great opportunities.

Real Estate Variety

Another pro that a lot of people miss about Greenwich is the diversity of real estate. It is a very large town. That means that you can be near the coast with more of a beach lifestyle, perhaps closer knit homes closer together. And as you move north in town, the homes start to spread apart. It gets a bit more peaceful.

And so there’s an array of different types of living and you can figure out which one is the best for you.

Contractor Pricing

Another con that people often bring up to me are the high prices for home repairs and contractors. If you're not aware, in my past life before I was a realtor, I owned a construction business. We covered Greenwich and other areas across the Gold Coast.

Let me shed a little bit of light on this. There is some reality to the fact that some contractors will come to town and will price the job based on the fact that it's in Greenwich with the assumption that you could afford it more than, say, the guy in the next town.

However, what is also true is that you most likely have a higher standard than someone else, let's say, in a different town with a more modest home. That means that we need to bring better contractors. That means that contractor needs to bring his best guys. He probably needs to allow a little more time for the higher quality of job.

So it's not that you're not getting anything for the extra money. You are getting higher caliber of work. Assuming that you're doing your research to find a great contractor. And so it’s not all that money going to waste. Quite frankly, you're getting a nicer home.

Next Steps

So what's your next step beyond looking for properties? Get out and explore Greenwich and 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 a visit so I can show you where you’ll most likely find what you’re looking for. That way you won’t waste any time or miss anything important.

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