If you're reading this, you're probably sitting in your Manhattan apartment (or maybe Brooklyn, or Queens) scrolling through Zillow at 11pm, wondering if Greenwich is really worth it. The commute. The schools. The lifestyle change. The price tag.
I get it. I was you five years ago. And I'm going to tell you the things I wish someone had told me, the stuff that doesn't show up in those glossy relocation guides or on Zillow listings.
This isn't a sales pitch. I'm not trying to convince you to move here. I'm just going to be honest about what Greenwich is, what it isn't, and whether it might be right for you.
The Commute: Let's Be Real
Everyone asks about the commute first, and for good reason. Here's the truth: it's not terrible, but it's not nothing either.
From most Greenwich neighborhoods, you're looking at 45-55 minutes to Grand Central on the Metro-North. That's door-to-door, including the drive to the station and the walk to your office. If you're in Old Greenwich or Riverside, you might shave off 5-10 minutes. If you're in backcountry Greenwich, add 10-15 minutes.
The trains are generally reliable (way more than the subway), and you can actually get work done. But here's what they don't tell you: that 45 minutes feels longer when you're doing it twice a day, five days a week. And if you're used to a 20-minute subway ride, it's an adjustment.
The good news? If you can work from home even two days a week, the commute becomes totally manageable. And honestly, most people I know who moved here during or after COVID are doing hybrid schedules anyway.
The Neighborhoods: They're Not All the Same
This is where Greenwich gets interesting. Each neighborhood has its own personality, and choosing the wrong one can make or break your experience.
Riverside
Feels like a village. Walkable, community-oriented, great for families. The train station is right there, which is huge. Houses are expensive (we're talking $1.5M+ for something decent), but you're paying for location and that village feel.
Best for: Families who want that small-town feel but still need easy city access.
Old Greenwich
Beach town vibes. If you're coming from the Hamptons or just love that coastal energy, this might be your spot. The beach is actually a thing here, people go, it's not just for show. Also walkable, also expensive.
Best for: People who want that beach-town lifestyle but still need to get to the city.
Cos Cob
More affordable (relatively speaking), more diverse, feels less polished but more real. The harbor area is charming. Good schools, but maybe not the "best" schools if that's your priority. Great value if you're willing to trade some prestige for practicality.
Best for: Families who want Greenwich without the Greenwich price tag (or attitude).
Backcountry Greenwich
Bigger properties, more privacy, more space. But you're further from the train, further from town, and it can feel isolated. If you're coming from a big apartment and want land, this is where you'll find it.
Best for: People who want space and privacy and don't mind being a bit removed from the action.
The thing is, you can't really know which neighborhood fits until you've spent time in each one. That's where I come in. I can help you figure out which areas match your lifestyle, not just your budget.
The Schools: They're Good, But...
Greenwich public schools are consistently ranked among the best in Connecticut, which means they're among the best in the country. The high school sends kids to Ivy Leagues every year. The elementary schools are well-funded and well-staffed.
But here's what you need to know: there's pressure. These are high-achieving communities, and that trickles down to the kids. If you're coming from a more laid-back school environment, your kids might feel it. The competition is real, and it starts early.
Also, while the schools are great, they're not all the same. Some elementary schools are more competitive than others. Some have better resources. The district does a good job, but there are still differences.
If schools are your top priority (and they probably are if you're moving here), I can help you understand which neighborhoods feed into which schools, and which schools might be the best fit for your kids' personalities and learning styles.
The Lifestyle: What Actually Changes
This is the part that's hardest to explain until you've lived it. The pace is different. The social scene is different. The way you spend your weekends is different.
In NYC, you might grab dinner at a new restaurant on a Tuesday night just because. In Greenwich, you're more likely to plan things. People make reservations. They schedule playdates. The spontaneity of city life gets replaced with... structure.
But here's what I love: the space. Having a yard. Being able to walk to the beach. The community feel, like actual community, where you know your neighbors and they know you. The kids can ride bikes. You can have people over without worrying about noise complaints.
The trade-off is that you lose some of that city energy. The "anything can happen" feeling. The 24/7 options. The anonymity (which can be good or bad, depending on how you feel about it).
Whether that's worth it depends entirely on what you want. If you're ready for a slower pace, more space, and a community-focused lifestyle, Greenwich might be perfect. If you're still craving that city buzz, you might want to wait.
The Cost: Let's Talk Numbers
I'm not going to sugarcoat this: Greenwich is expensive. A decent family home in a good neighborhood? You're looking at $1.5M minimum, and realistically more like $2M+ for something that doesn't need major work.
But here's the thing: if you're coming from NYC, you're probably already paying a lot for housing. The question isn't whether Greenwich is expensive (it is), but whether you're getting more for your money here than you were in the city.
In Greenwich, $2M gets you an actual house with a yard, good schools, and a community. In Manhattan, $2M gets you... well, you know what it gets you. The value proposition is different.
Property taxes are high (we're talking $20K-$40K+ per year depending on the house), but you're not paying city income tax. So there's that. The math works out for a lot of people, but it's worth running the numbers for your specific situation.
Is Greenwich Right for You?
Here's my honest take: Greenwich is amazing if you're ready for suburban life and you can afford it. It's not amazing if you're still holding onto city life or if you're stretching your budget to make it work.
Greenwich might be right if:
- You're ready for a slower pace and more space
- Schools are a top priority
- You can work from home at least part of the week
- You want a community feel, not just a collection of houses
- You're financially comfortable (not house-poor)
- You're okay trading some city energy for suburban benefits
Greenwich might not be right if:
- You need to be in the city five days a week
- You're still craving that 24/7 city energy
- The budget is tight (there are other great CT towns that are more affordable)
- You want a more diverse community (Greenwich is pretty homogenous)
- You're not ready to commit to suburban life
Still Not Sure? Let's Talk
I know this is a big decision. I've been there. If you want to talk through your specific situation, your commute, your budget, your priorities, I'm here to help. No pressure, no sales pitch, just honest advice from someone who's made the same move.