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.
Benefits of Moving from NYC to Greenwich CT
People move from New York City to Greenwich for lots of reasons. Here are the main benefits that draw families here:
More Affordable Housing with Way More Space
Are you tired of paying New York City rental prices? In Connecticut, you can actually afford to buy property. House prices in Connecticut are above the national average, but they're way lower than in New York City. In some areas, median house prices can be up to 50% cheaper than in the city.
You don't need to buy to enjoy the benefits. Average rent in Connecticut is much cheaper than what New Yorkers pay. And you'll often get more space too. A $2 million Greenwich home gives you 3,000 square feet or more. In Manhattan, that same money gets you maybe 1,200 square feet.
Better Cost of Living Overall
People who move from NYC to Connecticut don't just save on real estate. They tend to save on everything. If you've lived in New York for a while, you know how expensive groceries, dining, and entertainment can be. Those costs add up fast.
Connecticut, while more expensive than the national average, is more affordable than New York City. It's also more affordable than most other places in New England. You'll spend less on daily expenses, which helps offset the higher property taxes.
Excellent Public Schools (Save on Private School)
Greenwich has some of the best public schools in the country. The district gets an A+ rating from Niche. Greenwich High School sends students to top colleges every year. The elementary and middle schools are well-funded and well-staffed.
If you're paying for private school in NYC, moving to Greenwich could save you $50,000 or more per year. The public schools here are that good. Many families who were planning to go private end up choosing public school instead.
Enjoy All Four Seasons
New York City gets four seasons, but you don't experience them the same way as in Connecticut. Connecticut lets you fully enjoy each season. Spring brings blossoming flowers. Summer brings outdoor activities. Fall brings stunning foliage. Winter brings snowy, chilly weather.
The state offers incredible natural beauty. There are countless state parks, the Appalachian Trail, and plenty of coastlines. You can form a closer connection to the outdoors than you could in New York City. After years of city living, that's a huge change.
Great Location Without Being Too Far
Moving from NYC to Connecticut is a change, but it's not like moving to the moon. New York and Connecticut are neighbors. Lots of people live in Connecticut but work in New York City. Even if you find a job in Connecticut, you'll still have all the culture and advantages of NYC nearby.
You can think of Connecticut as offering the best of all worlds. You get affordable properties with plenty of space, lots of nature, and a world-class city on your doorstep. Boston and other New England highlights are also just an easy car or train ride away.
Lots of Things To Do
New York City offers plenty of cultural and sporting events. But since Connecticut is so close, you can still make the trip into the city when your favorite artist is in town. You don't have to give up city culture completely.
When you move to Connecticut, you gain activities that New York City can't offer. The state is popular with outdoor recreation lovers thanks to forests, preserves, and coastline. Hiking, biking, camping, kayaking, fishing, and birdwatching are just some of the popular activities Connecticut residents enjoy on weekends.
Slower Pace of Life
Finally, Connecticut offers a more peaceful pace of life. It's a breath of fresh air compared to the non-stop energy of New York City. The state lets you slow down, enjoy the simple things, and worry less about optimizing every minute.
New York City is exciting, but it can be stressful. Most people decide to leave after a number of years. Connecticut offers the perfect place to escape. You can still work in the city if you want, but you don't have to live in the chaos.
Your 6-Month Moving Timeline
Moving from NYC to Greenwich is a big process. Here's a timeline to help you plan. Start early, and you'll avoid last-minute stress.
6 Months Before You Move
- Research Greenwich neighborhoods online
- Visit during different seasons to see what it's really like
- Research schools, both public and private
- Get pre-approved for a mortgage if you're buying
- Start private school applications if you're going that route
- Talk to a real estate agent who knows Greenwich
3 Months Before You Move
- Work with your real estate agent to find homes
- Make offers and negotiate
- Schedule school tours for your kids
- Research moving companies and get quotes
- Plan your work commute and test it out
- Start decluttering and packing non-essentials
1 Month Before You Move
- Finalize your home purchase or rental
- Schedule movers and confirm dates
- Change your address with the post office
- Set up utilities in your new home
- Register your kids for school
- Transfer medical records and find new doctors
- Update your driver's license and car registration
Moving Week
- Pack an essentials bag with clothes and important items
- Confirm all moving details with your movers
- Say goodbye to your NYC friends and favorite spots
- Do a final walkthrough of your new home
- Move to Greenwich
- Unpack essentials and get settled
First Month After Moving
- Finish unpacking and organizing
- Explore your new neighborhood
- Join local groups or the PTA
- Get to know your neighbors
- Find your new favorite restaurants and shops
- Enjoy your new life in Greenwich
My Take: Don't try to do everything at once. Moving is stressful enough. Focus on the big stuff first, like finding a home and schools. The rest can wait. And remember, it takes time to feel settled. Give yourself at least six months to adjust. You'll get there.
Greenwich at a Glance (2025)
45 min
Train to Grand Central
61,000+
Population
1,500+
Acres of Parkland
4
Metro-North Stations
Transportation and Commuting
Everyone asks about the commute first, and for good reason. Here's the truth: it's not terrible, but it's not nothing either.
Greenwich is served by four Metro-North stations: Greenwich (main), Cos Cob, Riverside, and Old Greenwich. Express trains reach Grand Central Terminal in about 45 minutes. If you're in Old Greenwich or Riverside, you're practically at the station. If you're in backcountry Greenwich, add 10-15 minutes for the drive.
My Take: That 45 minutes feels longer when you're doing it twice a day, five days a week. But unlike the subway, you can actually get work done. I've watched people close deals, prep presentations, and catch up on reading. The trains are generally reliable—way more than the MTA.
For drivers, Greenwich connects directly to I-95 and the Merritt Parkway (Route 15). You're about 30 miles from Manhattan and 5 miles from Stamford's corporate district—home to major companies like Charter Communications, WWE, and NBC Sports.
The 2025 reality? Most families I work with are doing hybrid schedules—2-3 days in the city, the rest from home. If you can work remotely even two days a week, the commute becomes totally manageable.
Neighborhoods to Explore in Greenwich
Greenwich is made up of several distinct neighborhoods, each with its own appeal. Choosing the wrong one can make or break your experience—so here's the honest breakdown:
Downtown Greenwich
A lively area with upscale shopping, restaurants, and cultural attractions. Greenwich Avenue (locals call it "The Ave") rivals Rodeo Drive for designer boutiques and high-end dining. Walkable, vibrant, and convenient.
Price range: $800K-$3M+ (condos and townhomes)
Best for: Professionals who want walkability and urban energy without the NYC chaos.
Riverside →
Feels like a village. Walkable, community-oriented, great for families. The train station is right there, which is huge. Houses are expensive, but you're paying for location and that village feel. The elementary school is excellent.
Price range: $1.5M-$5M+
Best for: Families who want that small-town feel but still need easy city access.
Old Greenwich →
Beach town vibes with a quaint, walkable downtown. If you're coming from the Hamptons or just love that coastal energy, this might be your spot. The beach at Greenwich Point Park (Tod's Point) is actually a thing here—people go, it's not just for show.
Price range: $1.5M-$8M+
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. A charming village with a strong arts scene—this was Connecticut's first art colony. The harbor area is beautiful. Great value if you're willing to trade some prestige for practicality.
Price range: $900K-$3M+
Best for: Families who want Greenwich without the Greenwich price tag (or attitude).
Backcountry Greenwich
Ideal for those seeking privacy and luxury estates on larger properties—we're talking 2-10+ acres. But you're further from the train, further from town, and it can feel isolated. If you're coming from a cramped apartment and want land, this is where you'll find it.
Price range: $2M-$20M+
Best for: People who want space and privacy and don't mind being a bit removed from the action.
Belle Haven →
One of the most exclusive gated communities on the East Coast. Waterfront estates, private beach club, old money vibes. This is where the hedge fund managers and CEOs live. Beautiful, but very particular.
Price range: $5M-$50M+
Best for: Those seeking ultra-luxury waterfront living with maximum privacy.
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.
Weather and Seasonal Changes
Like much of New England, Greenwich experiences all four seasons, each with its own beauty and challenges:
- ❄️Cold, snowy winters – Bundle up and prepare for snow between December and February. The town does a great job with snow removal.
- 🍂Beautiful autumns – Fall foliage creates postcard-worthy views. The backcountry roads are stunning in October.
- ☀️Warm, sunny summers – Perfect for enjoying beaches, marinas, and outdoor activities. Greenwich Point Park is packed on weekends.
- 🌸Variable springs – Expect a mix of rain, cool days, and gradual warmth. The cherry blossoms at Bruce Park are worth seeing.
My Take: If you're planning a winter move, factor in weather delays. If you're house hunting in winter, you won't see the yards and landscaping at their best—but you will see how the house handles cold weather. There's value in that.
Tax Benefits: The NYC to Greenwich Math
Let's talk about what everyone's really curious about: the money. Unlike New York, Connecticut has no local income tax—you're not paying that 3.9% NYC resident tax anymore.
For high earners, this can mean significant savings. If you're making $500K+, you could save $20-40K+ per year just by eliminating that NYC tax. Some families use these savings to offset higher property taxes or simply pocket the difference.
Quick Tax Comparison
NYC: 3.078%-3.876% city income tax + NY state tax
Greenwich: CT state tax only (6.99% top rate) + property tax (~1.1% of assessed value)
*Property taxes in Greenwich average $20K-$40K+ annually depending on home value.
The math works out for a lot of people, but it's worth running the numbers for your specific situation. I can connect you with CPAs who specialize in NYC-to-CT relocations if you want a proper analysis.
Education: Public and Private Options
Education remains a top priority for families moving to Greenwich—and for good reason. The town offers some of the best-ranked public schools in Connecticut (and the country), plus excellent private school options.
Greenwich Public Schools
Greenwich High School serves around 2,600 students and offers 200+ courses including 30 AP options. The graduation rate is 94%+, and the school sends students to Ivy League schools every year. The elementary schools are well-funded and well-staffed.
Private School Options
Greenwich is also home to elite private schools like Brunswick School (boys), Greenwich Academy (girls), and Sacred Heart Greenwich. These offer exceptional academics, arts, and athletics—with tuition to match ($50K+/year).
My Take: Here's what you need to know—there's pressure. These are high-achieving communities, and it trickles down to the kids. If you're coming from a more laid-back school environment, your kids might feel it. Some elementary schools are more competitive than others. I can help you understand which schools match your kids' personalities and learning styles.
Nature, Beaches, and Outdoor Living
Greenwich offers over 1,500 acres of parkland, 20 miles of coastline, and four public beaches, including the popular Greenwich Point Park (Tod's Point). After years of cramped city living, this might be the biggest lifestyle upgrade.
- •Greenwich Point Park – 147 acres with beach access, walking trails, and picnic areas
- •Bruce Park – 60 acres with ponds, tennis courts, and beautiful cherry blossoms
- •Mianus River Park – 400+ acres for hiking and nature exploration
- •Golf clubs – Multiple private clubs and one public course
- •Marinas – For sailing and boating enthusiasts
For families relocating in 2025, Greenwich's natural beauty and outdoor access are huge draws—especially after years of urban lockdowns or cramped city apartments.
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.
Dining, Shopping & Arts
Greenwich Avenue offers high-end shopping, world-class restaurants, art galleries, and cultural events year-round. The Bruce Museum, Greenwich Symphony Orchestra, and Greenwich International Film Festival keep the cultural calendar full. You're not giving up sophistication—just the 24/7 options.
Community Events
From the Greenwich Town Party (Memorial Day weekend) to farmers markets, polo matches, and holiday parades, there's always something happening. People actually show up. You'll see the same faces, build friendships, and become part of something.
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.
Housing and Real Estate: 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.
2025 Price Ranges by Area
Condos/Townhomes: $500K-$2M
Cos Cob: $900K-$3M
Riverside: $1.5M-$5M+
Old Greenwich: $1.5M-$8M+
Backcountry: $2M-$20M+
Belle Haven: $5M-$50M+
But here's the thing: if you're coming from NYC, you're probably already paying a lot for housing. In Manhattan, $2M gets you... well, you know what it gets you. In Greenwich, $2M gets you an actual house with a yard, good schools, and a community.
Property taxes average around 1.1% of assessed value—roughly $20K-$40K+ per year depending on the house. But remember: you're not paying NYC income tax anymore. For many families, the math works out.
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.