Moving from Toronto to Greenwich is a popular path for Canadians relocating for work in NYC or Stamford. You get the proximity to the city, but with more space and better schools—similar to moving from downtown Toronto to Oakville, but on a grander scale.
But let's be honest: moving across the border adds a layer of complexity. You're trading OHIP for health insurance, the CRA for the IRS, and the TTC for Metro-North.
The Big Shifts: Canada vs USA
Healthcare (Goodbye OHIP)
The biggest adjustment for us Canadians. In Greenwich, you will likely be on a private health insurance plan through your employer. The good news? The quality of care is exceptional. Greenwich Hospital is world-class, and you have access to NYC specialists.
Tip: Understand your "deductible" and "out-of-pocket max" before you select a plan. It's very different from showing your health card.
Taxes (Hello IRS)
Generally, your income tax burden will be lower in Connecticut than in Ontario. The absolute top combined rate (Federal + CT) is often lower than the top Ontario marginal rate (53%+).
However, you must file a final tax return in Canada (look up "departure tax" and "deemed disposition"). Talk to a cross-border accountant. Do this before you move.
Credit History
Your Canadian credit score doesn't automatically follow you. Use services like Amex Global Transfer or cross-border banking (RBC/TD/BMO have US branches) to establish US credit using your Canadian history. Without this, getting a mortgage or even a lease can be tough.
Your Cross-Border Timeline
Moving internationally takes more planning than a domestic move. Here's a modified timeline for Canadians.
6 Months Before
- Visas: Confirm your status (L1, TN, H1B, Green Card). You cannot live here without this sorted.
- Research Greenwich schools (they rival top Toronto private schools like UCC or Havergal).
- Talk to a cross-border tax specialist.
Moving Week
- Pack an essentials bag with all immigration documents (Passports + Visas!). Do not pack these in the truck!
- Confirm details with your international movers (customs forms are required).
- Say goodbye in style: Before you leave top-tier Toronto life, you'll want to throw a proper farewell party. If you need a Mobile bartender in Toronto, check out Bartending Canada to send you off in style.
- Do a final walkthrough of your home.
- Cross the border (expect a wait for visa processing if doing it at the POE).
Greenwich Neighborhoods: The Toronto Equivalent
Trying to map Greenwich to Toronto? It's not perfect, but here's a rough guide:
Backcountry = The Bridle Path
Large estates, privacy, long driveways. Multi-acre properties.
Old Greenwich = The Beaches
Walkable, coastal, distinct village feel, very family-oriented.
Downtown Greenwich = Yorkville
High-end shopping, dining, condos, and walkability.
Riverside = Lawrence Park
Prestigious, great schools, tight-knit community feel.
Welcome to Your New Home
I've helped many families make the move from Canada. I understand the specific challenges you're facing. Let's chat about finding your perfect spot in Greenwich.