Moving from Toronto to Greenwich CT 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 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.
Housing: Greenwich vs Toronto
Greenwich housing prices are comparable to Toronto's top neighborhoods like Rosedale and Forest Hill. A detached family home starts around $1.5M–$2M+ USD, similar to what you'd pay in midtown Toronto, but you get significantly more land (0.25–2+ acres vs a typical Toronto lot).
2026 Greenwich Price Ranges
Condos/Townhomes: $600K–$2M
Cos Cob: $900K–$3M+
Riverside: $1.5M–$5M+
Old Greenwich: $1.5M–$8M+
Backcountry: $2M–$20M+
August 2026 single-family median: $3.95M. Property tax mill rate: 10.12 (~0.71% of market value after the 70% assessment).
August 2026 Greenwich MLS
The market right now, not last winter
Single-family inventory is historically tight. Condos are the pressure valve: August condo/co-op median was $1.16M, and new condo listings jumped 91% year over year.
$3.95M
August SF median
Up 41% vs Aug 2025. One month, not a year.
17 days
Days on market
Was 55 days a year earlier.
83 homes
Active SF inventory
Down 29% year over year.
103.6%
Sale-to-list
Buyers still paying over ask.
Like-for-like, not medians
Annual tax on the same $2 million home
Connecticut towns assess at 70% of market, then multiply by the mill rate. New York towns use an effective rate on market value. Same $2M house, different bill.
FY2026-27. Lowest mill in Connecticut.
Also just revalued. Mill dropped; assessments jumped.
Same $2M house, about $7,500 more per year.
Remember, all prices are in USD. At current exchange rates, your CAD budget goes about 25–30% less far. However, US salaries are typically higher, and combined income taxes (Federal + CT) are often lower than Ontario's 53%+ top marginal rate, so the math works out for most families.
Schools: Your Kids Will Thrive
Greenwich Public Schools rival the top Toronto private schools (UCC, Havergal, Crescent) in facilities, university matriculation, and sports programs. Greenwich High School is ranked #5 in Connecticut and #268 nationally by Niche (2026), with 200+ courses including 30 AP options.
Many Canadian families who were paying $30K–$40K CAD per year for private school in Toronto switch to Greenwich public schools and save that tuition entirely. The public schools are that good.
If you still prefer private education, Greenwich offers elite options: Brunswick School (boys), Greenwich Academy (girls), and Sacred Heart Greenwich, with tuition around $50K+ USD/year.
Tip: Register your kids for school as early as possible. The Greenwich Public Schools website has clear enrollment guides for international families. Bring proof of residence, immunization records, and previous school transcripts.
Buy the feeder, not just the house
Greenwich public school map, in one table
Address assigns the elementary and middle school. There is no town-wide lottery. All three middle schools feed Greenwich High School. Confirm the specific address on the Greenwich Public Schools site before you bid.
| Neighborhood | Elementary | Middle | What parents actually say |
|---|---|---|---|
| Old Greenwich | Old Greenwich School | Eastern | Walkable village. Late elementary start is common. |
| Riverside | Riverside School | Eastern | Early drop exists (~7:30). Strong PTA. |
| Cos Cob | Cos Cob School | Eastern / Central | Locals praise it. Walkable to shops and the station. |
| North Mianus | North Mianus School | Eastern | Parents often call this the strongest public combo in town. |
| Downtown | Julian Curtiss | Central | Most international. New Central Middle opened Aug 2026. |
| Backcountry | Parkway / North Street | Western | Drive to everything, including the train. |
If both parents commute
Budget a 12-hour nanny or au pair
Several Greenwich elementary schools start around 9am. A 7:45 train and a 9am bell do not mix. Riverside has an early drop around 7:30. Sick-day pickup is under an hour.
If you work in Midtown
Live walking distance to a station
Express from Greenwich station can be ~40–45 minutes. Locals from Cos Cob, Riverside, and Old Greenwich often run 50–75. Backcountry plus a 15-minute drive is a different life.
If you work in FiDi or Hudson Yards
Ride it twice before you offer
Add the subway. Families who skip this test are the ones who move back to Westchester or the city. Scarsdale is faster. Greenwich is cheaper on taxes.
Weather: Better Than You Think
Great news: if you survived Toronto winters, Greenwich will feel mild. Winters are shorter, less windy, and rarely hit the -20°C extremes you're used to. Average January temps hover around -3°C to 2°C (26–36°F).
- ❄️Winters: Milder than Toronto. Less lake-effect snow. The town handles snow removal efficiently.
- 🍂Fall: Stunning New England foliage, arguably more picturesque than Ontario's. Peak in late October.
- ☀️Summers: Warm and coastal. Beach days at Tod's Point are a regular weekend activity. Slightly more humid than Toronto.
- 🌸Spring: Arrives earlier than Toronto. Cherry blossoms at Bruce Park in April are worth seeing.
Your Cross-Border Moving Timeline
Moving internationally takes more planning than a domestic move. Here's a step-by-step timeline for Canadians.
6 Months Before
- Visas: Confirm your status (L-1, TN, H-1B, 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 about departure tax and deemed dispositions.
- Start working with a Greenwich real estate agent.
- Begin establishing US credit (Amex Global Transfer, RBC/TD/BMO US branches).
3 Months Before
- Tour Greenwich neighborhoods and homes (we recommend visiting on weekdays and weekends to get the real feel).
- Get pre-approved for a US mortgage, cross-border lenders like RBC Bank or HSBC can use Canadian credit history.
- Schedule school tours for your kids.
- Get quotes from international movers (customs forms are required for cross-border moves).
1 Month Before
- Finalize your home purchase or rental agreement.
- File your final Canadian tax return and handle CRA departure formalities.
- Cancel OHIP coverage (it ends 3 months after you leave Ontario).
- Set up US health insurance through your employer.
- Set up utilities, internet, and services at your new Greenwich home.
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).
- Do a final walkthrough of your new home.
- Cross the border (expect a wait for visa processing if doing it at the POE).
First Month After Moving
- Get a US Social Security Number (apply at the Stamford SSA office).
- Get a Connecticut driver's license (you have 30 days to convert your Ontario license).
- Register your kids for school and set up their schedules.
- Open a US bank account (TD Bank and BMO Harris have seamless cross-border services).
- Explore your new neighborhood and find your new favourite spots, we mean favorite.
Pro Tip: Don't try to do everything at once. The first month is about settling in. Give yourself at least six months to fully adjust, you'll get there, eh?
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.
Let's Chat About Your Move
Tell me about your timeline, budget, and what matters most, and I'll send you a curated list of neighborhoods that could be your perfect fit.
Ester Zolotnitsky
Greenwich Relocation Expert & Real Estate Consultant
Ester helps families transition from city life to the Connecticut coast. With deep knowledge of Greenwich neighborhoods, schools, and lifestyle, she provides honest, no-pressure guidance to help you find your perfect community.