A move from Toronto to Greenwich CT often follows a finance job in NYC or Stamford. You may gain more land and access to public schools, but compare housing costs in USD before choosing a neighborhood.
Crossing the border is what makes this move harder. 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)
In Greenwich, Canadians usually switch from OHIP to a private employer plan. Greenwich Hospital and NYC specialists may be options if your network covers them. Check the deductible and out-of-pocket maximum before choosing a plan.
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)
Expect a lower income tax burden in Connecticut than in Ontario. The top combined rate (Federal + CT) sits below 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 is tough.
Housing: Greenwich vs Toronto
Map your budget to Rosedale or Forest Hill money, not midtown Toronto averages. The August 2026 single-family median in Greenwich was $3.95M. Walkable Riverside and Old Greenwich family houses typically start closer to $1.8M. The extra land comes with a high purchase price.
2026 Greenwich Price Ranges
Condos/Townhomes: $600K-$2M
Cos Cob: $1M-$3.5M+
Riverside: $1.8M-$6M+
Old Greenwich: $1.8M-$8M+
Backcountry: $2M-$20M+
August 2026 single-family median: $3.95M. Property tax mill rate: 10.125 (~0.71% of market value after the 70% assessment).
September 1, 2026 Greenwich MLS
The market right now, not last winter
On September 1 there were 80 single-family homes for sale and 26 condos, the highest condo count of 2026 against a year average near 17. Through July the town-wide single-family median was $3.60M, up 14% from $3.15M, with average days on market at 59 (July alone averaged 36). August closings for context: $3.95M median, 83 active SF at month-end, 103.6% of list (GAR MLS).
$3.60M
YTD SF median (thru July)
Up 14% from $3.15M a year earlier.
59 days
YTD avg days on market
July alone averaged 36 days.
80 homes
Active SF (Sep 1)
Late August town-wide sat near 130 listings.
26 units
Condos for sale
Highest condo count of 2026; year avg ~17.
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 $8,300 more per year.
All prices are in USD. A CAD budget buys less at current exchange rates, roughly a quarter less. US base pay for finance and tech roles is usually higher, and the top combined Federal + CT rate is still below Ontario's 53%+ marginal top. Run the numbers with a cross-border accountant before you underwrite a $3M house on Canadian savings.
Schools: Public vs Toronto Private Money
A lot of Toronto families pay $30K-$40K CAD a year for UCC, Havergal, or Crescent. Greenwich Public Schools are why many of them stop writing that cheque. Greenwich High School is ranked #5 in Connecticut and #268 nationally by Niche (2026), with 200+ courses including 30 AP options. Start with the schools guide and the east-side feeder people actually name: North Mianus into Eastern Middle.
Using public schools removes private tuition from your budget, but you'll still pay property taxes and the housing costs of your chosen neighborhood. Confirm the elementary catchment before making an offer.
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 with 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 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 runs ~40-45 minutes. Locals from Cos Cob, Riverside, and Old Greenwich run 50-75. Backcountry adds a 15-minute drive before you reach the train.
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.
If both parents will be on a 7:45 train most weekdays, plan childcare costs before optional renovations. Several elementary schools start around 9am. Dual-commuter families here usually need a 12-hour nanny or an au pair, not a 9-to-5 daycare. Experienced Greenwich-area nanny rates in recent local chatter land around the mid-$30s per hour. See the cost of living breakdown and the long-distance movers guide before you lock dates.
Weather: Milder Than Toronto Winters
If you survived Toronto winters, Greenwich feels milder. Less lake-effect snow, fewer deep freezes, January averages roughly -3°C to 2°C (26-36°F). Summers are more humid and coastal.
- ❄️Winters: Milder than Toronto. Less lake-effect snow. Budget for a plow contract anyway once you have a driveway.
- 🍂Fall: New England foliage peaks late October. Litchfield is the day trip; Tod's Point is the Sunday walk.
- ☀️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 (visit on a weekday and a weekend to get the real feel).
- Get pre-approved for a US mortgage. Cross-border lenders like RBC Bank or HSBC can use your 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 both run cross-border setups Canadians actually use).
- Explore your new neighborhood and find your new favourite spots, we mean favorite.
Practical note: Do not try to finish immigration, school registration, and furniture in the same week. The first month is utilities, SSN, license, and getting the kids on a schedule.
Next step
Storage for a cross-border move.
Storage while you cross the border
Park household goods while visas, closing, and customs timing line up.
Find storage nearbyGreenwich Neighborhoods: The Toronto Equivalent
Here's a rough Toronto translation for each Greenwich neighborhood:
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. Let's chat about finding your spot in Greenwich.
Let's Chat About Your Move
Tell me your timeline, budget, and priorities, and I'll suggest neighborhoods to compare.
Ester Zolotnitsky
Greenwich Relocation Expert & Real Estate Consultant
Ester helps families move from city life to the Connecticut coast. She offers guidance on Greenwich neighborhoods, schools, and daily life as you compare places to live.
More Greenwich Resources
- 🏙️ Moving from NYC to Greenwich CT
- 🏠 Best Suburbs Near NYC: Complete Comparison
- 🏡 Complete Greenwich Neighborhood Guide
- 🎓 Greenwich Public Schools CT Guide
- 💰 Cost of Living in Greenwich CT
- 📊 Greenwich CT Housing Market Update
- 🚚 Long Distance Moving Companies Connecticut
- 🏨 Hotels in Greenwich CT
- 🎉 Things to Do in Greenwich CT