Distance
350 miles
Major Shift
New Country, New Systems
Top Benefit
Lower Taxes & Better Schools
The Logistics
Trade the Gardiner Expressway for a 1-hour flight from Billy Bishop or Pearson to Westchester Airport. Or a scenic 8-hour drive. It's an international move, but one that thousands of Canadians make for NYC careers.
The Lifestyle Shift
Greenwich feels like a blend of Rosedale and Oakville, but on the ocean. You keep the safety, the excellent schools, and the 'village' feel, but gain US salaries and lower taxes.
Local Expert Insight
"Don't forget the 'departure tax' when leaving Canada. Speak to a cross-border accountant before you sell your principal residence."
Housing & Cost of Living
Greenwich housing prices are comparable to Toronto's top neighborhoods like Rosedale and Forest Hill. A detached family home starts around $1.5M–$2M+, similar to what you'd pay in midtown Toronto—but you get significantly more land (0.25–2+ acres vs a typical Toronto lot). Condos start around $600K–$2M. Property taxes run about 1.2% of assessed value (mill rate 12.041), which is lower than Toronto's rate but applied to higher assessed values.
Schools & Education
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). Many Canadian families who were paying $30K–$40K CAD for private school in Toronto switch to Greenwich public schools and save that tuition entirely.
Why Toronto Families Choose Greenwich
- 1
Tax Advantages
The difference between Ontario's 53% marginal rate and Connecticut's ~6.99% + US Federal rates is significant. Your take-home pay increases substantially.
- 2
Healthcare Quality
Access to world-class private healthcare with no wait times. Greenwich Hospital is affiliated with Yale New Haven Health.
- 3
Educational Standards
Greenwich Public Schools rival top Toronto private schools (UCC, Havergal) in terms of facilities, matriculation, and sports.
Planning Your Move from Toronto?
Let's discuss your specific timeline, budget, and school needs.
Best Greenwich Neighborhoods for Toronto Families
Based on what Toronto residents typically value, here are the neighborhoods we recommend exploring first.
Old Greenwich
Feels like The Beaches in Toronto—walkable, coastal, family-oriented
$1.5M–$8M+
Riverside
Similar to Lawrence Park—prestigious, tight-knit, top schools
$1.5M–$5M+
Downtown Greenwich
Yorkville energy—high-end shopping, dining, condos
$800K–$3M+
Cos Cob
Best value in Greenwich with a diverse, artistic community
$900K–$3M+
Common Questions
Is it hard to get a mortgage?
Without US credit history, yes. We recommend working with cross-border lenders like RBC Bank (Georgia) or HSBC who can use your Canadian history.
How does health insurance work?
It is usually employer-sponsored. You will have a deductible and copays, which is different from OHIP, but the access to specialists is immediate.
Are there other Canadians?
Yes, a very large community. You will find plenty of Leafs fans (and Rangers fans) at local sports bars.
What visa do I need to live in Greenwich?
Most Canadians relocate on an L-1 (intra-company transfer), H-1B (specialty occupation), or TN visa (USMCA professions). Your employer typically sponsors the visa. Green card holders can live and work freely.
How easy is it to fly back to Toronto?
Very easy. Flights from LaGuardia or JFK to Pearson or Billy Bishop take about 90 minutes. Westchester Airport (15 min from Greenwich) also has connecting flights. Many families visit monthly.
Let's Chat About Your Move
Tell me about your Toronto to Greenwich move—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.
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