Why You Should Look for a Nanny Job in Westchester and Connecticut

If you’re a nanny in the New York region thinking about your next career move, let us tell you about Westchester and Connecticut – areas with plenty of job opportunities and great potential. Whether you live in the City or outside, you know this is a region with loads of families looking for great in-home care, and Smart Sitting can help you book a position that fits your career goals. Let’s take a look! 

connecticut landscape in fall foliage in a post about nanny jobs in connecticut

Why Westchester & Connecticut Are Great Places to Work as a Nanny

Lots of Jobs

Westchester County and Connecticut communities (like Greenwich, Stamford, Darien, and Westport) consistently have lots of open nanny and babysitting jobs, both full-time and part-time. 

In our experience, families in these areas are paying competitive rates – comparable to New York City for the right candidate. Just like with most regular, long-term positions, these jobs often also include paid time off and other benefits. These are perks that signal long-term commitment and professional respect for caregiver roles – one of our cornerstone values. 

Variety of Roles 

This region doesn’t offer just one kind of job. Families are hiring for:

  • Full-time, live-out nanny positions with stable hours

  • Part-time & after-school roles

  • Weekend or flexible babysitting/nanny coverage

  • Rotational schedules or hybrid roles for families who travel

This variety allows you to find a position that fits your preferred schedule — whether you’re balancing other commitments or seeking stable full-time work. For many nannies, this translates into days where schedules are predictable, routines are respected, and you’re part of a household that values stability and care as much as you do.

For nannies planning on commuting out from the city, a heads-up: most of these positions will include some amount of driving and require that you are comfortable driving kids.

Lifestyle & Work/Life Balance

As a New York City based nanny agency, we obviously love the city’s hustle and energy. But even we can admit it, one of the big draws of Westchester and Connecticut is the lifestyle shift to a more relaxed, family-centered pace. 

Westchester has a mix of charming town centers, open spaces, and strong school communities. The greenery is strong in this one! Connecticut’s towns often attract families who value both a quieter environment and proximity to NYC for work or leisure – and while many areas have a high cost of living, nearby towns are much more affordable and still an easy commute to your nanny job. 

That said, both of these bedroom communities are still close enough to the city for easy access to culture, transit, and weekend adventures. So you could actually have both.

What Families in Westchester & Connecticut Are Looking For

We work with many professional families and high-profile families both in the city and in the areas around it. What we’ve found for nanny jobs in Westchester and Connecticut is that they’re looking for much of the same as our New York families: 

  • Solid experience with strong childcare references

  • Flexibility and good communication

  • Proven reliability  

  • A warm, engaging approach with children

As we mentioned before, one thing that does stand out when compared to NYC positions is a comfort with driving and a clean driving record. 

Are You Looking for a Tri-State Area Nanny Job?


Westchester County and Connecticut stand out as strong markets for nanny work for good reasons: 

  • Plenty of job opportunities in diverse roles

  • Competitive compensation

  • Quality of life 

  • Proximity to NYC 

We have nannies and babysitters who live in New York and commute to jobs in Westchester and Connecticut, and we’ve also helped caregivers who live in these areas find awesome nanny jobs that align with their own goals, so whether you’re local or not, this might be the place for you.

If you’re looking to grow your nanny career, explore flexible scheduling, or find a role that fits your life as well as your skills, and you’re curious about working in Westchester or Connecticut – get in touch with us. When you apply to Smart Sitting, we get to know your experience as well as your goals, so that we can connect you with the positions we think will be best suited for you. We only work with a select group of sitters so we can keep a personal touch to building nanny-family relationships that really succeed, wherever that may be! 

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Cajsa Landin