Greenwich & Westport

Homes that hold steady while you commute

Staffing the commuter estates of Fairfield County: households built around acreage, school calendars, and a principal who is often in the city.

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Fairfield County households are built around absence. One or both principals leave early, Metro-North from Greenwich or Westport, or a car into Manhattan, and the house has to run without them. That puts real weight on the people inside it: a household manager with genuine authority, a nanny who owns the school run, a housekeeper who doesn't need direction by text.

The properties here are a different animal than a city apartment. Back-country Greenwich estates carry acreage, pools, guest houses, barns, and a rotation of landscapers, arborists, and trades. Someone has to manage all of it. Families often arrive from the city with one housekeeper and discover within a year that the property needs a manager, not just more hands.

The rhythm follows the school calendar more than the seasons. September resets everything; summers empty toward the shore or the East End. Staff who understand that cadence, intense school years, flexible summers, the household quieting and refilling on schedule, tend to stay for years. We've been placing them in these towns since 2002, and tenure is still the measure we care about most.

Most requested

The roles Greenwich & Westport households hire.

Estate Manager

The operational lead for a significant property: staff, vendors, budgets, and projects, so your home simply works.

Hiring guide

Household Manager

The steady hand inside your home: staff, service, supplies, and schedules, managed to a standard you never have to restate.

Hiring guide

Nanny

A dedicated childcare professional who brings warmth, structure, and judgment to your children's daily rhythm.

Hiring guide

Housekeeper

Daily, devoted care of your home: rooms reset, laundry done properly, and fine things handled by someone who knows how.

Hiring guide

Private Chef

A home chef for hire should do more than prepare meals: a private chef builds daily menus around your household, manages the kitchen, and travels when the role requires it.

Hiring guide

Chauffeur

A professional driver whose real product is calm: safe, punctual, discreet transport for your family and guests.

Hiring guide

Family Assistant

A flexible right hand for the whole family: childcare, errands, logistics, and the hundred small things in between.

Hiring guide

Questions

Staffing in Greenwich & Westport, answered.

We just moved from the city. Where do most families start?

Usually with the realization that a suburban property asks more of you than an apartment did. Most families start with a strong housekeeper and a nanny, then add a household or estate manager once the acreage, vendors, and second properties make self-managing untenable. We'd rather scope one right hire than sell you a full team you don't need yet.

Do candidates commute from the city, or live locally?

Both. Metro-North makes reverse commuting workable for some roles, and a meaningful number of experienced candidates live in Westchester and Fairfield County already. For early-morning roles, nannies covering school runs, chauffeurs, local or live-in candidates are more dependable. We're candid about which commutes hold up through a winter and which quietly erode a placement.

Can one person manage a large back-country property?

Often, yes, if it's the right person. An experienced estate manager can run the vendor relationships, grounds, systems, and household staff of a substantial property. What doesn't work is asking a housekeeper to absorb that job informally. The title matters less than the mandate: clear authority, a real budget, and a direct line to you.

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Hiring in Greenwich & Westport?

Tell us about the household and the role. A senior advisor will be in touch within one business day.