The Fairfield County Town Scorecard breaks down eight Gold Coast towns on commute, schools, space, downtown, and taxes, then gives you a weighted worksheet that turns your family's priorities into a ranked short list.
Whether you're coming up from the city or outgrowing the house you're in.
The Scorecard is on its way. If it isn't there in a few minutes, check promotions or spam, then add chris@chrisgiolitto.com to your contacts.
Book a 15-Minute Town Strategy SessionMost town guides are a paragraph of adjectives and a Zillow link. This one is built to be scored, argued over, and brought to the car on Saturday.
Westport, Darien, New Canaan, Fairfield and Southport, Greenwich with its villages, Wilton, Weston, Ridgefield. Each gets the commute as it actually runs, station parking reality, the school feeder path, and a pros-and-cons list I'd say to your face.
Three tiers, $1.2M to $1.5M, $2.0M to $2.5M, and $3.5M and up, with square footage, lot size, and the neighborhoods and condition you should expect at each. No "charming starter home" language.
Current mill rates and the estimated annual bill on a $2.0M home in each town. The spread is more than $20,000 a year between the lowest and highest, and it should change where you look.
You rate five pillars and three secondary factors from 1 to 5. The towns are pre-scored. Multiply, add down, and the total tells you which towns deserve a Saturday and which you can skip without guilt.
Main line versus the New Canaan and Danbury branches, the express window, transfer rules, six parking waitlist workarounds, and a door-to-desk formula with worked examples.
A Brooklyn family solving commute versus yard, and a Fairfield family upsizing into a Greenfield Hill house that was never going to hit the MLS.
A sample from the worksheet: two full-time commuters with three kids who want a yard. Commute and schools weighted 5, space 4, downtown 3. Watch what happens to Westport versus Weston.
| Decision factor | Your weight | Westport | Product | Weston | Product |
|---|---|---|---|---|---|
| Express commute | 5 | 8 | 40 | 3 | 15 |
| School system scale | 5 | 10 | 50 | 9 | 45 |
| Lot and living space | 4 | 6 | 24 | 10 | 40 |
| Downtown vibe | 3 | 10 | 30 | 2 | 6 |
| Tax and value | 3 | 7 | 21 | 4 | 12 |
| Five-pillar total | 165 | 118 |
Drop the commute weight to 1 for a fully remote household and Weston closes to within a few points. That swing is the entire point of the exercise. The full worksheet adds beach access, walkability and tax savings, and scores all eight towns.
You've priced out Brooklyn, your office is hybrid, and everyone you know has an opinion about "Connecticut." You need the towns ranked by your life, not your coworker's.
You bought in 2018 or 2020, the kids got bigger, and the next house in your own town keeps going under contract before you see it. The question is whether to move towns or move within.
I've lived in Fairfield County my entire life. I'm raising young kids here, I sell homes here with William Raveis out of Southport, and I make the videos a lot of NYC families watch before they ever get on a train north.
This guide exists because almost nobody I meet is short on information. They have too much of it and no way to weigh it. Darien has the faster train, Fairfield has the lower price per square foot, Weston has the acreage, Greenwich has the lowest taxes. All true, and none of it tells you where to buy. The Scorecard does.
If you'd rather talk than read, book a 15-minute Town Strategy Session. You bring your top three towns, I bring what's actually for sale and a straight answer about whether your budget works where you want it to.
Chris
Instagram @chrisgiolitto and @fairfieldcountyliving · YouTube @FFLDCountyLiving
The guide is 31 pages and the pitch is one of them. The other 30 are train times, mill rates, school feeder paths, budget tiers and a worksheet. If you read it and never call me, it still did its job.
The budget tiers start at $1.2M because that's where the towns in this guide start to open up for families. The commute, school and tax sections apply at any price, but if your budget is well under that, I'd rather tell you now than have you feel misled on page six.
Mill rates are the FY 2026-27 figures, including the new post-revaluation rates in Westport, Fairfield and Greenwich. Train times and parking notes reflect fall 2026. Everything resets every July, so confirm with the town before you make an offer.
You'll get the guide, then my weekly Fairfield County newsletter: new developments, openings, market notes. One email a week, and the unsubscribe link works.
Both have neighborhoods that belong in this conversation, especially Rowayton, Shippan Point and North Stamford. Ask me about them on a strategy call, or watch for the micro-market addendum.
Enter your email, get the Scorecard, score the towns with your partner, and tour only the ones that earned it.