Fairfield County · Buyer & Seller Guide
What the Numbers Mean for You
A plain-English guide to the Fairfield County market
6 min read
This guide takes a large pile of real numbers and turns it into something you can actually use. We looked at 48,855 home sales in Fairfield, Westport, and Greenwich, from 2001 through 2023. You don't need a finance background to follow along. For each finding, you'll see the data first, then a plain-English read on what it means for you, whether you're buying or selling.
The big picture in one breath
Home prices in these three towns have climbed sharply since 2019. At the same time, fewer homes are selling each year. That combination—higher prices and fewer sales—means more buyers competing for fewer homes, and it keeps prices firm. This isn't a short-term mood swing; it's a shift that has held for years.
Prices climbed, and not gently
Here's the data. These are the median sale prices, which simply means the price right in the middle: half the homes sold for more, half sold for less. It's a better gut-check than an average, because one giant sale can't skew it.
We compare 2019 to 2023 on purpose, so you see the full shift. More on why in the notes at the end.
The home you're looking at likely costs meaningfully more than it would have a few years ago. That's not a fluke or a bad deal; it's the market. Budget for today's prices, not the prices you remember.
Your home has very likely gained real value since 2019. The starting point for pricing is higher than many owners expect.
Fewer homes are trading hands
Here's the data. The number of homes sold each year has dropped in all three towns:
The number of homes available to buy fell sharply after 2020 and hasn't recovered. So you have fewer homes for sale and plenty of people who still want to live here. When steady demand meets a smaller supply, two things follow: more competition among buyers, and prices that hold firm.
Expect fewer choices and more competition. The right home may not sit around waiting. Be ready to move when one fits.
A well-presented home in a tight market tends to draw serious attention. Scarcity is working in your favor.
How to compare homes fairly: price per square foot
Here's the idea. When two homes are different sizes, comparing their sticker prices tells you almost nothing. Price per square foot fixes that. It's the same trick as price-per-ounce at the grocery store: it lets you compare things of different sizes on equal footing.
Looking at sales from 2021 through 2023, the typical price per square foot was roughly:
One useful pattern: bigger homes usually cost less per square foot than smaller ones. You're often paying a higher rate per foot for a smaller home, and a lower rate for a larger one. Newer homes and homes in better condition also tend to command a premium, so a higher per-foot price often reflects real quality, not just hype.
Use price per square foot to sanity-check two homes against each other, but remember it's a starting point, not the whole story. Condition, age, and location move the number.
If your home is newer, larger, or in great shape, its per-foot value reflects that. The right comparison homes matter when you set your price.
Location is its own market
Here's the idea. Each town isn't one single market; it's several little markets sitting side by side. Where a home sits inside a town can matter as much as the town itself.
- —In Fairfield and Westport, waterfront homes carry a clear premium. Being near the water adds real value.
- —In Greenwich, it flips. The most expensive part of town isn't the shoreline; it's the inland “backcountry” estate area, which runs well above the near-shore middle price.
So a price that looks high or low only makes sense once you know exactly where the home sits.
Don't judge a price by the town name alone. A home two miles away may belong to a completely different price world. Ask where the value really lives.
Your location is part of your pitch. Whether it's water, a sought-after pocket, or quiet acreage, the right buyers will pay for the right spot.
If you're buying
- ■Budget for today's prices, not the prices you remember from a few years ago.
- ■Expect fewer homes for sale and real competition, so be ready to act when the right one appears.
- ■Use price per square foot to compare homes fairly, then adjust for age, condition, and location.
- ■Look closely at exactly where a home sits within its town; location is its own market.
- ■Lean on your agent to tell you when a price is fair for that specific street.
If you're selling
- ■Your home has likely gained real value since 2019; start from today's market, not the past.
- ■A tight market with few homes for sale tends to favor sellers who present well.
- ■Newer, larger, or well-kept homes earn a premium, so highlight what makes yours stand out.
- ■Your location and pocket within town are part of the story; price to reflect them.
- ■Price against the right comparison homes; your agent can pinpoint which ones truly match.
How to read this guide
A few honest notes, because clarity matters more than spin:
- ■These are past sales, not predictions. The numbers show what already happened. They're a strong guide, not a promise about next year.
- ■Every home and every street is different. Town-wide figures set the scene, but your specific home can sit above or below them for good reasons.
- ■A note on 2020. Public records are missing 2020 sales for Fairfield and Westport (a reporting gap during the COVID period). That's why we compare 2019 to 2023, so you see the full picture without a hole in the middle.
- ■Your situation is unique. The best read on your home, your budget, or your timing comes from a conversation, not a chart.
Let's talk
The numbers tell a story, but your story is the one that matters. If you're thinking about buying or selling in Fairfield, Westport, or Greenwich, let's sit down and talk through what all of this means for you.
Kate Cacciatore
Luxury Properties Specialist · William Raveis Real Estate