Greenwich, the long way up.

A decade of drift, then four years that reset the level.

The Town’s single-family median barely moved through the 2010s — $1.7M in 2013, $1.7M again in 2016, $1.86M in 2019. Then it stepped up every year from 2020: $2.075M, $2.30M, $2.45M, $2.50M, $2.87M, and $3.15M in 2025. The durable signal is that repricing, which held even as the number of sales fell back below its mid-2010s level.

The long view matters here more than in the other markets. Greenwich is the slowest fifty-year compounder of the six and it recovered from 2008 the slowest — the 2006 peak was not regained until 2022, sixteen years later. The four years since are the exception, not the trend.

Jobs and schools, not second homes.

The only genuine primary-residence market here. Three percent of Greenwich's housing units are seasonal, against 39% in the Town of Palm Beach and 47% in East Hampton. That makes Greenwich a jobs-and-schools market that happens to carry resort-level price points — so it turns on employment and commuting patterns, not on discretionary second-home appetite.

Price per square foot tells the same story from another angle: about $888/sf in 2025, up +57.4% since 2016. The Town is not adding meaningful new single-family supply, so a demand shock lands on price and speed rather than volume.

Fifty years, in six moments.

1. 1985-1986
   The Wall Street decade

   +20.9% then +26.5% — Greenwich's two best years on record, both in the 1980s. The market's beta to financial-services compensation is visible from the very start of the series.

2. 2006-2013
   Seven years down

   Peak 2006, trough 2013, -23.4%. Shallower than Florida but far longer, and the recovery is the slowest in the dataset: the 2006 level is not regained until 2022. Sixteen years.

3. 2012-2019
   Eight years of leakage

   The number nobody puts in a Greenwich pitch: Fairfield County ran a NEGATIVE net adjusted-gross-income balance with the rest of the country every single year from 2012 to 2019 — minus $1.38 billion in tax year 2011-12, minus $1.62 billion in TY2015-16, minus $578 million as late as TY2018-19. Greenwich was exporting wealth for eight straight years. It did not turn positive until TY2019-20, and only barely.

4. 2015-2019
   The lost half-decade

   The Greater Greenwich single-family record shows the malaise precisely: 601 sales in 2015 at a $1,856,250 median with 161 days on market and a 94.4% sale-to-list ratio; by 2019, 528 sales, a $1,858,333 median — statistically flat over five years — and 199 days on market.

5. 2020-2021
   Four years of change in eighteen months

   Sales go to 863 in 2020 and 1,006 in 2021, the highest on record. Days on market collapse from 199 (2019) to 109 (2021) to 64 (2024). Sale-to-list crosses 100% in 2022 and stays there. The town's conveyance-tax take hits $50.65 million in fiscal 2021-22 on 1,427 taxable conveyances.

6. 2022-2025
   Fewer, larger, faster

   Volume falls back to 501 sales in 2024 — fewer than 2015 — while the median rises from $2,450,000 (2022) to $3,150,000 (2025). Conveyance-tax receipts fall to $35.93 million on 1,011 conveyances in FY2022-23. The market is not slowing; it is running out of things to sell.

Where Greenwich prices hardest.

The waterfront neighborhoods — Old Greenwich, Riverside and Cos Cob — carry the Town’s highest single-family medians and its own tight sub-records. Each trades on its own count, which is why the Town figure moves in steps rather than a clean line.

The Town, neighborhood by neighborhood.

Neighborhood records vary in basis — some are single-family only, others cover all home types where that is how the area trades — so each row states which. Where a figure rests on a single reporting source it is marked as such and is never presented as corroborated.