October 2025 Fairfield County Luxury Real Estate Market Update

The opening month of Q4 revealed a rational, resilient market.

October marked the start of Q4, and while the air cooled, the market did not. Across Fairfield County’s nine luxury markets, the same imbalance held - demand still outweighs supply. What changed were the nuances - slightly longer marketing times, a more rational buyer pool, and a market that rewards preparation and precision above all else. 

The Executive Take 

Across Fairfield County (year-over-year): 

• Unit sales rose +11% - proof that buyers are still transacting even as headlines suggest fatigue.
• Median sale price climbed +20% to $1.825M, driven by a higher share of luxury trades (particularly in Westport and New Canaan).
• Days on Market (DOM) jumped +37% o 60 days, signaling selectivity, not softness.
• List-to-sale price ratio remained strong at 101.8% (down only 1.1 points).
• New listings fell –12% , confirming that scarcity continues to define the landscape. 

In short: buyers remain motivated, sellers remain advantaged - but both must navigate with skill, not luck. 

Signals Beneath the Surface 

1 | Inventory Tightness Still Rules 

We anticipated Q4 would open with subdued listing volume, and October confirmed it. 

New listings declined 12% year-over-year, perpetuating the self-reinforcing cycle: homeowners hesitate to sell because they see little to buy. 

Takeaway: 

• For sellers: scarcity continues to work in your favor - if your home is properly positioned.
• For buyers: waiting for a surge in inventory is wishful thinking. Be ready when quality appears. 

2 | DOM Is Rising - But Only for the Unprepared 

The 36.8% increase in Days on Market isn’t a sign of weakness - it’s segmentation. 

• Turn-key homes, staged and priced with discipline, still sell within weeks.
• Dated or mispriced listings linger for months. 

Westport (74 DOM, +80%) and Weston (110 DOM, +156%) show that higher-end homes can sit longer when they overshoot value or readiness. 

Takeaway: The market isn’t slowing - it’s penalizing indecision. 

3 | Pricing Power Remains Remarkably Resilient 

Despite longer timelines, sellers still achieved 101.8% of list on average - only a slight dip from 2024. 

• Wilton (104.3%) and Ridgefield (104.2%) led. 
• Even Greenwich (102.2%) improved year-over-year. 
• Only Weston and New Canaan (99.1%) fell below 100%, both due to listing mix. 

Takeaway: buyers are still paying up—but only for homes that justify it. 

4 | Median Price Growth Reflects Mix, Not Inflation 

A +20% median price gain sounds dramatic, but it’s compositional. 

• Westport’s median +87% to $2.9M (more $3M+ sales).
• Fairfield +56% to $1.29M.
• Greenwich –21%, a pullback in ultra-luxury closings. 

Takeaway: prices didn’t inflate; higher-end transactions simply dominated the month. 

An Emerging Pattern: A Rational Luxury Market 

2024 was emotional - fueled by scarcity and FOMO. 

2025 is analytical. Buyers still compete, but they walk from overpriced listings. Sellers still win, but they earn it through strategy and execution. 

This is a mature market, not a manic one. 

Looking Ahead | Setting Up for Q1 2026 

October’s patterns point to a first quarter defined by: 

• Continued low supply,
• Stable pricing for quality homes, and
• More balanced negotiation as logic tempers urgency. 

For Sellers: 

• Act now if absolutely necessary or prepare for January/February. The early-Q1 window captures pent-up demand and limited competition.
• Invest where ROI is clear. Small upgrades—lighting, paint, landscaping—compress DOM.
• Price truthfully. In a rational market, overpricing isn’t aspirational; it’s expensive. 

You’re still in control - but the playbook has evolved from “list and wait” to “prepare and perform.” 

For Buyers: 

• Be decisive and prepare financing. Well-positioned listings still move in days.
• Craft compelling offers. Flexibility with closing timing, rent-backs, and terms can often outperform a higher price.
• Look quietly. Off-market and “coming soon” inventory continues to expand. 

This isn’t the time to sit it out; it’s the time to be ready. 

A Note on New York City Migration 

We’ve been asked whether Zohran Mamdani’s election as Mayor of New York City could trigger another wave of migration from the city into Fairfield County - similar to what we saw during 2020–2022. 

The short answer: it’s too early, and perhaps too simple, to draw that conclusion. 

It’s worth remembering that markets, both real estate and financial, tend to anticipate change. By the time an election result is official, much of its impact is already priced in - just as equity markets often absorb an expected rate cut before it happens. 

So, while it’s possible that a few city homeowners may accelerate relocation plans in response, it’s unlikely to spark the kind of exodus we saw during COVID. That migration was driven by necessity and lifestyle shifts, not politics. 

But let’s suppose we’re wrong. What happens if Fairfield County does see another dramatic surge like 2020–2022? Here’s the rub: even if demand from New York rises, it doesn’t change the fundamental constraint - inventory. We can bring more buyers into Fairfield County, but we can’t conjure more homes for them to purchase. The limiting factor isn’t interest - it’s availability. 

The more telling moment will come in Q1 2026, when spring listings typically surface and open house activity peaks. Only then will we see whether buyer inflow from New York is anecdotal or material. 

Until then, it’s best to do what the best advisors always do - avoid forecasting, stay attentive, and prepare to act if the data warrants it. 

Final Thoughts 

The Fairfield County luxury market continues to defy the broader national slowdown - not by inflating, but by normalizing with discipline. 

In 2025, Fairfield County’s market is rewarding judgment. 

And for those who make smart, informed moves - it’s rewarding them handsomely. 

We’re aware that much of our advice sounds familiar. That’s because it’s meant to. Markets reward consistency of judgment more than novelty of opinion. 

Until the dynamics truly shift - until inventory normalizes, rates move meaningfully, or buyer psychology resets - the fundamentals remain our compass. 

Price truthfully. Prepare fully. Act decisively. 

The playbook hasn’t changed because the field hasn’t either.

To position yourself advantageously for Q1 2026, reach out to Cindy Raney & Team and start planning now.