Is Now a Good Time to Buy or Sell in Fairfield County, CT? A 2025 Luxury Market Breakdown

The Short answer:
Yes—2025 is a strategic time to both buy and sell luxury property in Fairfield County, CT, but for very different reasons. Sellers are benefiting from strong prices and limited high-end inventory, while buyers finally have a bit more time and choice than they did in the frenzy of 2021–2022.

Let's walk through what’s happening right now in the Fairfield County luxury market, town by town, and what it means if you’re thinking about buying or selling in 2025—especially in New Canaan, Weston, and Wilton.

2025 Fairfield County Luxury Market at a Glance

The broader Fairfield County market remains resilient:

• County-wide median sale price: about $650,000, up roughly 11–12% year-over-year as of late 2025.

• Average days on market: homes sell in about 44 days, only slightly slower than last year (43 days).

• Sales volume: the number of homes sold has ticked up, with 897 closed sales in October vs. 839 a year earlier, indicating healthy demand.

• Statewide context: Connecticut overall is still grappling with low inventory and high prices, but 2025 is on track for more total home sales than 2024.

For luxury homes (roughly $1.5M+ in these towns), the story is similar but amplified: prices are elevated, buyers are more discerning, and properly priced homes still move quickly.

Town-by-Town Luxury Snapshot

Here’s what the data is telling us in New Canaan, Weston, and Wilton.

New Canaan: High Demand, Thoughtful Buyers

• Recent median sale price: around $1.9M, up more than 12% year-over-year.

• Median days on market: roughly 35–60 days, depending on property type and time of year.

What it means:
New Canaan remains one of Fairfield County’s premier luxury destinations. Move-in-ready homes in central and walkable locations, or with updated kitchens, baths, and outdoor spaces, are still seeing strong interest and, in some cases, multiple offers—especially if they’re priced correctly from day one.

Good time to sell?
Yes, especially if your home is updated and you’re in a prime location (in-town, close to schools, or on coveted streets).

Good time to buy?
Yes, if you’re upgrading from a starter home or moving from the city and plan to stay at least 5–7 years. You’ll be buying into a market with proven long-term demand and limited buildable land.

Weston: Country Living with Solid Value

• Average home value: approximately $1.3M, up about 6–7% over the past year.

• 2025 reports show fluctuations in monthly median prices, but the overall trend over the past several years is upward.

What it means:
Weston attracts buyers seeking privacy, acreage, and top-rated schools. Two-acre zoning keeps density low and supports price stability. The luxury segment here includes both classic colonials and architect-designed modern homes.

Good time to sell?
Yes—particularly if you’ve updated older homes (70s/80s builds) with modern kitchens, windows, and systems. Today’s buyers still want land, but they don’t want a project at a premium price.

Good time to buy?
Yes for buyers who value space over walkability. Compared to some neighboring towns, Weston can offer more land per dollar while still showing long-term appreciation.

Wilton: Quietly Competitive Luxury

• Median sale price (Wilton area): roughly $1.35M, up close to 30% year-over-year, with brisk turnover.

• Median days on market: about 24 days, faster than many surrounding markets.

What it means:
Wilton is a standout for value-minded luxury buyers—strong school system, scenic neighborhoods, and relatively quick access to commuting routes. The big year-over-year price jump reflects both limited inventory and strong demand for turnkey homes.

Good time to sell?
Very much so, especially if you’re listing a renovated colonial or newer construction close to town or trains. Well-priced homes are still moving quickly.

Good time to buy?
Yes—but strategy is critical. Buyers should be pre-approved and ready to move quickly on quality listings. There is less “sitting around” inventory in Wilton’s sweet spots.

So…Is It a Good Time to Sell a Luxury Home in Fairfield County?

For many homeowners in New Canaan, Weston, and Wilton, the answer is yes—if you approach it strategically.

Why 2025 favors luxury sellers

1. Prices are elevated vs. pre-pandemic. Most towns have seen double-digit price growth over the last several years.

2. Limited quality inventory. Many owners are still holding onto low pandemic-era interest rates, so there’s not a flood of comparable listings hitting the market.

3. Strong buyer pool. Affluent buyers who delayed moves during rate spikes are re-entering, especially from NYC and other higher-cost metros.

4. Market still moves—when homes are positioned correctly. County-wide days on market remain reasonable, and in some sub-markets, they’re very fast.

When you might wait

• You purchased at the very top of a hyper-local mini-spike and would be selling again within 1–2 years.

• Your home needs major renovations that today’s buyers are unwilling to take on at a luxury price point.

• You’re not yet emotionally or financially ready to downsize or relocate, and forcing a timeline would create stress.

If you do decide to sell, the key is positioning:

• Lean into data-driven pricing rather than aiming unrealistically high.

• Invest in targeted prep—paint, landscaping, lighting, minor cosmetic updates—to make your home show like a model.

• Use high-end marketing: professional photography, video, floor plans, and neighborhood-specific storytelling that resonates with luxury buyers.

Is It a Good Time to Buy a Luxury Home in Fairfield County?

Surprisingly, yes—for the right kind of buyer.

Why 2025 can work for buyers

1. More breathing room than 2021–2022. You’re less likely to face 15-offer bidding wars on every listing, especially at higher price points.

2. Still-strong long-term fundamentals. Limited land, proximity to NYC, excellent schools, and enduring town character support long-term value.

3. Opportunities in “imperfect” homes. Properties that need cosmetic updates or are slightly mis-priced can sit longer, creating negotiation room.

4. Mortgage strategies have evolved. Buy-down programs, adjustable-rate options, and creative financing can help smooth monthly payments even if rates aren’t at their historical lows.

You’re a good candidate to buy in 2025 if…

• You plan to hold the home for 5+ years.

• You’re financially comfortable with your payment at today’s rates—even if they don’t drop.

• You’re willing to move quickly when the right property appears.

• You’re open to small projects (paint, fixtures, landscaping) to gain value.

Strategy: How Buyers & Sellers Win in This Market

For Sellers

• Time your launch. In our area, early spring and early fall often bring the strongest buyer activity, but truly special homes can perform well year-round.

• Price inside the market, not outside it. Pricing slightly behind the curve (instead of ahead) often generates more interest and stronger final sale prices.

• Tell the neighborhood story. Especially for luxury listings, buyers are buying lifestyle—schools, commute, recreation, dining—not just square footage.

For Buyers

• Get fully underwritten pre-approval. In competitive towns like Wilton and New Canaan, strong pre-approval is a must.

• Know your “must-have” vs. “nice-to-have.” Acreage vs. walkability, school district vs. commute, new construction vs. character—these choices can point you to the right town and neighborhood.

• Watch micro-markets, not “Fairfield County” as a whole. Conditions in New Canaan’s in-town market can be very different from, say, Weston’s 4-bedroom colonials on 2 acres.

• Use data, but decide with your life in mind. Charts and graphs help, but where you live is ultimately about how you want to spend your days.

Final Take: Is Now a Good Time to Buy or Sell in Fairfield County, CT?

• If you’re a luxury seller in New Canaan, Weston, or Wilton, 2025 offers a rare combination: strong pricing, limited direct competition, and a motivated buyer pool. With smart pricing and polished presentation, it is absolutely a good time to sell.

• If you’re a luxury buyer, 2025 may not feel “cheap,” but it can be an excellent time to secure a long-term home in a blue-chip town. You’re buying into markets with proven resilience and long-term upside, with more choice and slightly less frenzy than just a few years ago.

Thinking of Buying or Selling?

Every home—and every move—is unique.

If you’re considering a sale or purchase in New Canaan, Weston, Wilton, or elsewhere in Fairfield County, I can prepare a custom, data-driven market report for your specific property or search criteria, including:

• Recent comparable sales

• Current competing listings

• Recommended pricing or offer strategy

• Simple visuals you can actually understand

When you’re ready, we’ll turn the numbers into a clear plan that fits your life—not just the market.