The Berkshire real estate market in 2025 is anything but predictable. Unlike the past, when seasonal patterns dominated, today’s market is highly segmented, with some properties selling in hours while others linger for months. This new landscape is driven by a mix of shifting buyer demographics, post-pandemic economic factors, and changing housing priorities.
From Predictable Cycles to Year-Round Demand
Before COVID, the market in the Berkshires followed a steady rhythm:
• Local buyers supported a stable, year-round market.
• Seasonal buyers drove a summer surge, fueled by the region’s cultural attractions.
• Sellers typically listed in the spring and sold by fall, often moving on to retire in Florida.
That predictable cycle was upended when COVID redefined how people view homeownership. The pandemic made having a country home less of a luxury and more of a necessity, and as a result, buyer interest became less seasonal and more constant.
One of the biggest takeaways from this shift is that home values are no longer determined solely by traditional real estate metrics. Instead, buyers have been willing to pay tens—or even hundreds—of thousands more for properties that provide peace of mind.
New Buyer Streams & Market Pressures
The Berkshire market now features several distinct buyer groups, each influencing pricing and demand differently:
• Urban Transplants: Buyers from California, Colorado, coastal areas, and high-end enclaves like Nantucket and the Hamptons are seeking more affordable alternatives to their skyrocketing home markets. Their presence has pushed average home prices higher, even though transaction volume hasn’t kept pace with demand.
• Local Market Decline: Unfortunately, the number of full-time local buyers has dwindled. With fewer high-paying professional jobs available in the region, many would-be homebuyers are priced out, weakening this once-stable segment of the market.
• Investor Buyers: The past few years have also seen an influx of investors buying single-family homes—a trend that was rare before COVID, when investment interest was largely focused on commercial and multi-family properties. These investor purchases have further altered the traditional real estate cycle.
The Rise & Fall of the Airbnb Boom
A significant factor affecting today’s market is the shifting short-term rental landscape. During the pandemic, many first-time investors jumped into the Airbnb game, seeing it as a lucrative way to generate income. Some did well, but many others are now facing challenges.
With travel patterns normalizing and demand for short-term rentals softening, many Airbnb owners are struggling with lower occupancy rates, rising expenses, and a more competitive rental market. As a result, some of these properties are starting to hit the market again—not as traditional homes but as income-generating assets, which complicates pricing expectations.
A New Wave of Inventory—But at a Different Price Point
One of the biggest market shifts underway is the type of inventory coming back into play. Many homeowners who couldn’t logistically sell during COVID—whether due to travel restrictions, economic uncertainty, or stalled life events (like retirement or job changes)—are now listing their homes.
This emerging inventory can be divided into two categories:
1. The Fast Lane – Motivated sellers pricing their homes competitively, moving inventory quickly.
2. The Slow Lane – Sellers with unrealistic price expectations, hoping to recoup on investments or improvements, which could lead to longer days on market and a general slowdown in transactions.
Additionally, the homes hitting the market now are often at lower price points—think aging family homes where the owner has moved into assisted living. While this may bring down the average sale price and price per square foot, it doesn’t necessarily mean values are declining. Instead, it’s simply a shift in the type of homes being sold.
Market Outlook: A Statistical Softening, But Price Pressure Remains
Two long-term trends are likely to shape the market moving forward:
• Deferred Maintenance Costs: Many of the homes coming on the market have not been updated or maintained at the same level as in previous years. Buyers will need to factor in higher renovation costs, and sellers will need to be realistic about how those costs impact pricing.
• Supply & Demand Pressure: While the market may experience a statistical softening—longer days on market, lower median sale prices—the fundamental supply-and-demand dynamics of the Berkshires should keep price pressure steady overall.
Much like the post-9/11 market cycle, we’re likely entering a period where motivated sellers will keep transactions moving in one lane, while overpriced listings sit in another. As the year unfolds, the big question will be how buyers and sellers adjust to this evolving landscape.
The Berkshire real estate market is no longer a simple seasonal cycle—it’s a dynamic, multi-layered environment shaped by diverse buyer motivations and evolving economic forces. Only time will tell how these trends play out, but one thing is clear: the days of “list in the spring, sell by the fall” are long gone.
To share your thoughts or find out more about ACRES services for buyers & sellers in the Berkshires, please contact:
Dan Alden, Holistic Transactional Broker
413-335-9300
dan@berkshireacres.com