For over a century, the Berkshires have been a retreat for very wealthy individuals. But what makes our county in Western Massachusetts so attractive for those seeking a change, or a second home?
Dating back to the late 1800s, affluent individuals were coming to our area to build massive estates playfully called “The Berkshire Cottages.” Many of the people who resided in these mansions, either as a guest or the owner of the estate, remain well-known: Andrew Carnegie, the Vanderbilt family, Edith Wharton, and Daniel Chester French are just a few who called the Berkshires their home for at least part of the year. Most came to escape New York City for the summer in favor of scenic, bucolic views (and to show off their wealth to their guests and friends, of course!).
Despite the seemingly humble name, an estate typically needed to have over 20 rooms and be over 10,000 square feet to fall under the “Berkshire Cottage” umbrella. As you can imagine, these were very grand homes–some of which are still standing and retain elements of their unparalleled craftsmanship and historic charm.
Many of the Berkshire Cottages that remain have been transformed into public-facing properties, whether that be in the form of inns, museums, or spas. But there are some that still remain as private, single-family residences.
These summer estates in the Gilded Age were just the start of a long tradition of beautifully crafted second homes. The historic charm of the area–both in the architecture of the homes and our quaint, timeless downtowns–continues to be a great draw to second-home owners.
Million Dollar Views in Berkshire County
Particularly for buyers coming in from Boston or New York, the natural beauty of our area is another great attraction to the Berkshires. Those seeking fresh air and wide open spaces will find plenty to love about living here. It’s not unusual to find property listings situated on hundreds of acres for sale, which is a great bonus for affluent home buyers looking for an ultra-secluded getaway or primary residence.
Like the original Berkshire Cottage part-timers, many second homebuyers come seeking properties that are well suited to hosting plenty of guests while they’re in town. Properties like my previous listing offer both breathing room and seclusion along a private waterfront where friends can enjoy lots of outdoor recreation with you.
Privacy for High-Profile Homeowners
The high level of privacy that’s achievable in the Berkshires attracts not only the wealthy but also well-known individuals. There are lots of actors, musicians, YouTubers, and other celebrities who are hidden in our hills. Some may be spotted walking through our downtowns or acting in local theatre festivals if they want to be seen–otherwise, you’d never know they live here! If you’re someone for whom privacy is a huge concern, know that it’s very important to me that my conversations with clients are confidential, especially when a secret getaway is the ultimate goal.
World-Renowned Arts & Culture
Celebrities and other wealthy people are also drawn to the Berkshires for our well-known, thriving arts and cultural scene. We have incredible dance performances at Jacob’s Pillow, musicians at Tanglewood (the summer home of the Boston Symphony Orchestra), and theatrical pieces at a variety of stages from Shakespeare & Company, to Williamstown Theatre Festival, to Barrington Stage Company and more. You can also enjoy a wide variety of visual arts, from more classic works at The Clark to incredible modern installations at Mass MoCA. Berkshire County is also home to the Norman Rockwell Museum, based out of a property in Stockbridge where Rockwell lived and created famous works from the 1950s until his death. And this isn’t even a comprehensive list of every single cultural attraction of the Berkshires! Patronizing these cultural institutions is something that many affluent families look forward to year after year.
Scenic Downtowns & Community Atmosphere
Those that enjoy poking around shops and galleries to find unique, conversation-starting pieces also find great joy in situating themselves close to our beautiful downtowns. Some of my favorites, such as Lenox, Stockbridge, and Great Barrington, attract locals and tourists alike by being walkable and full of unique stores and restaurants. And placing yourself near one of these downtowns is a great way to integrate yourself into the community. Many of my clients coming out of New York or Boston love to walk around every weekend, seeing familiar faces and making friends just by being a regular at their favorite local cafe or bar.
Finally, many enjoy making the Berkshires their getaway because of the social and political climate. Like most other areas of Massachusetts, this is a very left-leaning area. I have had second-home clients tell me they are looking into the Berkshires because of its reputation of being a great getaway for those who are seeking a more rural environment, but are also concerned about the area they live in being LGBTQ+ friendly. This intersection, at a convenient distance from Boston and New York, makes the Berkshires highly desirable for this subsection of second home buyers.
Are you ready to find your perfect getaway in the Berkshires? Either give me a call or click here to get the conversation started.
