Second Home Markets to Watch: The Berkshires

Second homes offer you a place to hit the “reset” button, gather friends for a long weekend, or family for the holidays. At LandVest we understand the need to find a place where your head can clear, you can reconnect with the out of doors, with yourself and with the people you love.

For some lucky folks, second homes become primary homes as the demands of work change. That shift can increase the importance of a vibrant community, while reinforcing the need for privacy, quiet, and beauty.

We serve second home communities from coastal Connecticut to DownEast Maine and the Adirondacks.

Let’s talk about the Berkshires, a haven since the Gilden Age, and a hotspot for culture as well as remarkable natural beauty.


The current inventory of seasonal homes in the Berkshires is expected to increase by a stunning 59% by 2030. Back in 1975, just 12% of homes in the region were seasonal. Since then, that number has grown to over 1/3. We expect to see steady and sustained growth over the next decade resulting in nearly 5,000 new homes by 2030. Yet careful development planning and a strong conservation ethos will retain the rural character of the Berkshires, while new growth generates vibrant town centers and culture.


Whether you are in the market to buy or build your ideal second home, LandVest is here to help. We know where to find you the quiet and beauty we all crave, close to Tanglewood, Jacobs Pillow or MassMOCA.

Check out a sample of some of our ideal second (or first!) homes and local insight into what to do, see, eat and drink. Enjoy!

Stockbridge, MA

Southmayd Farm | Stockbridge, MA | 33.00± Acres | 8 Beds | 10 Baths | 10,970 Sq.Ft

A grand and historic Gilded Age home close to Norman Rockwell’s town of Stockbridge.

How to enjoy Stockbridge? We suggest exploring the “Inventing America: Rockwell & Warhol” exhibit at the Norman Rockwell Museum, touring the Berkshire Botanical Garden, and catching a performance by the Berkshire Theater Group.


Pittsfield, MA

Morewood | Pittsfield, MA | 11.20± Acres | 6 Beds | 8 Baths | 10,000Sq.Ft.

A beautifully restored Gilded Age Estate with expansive gardens and lawns abutting the Pittsfield Country Club.

What to do in Pittsfield? Visit Heman Melville’s Arrowhead Farm, grab some local produce at the downtown farmer’s market, dine-out at District Kitchen & Bar where they serve up seasonal fare using locally sourced ingredients.

West Stockbridge, MA

42 East Alford Road | Stockbridge, MA | 15.00± Acres | 6 Beds | 7 Baths | 7,400 Sq.Ft.

Sitting high in West Stockbridge, this 2007 shingle style contemporary has unbeatable views of the Berkshire Mountains. 6 bedrooms, 7400± sq.ft. of living space, and a pool.

Worthy of its “Best coffee stop in New England, 2016” honor by Yankee Magazine, No. 6 Depot is a must visit. With a guiding mission of “keep it simple and make it true” this gem of a café sources only natural coffees, teas, and salts–grown responsibly.


Richmond, MA

181 West Road | Richmond, MA | 7.50± Acres | 5 Beds | 5 Baths | 5,100 Sq.Ft.

Well landscaped with pool, this contemporary has 7 acres, large common rooms and 4-5 bedrooms.

Start your day off with a mouthwatering smoked salmon omelet from Haven Cafe & Bakery in the neighboring town of Lenox. Visit Hilltop Orchards to pick your own apples and enjoy an afternoon wine tasting.

Williamstown, MA

Purple Kings Land | Williamstown, MA | 59.95± Acres

A scenic 59.95± acres dominated by open fields, two ponds, beautiful forests and the best views possible of Mt. Greylock and the Taconic Range.


Williamstown, MA

Purple Kings Farm | Williamstown, MA | 15.76± Acres | 5 Beds | 3 Baths | 4,853 Sq.Ft.

On a scenic road in Williamstown, the original Purple Kings Farmhouse sits on 15 acres with never ending views of Greylock Mountain and the Hopper. Surrounded by meadows, it is pastoral with views.

Williamstown, MA

Swiss Meadows | Williamstown, MA | 28 Beds | 12 Baths | 13,230 Sq.Ft.

Many feasible and creative uses for the property exist, from private estate to campground, to school, to residential development, and more.

See Thomas Schütte’s large scale sculptures at The Clark Institute, catch a Williams College home football game, and explore the miles of trails in Hopkin’s Memorial Forest.

Berkshires, MA
Additional private listings available. LandVest offers land and estates for sale that are not marketed online.

Interested in learning more about these great listings, the Berkshire market, or other second home markets in New England? Contact luxury Berkshires broker Cindy Welch at or 413-329-3999.