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Built for Generations: Family Compounds Across New England & The Adirondacks05.12.2026

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Some properties are purchased for a moment in time. Others are held for generations.  Across New England and the Adirondacks, family compounds have long represented a distinct kind of ownership — properties designed not simply as homes, but as places to return to year after year. With [...]

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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.

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

Stockbridge

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.

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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!

SOUTHMAYD FARM - UNDER AGREEMENT Stockbridge, MA

MA1933_3 Southmayd Farm | Stockbridge, MA | 33.00 Acres | 8 Beds | 10 Baths | 10,970 Sq.Ft

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 Rockwells 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.

 

MOREWOOD Pittsfield, MA

MA1954_1 Morewood | Pittsfield, MA | 11.20 Acres | 6 Beds | 8 Baths | 10,000Sq.Ft.

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 Melvilles Arrowhead Farm, grab some local produce at the downtown farmers market, dine-out at District Kitchen & Bar where they serve up seasonal fare using locally sourced ingredients.  

42 EAST ALFORD ROAD - UNDER AGREEMENT West Stockbridge, MA

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

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 caf sources only natural coffees, teas, and salts--grown responsibly.

 

181 WEST ROAD Richmond, MA

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

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.  

PURPLE KINGS FARM LAND Williamstown, MA

Purple Kings Land | Williamstown, MA | 59.95 Acres

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.

 

PURPLE KINGS FARM Williamstown, MA

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

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.  

SWISS MEADOWS Williamstown, MA

MA2052_1_CC Swiss Meadows | Williamstown, MA | 28 Beds | 12 Baths | 13,230 Sq.Ft.

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 Schttes large scale sculptures at The Clark Institute, catch a Williams College home football game, and explore the miles of trails in Hopkins Memorial Forest.  

PRIVATE BERKSHIRE ESTATES Berkshires, MA MA2052_19_CC 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 cwelch@landvest.com or 413-329-3999.

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Cape Cod | Massachusetts | High-End Market Watch, First Half 202509.22.2025

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At the end of the second quarter, the high-end inventory of listings, active and pending, was up by 21% to a record318 listings compared to 263 last year and the previous record of 271 listings in 2016.

Middlesex County | Massachusetts High-End Market Watch, First Half 202509.22.2025

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