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LandVest Welcomes Joshua McDorman to Lead Mitigation Banking & Environmental Crediting Efforts06.04.2026

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  LandVest is pleased to welcome Joshua McDorman as Project Manager, Mitigation Banking & Environmental Crediting, further expanding the firm’s expertise in natural capital, conservation, and environmental markets. Josh joins the [...]

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The Berkshires Gilded Age Re-Visited
A Tribute Parade

The vintage carriages were polished like mirrors, the brass buckles and harnesses gleamed, and the prancing horses were glistening against the fall foliage on a perfect day in the Berkshires.

Berkshires luxury real estate

Ladies and gents gather for the bi-annual coach parade. Photo courtesy of Andrea MacCallum.

The carriages gathered in the front of the 1870 Southmayd Farm in Stockbridge MA. The gents in top hats and the ladies(including Martha Stewart) in 20th-century finery departed the coach for a luncheon near the maze, gathering above the oxbow of the Housatonic River on land once owned by Henry Wadsworth Longfellow. It could be 1900, but its actually Columbus Day 2016 and its the bi-annual coach parade organized by Harvey Waller of Orleton Farm. A tribute to the Gilded Age.

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The Housatonic River runs through Southmayd Farm

The Berkshires (pronounced Berk-shers) first became popular for second or third homes during the post-Civil war era called the Gilded Age. Society people, largely from NY, and literary and artistic luminaries were drawn to the clear mountain air, pristine hills, valleys, and lakes - a true refuge. The Astors, Westinghouses, Vanderbilts and their peers spared no expense in building mansions that they dubbed cottages in deference to their less formal settings than Newport.

Berkshires luxury real estate

Southmayd Farm is a 33+ acre estate with additional land available for purchase.

According to Cindy Welch, Berkshire Project Manager for LandVest, Privately held extant Berkshire cottages, such as Southmayd, are a rarity. Most have either become museums or been developed as resorts.

Berkshires luxury real estate

The Bellefontaine Mansion is now part of Canyon Ranch in Lenox, MA. Photo courtesy of Canyon Ranch.

One such cottage is Shadowbrook, which was built by Mr. Anson Phelps Stokes. At 410 long in 1894, it was the biggest house in America. In 1956 the house burned to the ground. It is now the site of world famous Kripalu. Bellefontaine is now Canyon Ranch. Colbrook is now Cranwell Resort. Blantyre and Wheatleigh are now resorts. Naumkeag is owned by the Trustees of Reservations. The Mount, once owned by Edith Wharton, is a popular public visitors site.

Berkshires luxury real estate

Visitors stroll through Whartons restored gardens at The Mount. Photo courtesy of The Mounts Facebook page.

Welch has sold two Gilded Age properties in Lenox, MA. One with ten bedrooms was sold to a Brooklyn, NY couple who plan to use it as second home for their large extended family. The other property was sold to a Boston couple who will also use it as a second home.

FEATURED BERKSHIRE LISTINGS

Currently, Cindy has 3 Cottages listed with LandVest, the grandest of which is Southmayd Farm on 33 acres in Stockbridge.

Southmayd Farm | Stockbridge, MA | $7,900,000

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The house, studio, pool, barns and greenhouse, set on 33+ acres, have been authentically restored to the finest detail. It is museum quality for comfortable country living.

Clipston Grange | Lenox, MA | $1,995,000

Berkshires luxury real estate Clipston Grange is in a walk-to Lenox town location and is in move-in condition, ideal for entertaining.

Morewood | Pittsfield, MA | $3,800,000

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The Morewood is adjacent to the Pittsfield Country Clubs golf course and has, like Southmayd, been lovingly restored to magnificence.


Despite the passing of a century, New Yorkers still comprise the largest single segment of second home owners in the Berkshires.

To find out more about these listings or other Berkshires Luxury Real Estate listings, contact broker Cindy Welch at cwelch@landvest.com

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