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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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Woodstock Vermont

Market Insights

The Woodstock area is perhaps the most valuable second home market in New England not on the water or slopeside. Beautiful farms, quiet gravel roads, and rolling countryside have been the perfect antidote to hectic urban life since the Rockefellers started buying up and preserving land in Woodstock in the 19th century.

LandVests focus on great properties and global marketing supports our dominance of the Vermont market for sales in the luxury market above $1m.

Gross sales volumes fell 21% in the Woodstock area, a function of tightening supply of great properties on the market. There is a pool of active LandVest buyers looking for special properties. The top 2019 Woodstock sale of $3.25 million did not match 2018s top sale at $5.3 million, but a major private sale in early 2020 reaffirms that realm of sales price for truly exceptional properties. All of these sales were led by LandVest.

Days on market shortened by 9 days to 169 days in 2019. Its important to note that the top sales had much shorter days on market due to accurate pricing. There is a huge disparity between the years on market of overpriced properties versus days (or hours) for those that come on with realistic pricing.

Sales by tier dropped slightly in 2019, with 12 sales over $1 million, 2 sales over $2 million and 1 sale north of $3 million (13/3/1 in 2018). The private transaction mentioned above was contracted in the late summer of 2019 with a delayed closing, so it will show up in the 2020 numbers.

Vermont Market Trends

Statewide, 2019 represented another strong or solid year for Vermonts high-end real estate market ($1m+):

  • As in Woodstock, gross sales fell slightly statewide, by about 2%, reflecting fewer great homes available for sale despite strong demand;
  • Median sale prices statewide fell slightly, with the top sale at $3.71 million below 2018s top sale of $10.5 million;
  • Days on market for properties over $1 million throughout Vermont fell by a notable 15 days to 182 days, again reflecting tighter inventory conditions;.and
  • The number of sales rose slightly to 105 sales over $1 million, 19 over $2 million and 4 over $3 million (102/14/2 in 2018). Chittenden County in Burlington and along Lake Champlain showed the strongest increases see our update on that market here.

2020 Outlook

The early months of 2020 have been very active, though a shortage of great properties on the market has resulted in a slower pace of sales than buyers would like.

Despite a tighter supply/demand situation than there has been for years, that hasnt translated into better pricing for marginal properties. In a market which is largely discretionary, buyers simply wont step up for properties they dont like or dont represent compelling value.

We are seeing a much greater appetite for land, despite very high prices for new construction, often three to four times the cost of purchasing existing properties. The driving factors are privacy and buyer preference for greener, more modern construction.

Looking forward, the major unknown is the impact of uncertainty around pandemics, the election and the equity markets. It is encouraging that coming into these potential headwinds, the market is structurally in the best shape that it has been for over a decade.


Got questions? Want to know more? Wed love to help! Contact any member of our Woodstock team: Dia Jenks, Story Jenks, Chris Lang or Ruth Kennedy Sudduth.

 

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The Paul & Bunny Mellon Estate11.21.2025

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Its easy to understand why Paul and Bunny Mellon chose this site for their storied summer home. Situated on a bluff, overlooking Nantucket Sound, the southwesterly trade winds, gentle but constant, drive the tempo of the sea just beyond a protected barrier island. No doubt the Mellons [...]

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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  HIGH-END $2,000,000+ MARKET HIGHLIGHTS Inventory up 12% (Record 514 vs record 458 last year). Sales up 23% (Record 423 vs record 345 last year). Top Sale: $10,500,000, 10 Appleton Street, Cambridge. Buyers and sellers continue to increase their activity resulting in record inventories and [...]

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