Chester Forest & Farm is an Earth Asset "curated portfolio" property. Our "curated portfolio" features properties that we have experience with, believe are exceptional investment opportunities, and are for sale and exclusively represented by other real estate firms. The in-house knowledge we have about these properties makes us well-positioned to provide informed, trusted counsel to a buyer. To learn about our exclusive buyer representation arrangement, contact Shawn at shawn@earthasset.com or (802) 434-7798.

Our Experience With This Property: Earth Asset's decade-long real estate counseling and valuation work for the owners provides our basis of intimate knowledge about the property, including its value integrity, historic use and management, potential to support a variety of new uses, income-generating opportunities, and conservation possibilities. Without infringing on the confidentiality we owe to the owners, we can leverage our wisdom to benefit a buyer. Save time, money, and avoid costly mistakes by partnering with us in the acquisition of this keystone property.

Why We Like This Property: Unfragmented landscape; water security & quality guaranteed by watershed control; rich wildlife habitat; robust wildlife population; excellent peripheral & internal access; field & edge openings; variable topography; variable solar aspect; diverse forest and NTFP (non-timber forest products) species for medicinal/food/fuel wildcrafting & foraging (eg. medicinal, edible fungi & plants like Reishi, red-belted polypore, birch polypore, stinging nettles); not over-improved with buildings; low carrying costs for a property of this size, quality & proximity to major metropolitan areas; easy access to major travel corridors and services; beauty; privacy.

Spanning nearly 2,000 acres, Chester Forest & Farm's size, contiguousness, 1.5-mile internal private road, diverse soil types and slope aspects, plentiful water resources, and close proximity to key regional markets like New York City and Boston, are its most valuable assets. Complementing them are excellent site access and privacy. Used as a family retreat, with the land managed primarily as a working forest, the property is in pristine condition.

The property is offered in three ways:

Offering 1 - $3,940,000 (formerly $4,650,000) | Chester Forest & Farm - 1,881± acres and all improvements; link to listing

Offering 2 - $3,150,000 (formerly $3,750,000) | Chester Forest - 1,807± acres and cabin; link to listing

Offering 3 - $790,000 (formerly $990,000) | Chester Farm - 73.7± acres and some improvements; link to listing


Active; seller represented by LandVest


Offering 1 | $3,940,000

Offering 2 | $3,150,000

Offering 3 | $790,000


Offering 1 | 1,881± acres

Offering 2 | 1,807± acres

Offering 3 | 73.7± acres


New England | Northeastern USA


Town of Chester, Windsor County, Southeastern Vermont

Access & Distances

Albany International Airport, Albany, NY, 2hr drive (commercial)
Bradley International Airport, Hartford, CT, 2hr drive (commercial)


Hartford, CT & Albany NY, 2hrs; Boston, MA, 2.5 hrs; NYC, 4.5 hrs

Off town-maintained roads

Built Environment

Main Residence

4,930-SF; c. 1819 2-story 6-bedrooms & 4.5 baths, views of hayfields, forestland & stone walls

Guest Residence

2,146-SF; c. 2000 2-story 2-bedrooms & 2 baths, attached garage, private

Guest Cottage

2-bedrooms, 1-bath, kitchen


Loft sleeping quarters, kitchen, orchard & mountain views, secluded

Antique Barns/2

Animal quarters, equipment & hay storage, workshop

Internal Road

1.5 miles, private, commercial-grade design & construction, gated

Natural Environment

Land Cover

80% forested, 20% hayfield, pasture & orchard

Trout Pond

Private, 23-foot depth, 2-aerators, dam


5 significant internal streams and 1 waterfall system


2 beaver-made wetland complexes

Wood Roads/Trails

Extensive internal working roads and trails system excellent for forest management, boundary supervision & recreational uses

Conservation Values

Unspoiled, intact northern forest ecosystem, headwaters of 9 distinct watersheds, 31 forest types, 20 soil types, and a healthy and abundant wildlife population.

Conserved Status

Not encumbered by a conservation easement