Set at the end of a -mile private drive and surrounded by 11 acres of open meadow and protected farmland, this Mid-Century three-bedroom, two-bathroom cottage offers privacy, charm, and country comfort in an estate-like setting. The compound is shared with a turn of the century former private school, now converted into 6 residences.

Property Highlights

Three bedrooms / two full bathrooms

Spacious second-floor suite with full bathroom, a wall of generous closets, built-in storage, and a bright nook perfect for a home office or creative space

Wood-paneled three-season room with a wood-burning stove, ideal for cozy mornings, entertaining, or quiet evenings

Inviting living area with warm natural light and country character

Separate dining room off kitchen

Mudroom entry, ideal for coats, boots, and outdoor gear

Back deck and stone patio, perfect for grilling and outdoor dining

Ample space to revive the former vegetable garden and enjoy the open land

Full, dry basement with washer and dryer.

Serene private location, yet just minutes from Sheffield town center, Great Barrington and North Canaan

Utilities & Services

Included in rent: Garbage removal, lawn maintenance, and snow plowing

Tenant responsible for: Heat, electricity, and internet

About This Lister

La Villa Holdings is a family-run venture rooted in the Southern Berkshires, dedicated to offering a range of thoughtfully maintained rental properties that reflect the character and charm of the area. As local owners, we’re never more than five miles from any property at any given time — always nearby and easily accessible to our tenants and neighbors.