You can make your dream of owning a home in the Berkshires come true, and you can do it for under $500K.
An ideal choice for first-time homebuyers to downsizers to buyers looking for a second home or vacation retreat, homes in the Berkshires offer a spectacular natural setting, easy access from Boston, Albany, and New York City, and close proximity to vibrant and historic communities like Pittsfield, Lenox, and Stockbridge.
The Berkshires is a time-honored vacation destination as well as a place to call home all year round. Berkshire homes for sale priced under $500K run the gamut from compact to expansive. Which one will become yours? Here’s a sampling of three exclusive properties in this attainable price range.
6 Beacon Hill, Great Barrington, MA, $395,000
The first standout feature you’ll notice about this 3-bedroom home is the enclosed porch with three walls of windows that flood the entry with light. The second impressive feature is the detailing that graces every room, from carvings on the mantlepiece to the coffered ceiling in the kitchen. Located along the Housatonic River in Great Barrington, this beautifully maintained home is in walking distance to the charming village of Housatonic and an easy drive to nearly every Berkshire attraction and activity.

438 Shaker Ridge Drive, Canaan, NY $439,000
This contemporary-style home offers 3,000 square feet of extraordinary living spaces. With five bedrooms and four baths, there’s plenty of room for everyone. And this home checks all the boxes for home features that delight. The chef’s kitchen glows with warm woods and high-end stainless steel appliances. The open floor plan features a living area with a gorgeous stone fireplace. The master suite comes with its own private sunroom. Multiple decks make this a home for outdoor relaxation and entertaining. Set on 5.8 acres, this property is an amazing value.

17 Glendale Road West, Stockbridge, MA, $495,000
This three-bedroom, two-bath home set on just over three acres offers a private setting on a quiet country road central to the multitude of cultural and recreational venues for which Stockbridge is famous. Beautifully updated and in move-in condition, this home features an open living room and dining room with two-sided stone fireplace. But what’s truly special about this home are the living spaces designed for well-appointed year-round living in the Berkshires. Such as: brand-new central AC, a four-season sunroom, a mud room, a family room with wood stove, and a laundry room with cupboards, sink and granite counters, and easy-care wood, tile, and slate floors throughout. Beautiful stone pathways and a wrap-around deck set off the dramatic rock outcroppings and naturalized landscaping.
