6 homes with glorious fall foliage
Featuring a house in the Berkshires that has a cupola with 360-degree treetop views and an 80-acre Oregon estate with a restored barn and riding arena
Stratton, Vt.
This 2004 timber-frame home in southern Vermont is on more than 5 acres and abuts the Green Mountain National Forest. The five-bedroom’s great room features a block-stone fireplace, a wall of windows, and a kitchen with a pantry, while a lower level has a live-edge billiards table, wet bar, and media room.
A screened porch and deck overlook the woods, and the property also includes a firepit, hot tub, and barn with a gym. $2,700,000. Betsy Wadsworth, Four Seasons Sotheby’s International Realty, (802) 579-8689
Woodstock, N.Y.
Five minutes from town and Cooper Lake, this 1973 contemporary mountain home sits on more than 6 wooded acres. The renovated four-bedroom’s living room has an Italian plaster fireplace, oak beams, and pale wood floors. The open kitchen includes soapstone counters, and the primary bath has a soaker tub and heated floors.
The Week
Escape your echo chamber. Get the facts behind the news, plus analysis from multiple perspectives.
Sign up for The Week's Free Newsletters
Join more than 350,000 subscribers and keep yourself informed with a selection of The Week’s most interesting, enlightening and entertaining stories - plus daily puzzles.
Join more than 350,000 subscribers and keep yourself informed with a selection of The Week’s most interesting, enlightening and entertaining stories - plus daily puzzles.
A screened porch opens to a pool and deck, and there’s a newly built garage. $2,395,000. Laurie Ylvisaker and Leslie Foti, Coldwell Banker Village Green Realty, (845) 901-6129
New Marlborough, Mass.
On more than 9 acres in the Berkshires, about 20 minutes from Great Barrington, this 2025 four-bedroom modern double-dome home features a main dome with vaulted, wood-clad ceilings with windowed panels, plus a loft that connects to a cupola with 360-degree treetop and East Mountain views.
A theater, gym, sauna, two kitchens, and bonus space fill out the interior. Outside are yards, a deck, a garage, and a brook. $3,250,000. Tim Lovett, Compass, (413) 446-0059
Darby, Mont.
This 2005 forested estate on more than 20 acres in the Bitterroot Valley includes two creeks. The three-bedroom main mountain home has hardwood floors, ceilings with exposed timber trusses, a chef’s kitchen with Wolf and Sub-Zero appliances, and an upstairs bunk room.
A free daily email with the day’s biggest news and analysis – and the best features from TheWeek.com
Sharing the land are a two-bedroom guesthouse, patios, a pizza oven, a hot tub, a three-car garage with a studio, and parklike grounds. $5,950,000. Dawn Maddux, Engel & Völkers Western Frontier—Missoula, (406) 550-4131
Oregon, Wis.
Started as a homestead in 1837, Five Bridges Farm, an 80-acre estate about 15 minutes from Madison, is dotted with many tree varieties, with Swan Creek running throughout. The 2018 modern four-bedroom has a 30-foot-high central room with floating stairs, floor-to-ceiling windows, and a woodstove.
The land includes prairie, pasture, and forest and has a restored barn, a riding arena with paddocks, a studio, and a tree house. $6,000,000. Melissa LeGrand, Christie’s International Real Estate @properties elleven, (608) 438-2130
Egremont, Mass
This 1970 gambrel-roof A-frame in the Berkshires is on almost an acre surrounded by mature deciduous trees. The onebedroom has wood-clad walls, vaulted ceilings, a mid-century modern fireplace, a bedroom loft, and a wall of windows framing leafy views. A basement has room for guests, a den, and an office.
A screened porch and deck look out onto the property, which is less than 10 minutes from Catamount Mountain Resort. $589,000. Antonio Segalla, William Pitt Sotheby’s International Realty, (413) 329-4075


