Encompassing over 200 acres of pasture and forest, Timberland Farm is anchored by an early 1800s farmhouse that feels at once timeless and lived-in, a place shaped by centuries of stories, music, and shared meals. The living spaces feel both intimate and generous, framed by hand-hewn beams and original wide pine floors. From the dining room to the music room, wood-burning fireplaces crowned with antique mantels add warmth and character, while the expansive kitchen hearth draws one in for easy conversation and board games. Built-in bookcases, plaster walls, wood paneling, and windows overlooking the land lend the house a quiet, grounded grace. The farmhouse also includes a lower-level guest apartment with a private entrance. Nearby, a charming guest cabin, once the town’s blacksmith shop, provides a private haven for visitors. The barn has been thoughtfully reimagined and now houses a commercial kitchen, gym, and offices, offering flexibility for creative enterprise and agricultural ventures. A separate barn includes a woodworking shop. In recent years, pastureland surrounding the home and pond was reclaimed for grazing goats, restoring the agrarian rhythm of the property. Wildflowers and apple trees scatter the fields. A three-quarter-mile hike through the wood reveals a cool swimming hole. Additional woodland trails invite walking, snowshoeing, and foraging for berries, mushrooms and fiddleheads. Timberland Farm is a legacy holding, and very private, yet within easy reach of Stratton, Bromley, Magic Mtn. and Okemo. 17 miles from Manchester and 26 miles from Rutland Airport. 3 h from Boston and 4 h from New York. No showings through May 16th, 2026. Showings are by APPOINTMENT ONLY. Do not drive up the driveway to view the property. Home is owner-occupied and surveillance is in effect.
| MLS # | 5077331 |
|---|---|
| Listing Type | For Sale |
| Style | House |
| Sub-Type | Resale |
| Status | (10) Active - Active |
| Year | 1812 |
| Days On Site | 183 |
| Listing Provided By | LandVest, Inc/Woodstock | T Story Jenks |
| Bed(s) | 7 |
|---|---|
| Bath(s) | 5 Total |
| Garage | 3 |
| Basement | Y |
| Story(s) | 3 |
| Zoning | Residential |
| Acreage | 211.45 |
| Rooms Total | 10 |
|---|---|
| Cooling | Mini Split, Other |
| Heating | Propane, Oil, Electric, Heat Pump, Hot Air, Steam |
| Roof | Metal, Standing Seam |
|---|---|
| Construction Materials | Post and Beam, Wood Frame, Clapboard, Wood Siding |
| Foundation Details | Gravel/Pad, Stone |
| Lot Features | Country Setting, Farm, Horse/Animal Farm, Open Lot, Pond, Sloped, Timber, Trail/Near Trail, Views, Wooded, Mountain |
| Garage Yes / No | Yes |
|---|
| Utilities | Cable, Satellite |
|---|---|
| Electric | 200+ Amp Service, Circuit Breakers |
| Sewer | Concrete, On-Site Septic Exists, Private Sewer |
| Tax Annual Amount | 17739.1 |
|---|---|
| Tax Year | 2025 |
| State | VT |
|---|---|
| County | Windham |
| City | Londonderry |
| Zip Code | 05148 |
| Area | VT Windham |
| Listing VS Median (in 05148) | |
Price: $1,498,500 low | high Med: $850,000 On site: 183 low | high Med: 483 | |
| State | VT |
|---|---|
| County | Windham |
| City | Londonderry |
| Zip Code | 05148 |
| Area | VT Windham |
| Listing VS Median (in 05148) | |
Price: $1,498,500 low | high Med: $850,000 On site: 183 low | high Med: 483 | |