SoldAug 27, 2026

Listed by Kristen Taylor from Brattleboro Area Realty

Bought with Mickey Hipp from BHG Masiello Brattleboro

Source: PrimeMLS #5090867

442 Brookline Road, Windham County, VT, 05345

$374,000

3
2
2500 sq. ft.
557568 sq. ft.

SingleFam

23 days on the market

Sold: Aug 27, 2026

What's around 442 Brookline Road

About this property

MOTIVATED SELLER! Welcome to the Green Mountains! Nestled on 12.8 private acres, this quintessential, one-of-a-kind timber frame cabin offers a rare blend of craftsmanship and nature. Bordering the protected Pinnacle Association preserve, you can walk right out your front door to explore amazing trails and local wildlife. Lovingly constructed by local artist and builder Nathan Guest, the home’s creative vision is evident in every detail rom the 1800s wagon wheel chandelier to the handcrafted dining table. The main floor features two bedrooms, a full bath, and an inviting living room anchored by a Quadra-Fire Explorer wood stove and a custom bar, perfect for entertaining. The amazing kitchen flows directly out to a splendid deck, where you can take in the fresh Vermont air and listen to the flowing brook—which features natural pools large enough for a dip. The main level also offers a large dining room and a cozy sitting room. Energy-efficient mini-splits provide additional heating and cooling for all of Vermont’s picturesque seasons. Upstairs, you’ll find a spacious and charming primary suite. Outside, the property includes a dedicated workshop and an adorable tiny guesthouse, ideal for meditation, relaxation, or hosting occasional visitors. This ultimate Vermont getaway is less than an hour from Bromley, Stratton, and Mount Snow. A truly special place to call home.

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