
Land with Home for Sale in Brookline, Vermont
1382 Grassy Brook Rd, Brookline, VT 05345
Beautiful Brookline! Lovingly developed by the current owners over the past 40 years, this remarkable property offers a rare opportunity--ideal for a builder, contractor, skier, snowmobiler, or anyone seeking space for equipment storage. Arrive by crossing a charming stream and following a gentle rise to the main home, which includes a one-car attached garage in the basement. Inside, the finished lower level features a comfortable sitting/TV room, laundry area, large storage closet, and utility room. Upstairs, the first floor opens into a warm, open-concept kitchen, dining, and living space centered around a striking wood-burning fireplace with a glass door enclosure. To the south, a spacious three-season sunroom invites relaxation in every season. The primary bedroom, with an en-suite bath, is conveniently located on this level. A great office space is here, too. The upper floor features two spacious bedrooms, each equipped with ample storage space. Outdoors, the property shines: a large trout pond graces the north side of the home, while the land abuts the Windmill Hill Pinnacle Association, offering direct access to miles of scenic hiking trails. Snowmobile enthusiasts will also appreciate nearby trail access. A separate three-car garage expands the possibilities--imagine a future guest house, in-law suite, or artist studio! This unique Brookline property must be experienced in person to be fully appreciated.
Location
- Street address
- 1382 Grassy Brook Rd
- County
- Windham County
- School district
- Windham Southeast
- Elevation
- 794 feet
Directions
FROM BRATTLEBORO, follow VT-30 N 11.7 mi Turn right onto Radway Hill Rd 0.4 mi Continue onto Brookline Rd/Grassy Brook Rd 1.0 mi Turn left to stay on Brookline Rd/Grassy Brook Rd 5.9 mi 1382 Grassy Brook Rd. ON RIGHT. SEE SIGN
Property details
- Acreage
- 44.3 acres
- Zoning
- Residential
- MLS #
- NNEREN 5062413
- Posted
Property taxes
- 2025
- $9,499
Resources
Details and features
Listing
- Type
- Residential
- Subtype
- Single Family Residence
Exterior
- Parking Spaces
- 3
- Parking
- Garage
Structure
- Stories
- 1
- Heating
- Forced Air, Oil
- Cooling
- Central Air
- Roof
- Asphalt, Metal, Shingle
Interior
- Room Count
- 6
- Rooms
- Basement, Bathroom x 3, Bedroom x 3, Kitchen, Office
- Flooring
- Carpet, Hardwood, Wood
- Appliances
- Dishwasher, Dryer, Freezer, Gas Range, Microwave, Range, Refrigerator, Washer
Nearby schools
| Name | Level | District | Description |
|---|---|---|---|
| Newbrook Elementary School | Elementary | Windham Southeast | — |
| Leland Gray Union Middle/High | Middle | Windham Southeast | — |
| Leland Gray | High | Windham Southeast | — |
Listing history
| Date | Event | Price | Change | Source |
|---|---|---|---|---|
| Sept 22, 2025 | New listing | $639,000 | — | NNEREN |





































