Hillwinds Rd, Brattleboro, VT Property Records

Brattleboro Town and Whitingham Town property records for 26 addresses on Hillwinds Rd, Brattleboro, VT · Last verified August 2026

Hillwinds Rd Highlights

Properties 26
Median Sale Price $476,000
Deeds and Mortgages on File 20
Median Price per Sqft $244
Owner Occupied 100%
Median Annual Tax Bill $6,021
Median Year Built 1975
Median Ownership Tenure 10 years

Properties on Hillwinds Rd

Owner names and prior sale amounts shown locked below are available instantly with a free trial.

78 Hillwinds Rd

4 bd · 2 ba · 2,646 sqft · 5.9 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$17,500Jan 1999 $6,7112025 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

122 Hillwinds Rd

3 bd · 1.5 ba · 1,330 sqft · 1.95 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$250,000Jul 2005 $5,3442025 Amount on Record Jun 1993 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

143 Hillwinds Rd

5 bd · 3.5 ba · 2,520 sqft · 1.18 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$615,000Jul 2026 $6,6762025 Amount on Record Oct 2023 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

161 Hillwinds Rd

4 bd · 4.5 ba · 2,504 sqft · 1.08 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$330,500Dec 2016 $6,6862025 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

177 Hillwinds Rd

4 bd · 2.5 ba · 2,493 sqft · 1.36 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$357,500Nov 2016 $6,7702025 —Nov 2016 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

187 Hillwinds Rd

3 bd · 3.5 ba · 2,372 sqft · 1.3 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$476,000Nov 2025 $6,1832025 Amount on Record Apr 2007 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

203 Hillwinds Rd

3 bd · 2 ba · 1,404 sqft · 1.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$370,000Nov 2022 $4,3242025 Amount on Record Jul 2016 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

219 Hillwinds Rd

4 bd · 2.5 ba · 2,400 sqft · 2.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$180,000Aug 1993 $5,5372025 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

244 Hillwinds Rd

4 bd · 1.5 ba · 1,440 sqft · 1.63 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$21,000May 2001 $3,7842025 Amount on Record Apr 2000 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

250 Hillwinds Rd

2 bd · 2 ba · 817 sqft · 14.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,1662025 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

265 Hillwinds Rd

3 bd · 2 ba · 800 sqft · 1.5 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$192,500Jul 2012 $3,5242025 —Jul 2012 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

288 Hillwinds Rd

3 bd · 2.5 ba · 2,652 sqft · 1.16 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$370,000Aug 2014 $6,0212025 Amount on Record May 2011 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

297 Hillwinds Rd

3 bd · 2 ba · 1,408 sqft · 1.76 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$279,900Dec 2005 $5,2462025 Amount on Record May 1995 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

306 Hillwinds Rd

4 bd · 3.5 ba · 2,590 sqft · 1.33 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$230,000Oct 1997 $7,8242025 Amount on Record Aug 1991 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

321 Hillwinds Rd

4 bd · 2.5 ba · 2,464 sqft · 2.5 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$6,7002025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

335 Hillwinds Rd

4 bd · 3.5 ba · 2,544 sqft · 1.58 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$466,000Mar 2024 $7,5692025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

336 Hillwinds Rd

4 bd · 3 ba · 2,529 sqft · 1.18 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$705,000Apr 2024 $7,7992025 Amount on Record May 2019 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

345 Hillwinds Rd

3 bd · 2 ba · 2,650 sqft · 1.4 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$155,000Aug 1994 $10,6522024 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

348 Hillwinds Rd

2 bd · 2 ba · 1,138 sqft · 1.1 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$56,652Apr 2025 $4,5232025 —Sep 2018 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

357 Hillwinds Rd

1 bd · 2 ba · 1,380 sqft · 1.5 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Dec 2018 $4,8262025 Amount on Record Nov 2015 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

373 Hillwinds Rd

3 bd · 3 ba · 1,292 sqft · 1.03 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$5,1342025 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

388 Hillwinds Rd

4 bd · 2.5 ba · 2,673 sqft · 1.5 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$350,000Jun 2013 $7,2042025 Amount on Record Nov 2005 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

395 Hillwinds Rd

4 bd · 2 ba · 2,226 sqft · 1.25 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$668,000Aug 2025 $5,8982025 Amount on Record Apr 2022 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

409 Hillwinds Rd

3 bd · 1.5 ba · 1,638 sqft · 0.51 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$294,000Jun 2021 $4,3982025 Amount on Record Jul 2000 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

410 Hillwinds Rd

5 bd · 2 ba · 3,158 sqft · 1.4 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$450,000Jul 2019 $7,5992025 Amount on Record Aug 1993 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

414 Hillwinds Rd

3 bd · 2 ba · 1,504 sqft · 1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$295,000Dec 2005 $4,3542025 Amount on Record Nov 2000 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

Wildfire Risk on Hillwinds Rd

Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020

Wildfire RiskLow
this street's cells rank above 20% of the US · above 52% of Vermont
Wildfire LikelihoodAbout 1 in 10,000 per year
ExposureDirect
4 of 6 cells directly exposed · 6 adjoin burnable vegetation

Property Records in Nearby Streets