Winding Hill Rd, Brattleboro, VT Property Records

Brattleboro Town property records for 32 addresses on Winding Hill Rd, Brattleboro, VT · Last verified October 2026

Winding Hill Rd Highlights

Properties 32
Median Sale Price $32,500
Deeds and Mortgages on File 12
Median Price per Sqft $35
Owner Occupied 63%
Median Annual Tax Bill $610
Median Year Built 1978
Median Ownership Tenure 9 years

Properties on Winding Hill Rd

Owner names and exact recorded amounts are on file and can be viewed instantly on this page with a free 10-day trial.

1 Winding Hill Rd

2 bd · 1 ba · 967 sqft · built 1980

Last Sale Tax Bill Prior Sale Owner Records
—Jul 2017 $7402025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

2 Winding Hill Rd

3 bd · 1 ba · 804 sqft · built 1969

Last Sale Tax Bill Prior Sale Owner Records
$3562025 Owner on Record Owner Occupied AssessorUpdated Aug 2026

3 Winding Hill Rd

2 bd · 1 ba · 792 sqft · built 1970

Last Sale Tax Bill Prior Sale Owner Records
$17,500Sep 2014 $3762025 Owner on Record Owner Occupied AssessorUpdated Oct 2026

4 Winding Hill Rd

2 bd · 1 ba · 516 sqft · built 1966

Last Sale Tax Bill Prior Sale Owner Records
$10,000Mar 2011 $1822025 Owner on Record AssessorUpdated Aug 2026

5 Winding Hill Rd

2 bd · 1 ba · 1,032 sqft · built 1974

Last Sale Tax Bill Prior Sale Owner Records
$69,900Oct 2015 $1,0152025 Amount on Record Mar 2005 Owner on Record Owner Occupied AssessorUpdated Aug 2026

6 Winding Hill Rd

3 bd · 1 ba · 924 sqft · built 2004

Last Sale Tax Bill Prior Sale Owner Records
$8692025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

7 Winding Hill Rd

3 bd · 2 ba · 1,056 sqft · built 1996

Last Sale Tax Bill Prior Sale Owner Records
$7542025 Owner on Record Owner Occupied AssessorUpdated Oct 2026

8 Winding Hill Rd

2 bd · 1 ba · 744 sqft · built 1972

Last Sale Tax Bill Prior Sale Owner Records
$2982025 Owner on Record AssessorUpdated Oct 2026

9 Winding Hill Rd

3 bd · 1 ba · 924 sqft · built 1976

Last Sale Tax Bill Prior Sale Owner Records
$3232025 Owner on Record Owner Occupied AssessorUpdated Aug 2026

11 Winding Hill Rd

3 bd · 1 ba · 672 sqft · built 1969

Last Sale Tax Bill Prior Sale Owner Records
$20,000Apr 2023 $2022025 Amount on Record Feb 2016 Owner on Record Assessor + 2 DocumentsUpdated Aug 2026

12 Winding Hill Rd

3 bd · 2 ba · 924 sqft · built 1980

Last Sale Tax Bill Prior Sale Owner Records
$9002021 Owner on Record AssessorUpdated Jun 2023

13 Winding Hill Rd

2 bd · 2 ba · 1,120 sqft · built 1988

Last Sale Tax Bill Prior Sale Owner Records
$79,000Dec 2025 $1,1382025 Amount on Record Oct 2019 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
$10,501May 2015 2 Owners on Record Owner Occupied AssessorUpdated Jun 2023
Last Sale Tax Bill Prior Sale Owner Records
$4342025 Owner on Record AssessorUpdated Aug 2026

15 Winding Hill Rd

2 bd · 1.5 ba · 953 sqft · built 1984

Last Sale Tax Bill Prior Sale Owner Records
$65,000Jun 2020 $7692025 Owner on Record Assessor + 1 DocumentUpdated Aug 2026

16 Winding Hill Rd

3 bd · 2 ba · 1,248 sqft · built 2019

Last Sale Tax Bill Prior Sale Owner Records
—Apr 2018 $1,2332025 Amount on Record Dec 2003 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

17 Winding Hill Rd

2 bd · 1 ba · 684 sqft · built 1967

Last Sale Tax Bill Prior Sale Owner Records
$3352025 Owner on Record Owner Occupied AssessorUpdated Aug 2026

18 Winding Hill Rd

2 bd · 1.5 ba · 952 sqft · built 1978

Last Sale Tax Bill Prior Sale Owner Records
$6222025 Owner on Record AssessorUpdated Aug 2026

19 Winding Hill Rd

4 bd · 2 ba · 1,836 sqft · built 2005

Last Sale Tax Bill Prior Sale Owner Records
—Oct 2006 $1,7412025 Amount on Record Sep 2005 Owner on Record AssessorUpdated Oct 2026

20 Winding Hill Rd

2 bd · 2 ba · 1,018 sqft · built 1983

Last Sale Tax Bill Prior Sale Owner Records
—Jun 2017 $5162025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

21 Winding Hill Rd

2 bd · 1 ba · 924 sqft · built 1986

Last Sale Tax Bill Prior Sale Owner Records
$30,000Dec 2022 $6832025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

22 Winding Hill Rd

2 bd · 1 ba · 854 sqft · built 1977

Last Sale Tax Bill Prior Sale Owner Records
$16,500Oct 2013 $4112025 Owner on Record Owner Occupied AssessorUpdated Oct 2026

23 Winding Hill Rd

2 bd · 1 ba · 924 sqft · built 1986

Last Sale Tax Bill Prior Sale Owner Records
$8262025 Owner on Record Owner Occupied AssessorUpdated Aug 2026

24 Winding Hill Rd

3 bd · 2 ba · 1,084 sqft · built 1982

Last Sale Tax Bill Prior Sale Owner Records
$6562025 Owner on Record Owner Occupied AssessorUpdated Aug 2026

25 Winding Hill Rd

2 bd · 1 ba · 924 sqft · built 1985

Last Sale Tax Bill Prior Sale Owner Records
$25,000Jul 2022 $5732025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

26 Winding Hill Rd

2 bd · 1 ba · 1,172 sqft · built 1978

Last Sale Tax Bill Prior Sale Owner Records
$11,000Mar 2025 $6102025 Owner on Record AssessorUpdated Aug 2026

27 Winding Hill Rd

2 bd · 1 ba · 720 sqft · built 1969

Last Sale Tax Bill Prior Sale Owner Records
$2872025 Owner on Record AssessorUpdated Sep 2026

28 Winding Hill Rd

2 bd · 1 ba · 903 sqft · built 1966

Last Sale Tax Bill Prior Sale Owner Records
$32,500Jul 2015 $3432025 Amount on Record Oct 2006 Owner on Record Owner Occupied AssessorUpdated Oct 2026

29 Winding Hill Rd

3 bd · 1.5 ba · 924 sqft · built 2001

Last Sale Tax Bill Prior Sale Owner Records
$40,000Jul 2005 $8362025 —Jun 2005 Owner on Record Owner Occupied AssessorUpdated Aug 2026

30 Winding Hill Rd

2 bd · 2 ba · 1,222 sqft · built 1973

Last Sale Tax Bill Prior Sale Owner Records
$6982025 Owner on Record Assessor + 1 DocumentUpdated Aug 2026

32 Winding Hill Rd

2 bd · 1 ba · 832 sqft · built 1966

Last Sale Tax Bill Prior Sale Owner Records
$3792025 Owner on Record AssessorUpdated Aug 2026

34 Winding Hill Rd

2 bd · 1 ba · 840 sqft · built 1978

Last Sale Tax Bill Prior Sale Owner Records
$11,500Nov 2006 $4312025 Owner on Record Owner Occupied AssessorUpdated Aug 2026

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