Windy Hill Rd, Oak Bluffs, MA Property Records

Dukes County and Oak Bluffs Town property records for 16 addresses on Windy Hill Rd, Oak Bluffs, MA · Last verified October 2026

Windy Hill Rd Highlights

Properties 16
Median Sale Price $548,000
Deeds and Mortgages on File 18
Median Price per Sqft $460
Median Annual Tax Bill $4,003
Median Year Built 1973
Median Ownership Tenure 11 years

Properties on Windy Hill Rd

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

7 Windy Hill Rd

built 2013 · 0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$282,000Oct 2018 $2,5292025 Amount on Record Oct 2018 2 Owners on Record AssessorUpdated Oct 2026

10 Windy Hill Rd

3 bd · 2 ba · 1,456 sqft · built 1990 · 0.459 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,4142025 Owner on Record AssessorUpdated Oct 2026

11 Windy Hill Rd

0.48 acres

Last Sale Tax Bill Prior Sale Owner Records
$465,000Dec 2003 $5,8162024 Owner on Record Assessor + 1 DocumentUpdated May 2024

12 Windy Hill Rd

0.275 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,4692025 Owner on Record AssessorUpdated Apr 2026

14 Windy Hill Rd

0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,4392025 Owner on Record AssessorUpdated Aug 2026

15 Windy Hill Rd

3 bd · 2 ba · 1,564 sqft · built 1988 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$45,000Jun 1987 $4,7952025 2 Owners on Record Assessor + 1 DocumentUpdated Oct 2026

16 Windy Hill Rd

3 bd · 2 ba · 1,120 sqft · built 1975 · 0.25 acres

Last Sale Tax Bill Prior Sale Owner Records
—Oct 2018 $4,0032025 2 Owners on Record Assessor + 1 DocumentUpdated Oct 2026

18 Windy Hill Rd

2 bd · 2.5 ba · 1,714 sqft · built 2015 · 0.369 acres

Last Sale Tax Bill Prior Sale Owner Records
$665,000Jan 2017 $5,9622025 Amount on Record Jun 2015 2 Owners on Record Assessor + 3 DocumentsUpdated Oct 2026

19 Windy Hill Rd

3 bd · 2 ba · 1,612 sqft · built 1987 · 0.855 acres

Last Sale Tax Bill Prior Sale Owner Records
—Feb 2015 $4,9062025 Amount on Record Mar 1983 2 Owners on Record Assessor + 1 DocumentUpdated Oct 2026

20 Windy Hill Rd

4 bd · 1.5 ba · 1,189 sqft · built 1970 · 0.401 acres

Last Sale Tax Bill Prior Sale Owner Records
$548,000Feb 2021 $3,0862025 Owner on Record Assessor + 3 DocumentsUpdated Oct 2026

21 Windy Hill Rd

3 bd · 1.5 ba · 888 sqft · built 1970 · 0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jun 2010 $3,8702025 Owner on Record AssessorUpdated Oct 2026

22 Windy Hill Rd

3 bd · 1 ba · 1,014 sqft · built 1973 · 0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$590,000Dec 2019 $3,8352025 Amount on Record Dec 2004 2 Owners on Record Assessor + 2 DocumentsUpdated Oct 2026

25 Windy Hill Rd

3 bd · 1 ba · 960 sqft · built 1971 · 0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$982,000Dec 2025 $3,9282025 2 Owners on Record Assessor + 2 DocumentsUpdated Oct 2026

28 Windy Hill Rd

3 bd · 1 ba · 960 sqft · built 1973 · 0.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$389,000Aug 2015 $3,8762025 Amount on Record Sep 2002 Owner on Record Assessor + 4 DocumentsUpdated Oct 2026

29 Windy Hill Rd

3 bd · 1 ba · 1,008 sqft · built 1972 · 0.25 acres

Last Sale Tax Bill Prior Sale Owner Records
$34,000Mar 1979 $4,1402025 2 Owners on Record AssessorUpdated Oct 2026

32 Windy Hill Rd

4 bd · 2 ba · 1,687 sqft · built 1968 · 0.495 acres

Last Sale Tax Bill Prior Sale Owner Records
$375,000Feb 2004 $4,5722025 Owner on Record AssessorUpdated Oct 2026

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