Windsor Rd, Wellesley Hills, MA Property Records

Norfolk County and Wellesley Town property records for 28 addresses on Windsor Rd, Wellesley Hills, MA · Last verified October 2026

Windsor Rd Highlights

Properties 28
Median Sale Price $2,515,000
Deeds and Mortgages on File 48
Median Price per Sqft $687
Owner Occupied 75%
Median Annual Tax Bill $24,405
Median Year Built 1928
Median Ownership Tenure 10 years

Properties on Windsor Rd

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

8 Windsor Rd

6 bd · 5 ba · 4,921 sqft · built 1920 · 0.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$855,000Mar 1999 $26,4712025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

11 Windsor Rd

4 bd · 2.5 ba · 2,119 sqft · built 1911 · 0.219 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,225,000Aug 2008 $15,2352025 Amount on Record Jun 1999 2 Owners on Record AssessorUpdated Jul 2026

14 Windsor Rd

6 bd · 3.5 ba · 3,787 sqft · built 1916 · 0.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,800,000Jul 2006 $22,0302025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

15 Windsor Rd

5 bd · 4.5 ba · 3,506 sqft · built 1913 · 0.465 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,175,000Jun 1999 $23,3052025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

20 Windsor Rd

6 bd · 5 ba · 5,393 sqft · built 1935 · 0.344 acres

Last Sale Tax Bill Prior Sale Owner Records
$710,000Nov 1995 $26,2652025 —May 1995 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

21 Windsor Rd

5 bd · 4 ba · 4,098 sqft · built 1913 · 0.544 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,335,000Nov 2023 $24,4052025 Amount on Record Jun 2019 2 Owners on Record Assessor + 5 DocumentsUpdated Jul 2026

24 Windsor Rd

5 bd · 4 ba · 3,741 sqft · built 1915 · 0.382 acres

Last Sale Tax Bill Prior Sale Owner Records
$20,0772025 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

27 Windsor Rd

6 bd · 3 ba · 2,891 sqft · built 1916 · 0.781 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,180,000Dec 2012 $22,7292025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

28 Windsor Rd

5 bd · 6.5 ba · 5,287 sqft · built 1916 · 0.695 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,850,000Dec 2016 $39,4442025 Amount on Record Aug 2005 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

33 Windsor Rd

5 bd · 4.5 ba · 4,601 sqft · built 1928 · 1.76 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,180,000Sep 1993 $38,6732025 Amount on Record Feb 1991 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

38 Windsor Rd

5 bd · 7 ba · 5,497 sqft · built 2019 · 0.619 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,211,250Nov 2020 $53,0042025 Amount on Record Jan 2019 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

39 Windsor Rd

5 bd · 7 ba · 6,541 sqft · built 2004 · 0.546 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,625,000Jul 2012 $31,8782025 Amount on Record Jul 2004 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

45 Windsor Rd

4 bd · 3 ba · 2,815 sqft · built 1927 · 0.78 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,412,500Oct 2025 $23,9732025 Owner on Record Assessor + 2 DocumentsUpdated Jul 2026

46 Windsor Rd

5 bd · 4 ba · 3,451 sqft · built 1929 · 0.433 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,687,500Sep 2020 $28,7742025 Amount on Record Aug 1992 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

49 Windsor Rd

3 bd · 4 ba · 3,541 sqft · built 1936 · 0.837 acres

Last Sale Tax Bill Prior Sale Owner Records
$695,000Aug 1993 $26,0392025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

50 Windsor Rd

5 bd · 4 ba · 3,540 sqft · built 1939 · 0.376 acres

Last Sale Tax Bill Prior Sale Owner Records
$585,000Dec 1992 $21,0642025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

53 Windsor Rd

3 bd · 4.5 ba · 3,272 sqft · built 1926 · 0.543 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,900,000Jul 2025 $26,0352026 Amount on Record Apr 2021 2 Owners on Record Owner Occupied Assessor + 6 DocumentsUpdated Oct 2026

56 Windsor Rd

6 bd · 7 ba · 6,581 sqft · built 2008 · 0.525 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,930,000Jul 2016 $38,8892025 Amount on Record Jun 2008 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

57 Windsor Rd

5 bd · 5.5 ba · 4,381 sqft · built 1929 · 0.297 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,515,000Jan 2022 $27,0012026 Amount on Record Jan 2010 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

59 Windsor Rd

3 bd · 2.5 ba · 1,824 sqft · built 1929 · 0.275 acres

Last Sale Tax Bill Prior Sale Owner Records
$680,000Dec 1999 $14,4542025 Amount on Record Sep 1994 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

59R Windsor Rd

0.354 acres

Last Sale Tax Bill Prior Sale Owner Records
Owner on Record AssessorUpdated Apr 2026

60 Windsor Rd

5 bd · 7 ba · 5,158 sqft · built 2023 · 0.476 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,000,000Nov 2024 $53,3222025 Amount on Record Aug 2022 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

61 Windsor Rd

4 bd · 5.5 ba · 3,132 sqft · built 1930 · 0.293 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,925,000Aug 2017 $23,3052025 Amount on Record Oct 2003 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

62 Windsor Rd

6 bd · 3.5 ba · 3,733 sqft · built 1929 · 0.344 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,850,000Aug 2017 $24,1272025 Amount on Record Jun 2009 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

65 Windsor Rd

3 bd · 2.5 ba · 2,062 sqft · built 1914 · 0.45 acres

Last Sale Tax Bill Prior Sale Owner Records
$16,4382025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

66 Windsor Rd

5 bd · 6 ba · 5,004 sqft · built 1924 · 0.569 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,050,000Jul 2022 $31,4982025 Amount on Record Aug 2021 Owner on Record Assessor + 7 DocumentsUpdated Jul 2026

70 Windsor Rd

0.267 acres

Last Sale Tax Bill Prior Sale Owner Records
$900,000Jun 2025 $5962025 Amount on Record Jan 1999 2 Owners on Record Assessor + 1 DocumentUpdated Apr 2026

72 Windsor Rd

3 bd · 2.5 ba · 2,618 sqft · built 1928 · 0.436 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,800,000Jun 2025 $21,8142025 2 Owners on Record Assessor + 1 DocumentUpdated Jul 2026

Property Records in Nearby Streets