Chestnut St, Weston, MA Property Records

Middlesex County and Weston Town property records for 32 addresses on Chestnut St, Weston, MA · Last verified August 2026

Chestnut St Highlights

Properties 32
Median Sale Price $1,828,000
Deeds and Mortgages on File 38
Median Price per Sqft $587
Owner Occupied 75%
Median Annual Tax Bill $52,834
Median Year Built 1992
Median Ownership Tenure 10 years

Properties on Chestnut St

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

1 Chestnut St

4 bd · 5.5 ba · 5,375 sqft · 2.98 acres

Last Sale Tax Bill Prior Sale Owner Records
$59,7022025 Owner on Record Owner Occupied AssessorUpdated Apr 2026

7 Chestnut St

5 bd · 5 ba · 4,773 sqft · built 1978 · 1.97 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,350,000Jul 2000 $52,8342025 Owner on Record Owner Occupied AssessorUpdated Apr 2026

21 Chestnut St

6 bd · 8 ba · 9,310 sqft · built 2023 · 2.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$11,000,000Dec 2025 $120,8072026 Amount on Record Dec 2020 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

27 Chestnut St

8 bd · 6 ba · 5,426 sqft · built 1934 · 3.06 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,950,000Apr 2018 $38,6422025 —Dec 2012 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

34 Chestnut St

5 bd · 3 ba · 2,304 sqft · built 1931 · 2.25 acres

Last Sale Tax Bill Prior Sale Owner Records
$535,000Oct 2020 $12,1532025 2 Owners on Record Assessor + 1 DocumentUpdated Apr 2026

36 Chestnut St

3 bd · 2 ba · 1,620 sqft · built 1939 · 0.345 acres

Last Sale Tax Bill Prior Sale Owner Records
$680,000Sep 2020 $8,6192025 2 Owners on Record Assessor + 2 DocumentsUpdated Jul 2026

38 Chestnut St

4 bd · 2 ba · 2,270 sqft · built 1930 · 0.395 acres

Last Sale Tax Bill Prior Sale Owner Records
$700,000Jun 2022 $9,6282025 2 Owners on Record Assessor + 2 DocumentsUpdated Jul 2026

40 Chestnut St

3 bd · 2.5 ba · 3,320 sqft · built 1920 · 0.389 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,300,000Jul 2020 $14,9892025 Amount on Record Dec 1999 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

44 Chestnut St

4 bd · 4.5 ba · 5,018 sqft · built 1895 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,490,000Jun 2015 $22,5332025 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

52 Chestnut St

6 bd · 5 ba · 7,827 sqft · built 1998 · 0.438 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,075,000Jun 2014 $68,2952025 Amount on Record Jul 1999 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

55 Chestnut St

6 bd · 8 ba · 7,948 sqft · built 1964 · 1.42 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,100,000Jun 2021 $60,5752025 Amount on Record Apr 2004 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

56 Chestnut St

4 bd · 6 ba · 4,823 sqft · built 2006 · 2.19 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,600,000Dec 2015 $35,1272025 Amount on Record Jun 2008 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

70 Chestnut St

3 bd · 2.5 ba · 3,757 sqft · built 1920 · 1.33 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,550,000Aug 2025 $15,2082025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

72 Chestnut St

3 bd · 2.5 ba · 2,228 sqft · built 1928 · 1.68 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,285,000Aug 2017 $15,0722025 Amount on Record Oct 2000 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

73 Chestnut St

7 bd · 10 ba · 8,753 sqft · built 1952 · 2.77 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,200,000Dec 2017 $66,2962025 Amount on Record Oct 1993 Owner on Record Assessor + 2 DocumentsUpdated Jul 2026

74 Chestnut St

5 bd · 3.5 ba · 3,112 sqft · built 1881 · 2.34 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,828,000Apr 2025 $17,2652025 Amount on Record Aug 1997 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

77 Chestnut St

6 bd · 8.5 ba · 7,739 sqft · built 2012 · 2.99 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,534,500Oct 2011 $73,5522025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

78 Chestnut St

5 bd · 7 ba · 6,273 sqft · built 2015 · 2.62 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,960,000Aug 2016 $64,0102025 Amount on Record Mar 2016 Owner on Record Owner Occupied AssessorUpdated Jul 2026

81 Chestnut St

5 bd · 7 ba · 8,438 sqft · built 2002 · 2.02 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,400,000Jul 2001 $66,9242025 Amount on Record Aug 1990 Owner on Record Owner Occupied AssessorUpdated Jul 2026

84 Chestnut St

5 bd · 6 ba · 5,644 sqft · built 1993 · 1.96 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,717,500Jul 2021 $55,4832025 Amount on Record Jun 2012 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

85 Chestnut St

6 bd · 9.5 ba · 7,794 sqft · built 2001 · 3.39 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,600,000May 2014 $60,9282025 Amount on Record Mar 1998 Owner on Record Owner Occupied AssessorUpdated Jul 2026

88 Chestnut St

3 bd · 3.5 ba · 3,990 sqft · built 1913 · 8.41 acres

Last Sale Tax Bill Prior Sale Owner Records
$600,000Jun 1992 $51,9192025 Owner on Record Assessor + 1 DocumentUpdated Apr 2026

99 Chestnut St

4 bd · 4 ba · 1,763 sqft · built 1959 · 1.44 acres

Last Sale Tax Bill Prior Sale Owner Records
$20,0502025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

100 Chestnut St

5 bd · 6.5 ba · 7,064 sqft · built 1992 · 3.38 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,255,000Oct 2025 $64,8262025 Amount on Record Feb 2015 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

109 Chestnut St

7 bd · 8 ba · 7,895 sqft · built 2008 · 1.72 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,500,000Jun 2024 $92,7632025 Amount on Record Feb 2010 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

115 Chestnut St

5 bd · 8 ba · 7,579 sqft · built 2009 · 3.44 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,300,000Jul 2016 $98,1452025 Amount on Record Jul 2008 Owner on Record AssessorUpdated Apr 2026

118 Chestnut St

6 bd · 9 ba · 11,406 sqft · built 2004 · 6.85 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,800,000Jun 2004 $149,2782025 Owner on Record Owner Occupied AssessorUpdated Apr 2026

121 Chestnut St

4 bd · 5.5 ba · 6,981 sqft · built 1992 · 1.67 acres

Last Sale Tax Bill Prior Sale Owner Records
—Dec 2012 $47,7062025 Amount on Record Aug 2000 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

140 Chestnut St

1.51 acres

Last Sale Tax Bill Prior Sale Owner Records
—Sep 2004 $14,1742025 Owner on Record AssessorUpdated Apr 2026

150 Chestnut St

4 bd · 5 ba · 4,653 sqft · built 1967 · 6.55 acres

Last Sale Tax Bill Prior Sale Owner Records
$30,000Sep 2004 $48,1142025 Amount on Record Apr 1994 Owner on Record Owner Occupied AssessorUpdated Apr 2026

155 Chestnut St

7 bd · 8 ba · 7,533 sqft · built 1995 · 3.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,950,000May 2015 $58,4712025 Amount on Record Aug 2004 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

157 Chestnut St

4 bd · 4 ba · 5,017 sqft · built 1994 · 1.61 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,725,000Sep 1996 $37,9792025 Amount on Record Jul 1995 Owner on Record AssessorUpdated Jul 2026

Property Records in Nearby Streets