Overlook Dr, Holliston, MA Property Records

Middlesex County and Holliston Town property records for 15 addresses on Overlook Dr, Holliston, MA · Last verified October 2026

Overlook Dr Highlights

Properties 15
Median Sale Price $585,000
Deeds and Mortgages on File 24
Median Price per Sqft $197
Owner Occupied 93%
Median Annual Tax Bill $11,773
Median Year Built 1985
Median Ownership Tenure 14 years

Properties on Overlook Dr

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

27 Overlook Dr

4 bd · 2.5 ba · 2,550 sqft · built 1985 · 1.1 acres

Last Sale Tax Bill Prior Sale Owner Records
—Apr 2014 $11,9182025 Amount on Record Sep 1992 Owner on Record Owner Occupied AssessorUpdated Sep 2026

37 Overlook Dr

3 bd · 2.5 ba · 2,419 sqft · built 1983 · 1.06 acres

Last Sale Tax Bill Prior Sale Owner Records
$587,000Dec 2015 $12,1872025 Amount on Record Aug 2007 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2026

47 Overlook Dr

4 bd · 2.5 ba · 4,770 sqft · built 1985 · 2.43 acres

Last Sale Tax Bill Prior Sale Owner Records
$45,000May 1984 $16,7382025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

57 Overlook Dr

4 bd · 2.5 ba · 2,662 sqft · built 1985 · 1.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$525,000Jun 2010 $11,5192025 Amount on Record Jul 1992 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

67 Overlook Dr

4 bd · 2.5 ba · 2,464 sqft · built 1986 · 1.6 acres

Last Sale Tax Bill Prior Sale Owner Records
$480,000Aug 2011 $11,5902025 Amount on Record Mar 2011 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

75 Overlook Dr

4 bd · 2.5 ba · 2,872 sqft · built 1985 · 1.63 acres

Last Sale Tax Bill Prior Sale Owner Records
$295,000Oct 1994 $11,7732025 Amount on Record Oct 1990 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

85 Overlook Dr

4 bd · 2.5 ba · 2,510 sqft · built 1985 · 1.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$442,001Oct 2012 $10,8912025 Amount on Record — 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

95 Overlook Dr

4 bd · 3.5 ba · 2,934 sqft · built 1986 · 1.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$599,000Jun 2016 $14,5172025 Amount on Record May 1997 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Sep 2026

105 Overlook Dr

4 bd · 3 ba · 3,000 sqft · built 1986 · 1.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$585,000Dec 2017 $12,7432025 —Mar 2012 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Sep 2026

115 Overlook Dr

4 bd · 2.5 ba · 2,964 sqft · built 1986 · 1.33 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jan 2015 $12,4132025 Amount on Record Jun 2000 Owner on Record Owner Occupied AssessorUpdated Jul 2026

125 Overlook Dr

4 bd · 2.5 ba · 2,292 sqft · built 1985 · 1.38 acres

Last Sale Tax Bill Prior Sale Owner Records
$659,125May 2021 $10,5552025 Amount on Record May 2013 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

135 Overlook Dr

3 bd · 2.5 ba · 2,674 sqft · built 1993 · 1.35 acres

Last Sale Tax Bill Prior Sale Owner Records
$387,500Nov 2000 $11,6392025 2 Owners on Record AssessorUpdated Jul 2026

143 Overlook Dr

3 bd · 2.5 ba · 2,541 sqft · built 1984 · 1.51 acres

Last Sale Tax Bill Prior Sale Owner Records
$272,500Aug 1998 $9,8302025 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

153 Overlook Dr

4 bd · 2.5 ba · 2,133 sqft · built 1984 · 1.33 acres

Last Sale Tax Bill Prior Sale Owner Records
$225,000May 1985 $10,7022025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

163 Overlook Dr

4 bd · 2.5 ba · 3,170 sqft · built 1985 · 1.38 acres

Last Sale Tax Bill Prior Sale Owner Records
$515,000Jul 2013 $13,4822025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

Property Records in Nearby Streets