Dennett Rd, Winchester, MA Property Records

Middlesex County and Winchester Town property records for 11 addresses on Dennett Rd, Winchester, MA · Last verified August 2026

Dennett Rd Highlights

Properties 11
Median Sale Price $951,000
Deeds and Mortgages on File 20
Median Price per Sqft $446
Owner Occupied 100%
Median Annual Tax Bill $172
Median Year Built 1964
Median Ownership Tenure 15 years

Properties on Dennett Rd

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

3 Dennett Rd

4 bd · 2.5 ba · 2,128 sqft · 0.391 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$951,000May 2018 $16,8712025 2 Names on Record Owner Occupied Assessor + 8 DocumentsUpdated Apr 2026

5 Dennett Rd

4 bd · 4.5 ba · 3,555 sqft · 0.265 acres

Last Sale Tax Bill Prior Sale Owner Records
$950,000Jul 2014 $1702025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

6 Dennett Rd

3 bd · 2.5 ba · 2,643 sqft · 0.344 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$470,000Apr 1999 $1642025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

7 Dennett Rd

4 bd · 3.5 ba · 3,282 sqft · 0.346 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,499,000Apr 2019 $21,3322025 Amount on Record Jan 2009 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

10 Dennett Rd

4 bd · 3.5 ba · 2,485 sqft · 0.346 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,150,000Dec 2020 $1652025 Amount on Record Sep 1988 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

14 Dennett Rd

3 bd · 2.5 ba · 2,485 sqft · 0.344 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$690,925May 2010 $1572025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

17 Dennett Rd

3 bd · 2.5 ba · 2,010 sqft · 0.351 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,500,000Oct 2025 $15,9652025 Amount on Record Jan 2018 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

19 Dennett Rd

4 bd · 3 ba · 2,706 sqft · 0.362 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$722,000Feb 2009 $1722025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

20 Dennett Rd

4 bd · 2.5 ba · 3,442 sqft · 0.351 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$425,000Dec 1986 $1722025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

21 Dennett Rd

3 bd · 3.5 ba · 4,980 sqft · 0.364 acres

Last Sale Tax Bill Prior Sale Owner Records
$775,000Mar 2003 $1862025 Amount on Record Aug 1999 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

23 Dennett Rd

4 bd · 2.5 ba · 2,397 sqft · 0.346 acres

Last Sale Tax Bill Prior Sale Owner Records
$715,000Jun 2011 $1672025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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