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Jefferson Rd, Winchester, MA Property Records

Middlesex County and Winchester Town property records for 30 addresses on Jefferson Rd, Winchester, MA · Last verified August 2026

Jefferson Rd Highlights

Properties 30
Median Sale Price $1,850,000
Deeds and Mortgages on File 58
Median Price per Sqft $585
Owner Occupied 93%
Median Annual Tax Bill $199
Median Year Built 1948
Median Ownership Tenure 11 years

Properties on Jefferson Rd

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

3 Jefferson Rd

4 bd · 2 ba · 3,301 sqft · built 1948 · 0.359 acres

Last Sale Tax Bill Prior Sale Owner Records
$930,000Jun 2015 $1842025 —Sep 2007 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

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6 Jefferson Rd

4 bd · 2.5 ba · 3,201 sqft · built 1930 · 0.252 acres

Last Sale Tax Bill Prior Sale Owner Records
—Sep 2018 $1772025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

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7 Jefferson Rd

4 bd · 3.5 ba · 2,704 sqft · built 1955 · 0.342 acres

Last Sale Tax Bill Prior Sale Owner Records
$882,750Aug 2004 $1962025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

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10 Jefferson Rd

3 bd · 2.5 ba · 3,248 sqft · built 1936 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,245,000Jul 2014 $1732025 Amount on Record Aug 1991 1 Name on Record Owner Occupied Assessor + 5 DocumentsUpdated Apr 2026

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11 Jefferson Rd

6 bd · 2.5 ba · 5,052 sqft · built 2005 · 0.33 acres

Last Sale Tax Bill Prior Sale Owner Records
$3222025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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14 Jefferson Rd

3 bd · 3.5 ba · 3,190 sqft · built 1941 · 0.385 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,250,000May 2015 $1992025 —May 2014 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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15 Jefferson Rd

4 bd · 3.5 ba · 2,975 sqft · built 1936 · 0.307 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,300,000Apr 2008 $1952025 —Nov 2003 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

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17 Jefferson Rd

3 bd · 2.5 ba · 2,486 sqft · built 1939 · 0.26 acres

Last Sale Tax Bill Prior Sale Owner Records
$685,000May 2004 $1842025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

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19 Jefferson Rd

5 bd · 3.5 ba · 4,594 sqft · built 1929 · 0.262 acres

Last Sale Tax Bill Prior Sale Owner Records
$925,000Jul 2013 $2082025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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20 Jefferson Rd

4 bd · 2.5 ba · 3,574 sqft · built 1927 · 0.326 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,035,000Nov 2015 $1972025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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21 Jefferson Rd

3 bd · 2.5 ba · 2,827 sqft · built 1945 · 0.245 acres

Last Sale Tax Bill Prior Sale Owner Records
$905,000Feb 2008 $1832025 Amount on Record Sep 2002 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

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23 Jefferson Rd

5 bd · 4.5 ba · 3,118 sqft · built 1929 · 0.369 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,345,000Dec 2015 $2152025 Amount on Record Jan 2005 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

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25 Jefferson Rd

3 bd · 4.5 ba · 3,325 sqft · built 1950 · 0.306 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,350,263Sep 2022 $1752025 Amount on Record Jul 2003 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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26 Jefferson Rd

5 bd · 3.5 ba · 4,014 sqft · built 1938 · 0.475 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,300,000Aug 2018 $2222025 —Jan 2012 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Apr 2026

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30 Jefferson Rd

5 bd · 5.5 ba · 4,358 sqft · built 2020 · 0.255 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,550,000Mar 2021 $3032025 Amount on Record Sep 2018 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Jun 2026

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34 Jefferson Rd

4 bd · 2.5 ba · 3,340 sqft · built 1940 · 0.243 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,420,000Nov 2019 $1912025 Amount on Record Jun 1999 2 Names on Record Assessor + 1 DocumentUpdated Apr 2026

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35 Jefferson Rd

7 bd · 6.5 ba · 6,131 sqft · built 2016 · 0.321 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,150,000Apr 2018 $2912025 Amount on Record Mar 2016 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

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38 Jefferson Rd

3 bd · 2.5 ba · 3,485 sqft · built 1943 · 0.261 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,100,000Dec 2017 $1832025 Amount on Record Dec 1985 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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41 Jefferson Rd

4 bd · 3 ba · 3,155 sqft · built 1950 · 0.231 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,650,000Aug 2022 $1862025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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42 Jefferson Rd

4 bd · 3.5 ba · 3,262 sqft · built 1948 · 0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$875,400Jan 2011 $2042025 Amount on Record Dec 1989 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

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43 Jefferson Rd

4 bd · 3 ba · 2,515 sqft · built 1955 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$741,000Jul 2003 $1632025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

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46 Jefferson Rd

4 bd · 2.5 ba · 3,713 sqft · built 1940 · 0.34 acres

Last Sale Tax Bill Prior Sale Owner Records
$980,000Jul 2015 $1982025 —Nov 2009 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

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47 Jefferson Rd

4 bd · 2.5 ba · 2,512 sqft · built 1951 · 0.233 acres

Last Sale Tax Bill Prior Sale Owner Records
$367,000Sep 1992 $17,2372025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

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49 Jefferson Rd

5 bd · 4 ba · 4,175 sqft · built 1951 · 0.246 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,839,000Feb 2018 $2412025 Amount on Record Oct 2016 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

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50 Jefferson Rd

5 bd · 3.5 ba · 3,858 sqft · built 1948 · 0.27 acres

Last Sale Tax Bill Prior Sale Owner Records
$185,000Sep 1984 $2022025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

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52 Jefferson Rd

4 bd · 2.5 ba · 3,217 sqft · built 1948 · 0.318 acres

Last Sale Tax Bill Prior Sale Owner Records
—Mar 2014 $1932025 Amount on Record Feb 1994 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

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56 Jefferson Rd

3 bd · 2.5 ba · 3,252 sqft · built 1984 · 0.392 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,200,000Mar 2025 $22,8942025 Amount on Record Oct 1997 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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57 Jefferson Rd

5 bd · 2.5 ba · 2,779 sqft · built 1985 · 0.35 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,359,000Jun 2025 $20,3732025 Amount on Record Sep 2010 2 Names on Record Assessor + 6 DocumentsUpdated Apr 2026

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58 Jefferson Rd

5 bd · 2.5 ba · 2,910 sqft · built 1984 · 0.438 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,850,000Apr 2026 $20,0502025 Amount on Record Nov 1984 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

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60 Jefferson Rd

3 bd · 2.5 ba · 4,855 sqft · built 1987 · 0.601 acres

Last Sale Tax Bill Prior Sale Owner Records
—Dec 2015 $2172025 —May 2008 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Apr 2026

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Wildfire Risk on Jefferson Rd

Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020

Wildfire RiskLow
this street's cells rank above 24% of the US · above 72% of Massachusetts
Wildfire LikelihoodAbout 1 in 7,143 per year
ExposureDirect
1 of 3 cells directly exposed · 3 adjoin burnable vegetation

Property Records in Nearby Streets