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Brookside Ave, Winchester, MA Property Records

Middlesex County and Winchester Town property records for 34 addresses on Brookside Ave, Winchester, MA · Last verified August 2026

Brookside Ave Highlights

Properties 34
Median Sale Price $995,000
Deeds and Mortgages on File 46
Median Price per Sqft $451
Owner Occupied 94%
Median Annual Tax Bill $121
Median Year Built 1940
Median Ownership Tenure 11 years

Properties on Brookside Ave

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

3 Brookside Ave

4 bd · 2.5 ba · 2,269 sqft · 0.151 acres

Last Sale Tax Bill Prior Sale Owner Records
$750,000Aug 2018 $1282025 Amount on Record Aug 2010 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

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6 Brookside Ave

3 bd · 2.5 ba · 2,585 sqft

Last Sale Tax Bill Prior Sale Owner Records
$995,000Jun 2020 $1212025 Amount on Record Mar 2017 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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8 Brookside Ave

3 bd · 2.5 ba · 2,574 sqft

Last Sale Tax Bill Prior Sale Owner Records
$1202025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

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8 Brookside Ave, #8

Last Sale Tax Bill Prior Sale Owner Records
$895,000Mar 2017 2 Names on Record AssessorUpdated Jun 2023

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9 Brookside Ave

4 bd · 1.5 ba · 2,747 sqft · 0.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$13,2492025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

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14 Brookside Ave

4 bd · 3.5 ba · 2,592 sqft · 0.2 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,250,000Aug 2019 $1702025 Amount on Record Dec 2014 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

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15 Brookside Ave

2 bd · 2 ba · 2,104 sqft · 0.177 acres

Last Sale Tax Bill Prior Sale Owner Records
$780,000Dec 2013 $1392025 Amount on Record May 2002 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

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18 Brookside Ave

3 bd · 1.5 ba · 1,547 sqft · 0.088 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,207,500Jul 2025 $11,8412025 Amount on Record May 2022 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

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19 Brookside Ave

3 bd · 2.5 ba · 2,013 sqft · 0.305 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$650,000Jan 2009 $922025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

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20 Brookside Ave

4 bd · 2.5 ba · 2,775 sqft · 0.148 acres

Last Sale Tax Bill Prior Sale Owner Records
$832,500Jun 2013 $1642025 Amount on Record Sep 2012 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

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21 Brookside Ave

3 bd · 1.5 ba · 1,550 sqft

Last Sale Tax Bill Prior Sale Owner Records
$580,000Sep 2014 $832025 —May 2007 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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24 Brookside Ave

3 bd · 2.5 ba · 2,309 sqft · 0.127 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,211,000Nov 2022 $1382025 Amount on Record Mar 2019 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Apr 2026

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25 Brookside Ave

4 bd · 2 ba · 1,344 sqft · 0.149 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$325,000Sep 2014 $1062025 Amount on Record Aug 2007 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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28 Brookside Ave

3 bd · 2 ba · 1,714 sqft · 0.22 acres

Last Sale Tax Bill Prior Sale Owner Records
$900,000Sep 2022 $1152025 Amount on Record Mar 1964 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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29 Brookside Ave

3 bd · 2.5 ba · 2,573 sqft · 0.146 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$667,000Jun 2008 $1232025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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31 Brookside Ave

3 bd · 2.5 ba · 2,573 sqft · Garage

Last Sale Tax Bill Prior Sale Owner Records
$645,000May 2003 $1232025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

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37 Brookside Ave

5 bd · 3.5 ba · 2,219 sqft · Garage

Last Sale Tax Bill Prior Sale Owner Records
$652,000May 2009 $1202025 Amount on Record Apr 2004 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

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38 Brookside Ave

3 bd · 1.5 ba · 2,135 sqft · 0.246 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1452025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

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39 Brookside Ave

5 bd · 3.5 ba · 2,219 sqft · 0.539 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$949,000Dec 2019 $1202025 Amount on Record Jul 2016 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

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42 Brookside Ave

3 bd · 2.5 ba · 1,753 sqft · 0.197 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Sep 2015 $1272025 Amount on Record Sep 1999 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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43 Brookside Ave

4 bd · 2.5 ba · 2,930 sqft · 0.248 acres

Last Sale Tax Bill Prior Sale Owner Records
$610,000May 2010 $1282025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

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44 Brookside Ave

0.242 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,700,000Jun 2022 $1972025 Amount on Record Dec 1995 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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49 Brookside Ave

3 bd · 1.5 ba · 2,331 sqft · 0.096 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$67,500Jul 1979 $10,5982025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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52 Brookside Ave

3 bd · 2.5 ba · 1,403 sqft · 0.234 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1192025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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53 Brookside Ave

4 bd · 2.5 ba · 2,106 sqft · 0.387 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$475,000Nov 2008 $822025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

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55 Brookside Ave

3 bd · 1 ba · 1,120 sqft · 0.149 acres

Last Sale Tax Bill Prior Sale Owner Records
—Oct 2004 $692025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

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61 Brookside Ave

3 bd · 1 ba · 1,274 sqft · 0.239 acres

Last Sale Tax Bill Prior Sale Owner Records
—Nov 2016 $7,8842025 Amount on Record Jun 1988 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

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65 Brookside Ave

3 bd · 1.5 ba · 1,527 sqft · 0.156 acres

Last Sale Tax Bill Prior Sale Owner Records
$690,000Aug 2020 $872025 Amount on Record Nov 2013 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

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66 Brookside Ave

2 bd · 1.5 ba · 1,109 sqft · 0.119 acres

Last Sale Tax Bill Prior Sale Owner Records
$982025 2 Names on Record Assessor + 2 DocumentsUpdated Apr 2026

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71 Brookside Ave

4 bd · 2.5 ba · 1,944 sqft · 0.156 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$260,150Jun 1991 $952025 Amount on Record May 1987 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

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75 Brookside Ave

3 bd · 1.5 ba · 1,482 sqft · 0.149 acres

Last Sale Tax Bill Prior Sale Owner Records
$692025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

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77 Brookside Ave

4 bd · 2.5 ba · 1,740 sqft · 0.149 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$750,000Jan 2018 $10,5992025 Amount on Record May 2006 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

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81 Brookside Ave, #83

3 bd · 2 ba · 2,258 sqft · 0.115 acres

Last Sale Tax Bill Prior Sale Owner Records
$772025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

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85 Brookside Ave

5 bd · 2.5 ba · 1,931 sqft · 0.168 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$718,000Dec 2019 $942025 Amount on Record Jan 2008 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Apr 2026

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