Charles Rd, Winchester, MA Property Records

Middlesex County and Winchester Town property records for 45 addresses on Charles Rd, Winchester, MA · Last verified August 2026

Charles Rd Highlights

Properties 45
Median Sale Price $648,000
Deeds and Mortgages on File 60
Median Price per Sqft $528
Owner Occupied 56%
Median Annual Tax Bill $59
Median Year Built 1963
Median Ownership Tenure 11 years

Properties on Charles Rd

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

1 Charles Rd

2 bd · 1 ba · 968 sqft

Last Sale Tax Bill Prior Sale Owner Records
$475,000Aug 2020 $532025 Amount on Record Dec 2006 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

2 Charles Rd

3 bd · 1.5 ba · 968 sqft

Last Sale Tax Bill Prior Sale Owner Records
$277,000Dec 2010 $542025 Amount on Record Nov 2009 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

3 Charles Rd

2 bd · 2 ba · 968 sqft

Last Sale Tax Bill Prior Sale Owner Records
$562025 1 Name on Record Assessor + 4 DocumentsUpdated Apr 2026

4 Charles Rd

3 bd · 1.5 ba · 968 sqft

Last Sale Tax Bill Prior Sale Owner Records
$283,000Sep 2011 $542025 Amount on Record Jul 2007 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

5 Charles Rd

2 bd · 1 ba · 968 sqft · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$670,000Oct 2024 $532025 Amount on Record Jul 2007 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

6 Charles Rd

2 bd · 2 ba · 1,452 sqft

Last Sale Tax Bill Prior Sale Owner Records
$445,000Aug 2016 $672025 Amount on Record Jun 2006 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

7 Charles Rd

2 bd · 2 ba · 1,162 sqft

Last Sale Tax Bill Prior Sale Owner Records
$335,900Oct 2005 $592025 Amount on Record Oct 2001 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

8 Charles Rd

3 bd · 2.5 ba · 2,134 sqft

Last Sale Tax Bill Prior Sale Owner Records
$623,000Jun 2020 $842025 Amount on Record Jun 2005 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

9 Charles Rd

3 bd · 2 ba · 968 sqft

Last Sale Tax Bill Prior Sale Owner Records
$681,888Mar 2026 $562025 Amount on Record May 2007 2 Names on Record Assessor + 1 DocumentUpdated Jul 2026

10 Charles Rd

2 bd · 2 ba · 1,210 sqft

Last Sale Tax Bill Prior Sale Owner Records
$330,000Jun 2010 $592025 Amount on Record Jun 2005 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

11 Charles Rd

2 bd · 2 ba · 968 sqft

Last Sale Tax Bill Prior Sale Owner Records
$325,000Feb 2015 $562025 Amount on Record Mar 2007 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

12 Charles Rd

2 bd · 1.5 ba · 1,002 sqft

Last Sale Tax Bill Prior Sale Owner Records
$349,000Jul 2015 $622025 Amount on Record Jun 2005 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

14 Charles Rd

2 bd · 1.5 ba · 1,008 sqft

Last Sale Tax Bill Prior Sale Owner Records
$305,000Jul 2007 $552025 2 Names on Record AssessorUpdated Apr 2026

15 Charles Rd

2 bd · 2 ba · 968 sqft

Last Sale Tax Bill Prior Sale Owner Records
$680,000May 2025 $5,7352025 Amount on Record Nov 2018 1 Name on Record Assessor + 4 DocumentsUpdated Apr 2026

16 Charles Rd

2 bd · 1 ba · 1,470 sqft

Last Sale Tax Bill Prior Sale Owner Records
$305,000Nov 2009 $612025 Amount on Record May 2008 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

17 Charles Rd

2 bd · 2 ba · 968 sqft

Last Sale Tax Bill Prior Sale Owner Records
$645,000Jun 2026 $582025 Amount on Record Aug 2016 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

18 Charles Rd

2 bd · 2 ba · 968 sqft

Last Sale Tax Bill Prior Sale Owner Records
$300,000Feb 2007 $562025 2 Names on Record AssessorUpdated Apr 2026

20 Charles Rd

3 bd · 2 ba · 1,355 sqft

Last Sale Tax Bill Prior Sale Owner Records
$700,000Apr 2026 $602025 Amount on Record Mar 2018 2 Names on Record Assessor + 1 DocumentUpdated Jul 2026

22 Charles Rd

2 bd · 1 ba · 1,210 sqft

Last Sale Tax Bill Prior Sale Owner Records
$318,900Apr 2014 $572025 Amount on Record Jun 2005 2 Names on Record Assessor + 1 DocumentUpdated Apr 2026

23 Charles Rd

2 bd · 2 ba · 968 sqft

Last Sale Tax Bill Prior Sale Owner Records
$479,000Mar 2020 $552025 Amount on Record May 2014 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

24 Charles Rd

3 bd · 1 ba · 968 sqft

Last Sale Tax Bill Prior Sale Owner Records
$660,000Aug 2025 $5,3522025 Amount on Record Jun 2019 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Jul 2026

25 Charles Rd

3 bd · 1.5 ba · 1,307 sqft

Last Sale Tax Bill Prior Sale Owner Records
$328,900Jul 2005 $612025 2 Names on Record Assessor + 2 DocumentsUpdated Apr 2026

26 Charles Rd

3 bd · 1 ba · 1,002 sqft

Last Sale Tax Bill Prior Sale Owner Records
$525,000Jun 2021 $562025 Amount on Record Jul 2017 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

28 Charles Rd

2 bd · 1 ba · 1,283 sqft

Last Sale Tax Bill Prior Sale Owner Records
$450,000Sep 2018 $572025 Amount on Record Jul 2013 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Apr 2026

30 Charles Rd

3 bd · 1 ba · 968 sqft

Last Sale Tax Bill Prior Sale Owner Records
$317,500Sep 2007 $532025 2 Names on Record AssessorUpdated Apr 2026

32 Charles Rd

2 bd · 1.5 ba · 968 sqft

Last Sale Tax Bill Prior Sale Owner Records
$580,000Jul 2024 $542025 Amount on Record Jun 2005 2 Names on Record AssessorUpdated Apr 2026

34 Charles Rd

3 bd · 1.5 ba · 968 sqft

Last Sale Tax Bill Prior Sale Owner Records
$296,000May 2010 $542025 Amount on Record Apr 2006 2 Names on Record Assessor + 2 DocumentsUpdated Apr 2026

36 Charles Rd

3 bd · 1 ba · 968 sqft

Last Sale Tax Bill Prior Sale Owner Records
$410,000Oct 2017 $542025 Amount on Record Aug 2011 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

38 Charles Rd

3 bd · 1.5 ba · 968 sqft

Last Sale Tax Bill Prior Sale Owner Records
$435,000Aug 2019 $542025 Amount on Record Jun 2005 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

40 Charles Rd

3 bd · 1.5 ba · 1,210 sqft

Last Sale Tax Bill Prior Sale Owner Records
$323,900Jul 2005 $592025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

42 Charles Rd

2 bd · 2 ba · 968 sqft

Last Sale Tax Bill Prior Sale Owner Records
$349,900Aug 2005 $562025 2 Names on Record AssessorUpdated Apr 2026

44 Charles Rd

2 bd · 1 ba · 968 sqft

Last Sale Tax Bill Prior Sale Owner Records
$245,500Jul 2012 $532025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

46 Charles Rd

3 bd · 1 ba · 968 sqft

Last Sale Tax Bill Prior Sale Owner Records
$284,000Apr 2008 $532025 2 Names on Record AssessorUpdated Apr 2026

48 Charles Rd

2 bd · 1 ba · 968 sqft

Last Sale Tax Bill Prior Sale Owner Records
$500,100Sep 2023 $5,3522025 Amount on Record Apr 2017 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Apr 2026

50 Charles Rd

3 bd · 1.5 ba · 1,227 sqft

Last Sale Tax Bill Prior Sale Owner Records
$648,000Nov 2020 $652025 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

51 Charles Rd, #53

6 bd · 3 ba · 2,700 sqft · 0.303 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,160,000Jul 2024 $1412025 1 Name on Record Assessor + 2 DocumentsUpdated Jul 2026

52 Charles Rd

3 bd · 1.5 ba · 1,819 sqft

Last Sale Tax Bill Prior Sale Owner Records
$752025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

54 Charles Rd

3 bd · 1.5 ba · 1,232 sqft

Last Sale Tax Bill Prior Sale Owner Records
$652025 2 Names on Record AssessorUpdated Apr 2026

55 Charles Rd

3 bd · 1.5 ba · 1,225 sqft

Last Sale Tax Bill Prior Sale Owner Records
$355,000Nov 2002 $722025 2 Names on Record AssessorUpdated Aug 2026

56 Charles Rd

3 bd · 1.5 ba · 1,232 sqft

Last Sale Tax Bill Prior Sale Owner Records
$510,000Oct 2015 $652025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

57 Charles Rd

3 bd · 1.5 ba · 1,200 sqft

Last Sale Tax Bill Prior Sale Owner Records
$394,500May 2006 $742025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

58 Charles Rd

3 bd · 2.5 ba · 1,553 sqft

Last Sale Tax Bill Prior Sale Owner Records
$722025 2 Names on Record AssessorUpdated Apr 2026

59 Charles Rd

3 bd · 1.5 ba · 1,224 sqft

Last Sale Tax Bill Prior Sale Owner Records
$750,000Jun 2024 $652025 Amount on Record Oct 2020 1 Name on Record AssessorUpdated Aug 2026

60 Charles Rd

3 bd · 1.5 ba · 1,242 sqft

Last Sale Tax Bill Prior Sale Owner Records
$662025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

61 Charles Rd

3 bd · 1.5 ba · 1,224 sqft

Last Sale Tax Bill Prior Sale Owner Records
$652025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

Wildfire Risk on Charles Rd

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

Wildfire Risk to HomesNot rated
no burnable land in reach
Wildfire LikelihoodNegligible
ExposureNone
beyond ember reach of burnable land

Property Records in Nearby Streets