Coolidge Rd, Winchester, MA Property Records

Middlesex County and Winchester Town property records for 21 addresses on Coolidge Rd, Winchester, MA · Last verified August 2026

Coolidge Rd Highlights

Properties 21
Median Sale Price $1,200,000
Deeds and Mortgages on File 16
Median Price per Sqft $329
Owner Occupied 95%
Median Annual Tax Bill $179
Median Year Built 1981
Median Ownership Tenure 23 years

Properties on Coolidge Rd

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

5 Coolidge Rd

3 bd · 2 ba · 2,544 sqft · 0.46 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$399,000Dec 1987 $1422025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

7 Coolidge Rd

4 bd · 2.5 ba · 4,159 sqft · 0.462 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$915,000Jun 2003 $1942025 Amount on Record Apr 2000 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

8 Coolidge Rd

3 bd · 2.5 ba · 1,934 sqft · 0.588 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$145,000May 1983 $1562025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

9 Coolidge Rd

4 bd · 2.5 ba · 3,879 sqft · 0.46 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$500,000Dec 1997 $1922025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

10 Coolidge Rd

4 bd · 3 ba · 3,466 sqft · 0.562 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Jul 2016 $1912025 —Jan 2007 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

11 Coolidge Rd

4 bd · 2.5 ba · 3,324 sqft · 0.516 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$331,000Dec 1990 $1682025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

12 Coolidge Rd

4 bd · 3 ba · 3,974 sqft · 0.538 acres

Last Sale Tax Bill Prior Sale Owner Records
$900,000Nov 2013 $1862025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

14 Coolidge Rd

4 bd · 3.5 ba · 3,516 sqft · 0.47 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$315,000Apr 1991 $1592025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

15 Coolidge Rd

3 bd · 2.5 ba · 2,800 sqft · 0.503 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$700,000Aug 2008 $1622025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

19 Coolidge Rd

3 bd · 2.5 ba · 2,218 sqft · 0.483 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$378,000Aug 1995 $1572025 Amount on Record Jul 1987 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

20 Coolidge Rd

5 bd · 3.5 ba · 3,320 sqft · 0.464 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,251,500Nov 2020 $1692025 Amount on Record Aug 2014 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

21 Coolidge Rd

3 bd · 3.5 ba · 3,965 sqft · 0.56 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,200,000Apr 2021 $1822025 —Sep 2014 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

25 Coolidge Rd

4 bd · 2.5 ba · 2,614 sqft · 0.497 acres

Last Sale Tax Bill Prior Sale Owner Records
$185,000Nov 1982 $1792025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

26 Coolidge Rd

3 bd · 3 ba · 2,970 sqft · 0.501 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$875,000Jul 2004 $1732025 2 Names on Record AssessorUpdated Apr 2026

28 Coolidge Rd

4 bd · 2.5 ba · 2,782 sqft · 1.68 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jan 2004 $1802025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

29 Coolidge Rd

4 bd · 2.5 ba · 3,400 sqft · 0.464 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$477,500Jun 1997 $1892025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

30 Coolidge Rd

4 bd · 3 ba · 2,329 sqft · 0.507 acres

Last Sale Tax Bill Prior Sale Owner Records
$378,000Jun 1995 $1802025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

31 Coolidge Rd

4 bd · 2.5 ba · 3,639 sqft · 0.483 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,000,000Apr 2025 $18,9182025 Amount on Record Aug 2008 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Jul 2026

32 Coolidge Rd

3 bd · 2.5 ba · 2,829 sqft · 0.473 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$931,000Nov 2012 $1752025 Amount on Record Mar 2000 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

33 Coolidge Rd

3 bd · 2.5 ba · 3,400 sqft · 0.462 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$635,000Feb 2002 $1622025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

34 Coolidge Rd

4 bd · 2.5 ba · 3,338 sqft · 0.461 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,650,000Jun 2025 $18,0732025 Amount on Record Dec 1978 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

Property Records in Nearby Streets