Winslow Rd, Brookline, MA Property Records

Norfolk County and Brookline Town property records for 16 addresses on Winslow Rd, Brookline, MA · Last verified July 2026

Winslow Rd Highlights

Properties 39
Median Sale Price $1,500,000
Deeds and Mortgages on File 45
Median Price per Sqft $774
Owner Occupied 31%
Median Annual Tax Bill $6,183
Median Year Built 1944
Median Ownership Tenure 16 years

Properties on Winslow Rd

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

16 Winslow Rd

4 bd · 4.5 ba · 3,893 sqft · built 1890 · 0.151 acres

Last Sale Tax Bill Prior Sale Owner Records
$600,000Sep 2016 $20,4282025 Amount on Record Oct 1993 1 Name on Record AssessorUpdated Apr 2026

18 Winslow Rd, #20

12 bd · 4 ba · 4,260 sqft · built 1880 · 0.144 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jan 2014 $33,1232025 —May 2006 1 Name on Record Assessor + 3 DocumentsUpdated Jul 2026

22 Winslow Rd

5 bd · 3.5 ba · 2,188 sqft · built 1900 · 0.07 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,500,000Jun 2023 $16,4932025 Amount on Record Jun 2006 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

23 Winslow Rd, #1

3 bd · 3 ba · 1,466 sqft · built 1928 · 0.127 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,650,000Jun 2024 $18,1082025 Amount on Record Jul 2021 1 Name on Record Assessor + 1 DocumentUpdated Jul 2026

23 Winslow Rd, #2

4 bd · 3 ba · 2,205 sqft · built 1928 · 0.127 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,642,725Nov 2020 $17,0402025 1 Name on Record AssessorUpdated Jul 2026

24 Winslow Rd

5 bd · 4.5 ba · 1,964 sqft · built 1900 · 0.074 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,730,000Jul 2021 $18,1172025 Amount on Record Sep 2019 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Apr 2026

27 Winslow Rd

7 bd · 3.5 ba · 3,632 sqft · built 1905 · 0.167 acres

Last Sale Tax Bill Prior Sale Owner Records
$44,000Feb 1979 $22,0502025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

28 Winslow Rd

6 bd · 3.5 ba · 4,028 sqft · built 1900 · 0.158 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,500,000Dec 2025 $20,6702025 —Jan 2015 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

31 Winslow Rd

6 units · Built 1944 · 670 sq ft

Last Sale Median Tax Bill Median Sale    
$567,000May 2025 $5,9692025 $608,0006 units    

33 Winslow Rd

7 units · Built 1944 · 860 sq ft

Last Sale Median Tax Bill Median Sale    
$525,000Oct 2022 $6,6442025 $367,0007 units    

35 Winslow Rd

6 units · Built 1944 · 730 sq ft

Last Sale Median Tax Bill Median Sale    
$570,000Jun 2015 $6,0742025 $359,0006 units    

41 Winslow Rd

8 units · Built 1890 · 630 sq ft

Last Sale Median Tax Bill Median Sale    
$900,000Jun 2021 $5,6822025 $310,0008 units    

44 Winslow Rd

11 bd · 5 ba · 4,622 sqft · built 1910 · 0.166 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,855,800Jun 2022 $23,9892025 1 Name on Record Assessor + 4 DocumentsUpdated Apr 2026

45 Winslow Rd

7 bd · 4 ba · 2,256 sqft · built 1967 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
—Apr 2014 $17,8222025 Amount on Record Aug 2001 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

51 Winslow Rd

6 bd · 5 ba · 3,770 sqft · built 2004 · 0.143 acres

Last Sale Tax Bill Prior Sale Owner Records
$110,000Jul 1982 $36,6512025 1 Name on Record Assessor + 4 DocumentsUpdated Jun 2026

53 Winslow Rd

6 bd · 5 ba · 3,770 sqft · built 2004 · 0.143 acres

Last Sale Tax Bill Prior Sale Owner Records
$110,000Jul 1982 $36,6582025 1 Name on Record Assessor + 4 DocumentsUpdated Jul 2026

Wildfire Risk on Winslow Rd

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

Wildfire RiskNot rated
no burnable land in reach
Wildfire LikelihoodNegligible
ExposureNone
beyond ember reach

Property Records in Nearby Streets