Ann Dr, Pittsfield, MA Property Records

Berkshire County and Pittsfield City property records for 29 addresses on Ann Dr, Pittsfield, MA · Last verified August 2026

Ann Dr Highlights

Properties 29
Median Sale Price $500,000
Deeds and Mortgages on File 33
Median Price per Sqft $155
Owner Occupied 86%
Median Annual Tax Bill $8,529
Median Year Built 1960
Median Ownership Tenure 9 years

Properties on Ann Dr

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

21 Ann Dr

3 bd · 2 ba · 1,361 sqft · built 1955 · 0.475 acres

Last Sale Tax Bill Prior Sale Owner Records
$218,900Sep 2011 $6,9572025 Amount on Record May 2006 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

24 Ann Dr

5 bd · 2.5 ba · 3,142 sqft · built 1955 · 0.485 acres

Last Sale Tax Bill Prior Sale Owner Records
$440,000Jan 2024 $9,1762025 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

29 Ann Dr

4 bd · 2 ba · 1,656 sqft · built 1955 · 0.594 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,3642025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

39 Ann Dr

3 bd · 3 ba · 2,290 sqft · built 1951 · 0.57 acres

Last Sale Tax Bill Prior Sale Owner Records
$398,500Nov 2020 $8,7012025 Amount on Record Oct 2006 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

42 Ann Dr

3 bd · 2.5 ba · 2,750 sqft · built 1953 · 0.831 acres

Last Sale Tax Bill Prior Sale Owner Records
$140,000May 1999 $8,2562025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

51 Ann Dr

3 bd · 2.5 ba · 2,738 sqft · built 1950 · 0.831 acres

Last Sale Tax Bill Prior Sale Owner Records
$272,500May 2004 $11,0042025 Amount on Record Nov 2000 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

54 Ann Dr

3 bd · 2 ba · 1,347 sqft · built 1955 · 0.712 acres

Last Sale Tax Bill Prior Sale Owner Records
$207,875Nov 2017 $6,3012025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

66 Ann Dr

4 bd · 2 ba · 2,047 sqft · built 1955 · 0.712 acres

Last Sale Tax Bill Prior Sale Owner Records
$283,000Aug 2018 $7,8612025 Amount on Record Apr 1979 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

81 Ann Dr

4 bd · 2.5 ba · 2,201 sqft · built 1960 · 0.831 acres

Last Sale Tax Bill Prior Sale Owner Records
$310,000Jan 2017 $6,3332018 Amount on Record May 2014 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

88 Ann Dr

3 bd · 2 ba · 1,608 sqft · built 1955 · 0.712 acres

Last Sale Tax Bill Prior Sale Owner Records
—Mar 2017 $6,5162025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

89 Ann Dr

3 bd · 2.5 ba · 2,134 sqft · built 1965 · 0.712 acres

Last Sale Tax Bill Prior Sale Owner Records
$156,000Aug 1992 $8,4052025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

92 Ann Dr

3 bd · 2 ba · 1,483 sqft · built 1955 · 0.712 acres

Last Sale Tax Bill Prior Sale Owner Records
$250,000Feb 2005 $7,9132025 Amount on Record Oct 1997 2 Names on Record Assessor + 1 DocumentUpdated May 2026

95 Ann Dr

3 bd · 2.5 ba · 2,556 sqft · built 1965 · 0.712 acres

Last Sale Tax Bill Prior Sale Owner Records
$310,000Jun 2008 $9,4692025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

102 Ann Dr

2 bd · 1.5 ba · 1,423 sqft · built 1955 · 0.712 acres

Last Sale Tax Bill Prior Sale Owner Records
$264,500Aug 2016 $7,7342025 Amount on Record Jun 2009 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

105 Ann Dr

3 bd · 2 ba · 1,704 sqft · built 1960 · 0.594 acres

Last Sale Tax Bill Prior Sale Owner Records
$281,900Jun 2006 $7,4332025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

112 Ann Dr

3 bd · 2.5 ba · 1,864 sqft · built 1965 · 0.712 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,0822025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

115 Ann Dr

4 bd · 2.5 ba · 3,486 sqft · built 1968 · 0.594 acres

Last Sale Tax Bill Prior Sale Owner Records
$500,000Oct 2021 $10,5422025 Amount on Record Feb 2018 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

122 Ann Dr

4 bd · 3.5 ba · 1,580 sqft · built 1965 · 0.594 acres

Last Sale Tax Bill Prior Sale Owner Records
$230,000Feb 2017 $6,4102025 Amount on Record Apr 2016 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

123 Ann Dr

4 bd · 2.5 ba · 2,903 sqft · built 1968 · 0.594 acres

Last Sale Tax Bill Prior Sale Owner Records
$435,000Sep 2021 $8,7302025 Amount on Record Apr 2014 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

130 Ann Dr

4 bd · 2.5 ba · 2,416 sqft · built 1965 · 0.641 acres

Last Sale Tax Bill Prior Sale Owner Records
$285,000Jun 2012 $8,5292025 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

139 Ann Dr

6 bd · 3 ba · 2,927 sqft · built 1960 · 0.641 acres

Last Sale Tax Bill Prior Sale Owner Records
$530,000Mar 2025 $9,8202025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

140 Ann Dr

5 bd · 5.5 ba · 5,561 sqft · built 1975 · 1.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$22,3532025 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

147 Ann Dr

4 bd · 2.5 ba · 2,172 sqft · built 1961 · 0.641 acres

Last Sale Tax Bill Prior Sale Owner Records
$337,500Feb 2021 $7,3842025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

155 Ann Dr

4 bd · 2.5 ba · 3,441 sqft · built 1965 · 0.641 acres

Last Sale Tax Bill Prior Sale Owner Records
$660,000Aug 2023 $12,2402025 Amount on Record May 1994 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

160 Ann Dr

5 bd · 2.5 ba · 4,159 sqft · built 1970 · 0.641 acres

Last Sale Tax Bill Prior Sale Owner Records
$396,900Mar 2017 $11,5072025 Amount on Record Sep 2012 2 Names on Record AssessorUpdated Apr 2026

163 Ann Dr

6 bd · 3.5 ba · 3,404 sqft · built 1960 · 0.836 acres

Last Sale Tax Bill Prior Sale Owner Records
$410,000Sep 2011 $12,7982025 Amount on Record Feb 1990 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

170 Ann Dr

4 bd · 3.5 ba · 3,408 sqft · built 1965 · 0.679 acres

Last Sale Tax Bill Prior Sale Owner Records
$12,7632025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

175 Ann Dr

6 bd · 4 ba · 4,662 sqft · built 1970 · 1.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$563,000Nov 2019 $16,7812025 Amount on Record Jun 2015 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

180 Ann Dr

4 bd · 3.5 ba · 3,386 sqft · built 1965 · 0.628 acres

Last Sale Tax Bill Prior Sale Owner Records
$292,500May 1998 $14,8222025 Amount on Record Jun 1989 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

Wildfire Risk on Ann Dr

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

Wildfire RiskLow
this street's cells rank above 20% of the US · above 58% of Massachusetts
Wildfire LikelihoodAbout 1 in 10,000 per year
ExposureIndirect
0 of 4 cells directly exposed · 4 adjoin burnable vegetation

Property Records in Nearby Streets