Highland Ave, Pittsfield, MA Property Records

Berkshire County, Great Barrington Town and Otis Town property records for 87 addresses on Highland Ave, Pittsfield, MA · Last verified October 2026

Highland Ave Highlights

Properties 87
Median Sale Price $210,000
Deeds and Mortgages on File 75
Median Price per Sqft $142
Owner Occupied 87%
Median Annual Tax Bill $4,033
Median Year Built 1950
Median Ownership Tenure 12 years

Properties on Highland Ave

Address Details Last Sale Tax Bill Records Owner

14 Highland Ave

16 bd · 12 ba · 8,608 sqft built 2007 · 0.407 acres $935,000 Jul 2014 $13,810 2025 Assessor Updated Oct 2026 Owner on File
Address Details Last Sale Tax Bill Records Owner

18 Highland Ave

4 bd · 1 ba · 1,850 sqft built 1970 · 0.321 acres $111,000 Dec 2001 $6,765 2025 Assessor + 1 Document Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

21 Highland Ave

7 bd · 2.5 ba · 2,557 sqft built 1930 · 0.44 acres $136,000 Oct 2015 $4,797 2025 Assessor Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

27, #29 Highland Ave

4 bd · 2 ba · 2,244 sqft built 1890 · 0.248 acres $75,000 Sep 1992 $3,959 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

28 1/2 Highland Ave

3 bd · 2 ba · 1,318 sqft built 1900 · 0.313 acres $139,000 Jun 2013 $3,800 2025 Assessor + 1 Document Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

28 Highland Ave

3 bd · 2 ba · 1,890 sqft built 1910 · 0.186 acres $269,900 Dec 2024 $4,037 2025 Assessor Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

33 Highland Ave

3 bd · 1 ba · 1,128 sqft built 1930 · 0.2 acres $260,500 Nov 2025 $3,364 2025 Assessor + 2 Documents Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

36 Highland Ave

3 bd · 2 ba · 1,635 sqft built 1961 · 0.3 acres $180,000 Jun 2021 $3,864 2025 Assessor + 1 Document Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

37 Highland Ave

2.3 acres Assessor Updated Apr 2026 Owner on File
Address Details Last Sale Tax Bill Records Owner

41 Highland Ave

2 bd · 1 ba · 1,140 sqft built 1890 · 0.302 acres $210,000 Feb 2026 $3,197 2025 Assessor + 2 Documents Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

44 Highland Ave

2 bd · 1 ba · 768 sqft built 1949 · 0.333 acres — Jul 2018 $3,437 2025 Assessor + 1 Document Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

49 Highland Ave

2 bd · 1 ba · 850 sqft built 1953 · 0.295 acres $130,000 Mar 2014 $3,717 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

50 Highland Ave

2 bd · 1 ba · 704 sqft built 1940 · 0.19 acres $123,600 Aug 2012 $3,880 2025 Assessor + 1 Document Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

51 Highland Ave

2 bd · 1 ba · 884 sqft built 1960 · 0.18 acres $125,000 Jun 2011 $3,857 2025 Assessor Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

58 Highland Ave

3 bd · 1 ba · 1,425 sqft built 1940 · 0.19 acres $189,900 Oct 2020 $4,422 2025 Assessor + 1 Document Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

70 Highland Ave

1 bd · 1 ba · 678 sqft built 1930 · 0.16 acres $119,000 Nov 2007 $2,397 2025 Assessor Updated Oct 2026 2 Owners on File
Address Details Last Sale Tax Bill Records Owner

76 Highland Ave

3 bd · 1 ba · 1,152 sqft built 1920 · 0.368 acres $202,500 Aug 2019 $4,637 2025 Assessor + 2 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

84 Highland Ave

3 bd · 1 ba · 984 sqft built 1962 · 0.287 acres $135,000 Nov 2019 $4,141 2025 Assessor + 1 Document Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

87 Highland Ave

6 bd · 3.5 ba · 2,592 sqft built 1932 · 0.408 acres $115,000 Mar 2016 $3,330 2025 Assessor Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

90 Highland Ave

2 bd · 1 ba · 1,892 sqft built 1926 · 0.306 acres $110,000 May 2022 $4,444 2025 Assessor + 4 Documents Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

93 Highland Ave

3 bd · 2.5 ba · 1,960 sqft built 1987 · 0.575 acres $135,000 Feb 2001 $6,379 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

99 Highland Ave

3 bd · 1 ba · 1,512 sqft built 1955 · 0.222 acres $5,161 2025 Assessor + 1 Document Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

109 Highland Ave

2 bd · 1 ba · 1,505 sqft built 1940 · 0.115 acres $190,000 Jan 2025 $4,006 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

110 Highland Ave

3 bd · 1.5 ba · 1,754 sqft built 1965 · 0.311 acres $5,005 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

114 Highland Ave

2 bd · 1 ba · 1,056 sqft built 1940 · 0.133 acres $96,000 Sep 2007 $3,175 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

117 Highland Ave

2 bd · 1 ba · 1,386 sqft built 1940 · 0.275 acres $3,888 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

120 Highland Ave

2 bd · 1 ba · 857 sqft built 1965 · 0.275 acres — Sep 2018 $3,473 2025 Assessor + 1 Document Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

123 Highland Ave

4 bd · 3 ba · 3,932 sqft built 1950 · 0.373 acres $445,000 Sep 2024 $8,245 2025 Assessor + 1 Document Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

126 Highland Ave

0.725 acres $30,000 Mar 2012 $61 2025 Assessor Updated Apr 2026 2 Owners on File
Address Details Last Sale Tax Bill Records Owner

133 Highland Ave

4 bd · 1.5 ba · 1,571 sqft built 1948 · 0.192 acres $50,000 Jul 1987 $4,673 2025 Assessor + 1 Document Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

138 Highland Ave

3 bd · 2 ba · 1,226 sqft built 2004 · 0.277 acres $193,000 Feb 2006 $4,894 2025 Assessor + 1 Document Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

139 Highland Ave

3 bd · 2 ba · 1,428 sqft built 1945 · 0.216 acres $80,000 Nov 2001 $4,336 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

140 Highland Ave

3 bd · 1 ba · 1,368 sqft built 1960 · 0.254 acres $3,952 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

145 Highland Ave

3 bd · 1 ba · 1,300 sqft built 1962 · 0.273 acres $50,000 Apr 2004 $4,847 2025 Assessor + 2 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

150 Highland Ave

3 bd · 1 ba · 1,804 sqft built 1940 · 0.178 acres $4,289 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

166 Highland Ave

2 bd · 1 ba · 1,008 sqft built 1923 · 0.146 acres $133,000 Dec 2018 $3,082 2025 Assessor + 2 Documents Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

167 Highland Ave

3 bd · 1.5 ba · 1,988 sqft built 1977 · 0.364 acres $110,000 Aug 1992 $5,438 2025 Assessor + 1 Document Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

171 Highland Ave

4 bd · 1 ba · 1,594 sqft built 1900 · 0.175 acres $80,600 Oct 1988 $3,488 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

175 Highland Ave

2 bd · 1 ba · 835 sqft built 1930 · 0.125 acres $140,000 Jul 2019 $3,206 2025 Assessor + 1 Document Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

176 Highland Ave

3 bd · 2 ba · 1,680 sqft built 1890 · 0.224 acres $3,690 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

178 Highland Ave

2 bd · 1 ba · 1,175 sqft built 1930 · 0.216 acres $184,000 Apr 2022 $3,425 2025 Assessor + 3 Documents Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

179 Highland Ave

3 bd · 1 ba · 1,341 sqft built 1925 · 0.196 acres $124,000 Oct 2009 $3,862 2025 Assessor + 3 Documents Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

184 Highland Ave

3 bd · 1 ba · 1,014 sqft built 1955 · 0.415 acres $66,000 Apr 2015 $3,843 2025 Assessor Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

185 Highland Ave

3 bd · 1.5 ba · 1,715 sqft built 1970 · 0.288 acres $224,000 Jan 2021 $5,561 2025 Assessor + 5 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

196 Highland Ave

3 bd · 1.5 ba · 1,388 sqft built 1960 · 0.24 acres $169,900 Jun 2014 $4,752 2025 Assessor Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

204 Highland Ave

3 bd · 2.5 ba · 2,035 sqft built 1946 · 0.319 acres $95,000 Jun 1994 $6,076 2025 Assessor + 1 Document Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

205 Highland Ave

3 bd · 2.5 ba · 1,901 sqft built 1997 · 7.9 acres $70,000 May 1996 $7,348 2025 Assessor + 1 Document Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

210 Highland Ave

1 bd · 1 ba · 560 sqft built 1910 · 0.235 acres $77,000 Feb 2019 $2,052 2025 Assessor + 2 Documents Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

211 Highland Ave

2 bd · 1 ba · 1,254 sqft built 1940 · 0.429 acres $48,000 Nov 2017 $3,861 2025 Assessor + 1 Document Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

214 Highland Ave

672 sqft built 1920 · 0.117 acres — Nov 1971 $1,726 2017 Assessor Updated Jun 2023 2 Owners on File
Address Details Last Sale Tax Bill Records Owner

216 Highland Ave

3 bd · 1 ba · 1,164 sqft built 1900 · 0.21 acres $95,000 Apr 2017 $3,920 2025 Assessor + 2 Documents Updated Oct 2026 Owner on File
Address Details Last Sale Tax Bill Records Owner

218 Highland Ave

4 bd · 2 ba · 2,093 sqft built 1900 · 0.239 acres $139,000 May 2013 $5,391 2025 Assessor Updated Oct 2026 Owner on File
Address Details Last Sale Tax Bill Records Owner

219 Highland Ave

3 bd · 1.5 ba · 1,248 sqft built 1960 · 0.33 acres $3,538 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

224 Highland Ave

5 bd · 1.5 ba · 1,599 sqft built 1940 · 0.134 acres $37,100 Mar 2016 $1,545 2025 Assessor Updated Oct 2026 Owner on File
Address Details Last Sale Tax Bill Records Owner

225 Highland Ave

3 bd · 1 ba · 1,305 sqft built 1967 · 0.33 acres $200,000 Nov 2019 $5,280 2025 Assessor + 1 Document Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

230 Highland Ave

3 bd · 2 ba · 1,625 sqft built 1960 · 0.264 acres $170,000 Aug 2012 $5,212 2025 Assessor + 1 Document Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

231 Highland Ave

3 bd · 1 ba · 1,100 sqft built 1964 · 0.33 acres $79,000 Sep 1995 $4,033 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

234 Highland Ave

1 bd · 1 ba · 756 sqft built 1930 · 0.426 acres $105,000 Nov 2012 $3,299 2025 Assessor Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

237 Highland Ave

3 bd · 1 ba · 1,500 sqft built 1960 · 0.33 acres $48,000 Aug 1983 $3,536 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

239 Highland Ave

3 bd · 2 ba · 1,668 sqft built 1962 · 1.75 acres $400,000 Oct 2021 $7,436 2025 Assessor + 2 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

247 Highland Ave

4 bd · 2 ba · 2,046 sqft built 1960 · 0.295 acres $188,000 Mar 2005 $5,762 2025 Assessor + 2 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

250 Highland Ave

3 bd · 1 ba · 1,392 sqft built 1960 · 0.413 acres $297,000 Jul 2025 $4,808 2025 Assessor + 1 Document Updated Oct 2026 Owner on File
Address Details Last Sale Tax Bill Records Owner

257 Highland Ave

2 bd · 1 ba · 946 sqft built 1930 · 0.316 acres $208,900 Aug 2021 $4,130 2025 Assessor + 1 Document Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

260 Highland Ave

2 bd · 2 ba · 1,510 sqft built 1962 · 0.19 acres — Apr 2008 $4,982 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

261 Highland Ave

3 bd · 1 ba · 1,500 sqft built 1950 · 0.362 acres $270,000 Jul 2024 $4,176 2025 Assessor + 1 Document Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

266 Highland Ave

3 bd · 1 ba · 1,040 sqft built 1960 · 0.196 acres $34,000 Jun 1981 $3,233 2025 Assessor Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

267 Highland Ave

3 bd · 2 ba · 2,030 sqft built 1948 · 0.63 acres $169,500 May 2015 $5,439 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

268 Highland Ave

4 bd · 2.5 ba · 1,624 sqft built 1960 · 0.19 acres $4,930 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

270 Highland Ave

2 bd · 1 ba · 1,296 sqft built 1967 · 0.261 acres — Jun 2016 $4,688 2025 Assessor + 1 Document Updated Oct 2026 Owner on File
Address Details Last Sale Tax Bill Records Owner

275 Highland Ave

3 bd · 2 ba · 1,782 sqft built 2019 · 0.496 acres $6,553 2025 Assessor + 1 Document Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

279 Highland Ave

2 bd · 1 ba · 2,482 sqft built 1994 · 0.578 acres $85,000 Oct 1991 $7,221 2025 Assessor + 1 Document Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

285 Highland Ave

2 bd · 1 ba · 816 sqft built 1920 · 0.17 acres $68,285 Nov 2020 $2,112 2025 Assessor + 1 Document Updated Oct 2026 2 Owners on File
Address Details Last Sale Tax Bill Records Owner

291 Highland Ave

3 bd · 1 ba · 1,475 sqft built 1955 · 0.371 acres $3,543 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

300 Highland Ave

3 bd · 1 ba · 1,876 sqft built 1960 · 0.279 acres $87,500 Jul 1996 $4,246 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

305 Highland Ave

3 bd · 1 ba · 1,460 sqft built 1920 · 0.332 acres $90,000 Jun 1989 $3,703 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

306 Highland Ave

1 bd · 1 ba · 784 sqft built 1950 · 0.199 acres $53,500 Oct 1993 $3,852 2025 Assessor Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

309 Highland Ave

2 bd · 2.5 ba · 1,728 sqft built 1958 · 0.341 acres $140,000 May 2005 $4,548 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

312 Highland Ave

3 bd · 1.5 ba · 1,403 sqft built 1960 · 0.125 acres $220,000 Feb 2018 $5,710 2025 Assessor + 2 Documents Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

317 Highland Ave

2 bd · 2 ba · 1,459 sqft built 1950 · 0.379 acres $156,000 Sep 2007 $4,341 2025 Assessor + 3 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

318 Highland Ave

3 bd · 2 ba · 1,392 sqft built 1950 · 0.225 acres $107,900 Jun 1989 $5,070 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

323 Highland Ave

3 bd · 1 ba · 1,056 sqft built 1950 · 0.495 acres $3,923 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

326 Highland Ave

2 bd · 1.5 ba · 848 sqft built 1920 · 0.292 acres $63,000 Aug 2017 $2,628 2025 Assessor + 4 Documents Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

330 Highland Ave

2 bd · 1 ba · 990 sqft built 1940 · 0.256 acres $34,000 Jan 1987 $3,710 2025 Assessor Updated Oct 2026 2 Owners on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

331 Highland Ave

2 bd · 1 ba · 713 sqft built 1920 · 0.321 acres $95,000 Jul 2006 $2,478 2025 Assessor + 3 Documents Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

334 Highland Ave

3 bd · 2 ba · 1,494 sqft built 2002 · 0.568 acres $6,033 2025 Assessor Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

339 Highland Ave

3 bd · 1 ba · 1,440 sqft built 1940 · 0.33 acres $140,000 Mar 2021 $3,258 2025 Assessor + 3 Documents Updated Oct 2026 Owner on File Owner Occupied
Address Details Last Sale Tax Bill Records Owner

343 Highland Ave

3 bd · 1 ba · 1,200 sqft built 1940 · 0.123 acres $109,000 Aug 2015 $2,669 2025 Assessor + 1 Document Updated Oct 2026 Owner on File Owner Occupied

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