S Highland Ave, Ossining, NY Property Records

Westchester County and Ossining Town property records for 95 addresses on S Highland Ave, Ossining, NY · Last verified August 2026

S Highland Ave Highlights

Properties 95
Median Sale Price $735,000
Deeds and Mortgages on File 55
Median Price per Sqft $362
Owner Occupied 37%
Median Annual Tax Bill $14,254
Median Year Built 1928
Median Ownership Tenure 16 years

Properties on S Highland Ave

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

23 S Highland Ave

6 bd · 2 ba · 2,424 sqft · built 1850 · 0.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$12,6242025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

25 S Highland Ave

0.189 acres

Last Sale Tax Bill Prior Sale Owner Records
$11,7342025 2 Owners on Record AssessorUpdated May 2026

26 S Highland Ave

0.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$500,000Nov 2003 $110,1762025 2 Owners on Record Assessor + 1 DocumentUpdated Jun 2026

29 S Highland Ave

14.7 acres

Last Sale Tax Bill Prior Sale Owner Records
Owner on Record AssessorUpdated May 2026

30 S Highland Ave

0.58 acres

Last Sale Tax Bill Prior Sale Owner Records
$925,000Jun 2009 $27,7802025 Owner on Record AssessorUpdated May 2026

34 S Highland Ave

0.519 acres

Last Sale Tax Bill Prior Sale Owner Records
$27,8352025 Owner on Record AssessorUpdated May 2026

36 S Highland Ave

14 bd · 3 ba · 3,572 sqft · built 1860 · 0.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$925,000Nov 2018 $12,3552025 Amount on Record Feb 1997 Owner on Record Assessor + 1 DocumentUpdated May 2026

40 S Highland Ave

0.55 acres

Last Sale Tax Bill Prior Sale Owner Records
$13,3392025 Owner on Record AssessorUpdated Aug 2026

43 S Highland Ave

0.789 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,000,000Feb 2012 $12,1692025 Amount on Record Sep 2004 Owner on Record AssessorUpdated May 2026

45 S Highland Ave

0.6 acres

Last Sale Tax Bill Prior Sale Owner Records
$11,2062025 2 Owners on Record AssessorUpdated May 2026

46 S Highland Ave

2 bd · 2.5 ba · 1,736 sqft · built 1914 · 0.2 acres

Last Sale Tax Bill Prior Sale Owner Records
Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

47 S Highland Ave

0.489 acres

Last Sale Tax Bill Prior Sale Owner Records
$150,000Mar 1996 $17,4262025 Owner on Record AssessorUpdated May 2026

48 S Highland Ave

4 ba · 1,592 sqft · built 1922 · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$200,000Nov 1999 $10,6682025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

50 S Highland Ave

5 bd · 2 ba · 2,748 sqft · built 1912 · 0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,000Sep 2010 $10,9762025 Amount on Record Jul 2007 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

52 S Highland Ave

9 bd · 9 ba · 5,236 sqft · built 1923 · 0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$500,000Oct 2010 $11,6402025 Amount on Record Apr 2007 2 Owners on Record Owner Occupied AssessorUpdated May 2026

54 S Highland Ave

4 bd · 2.5 ba · 2,272 sqft · built 1942 · 0.239 acres

Last Sale Tax Bill Prior Sale Owner Records
$19,9212025 Owner on Record Assessor + 1 DocumentUpdated May 2026

56 S Highland Ave

0.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$10,3342025 Owner on Record AssessorUpdated Aug 2026

57 S Highland Ave

4 bd · 3 ba · 2,062 sqft · built 1920 · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$12,4052025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

58 S Highland Ave

0.769 acres

Last Sale Tax Bill Prior Sale Owner Records
$32,8262025 Owner on Record AssessorUpdated May 2026

62 S Highland Ave

0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$565,000Aug 2008 Amount on Record May 1999 Owner on Record AssessorUpdated May 2026

63 S Highland Ave

4 bd · 2 ba · 1,771 sqft · built 1885 · 0.13 acres

Last Sale Tax Bill Prior Sale Owner Records
$547,500Aug 2007 $25,3582025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

64 S Highland Ave

6 bd · 3 ba · 2,524 sqft · built 1900 · 0.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$11,2082025 Owner on Record Assessor + 1 DocumentUpdated May 2026

65 S Highland Ave

5 bd · 3.5 ba · 2,842 sqft · built 1930 · 0.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$15,3382025 2 Owners on Record AssessorUpdated May 2026

66 S Highland Ave

1 bd · 2 ba · 2,172 sqft · built 1900 · 0.139 acres

Last Sale Tax Bill Prior Sale Owner Records
$467,501Jul 2024 $11,9232025 Amount on Record May 2000 Owner on Record Assessor + 1 DocumentUpdated Aug 2026

67 S Highland Ave

4 bd · 3 ba · 2,166 sqft · built 1930 · 0.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$285,000Oct 2011 $14,4322025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

68 S Highland Ave

4 bd · 2 ba · 2,318 sqft · built 1900 · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$10,0902025 Owner on Record AssessorUpdated May 2026

69 S Highland Ave

3 bd · 2 ba · 2,510 sqft · built 1928 · 0.06 acres

Last Sale Tax Bill Prior Sale Owner Records
$205,000May 2001 $12,6992025 Owner on Record Owner Occupied AssessorUpdated May 2026

70 S Highland Ave

built 1890 · 0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$280,000Jun 1997 $8,5652025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

72 S Highland Ave

5 bd · 3 ba · 2,464 sqft · built 1880 · 0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$250,000Jan 2014 $18,2042025 Amount on Record Sep 2006 2 Owners on Record AssessorUpdated May 2026

75 S Highland Ave

0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$735,000Apr 2021 $12,2122025 Owner on Record Assessor + 1 DocumentUpdated May 2026

78 S Highland Ave

4 bd · 4 ba · 3,627 sqft · built 1900 · 0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$349,000Feb 2005 $11,7072025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

79 S Highland Ave

0.339 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,450,000Jun 2017 $100,9392025 Amount on Record May 2013 Owner on Record Assessor + 2 DocumentsUpdated May 2026

80 S Highland Ave

9 bd · 3 ba · 3,690 sqft · built 1872 · 0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$999,000Oct 2024 $10,7372025 Amount on Record Sep 2000 2 Owners on Record AssessorUpdated May 2026

82 S Highland Ave

3 bd · 3 ba · 2,244 sqft · built 1890 · 0.169 acres

Last Sale Tax Bill Prior Sale Owner Records
$450,000Sep 2004 $12,4832025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

84 S Highland Ave

5 bd · 3 ba · 2,767 sqft · built 1890 · 0.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$246,750Jan 2016 $13,6102025 Amount on Record Oct 2015 2 Owners on Record Owner Occupied AssessorUpdated May 2026

86 S Highland Ave

8 bd · 4 ba · 4,310 sqft · built 1870 · 0.389 acres

Last Sale Tax Bill Prior Sale Owner Records
$13,7282025 Owner on Record Assessor + 2 DocumentsUpdated May 2026

90 S Highland Ave

0.789 acres

Last Sale Tax Bill Prior Sale Owner Records
$605,000Oct 2021 $13,3162025 2 Owners on Record Assessor + 1 DocumentUpdated Jun 2026

92 S Highland Ave

0.33 acres

Last Sale Tax Bill Prior Sale Owner Records
$495,000Oct 2021 Amount on Record Apr 1996 2 Owners on Record AssessorUpdated Jun 2023

94 S Highland Ave

0.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$449,000Jan 2014 $26,1822025 Owner on Record AssessorUpdated May 2026

96 S Highland Ave

6 bd · 3.5 ba · 1,912 sqft · built 1900 · 0.13 acres

Last Sale Tax Bill Prior Sale Owner Records
$253,000Jun 2001 $12,1532025 2 Owners on Record AssessorUpdated May 2026

100 S Highland Ave

0.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$190,000Jan 2017 2 Owners on Record AssessorUpdated Feb 2024
Last Sale Tax Bill Prior Sale Owner Records
$2,3342020 Owner on Record Owner Occupied AssessorUpdated Jun 2023

122 S Highland Ave

5 bd · 3 ba · 1,698 sqft · built 1926 · 0.25 acres

Last Sale Tax Bill Prior Sale Owner Records
$615,000Jul 2022 $14,2542025 2 Owners on Record Assessor + 1 DocumentUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
$11,408,947Jun 1987 $425,0622020 Owner on Record Assessor + 2 DocumentsUpdated Jun 2023
Last Sale Tax Bill Prior Sale Owner Records
Owner on Record Owner Occupied AssessorUpdated May 2024

124 S Highland Ave

7 bd · 3 ba · 2,920 sqft · built 1926 · 0.339 acres

Last Sale Tax Bill Prior Sale Owner Records
$735,000Jan 2026 $14,6852025 2 Owners on Record Assessor + 1 DocumentUpdated Jul 2026

128 S Highland Ave

3 bd · 2 ba · 962 sqft · built 1963 · 0.169 acres

Last Sale Tax Bill Prior Sale Owner Records
$640,000Jul 2026 $8,9742025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

130 S Highland Ave

3 bd · 1 ba · 1,170 sqft · built 1961 · 0.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$153,000Mar 1996 $9,6302025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

132 S Highland Ave

3 bd · 2 ba · 836 sqft · built 1961 · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$631,000Jun 2025 $4,9182025 Amount on Record Mar 2000 Owner on Record Assessor + 2 DocumentsUpdated Aug 2026

140 S Highland Ave

0.489 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,820,000Aug 2024 $31,7372025 Owner on Record AssessorUpdated Jul 2026
Last Sale Tax Bill Prior Sale Owner Records
$1,300,000Nov 2022 $28,8002025 Owner on Record Assessor + 1 DocumentUpdated May 2026

150 S Highland Ave

0.169 acres

Last Sale Tax Bill Prior Sale Owner Records
$220,000Jun 1998 $13,2432025 Owner on Record AssessorUpdated May 2026

151 S Highland Ave

0.88 acres

Last Sale Tax Bill Prior Sale Owner Records
$128,500Jun 1998 $103,2502025 Amount on Record Mar 1998 Owner on Record Assessor + 1 DocumentUpdated May 2026

152 S Highland Ave

0.33 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,902,500Jan 2008 $30,4512025 Amount on Record Mar 2002 Owner on Record AssessorUpdated May 2026

153 S Highland Ave

0.25 acres

Last Sale Tax Bill Prior Sale Owner Records
$14,5162025 Owner on Record Assessor + 1 DocumentUpdated May 2026

154 S Highland Ave

0.25 acres

Last Sale Tax Bill Prior Sale Owner Records
$309,500May 2005 $15,0442025 Owner on Record AssessorUpdated May 2026

157 S Highland Ave

0.339 acres

Last Sale Tax Bill Prior Sale Owner Records
$23,3752025 Owner on Record AssessorUpdated May 2026

160 S Highland Ave

0.169 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,993,942Nov 2021 $38,4862025 Amount on Record Aug 2010 Owner on Record AssessorUpdated May 2026

170 S Highland Ave

0.769 acres

Last Sale Tax Bill Prior Sale Owner Records
$30,2162025 Owner on Record AssessorUpdated May 2026

174 S Highland Ave

1.06 acres

Last Sale Tax Bill Prior Sale Owner Records
$31,4192025 Owner on Record AssessorUpdated May 2026

176 S Highland Ave

4 bd · 1.5 ba · 1,080 sqft · built 1900 · 0.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$300,000May 2013 $9,4212025 Owner on Record AssessorUpdated May 2026

178 S Highland Ave

0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$11,6382025 Owner on Record AssessorUpdated May 2026

180 S Highland Ave

4 bd · 1.5 ba · 1,152 sqft · built 1922 · 0.13 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,9942025 Owner on Record AssessorUpdated May 2026

182 S Highland Ave

2 bd · 1 ba · 620 sqft · built 1930 · 0.169 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,5392025 Owner on Record AssessorUpdated May 2026

184 S Highland Ave

0.189 acres

Last Sale Tax Bill Prior Sale Owner Records
$203,000Jun 2000 $19,7392025 Owner on Record AssessorUpdated May 2026

186 S Highland Ave

0.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,6922025 Owner on Record AssessorUpdated May 2026

188 S Highland Ave

4 bd · 2 ba · 2,946 sqft · built 1900 · 0.169 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,7642025 Owner on Record AssessorUpdated May 2026

189 S Highland Ave

0.169 acres

Last Sale Tax Bill Prior Sale Owner Records
$210,000Oct 2001 $14,2822025 Owner on Record AssessorUpdated May 2026

190 S Highland Ave

0.119 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,800,000Apr 2023 $7,9772025 Owner on Record Assessor + 1 DocumentUpdated May 2026

194 S Highland Ave

0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$400,000Jul 1999 $29,6312025 Owner on Record AssessorUpdated May 2026

197 S Highland Ave

0.35 acres

Last Sale Tax Bill Prior Sale Owner Records
$600,000Dec 2013 $21,7652025 Owner on Record AssessorUpdated May 2026

200 S Highland Ave

0.51 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,800,000Apr 2023 $31,0252025 Amount on Record Dec 1995 Owner on Record AssessorUpdated May 2026

210 S Highland Ave

3.26 acres

Last Sale Tax Bill Prior Sale Owner Records
$115,7792025 Owner on Record Assessor + 1 DocumentUpdated May 2026

246 S Highland Ave

4.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$430,000Apr 2008 $256,2972025 Amount on Record Mar 1995 Owner on Record AssessorUpdated May 2026

252 S Highland Ave

3 bd · 2 ba · 1,676 sqft · built 1939 · 0.519 acres

Last Sale Tax Bill Prior Sale Owner Records
$10,5022025 Owner on Record Owner Occupied AssessorUpdated May 2026

256 S Highland Ave

3 bd · 1.5 ba · 1,482 sqft · built 1956 · 0.539 acres

Last Sale Tax Bill Prior Sale Owner Records
$185,000Feb 1994 $11,7612025 Owner on Record Owner Occupied AssessorUpdated May 2026

258 S Highland Ave

2 bd · 2 ba · 887 sqft · built 1952 · 0.53 acres

Last Sale Tax Bill Prior Sale Owner Records
$220,000Sep 2019 $11,5742025 Amount on Record Feb 2005 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

260 S Highland Ave

3 bd · 2.5 ba · 2,062 sqft · built 1971 · 0.76 acres

Last Sale Tax Bill Prior Sale Owner Records
$450,000Jul 2018 $13,7122025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

264 S Highland Ave

3 bd · 1.5 ba · 1,352 sqft · built 1963 · 0.719 acres

Last Sale Tax Bill Prior Sale Owner Records
$470,000Feb 2005 $11,3352025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

266 S Highland Ave

5 bd · 3.5 ba · 4,842 sqft · built 1949 · 1.13 acres

Last Sale Tax Bill Prior Sale Owner Records
$464,500Aug 2013 $21,2692025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

268 S Highland Ave

3 bd · 3 ba · 2,080 sqft · built 1980 · 0.65 acres

Last Sale Tax Bill Prior Sale Owner Records
$760,000Aug 2020 $18,6872025 Amount on Record Jun 2016 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

270 S Highland Ave

3 bd · 3 ba · 2,144 sqft · built 1956 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$615,000Mar 2006 $17,2502025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

272 S Highland Ave

3 bd · 2 ba · 1,856 sqft · built 1955 · 0.689 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,0932025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

282 S Highland Ave

3 bd · 3 ba · 2,366 sqft · built 1955 · 0.689 acres

Last Sale Tax Bill Prior Sale Owner Records
$14,2032025 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

284 S Highland Ave

4 bd · 2.5 ba · 2,352 sqft · built 1998 · 0.36 acres

Last Sale Tax Bill Prior Sale Owner Records
$17,0182025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

286 S Highland Ave

4 bd · 2.5 ba · 2,352 sqft · built 1998 · 0.339 acres

Last Sale Tax Bill Prior Sale Owner Records
$500,000Oct 2006 $16,1302025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

288 S Highland Ave

4 bd · 2.5 ba · 2,650 sqft · built 1991 · 0.319 acres

Last Sale Tax Bill Prior Sale Owner Records
$16,8382025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

290 S Highland Ave

4 bd · 2.5 ba · 2,538 sqft · built 1991 · 0.339 acres

Last Sale Tax Bill Prior Sale Owner Records
$16,0142025 Owner on Record Owner Occupied AssessorUpdated May 2026

292 S Highland Ave

4 bd · 2.5 ba · 2,500 sqft · built 1989 · 0.339 acres

Last Sale Tax Bill Prior Sale Owner Records
$380,000May 2009 $16,9982025 Amount on Record Nov 2008 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

294 S Highland Ave

4 bd · 2.5 ba · 2,500 sqft · built 1989 · 0.31 acres

Last Sale Tax Bill Prior Sale Owner Records
$244,000Sep 1997 $15,4362025 Amount on Record Nov 1994 Owner on Record Owner Occupied AssessorUpdated May 2026

8189 S Highland Ave

1.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$12,9272025 Owner on Record Assessor + 3 DocumentsUpdated Jul 2026
Last Sale Tax Bill Prior Sale Owner Records
$152,9332025 Owner on Record Assessor + 8 DocumentsUpdated May 2026
Last Sale Tax Bill Prior Sale Owner Records
$602,6312025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
$19,500Mar 1995 $336,1012025 Owner on Record Owner Occupied AssessorUpdated May 2026
Last Sale Tax Bill Prior Sale Owner Records
$380,9922025 Owner on Record AssessorUpdated May 2026

Property Records in Nearby Streets