Oakside Dr, Smithtown, NY Property Records

Suffolk County and Smithtown Town property records for 80 addresses on Oakside Dr, Smithtown, NY · Last verified August 2026

Oakside Dr Highlights

Properties 80
Median Sale Price $940,000
Deeds and Mortgages on File 92
Median Price per Sqft $343
Owner Occupied 85%
Median Annual Tax Bill $19,144
Median Year Built 1965
Median Ownership Tenure 13 years

Properties on Oakside Dr

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

97 Oakside Dr

3 bd · 1 ba · 1,574 sqft · 0.939 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$430,000Jun 2002 $15,0202024 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

99 Oakside Dr

2 ba · 2,125 sqft · 2 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$570,000Mar 2015 $19,4182024 Amount on Record Mar 2008 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

101 Oakside Dr

2 acres

Last Sale Tax Bill Prior Sale Owner Records
$10,4462024 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

102 Oakside Dr

1.78 acres

Last Sale Tax Bill Prior Sale Owner Records
$499,000Jul 2013 $13,6292024 1 Name on Record Assessor + 1 DocumentUpdated Aug 2026

103 Oakside Dr

3 bd · 2 ba · 2,443 sqft · 1.5 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$655,000Sep 2003 $17,8152024 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

104 Oakside Dr

3 bd · 1.5 ba · 1,570 sqft · 1.46 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$125,000Mar 1998 $14,7302024 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

105 Oakside Dr

3 bd · 1 ba · 1,444 sqft · 2.41 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$624,000Sep 2018 $15,4532024 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

106 Oakside Dr

4 bd · 1.5 ba · 1,744 sqft · 1.48 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$350,000Jun 2001 $14,7452024 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

107 Oakside Dr

4 bd · 2.5 ba · 2,403 sqft · 1.5 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,000Apr 2020 $15,1842024 Amount on Record Dec 1998 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

108 Oakside Dr

2 bd · 3 ba · 2,726 sqft · 2 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$370,000Apr 2000 $20,8742024 Amount on Record Mar 1998 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

109 Oakside Dr

4 bd · 2 ba · 2,283 sqft · 2 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,300,000May 2026 $28,6192024 Amount on Record Sep 2011 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

110 Oakside Dr

2 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,3412024 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

111 Oakside Dr

2 acres

Last Sale Tax Bill Prior Sale Owner Records
$690,500Nov 2023 $19,1872024 —May 2012 1 Name on Record Assessor + 1 DocumentUpdated Aug 2026

112 Oakside Dr

4 bd · 2.5 ba · 3,190 sqft · 2.01 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$945,000Mar 2021 $27,1422024 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

113 Oakside Dr

3 bd · 2 ba · 1,731 sqft · 1.5 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$535,000Oct 2017 $16,9602024 Amount on Record Aug 1999 1 Name on Record Assessor + 2 DocumentsUpdated Aug 2026

114 Oakside Dr

1.08 acres

Last Sale Tax Bill Prior Sale Owner Records
$712,000Dec 2005 $17,8902024 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

115 Oakside Dr

3 bd · 2 ba · 1,570 sqft · 1.5 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$215,000Apr 1997 $16,9042024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

115A Oakside Dr

2 acres

Last Sale Tax Bill Prior Sale Owner Records
$18,6542024 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

116 Oakside Dr

4 bd · 2.5 ba · 2,726 sqft · 1.46 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$672,000Feb 2003 $19,5492024 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

117 Oakside Dr

1 ba · 1,218 sqft · 1.53 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$200,000Sep 1993 $12,6742024 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

118 Oakside Dr

4 bd · 3 ba · 2,459 sqft · 2 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$16,2282024 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

119 Oakside Dr

4 bd · 2 ba · 2,940 sqft · 2.31 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$540,000May 2017 $18,9932024 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

120 Oakside Dr

2.88 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,0962024 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

121 Oakside Dr

4 bd · 2 ba · 2,169 sqft · 2 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$600,000Jun 2004 $19,2692024 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

123 Oakside Dr

4 bd · 2 ba · 1,893 sqft · 1.8 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$465,000Dec 2001 $15,7942024 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

125 Oakside Dr

1.81 acres

Last Sale Tax Bill Prior Sale Owner Records
$692,000Jan 2020 $20,4042024 Amount on Record Oct 2012 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

130 Oakside Dr

1.55 acres

Last Sale Tax Bill Prior Sale Owner Records
$120,000Oct 1994 $41,9022024 Amount on Record — 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

131 Oakside Dr

2 ba · 1,802 sqft · 1.86 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$320,000Oct 2024 $20,1412024 Amount on Record Apr 2022 2 Names on Record Assessor + 2 DocumentsUpdated Aug 2026

132 Oakside Dr

4 bd · 4.5 ba · 4,182 sqft · 2 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,350,000Oct 2021 $32,9312024 —Feb 2005 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

134 Oakside Dr

2.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$445,000Sep 1999 $24,5522024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

135 Oakside Dr

3 bd · 2.5 ba · 2,474 sqft · 1.61 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Dec 2010 $20,3422024 Amount on Record Jun 1996 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

136 Oakside Dr

3 bd · 2 ba · 3,028 sqft · 1.9 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$780,000Nov 2003 $23,2852024 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

137 Oakside Dr

4 bd · 4 ba · 4,717 sqft · 1.81 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$23,2672024 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

138 Oakside Dr

3 ba · 2,352 sqft · 1.8 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$950,000Dec 2021 $22,7402024 Amount on Record May 2002 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

139 Oakside Dr

3 bd · 2 ba · 1,551 sqft · 1.01 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$175,000Apr 1997 $15,3942024 Amount on Record — 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

140 Oakside Dr

3 bd · 1.5 ba · 1,941 sqft · 1.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$14,7612024 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

141 Oakside Dr

2.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$25,3092024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

143 Oakside Dr

1 acres

Last Sale Tax Bill Prior Sale Owner Records
$400,000Sep 2023 $13,2422024 Amount on Record Feb 2009 2 Names on Record Assessor + 2 DocumentsUpdated Aug 2026

143B Oakside Dr

4 bd · 3 ba · 3,072 sqft · 2 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$850,000Jan 2006 $22,4002024 Amount on Record Aug 2000 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

144 Oakside Dr

1.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,7802024 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

145 Oakside Dr

5 bd · 3 ba · 2,028 sqft · 1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Jan 2012 $12,8912024 Amount on Record Aug 1995 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

146 Oakside Dr

5 bd · 7.5 ba · 4,818 sqft · 2.88 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$2,790,000Aug 2024 $40,8162024 Amount on Record Oct 2000 2 Names on Record Assessor + 1 DocumentUpdated Aug 2026

147 Oakside Dr

3 bd · 1 ba · 1,749 sqft · 1.31 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$395,000Feb 2002 $14,0262024 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

148 Oakside Dr

4 bd · 2 ba · 2,422 sqft · 2 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,545,000Aug 2024 $19,6802024 Amount on Record Jun 2014 1 Name on Record AssessorUpdated Aug 2026

149 Oakside Dr

3 bd · 2 ba · 2,533 sqft · 3.4 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$25,7292024 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

150 Oakside Dr

5 bd · 3.5 ba · 3,925 sqft · 1.2 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$31,6132024 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

151 Oakside Dr

3 bd · 2 ba · 2,009 sqft · 1.61 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$308,019Jan 2005 $16,5722024 Amount on Record Feb 1999 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

152 Oakside Dr

2.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,3232024 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

154 Oakside Dr

4 bd · 5 ba · 4,679 sqft · 1.5 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$2,412,500Sep 2015 $43,6992024 Amount on Record Apr 2004 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

155 Oakside Dr

4 bd · 2 ba · 2,108 sqft · 1.61 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$320,000Jan 2000 $20,4292024 2 Names on Record Assessor + 2 DocumentsUpdated Aug 2026

156 Oakside Dr

5 bd · 2 ba · 2,178 sqft · 2 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$550,000May 2002 $20,6192024 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

158 Oakside Dr

4 bd · 2 ba · 3,420 sqft · 2.01 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$940,000Jul 2023 $19,6912024 Amount on Record Jun 2017 1 Name on Record Assessor + 5 DocumentsUpdated Aug 2026

159 Oakside Dr

1.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$13,6652024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

159A Oakside Dr

1.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$280,500Jan 1995 $21,5292024 Amount on Record May 1994 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

160 Oakside Dr

2 acres

Last Sale Tax Bill Prior Sale Owner Records
$14,4032024 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

161 Oakside Dr

4 bd · 2 ba · 2,348 sqft · 1.5 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$561,000Apr 2012 $18,5322024 Amount on Record May 2002 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

162 Oakside Dr

2 acres

Last Sale Tax Bill Prior Sale Owner Records
$667,000Aug 2024 $19,8482024 1 Name on Record Assessor + 2 DocumentsUpdated Aug 2026

163 Oakside Dr

4 bd · 2 ba · 1,749 sqft · 1.51 acres

Last Sale Tax Bill Prior Sale Owner Records
$495,000Nov 2018 $18,7322024 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

164 Oakside Dr

4 bd · 3.5 ba · 3,512 sqft · 2 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$26,7302024 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

165 Oakside Dr

3 bd · 1 ba · 1,700 sqft · 1.5 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$549,000Jul 2019 $17,7312024 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

166 Oakside Dr

3 bd · 2.5 ba · 2,701 sqft · 2 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$650,000Apr 2018 $20,0552024 Amount on Record May 2017 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

167 Oakside Dr

2.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$14,8702024 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

167 Oakside Dr, #A

5 bd · 3.5 ba · 3,625 sqft · 1.5 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$900,000Mar 2003 $22,4692024 Amount on Record Feb 2002 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

168 Oakside Dr

1.05 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,7622024 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

169 Oakside Dr

4 bd · 2.5 ba · 2,110 sqft · 1.5 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$675,000May 2019 $19,9302024 Amount on Record Nov 2006 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

170 Oakside Dr

4 bd · 2.5 ba · 1,998 sqft · 1.01 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$460,000Sep 2010 $13,7222024 Amount on Record Mar 1996 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

170A Oakside Dr

4 bd · 3 ba · 3,054 sqft · 1.46 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$500,000Oct 2017 $19,3672024 Amount on Record Jun 2003 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

171 Oakside Dr

2 acres

Last Sale Tax Bill Prior Sale Owner Records
$490,000Feb 2018 $17,2602024 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

172 Oakside Dr

3.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$900,000Sep 2006 $24,9192024 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

173 Oakside Dr

1.48 acres

Last Sale Tax Bill Prior Sale Owner Records
$879,000Oct 2024 $19,1362024 Amount on Record Aug 2020 2 Names on Record AssessorUpdated Aug 2026

175 Oakside Dr

2 ba · 2,825 sqft · 2 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$20,6842024 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

175 Oakside Dr, #A

4 bd · 3.5 ba · 3,396 sqft · 1.51 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$500,000Mar 2006 $31,7162024 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

176 Oakside Dr

4 bd · 2 ba · 1,806 sqft · 2 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$220,000Oct 1996 $14,9452024 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

178 Oakside Dr

4 bd · 2 ba · 2,213 sqft · 1.5 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$18,5042024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

180 Oakside Dr

5 bd · 3.5 ba · 3,811 sqft · 1.5 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,310,000Jul 2023 $34,1542024 Amount on Record Oct 2020 1 Name on Record Assessor + 3 DocumentsUpdated Aug 2026

181 Oakside Dr

4 bd · 3 ba · 2,711 sqft · 2 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$678,000Jul 2019 $19,4912024 Amount on Record Apr 2014 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

182 Oakside Dr

2.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$18,1082024 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

183 Oakside Dr

3 bd · 1.5 ba · 1,421 sqft · 1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$365,000May 2001 $13,2032024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

184 Oakside Dr

1 acres

Last Sale Tax Bill Prior Sale Owner Records
$649,000Nov 2016 $19,1442024 Amount on Record Mar 1994 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Aug 2026

186 Oakside Dr

3 bd · 2.5 ba · 2,449 sqft · 1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$641,000Oct 2013 $30,4892024 —Sep 2013 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

Wildfire Risk on Oakside Dr

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

Wildfire RiskLow
this street's cells rank at the 15th percentile of exposed land nationally · 41st in New York
Wildfire LikelihoodLow — about 1 in 6,587 per year
ExposureDirect
8 of 11 cells directly exposed · 11 adjoin burnable vegetation

Property Records in Nearby Streets