Hillside Dr, Oconomowoc, WI Property Records

Waukesha County property records for 22 addresses on Hillside Dr, Oconomowoc, WI · Last verified August 2026

Hillside Dr Highlights

Properties 22
Median Sale Price $385,000
Deeds and Mortgages on File 27
Median Price per Sqft $194
Owner Occupied 91%
Median Annual Tax Bill $4,404
Median Ownership Tenure 8 years

Properties on Hillside Dr

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

203 Hillside Dr

3 bd · 2 ba · 1,640 sqft · 0.289 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,3662025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

224 Hillside Dr

3 bd · 2.5 ba · 1,274 sqft · 0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,8562025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

227 Hillside Dr

3 bd · 1.5 ba · 1,800 sqft · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$231,500Apr 2016 $4,5632025 Amount on Record Jun 2010 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

230 Hillside Dr

0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$280,000Aug 2019 $4,2082025 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

235 Hillside Dr

3 bd · 2 ba · 1,232 sqft · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 2019 $3,5152025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

236 Hillside Dr

3 bd · 2 ba · 1,200 sqft · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$155,000Jul 1999 $4,4042025 —Aug 2020 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

239 Hillside Dr

3 bd · 2 ba · 1,976 sqft · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$385,000Jul 2024 $3,9882025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

240 Hillside Dr

3 bd · 1.5 ba · 1,352 sqft · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$178,000Sep 2002 $3,7822025 —Sep 2002 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

243 Hillside Dr

3 bd · 2 ba · 1,252 sqft · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$190,000Oct 2003 $4,0382025 Amount on Record Nov 1997 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

244 Hillside Dr

3 bd · 1.5 ba · 1,718 sqft · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,7422025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

245 Hillside Dr

3 bd · 2.5 ba · 2,213 sqft · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$534,900Apr 2025 $6,8972025 Amount on Record Nov 2018 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

246 Hillside Dr

3 bd · 2 ba · 2,094 sqft · 0.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$382,000May 2022 $4,6802025 Amount on Record Oct 2003 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

248 Hillside Dr

3 bd · 2 ba · 2,124 sqft · 0.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$202,000Aug 2015 $4,0362025 Amount on Record Aug 2013 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

250 Hillside Dr

3 bd · 2 ba · 1,628 sqft · 0.31 acres

Last Sale Tax Bill Prior Sale Owner Records
$172,000Sep 1998 $4,7612025 —Sep 1998 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

251 Hillside Dr

3 bd · 1 ba · 1,512 sqft · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$500,000Dec 2024 $5,1812025 Amount on Record Jun 2005 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

270 Hillside Dr

3 bd · 1.5 ba · 1,382 sqft · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$211,900Jul 2006 $4,4432025 Owner on Record AssessorUpdated Jul 2026

271 Hillside Dr

4 bd · 1.5 ba · 1,769 sqft · 0.289 acres

Last Sale Tax Bill Prior Sale Owner Records
$389,000May 2023 $4,3002025 Amount on Record Apr 1997 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

274 Hillside Dr

2 bd · 1.5 ba · 1,752 sqft · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,6122025 Owner on Record AssessorUpdated Jul 2026

280 Hillside Dr

2 bd · 2 ba · 1,340 sqft · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,8522025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

290 Hillside Dr

3 bd · 1.5 ba · 1,260 sqft · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$189,000Jun 2010 $3,5962025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

291 Hillside Dr

3 bd · 2 ba · 1,584 sqft · 0.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,6842025 —Nov 2000 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

296 Hillside Dr

3 bd · 2.5 ba · 1,772 sqft · 0.389 acres

Last Sale Tax Bill Prior Sale Owner Records
$295,000Aug 2018 $4,8122025 Amount on Record May 2012 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

Property Records in Nearby Streets