Oak Dr, New Windsor, NY Property Records

Orange County, New Windsor Town and Cornwall Town property records for 30 addresses on Oak Dr, New Windsor, NY · Last verified August 2026

Oak Dr Highlights

Properties 30
Median Sale Price $230,000
Deeds and Mortgages on File 22
Median Price per Sqft $196
Owner Occupied 80%
Median Annual Tax Bill $7,809
Median Year Built 1957
Median Ownership Tenure 8 years

Properties on Oak Dr

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

2 Oak Dr

4 bd · 2.5 ba · 1,863 sqft · built 1965 · 0.339 acres

Last Sale Tax Bill Prior Sale Owner Records
$240,000Jul 2013 $10,8472024 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5 Oak Dr

4 bd · 2 ba · 2,480 sqft · built 1939 · 0.51 acres

Last Sale Tax Bill Prior Sale Owner Records
1 Name on Record Owner Occupied AssessorUpdated Feb 2024

8 Oak Dr

6 bd · 5 ba · 4,407 sqft · built 1949 · 0.35 acres

Last Sale Tax Bill Prior Sale Owner Records
$375,000Jul 2008 $16,3612024 —Jun 2008 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

13 Oak Dr

2 bd · 1 ba · 816 sqft · built 1930 · 0.139 acres

Last Sale Tax Bill Prior Sale Owner Records
$160,000Mar 2021 $6,3502024 Amount on Record Jul 2017 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

300 Oak Dr

3 bd · 1 ba · 1,523 sqft · built 1949 · 0.141 acres

Last Sale Tax Bill Prior Sale Owner Records
$285,000Jul 2006 $7,4142024 1 Name on Record Owner Occupied AssessorUpdated May 2026

302 Oak Dr

3 bd · 2 ba · 1,150 sqft · built 1950 · 0.344 acres

Last Sale Tax Bill Prior Sale Owner Records
$230,000Nov 2021 $6,1692024 Amount on Record Aug 2002 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

303 Oak Dr

3 bd · 2 ba · 1,154 sqft · built 1940 · 0.317 acres

Last Sale Tax Bill Prior Sale Owner Records
$205,000Dec 2013 $4,6432024 1 Name on Record Owner Occupied AssessorUpdated May 2026

306 Oak Dr

3 bd · 2 ba · 1,040 sqft · built 1986 · 0.086 acres

Last Sale Tax Bill Prior Sale Owner Records
$404,900Sep 2021 $7,9562024 Amount on Record Jul 2016 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

309 Oak Dr

3 bd · 1 ba · 1,334 sqft · built 1940 · 0.246 acres

Last Sale Tax Bill Prior Sale Owner Records
$219,000Nov 2010 $6,3872024 1 Name on Record AssessorUpdated May 2026

314 Oak Dr

4 bd · 2 ba · 1,352 sqft · built 1950 · 0.12 acres

Last Sale Tax Bill Prior Sale Owner Records
$202,000Jun 2024 $4,6422024 Amount on Record Dec 1999 1 Name on Record AssessorUpdated May 2026

315 Oak Dr

3 bd · 2 ba · 1,568 sqft · built 1958 · 0.472 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,7212024 2 Names on Record Owner Occupied AssessorUpdated May 2026

320 Oak Dr

3 bd · 2 ba · 1,632 sqft · built 1974 · 0.215 acres

Last Sale Tax Bill Prior Sale Owner Records
$278,000Sep 2004 $7,9122024 Amount on Record Nov 1998 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

326 Oak Dr

4 bd · 2 ba · 1,392 sqft · built 1972 · 0.321 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,000Feb 2019 $2362024 Amount on Record Apr 2007 2 Names on Record AssessorUpdated May 2026

327 Oak Dr

3 bd · 2 ba · 1,248 sqft · built 1987 · 0.358 acres

Last Sale Tax Bill Prior Sale Owner Records
$430,000Nov 2023 $9,5092024 Amount on Record Jun 2004 2 Names on Record Assessor + 2 DocumentsUpdated May 2026

329 Oak Dr

2 bd · 1 ba · 900 sqft · built 1981 · 0.143 acres

Last Sale Tax Bill Prior Sale Owner Records
$184,900Feb 2004 $5,1232024 Amount on Record Dec 1999 2 Names on Record Owner Occupied AssessorUpdated May 2026

331 Oak Dr

4 bd · 1 ba · 2,000 sqft · built 1986 · 0.215 acres

Last Sale Tax Bill Prior Sale Owner Records
$163,000Feb 2024 $10,2012024 Amount on Record Nov 2007 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

333 Oak Dr

2 bd · 1 ba · 942 sqft · built 1957 · 0.215 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,000May 2022 $5,0362024 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

334 Oak Dr

4 bd · 1.5 ba · 1,652 sqft · built 1972 · 0.135 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,8092024 1 Name on Record Owner Occupied AssessorUpdated May 2026

335 Oak Dr

3 bd · 1.5 ba · 1,664 sqft · built 1986 · 0.071 acres

Last Sale Tax Bill Prior Sale Owner Records
$490,000Jul 2026 $8,0432024 Amount on Record Sep 2016 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

340 Oak Dr

2 bd · 1 ba · 1,096 sqft · built 1950 · 0.011 acres

Last Sale Tax Bill Prior Sale Owner Records
$112,500Jan 2000 $4,9922024 1 Name on Record Owner Occupied AssessorUpdated May 2026

353 Oak Dr

2 bd · 2 ba · 1,952 sqft · built 1983 · 0.43 acres

Last Sale Tax Bill Prior Sale Owner Records
$198,000Jun 2009 $10,3972024 2 Names on Record Owner Occupied AssessorUpdated May 2026

354 Oak Dr

3 bd · 1.5 ba · 3,084 sqft · built 1920 · 0.644 acres

Last Sale Tax Bill Prior Sale Owner Records
$159,000Dec 1999 $9,4382024 2 Names on Record Owner Occupied AssessorUpdated May 2026

357 Oak Dr

3 bd · 1 ba · 1,601 sqft · built 1956 · 0.143 acres

Last Sale Tax Bill Prior Sale Owner Records
$115,000Oct 2018 $4,9052024 —Feb 2017 1 Name on Record Assessor + 2 DocumentsUpdated May 2026

359 Oak Dr

3 bd · 1 ba · 1,069 sqft · built 1956 · 0.143 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,8882024 2 Names on Record Owner Occupied AssessorUpdated May 2026

360 Oak Dr

3 bd · 1.5 ba · 1,740 sqft · built 1982 · 0.373 acres

Last Sale Tax Bill Prior Sale Owner Records
$265,000Jun 2019 $8,7192024 Amount on Record Nov 2016 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

361 Oak Dr

5 bd · 3 ba · 2,404 sqft · built 1950 · 0.143 acres

Last Sale Tax Bill Prior Sale Owner Records
$461,250Jan 2025 $9,0892024 Amount on Record Nov 1994 1 Name on Record Assessor + 1 DocumentUpdated May 2026

362 Oak Dr

3 bd · 1.5 ba · 1,740 sqft · built 1982 · 0.363 acres

Last Sale Tax Bill Prior Sale Owner Records
$280,000Jan 2007 $8,4792024 1 Name on Record Owner Occupied AssessorUpdated May 2026

363 Oak Dr

2 bd · 1 ba · 814 sqft · built 1950 · 0.286 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,0892024 2 Names on Record Owner Occupied AssessorUpdated May 2026

364 Oak Dr

2 bd · 1 ba · 1,175 sqft · built 1942 · 0.325 acres

Last Sale Tax Bill Prior Sale Owner Records
$135,000Sep 2000 $5,6242024 2 Names on Record Owner Occupied AssessorUpdated May 2026

370 Oak Dr

3 bd · 2 ba · 1,708 sqft · built 1982 · 0.282 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,1332024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

Wildfire Risk on Oak Dr

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

Wildfire RiskLow
this street's cells rank above 12% of the US · above 31% of New York
Wildfire LikelihoodAbout 1 in 7,547 per year
ExposureIndirect
0 of 4 cells directly exposed · 4 adjoin burnable vegetation

Property Records in Nearby Streets