Chestnut Ave, New Windsor, NY Property Records

Orange County, New Windsor Town and Cornwall Town property records for 38 addresses on Chestnut Ave, New Windsor, NY · Last verified August 2026

Chestnut Ave Highlights

Properties 38
Median Sale Price $385,000
Deeds and Mortgages on File 31
Median Price per Sqft $214
Owner Occupied 76%
Median Annual Tax Bill $9,850
Median Year Built 1984
Median Ownership Tenure 10 years

Properties on Chestnut Ave

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

102 Chestnut Ave

4 bd · 3.5 ba · 1,945 sqft · built 1995 · 0.339 acres

Last Sale Tax Bill Prior Sale Owner Records
$210,000Dec 2001 $12,3962024 Amount on Record Mar 1999 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

112 Chestnut Ave

4 bd · 2 ba · 2,140 sqft · built 1964 · 0.339 acres

Last Sale Tax Bill Prior Sale Owner Records
$12,0092024 1 Name on Record Owner Occupied AssessorUpdated May 2026

115 Chestnut Ave

3 bd · 1 ba · 985 sqft · built 1953 · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$211,000Sep 2025 $5,6332024 Amount on Record Apr 2025 1 Name on Record Assessor + 4 DocumentsUpdated May 2026

116 Chestnut Ave

4 bd · 2.5 ba · 2,486 sqft · built 1970 · 0.369 acres

Last Sale Tax Bill Prior Sale Owner Records
$144,500Apr 1997 $12,1222024 Amount on Record Aug 1996 1 Name on Record Owner Occupied AssessorUpdated May 2026

117 Chestnut Ave

3 bd · 2 ba · 1,444 sqft · built 1997 · 0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$225,000Feb 2021 $10,1902024 Amount on Record Feb 2013 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

119 Chestnut Ave

5 bd · 2.5 ba · 1,660 sqft · built 1960 · 0.239 acres

Last Sale Tax Bill Prior Sale Owner Records
$284,000Aug 2004 $10,3442024 Amount on Record Feb 2002 1 Name on Record Owner Occupied AssessorUpdated May 2026

120 Chestnut Ave

0.389 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,0822024 1 Name on Record AssessorUpdated May 2026

121 Chestnut Ave

3 bd · 1.5 ba · 1,272 sqft · built 1952 · 0.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$326,000Mar 2022 $9,6102024 1 Name on Record Assessor + 1 DocumentUpdated May 2026

122 Chestnut Ave

0.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$1612024 1 Name on Record AssessorUpdated May 2026

123 Chestnut Ave

0.039 acres

Last Sale Tax Bill Prior Sale Owner Records
$3042024 1 Name on Record AssessorUpdated May 2026

125 Chestnut Ave

0.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$1612024 1 Name on Record AssessorUpdated May 2026

301 Chestnut Ave

2 bd · 1 ba · 1,184 sqft · built 1954 · 0.255 acres

Last Sale Tax Bill Prior Sale Owner Records
$263,000Jan 2005 $5,7772024 1 Name on Record Owner Occupied AssessorUpdated May 2026

305 Chestnut Ave

3 bd · 1.5 ba · 1,520 sqft · built 1963 · 0.287 acres

Last Sale Tax Bill Prior Sale Owner Records
$185,400Jun 2016 $7,3682024 1 Name on Record Owner Occupied AssessorUpdated May 2026

307 Chestnut Ave

3 bd · 2 ba · 2,512 sqft · built 1987 · 0.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$133,000Mar 2020 $7,5642024 Amount on Record Nov 2012 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

308 Chestnut Ave

3 bd · 2.5 ba · 2,405 sqft · built 2005 · 0.6 acres

Last Sale Tax Bill Prior Sale Owner Records
$412,050Jul 2005 $12,9902024 Amount on Record Nov 2004 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

313 Chestnut Ave

4 bd · 2 ba · 2,821 sqft · built 1966 · 0.468 acres

Last Sale Tax Bill Prior Sale Owner Records
$575,000Jul 2026 $10,4032025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

314 Chestnut Ave

3 bd · 1 ba · 1,576 sqft · built 1955 · 1.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$366,500Sep 2009 $9,1382024 Amount on Record Oct 1998 1 Name on Record Owner Occupied AssessorUpdated May 2026

317 Chestnut Ave

3 bd · 1.5 ba · 1,612 sqft · built 1985 · 0.447 acres

Last Sale Tax Bill Prior Sale Owner Records
$237,000Jan 2013 $9,0672024 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

321 Chestnut Ave

5 bd · 3 ba · 2,482 sqft · built 1969 · 0.424 acres

Last Sale Tax Bill Prior Sale Owner Records
$425,000Nov 2020 $10,7022024 Amount on Record Dec 2017 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

324 Chestnut Ave

3 bd · 1.5 ba · 1,414 sqft · built 1986 · 0.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$640,000Mar 2025 $9,0892024 Amount on Record Oct 2005 1 Name on Record AssessorUpdated May 2026

325 Chestnut Ave

3 bd · 1.5 ba · 1,660 sqft · built 1971 · 0.413 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,3262024 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

329 Chestnut Ave

3 bd · 2.5 ba · 1,812 sqft · built 1971 · 0.413 acres

Last Sale Tax Bill Prior Sale Owner Records
$227,000Nov 2016 $8,7842024 1 Name on Record Owner Occupied AssessorUpdated May 2026

333 Chestnut Ave

3 bd · 1 ba · 1,660 sqft · built 1972 · 0.413 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,4532024 1 Name on Record Owner Occupied AssessorUpdated May 2026

340 Chestnut Ave

4 bd · 1.5 ba · 1,984 sqft · built 1986 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$275,000Jan 2016 $10,0862024 Amount on Record Dec 2014 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

343 Chestnut Ave

4.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$9822024 1 Name on Record AssessorUpdated May 2026

344 Chestnut Ave

4 bd · 2.5 ba · 2,109 sqft · built 1985 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$230,000Jul 2015 $10,4482024 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

354 Chestnut Ave

3 bd · 1 ba · 1,196 sqft · built 1985 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,8502024 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

362 Chestnut Ave

3 bd · 2 ba · 1,479 sqft · built 1983 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,1502024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

364 Chestnut Ave

3 bd · 1.5 ba · 2,208 sqft · built 1985 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$14,8602024 2 Names on Record Owner Occupied AssessorUpdated May 2026

368 Chestnut Ave

4 bd · 2.5 ba · 2,544 sqft · built 1985 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$263,000Nov 2017 $12,7462024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

369 Chestnut Ave

3 bd · 3 ba · 1,384 sqft · built 1987 · 0.497 acres

Last Sale Tax Bill Prior Sale Owner Records
$385,000Dec 2020 $11,6172024 Amount on Record Dec 2007 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

372 Chestnut Ave

3 bd · 1 ba · 1,171 sqft · built 1983 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$160,000Jun 2017 $9,4142024 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

376 Chestnut Ave

3 bd · 2 ba · 2,016 sqft · built 1986 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$344,000Feb 2008 $11,3902024 Amount on Record Nov 2000 1 Name on Record Owner Occupied AssessorUpdated May 2026

377 Chestnut Ave

3 bd · 2.5 ba · 1,236 sqft · built 1986 · 0.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$156,500Oct 1998 $9,1112024 2 Names on Record Owner Occupied AssessorUpdated May 2026

382 Chestnut Ave

4 bd · 3 ba · 2,784 sqft · built 1985 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$348,900Aug 2005 $12,7852024 1 Name on Record Owner Occupied AssessorUpdated May 2026

383 Chestnut Ave

3 bd · 2.5 ba · 2,143 sqft · built 1984 · 0.356 acres

Last Sale Tax Bill Prior Sale Owner Records
$472,000Jan 2025 $10,2442024 Amount on Record Jun 2003 1 Name on Record AssessorUpdated May 2026

388 Chestnut Ave

3 bd · 1 ba · 1,583 sqft · built 1983 · 1.7 acres

Last Sale Tax Bill Prior Sale Owner Records
$10,3752024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

389 Chestnut Ave

4 bd · 3.5 ba · 2,040 sqft · built 1988 · 0.401 acres

Last Sale Tax Bill Prior Sale Owner Records
$302,500Jul 2018 $11,0072024 Amount on Record Apr 2015 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

Wildfire Risk on Chestnut Ave

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

Wildfire RiskLow
this street's cells rank above 17% of the US · above 48% of New York
Wildfire LikelihoodAbout 1 in 5,172 per year
ExposureDirect
4 of 6 cells directly exposed · 6 adjoin burnable vegetation

Property Records in Nearby Streets