Chestnut Dr, New Windsor, NY Property Records

Orange County and New Windsor Town property records for 17 addresses on Chestnut Dr, New Windsor, NY · Last verified August 2026

Chestnut Dr Highlights

Properties 17
Median Sale Price $340,000
Deeds and Mortgages on File 11
Median Price per Sqft $197
Owner Occupied 88%
Median Annual Tax Bill $6,808
Median Year Built 1946
Median Ownership Tenure 9 years

Properties on Chestnut Dr

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

100 Chestnut Dr

3 bd · 2 ba · 1,248 sqft · built 1974 · 0.203 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,2832024 2 Names on Record AssessorUpdated May 2026

101 Chestnut Dr

3 bd · 1.5 ba · 1,664 sqft · built 1940 · 0.273 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,2062024 1 Name on Record Owner Occupied AssessorUpdated May 2026

102 Chestnut Dr

2 bd · 1 ba · 1,512 sqft · built 1940 · 0.251 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,8662024 1 Name on Record Owner Occupied AssessorUpdated May 2026

103 Chestnut Dr

3 bd · 1 ba · 1,068 sqft · built 1948 · 0.176 acres

Last Sale Tax Bill Prior Sale Owner Records
$87,600Aug 1999 $6,4342024 1 Name on Record Owner Occupied AssessorUpdated May 2026

106 Chestnut Dr

3 bd · 1.5 ba · 2,740 sqft · built 1955 · 0.607 acres

Last Sale Tax Bill Prior Sale Owner Records
$340,000Jan 2007 $9,1252024 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

107 Chestnut Dr

2 bd · 2 ba · 3,332 sqft · built 1950 · 0.426 acres

Last Sale Tax Bill Prior Sale Owner Records
$10,0612024 2 Names on Record Owner Occupied AssessorUpdated May 2026

108 Chestnut Dr

3 bd · 1.5 ba · 1,930 sqft · built 1949 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$130,000Nov 1999 $6,5142024 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

109 Chestnut Dr

3 bd · 1 ba · 1,743 sqft · built 1954 · 0.117 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,9192024 1 Name on Record Owner Occupied AssessorUpdated May 2026

110 Chestnut Dr

4 bd · 2 ba · 1,546 sqft · built 1950 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,6232024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

111 Chestnut Dr

4 bd · 2 ba · 2,128 sqft · built 1948 · 0.194 acres

Last Sale Tax Bill Prior Sale Owner Records
$265,000Sep 2013 $7,1572024 Amount on Record Nov 2003 1 Name on Record Owner Occupied AssessorUpdated May 2026

112 Chestnut Dr

4 bd · 1.5 ba · 1,489 sqft · built 1942 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,7382024 1 Name on Record Owner Occupied AssessorUpdated May 2026

114 Chestnut Dr

3 bd · 2 ba · 1,484 sqft · built 1941 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$525,000Jun 2026 $7,1012025 Amount on Record Dec 2022 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

115 Chestnut Dr

4 bd · 2 ba · 1,906 sqft · built 1946 · 0.189 acres

Last Sale Tax Bill Prior Sale Owner Records
$500,000Oct 2024 $6,8082024 Amount on Record Jan 1999 2 Names on Record AssessorUpdated May 2026

116 Chestnut Dr

2 bd · 1.5 ba · 1,344 sqft · built 1941 · 0.333 acres

Last Sale Tax Bill Prior Sale Owner Records
$283,584Jul 2024 $7,0312024 Amount on Record Apr 2017 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

117 Chestnut Dr

2 bd · 1 ba · 1,590 sqft · built 1946 · 0.378 acres

Last Sale Tax Bill Prior Sale Owner Records
$149,000May 2017 $6,2002024 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

121 Chestnut Dr

3 bd · 2.5 ba · 2,116 sqft · built 1946 · 0.202 acres

Last Sale Tax Bill Prior Sale Owner Records
$179,000Jul 2001 $7,8382024 Amount on Record Jan 2000 1 Name on Record Owner Occupied AssessorUpdated May 2026

125 Chestnut Dr

3 bd · 1.5 ba · 1,768 sqft · built 1941 · 0.184 acres

Last Sale Tax Bill Prior Sale Owner Records
$350,000Nov 2021 $6,7382024 Amount on Record Jul 2006 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

Wildfire Risk on Chestnut Dr

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

Wildfire RiskNot rated
no burnable land in reach
Wildfire LikelihoodNegligible
ExposureNone
beyond ember reach

Property Records in Nearby Streets