Chestnut Ave, Middletown, NY Property Records

Orange County and Middletown City property records for 15 addresses on Chestnut Ave, Middletown, NY · Last verified August 2026

Chestnut Ave Highlights

Properties 15
Median Sale Price $299,900
Deeds and Mortgages on File 20
Median Price per Sqft $191
Owner Occupied 60%
Median Annual Tax Bill $7,220
Median Year Built 1960
Median Ownership Tenure 9 years

Properties on Chestnut Ave

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

3 Chestnut Ave

0.004 acres

Last Sale Tax Bill Prior Sale Owner Records
$282024 1 Name on Record AssessorUpdated May 2026

10 Chestnut Ave

0.264 acres

Last Sale Tax Bill Prior Sale Owner Records
$40,000Sep 2015 $1,9992024 Amount on Record Mar 2013 1 Name on Record AssessorUpdated May 2026

12 Chestnut Ave

6 bd · 3.5 ba · 2,756 sqft · 0.264 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$530,000Jan 2025 $10,0242024 Amount on Record Sep 2014 1 Name on Record Assessor + 1 DocumentUpdated May 2026

14 Chestnut Ave

6 bd · 3 ba · 2,784 sqft · 0.235 acres

Last Sale Tax Bill Prior Sale Owner Records
$220,000Jan 2017 $11,4682024 1 Name on Record Assessor + 1 DocumentUpdated May 2026

21 Chestnut Ave

3 bd · 1.5 ba · 1,632 sqft · 0.217 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$169,000Nov 2017 $7,8752024 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

22 Chestnut Ave

3 bd · 1.5 ba · 1,056 sqft · 0.284 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$202,460Jun 2019 $6,6642024 Amount on Record May 2018 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

23 Chestnut Ave

3 bd · 1.5 ba · 1,346 sqft · 0.209 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$232,500Dec 2008 $7,2202024 Amount on Record May 2003 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

24 Chestnut Ave

3 bd · 1.5 ba · 1,056 sqft · 0.12 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$340,000Feb 2022 $7,0812024 1 Name on Record Owner Occupied Assessor + 5 DocumentsUpdated May 2026

26 Chestnut Ave

3 bd · 1.5 ba · 1,056 sqft · 0.2 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$115,000Oct 2013 $6,4142024 2 Names on Record Owner Occupied AssessorUpdated May 2026

27 Chestnut Ave

4 bd · 2 ba · 1,618 sqft · 0.214 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$299,900Dec 2020 $8,3582024 Amount on Record Mar 1998 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

28 Chestnut Ave

3 bd · 1.5 ba · 1,100 sqft · 0.21 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$395,000Oct 2023 $7,3802024 Amount on Record Dec 2018 2 Names on Record Assessor + 4 DocumentsUpdated May 2026

29 Chestnut Ave

3 bd · 2 ba · 1,368 sqft · 0.13 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$7,9972024 2 Names on Record Owner Occupied AssessorUpdated May 2026

30 Chestnut Ave

3 bd · 1.5 ba · 1,056 sqft · 0.204 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$137,500Jul 2016 $7,2472024 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

31 Chestnut Ave

2 bd · 1 ba · 984 sqft · 0.189 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$159,000Jan 2003 $6,9142024 Amount on Record Feb 2002 1 Name on Record Owner Occupied AssessorUpdated May 2026

32 Chestnut Ave

3 bd · 1 ba · 1,066 sqft · 0.254 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$118,000Aug 2019 $6,1922024 Amount on Record Aug 2008 1 Name on Record Assessor + 1 DocumentUpdated Jun 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 at the 20th percentile of exposed land nationally · 55th in New York
Wildfire LikelihoodLow — about 1 in 10,000 per year
ExposureIndirect
0 of 2 cells directly exposed

Property Records in Nearby Streets