Main St, Chester, NY Property Records

Orange County, Chester Town and Deerpark Town property records for 85 addresses on Main St, Chester, NY · Last verified August 2026

Main St Highlights

Properties 85
Median Sale Price $350,000
Deeds and Mortgages on File 88
Median Price per Sqft $109
Owner Occupied 32%
Median Annual Tax Bill $9,026
Median Year Built 1910
Median Ownership Tenure 8 years

Properties on Main St

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

2 Main St

2,400 sqft · built 1935 · 0.032 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,9332024 1 Name on Record AssessorUpdated May 2026

3 Main St

0.319 acres

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

6 Main St

3,600 sqft · built 1935 · 0.051 acres

Last Sale Tax Bill Prior Sale Owner Records
$185,000Sep 2013 $9,9812024 1 Name on Record AssessorUpdated Jun 2026

10 Main St

3,600 sqft · built 1935 · 0.048 acres

Last Sale Tax Bill Prior Sale Owner Records
$140,000Feb 2024 $7,8942024 1 Name on Record Assessor + 1 DocumentUpdated May 2026

11 Main St

1,932 sqft · built 1950 · 0.033 acres

Last Sale Tax Bill Prior Sale Owner Records
$210,000Oct 2018 $7,5472024 Amount on Record Jul 2007 2 Names on Record Assessor + 2 DocumentsUpdated May 2026

14 Main St

3,940 sqft · built 1920 · 0.048 acres

Last Sale Tax Bill Prior Sale Owner Records
$140,000Feb 2024 $7,9012024 1 Name on Record Assessor + 1 DocumentUpdated May 2026

18 Main St, #20

2,160 sqft · built 1935 · 0.048 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,500Aug 1997 $5,7382024 1 Name on Record AssessorUpdated May 2026

19 Main St

5,166 sqft · built 1940 · 0.059 acres

Last Sale Tax Bill Prior Sale Owner Records
$13,5142024 1 Name on Record Assessor + 1 DocumentUpdated May 2026

22 Main St

2,160 sqft · built 1965 · 0.048 acres

Last Sale Tax Bill Prior Sale Owner Records
$120,000May 2000 $7,0952024 Amount on Record Nov 1996 2 Names on Record Assessor + 1 DocumentUpdated May 2026

23 Main St, #27

4,510 sqft · built 1940 · 0.041 acres

Last Sale Tax Bill Prior Sale Owner Records
$600,000May 2025 $11,2262024 Amount on Record Oct 1999 1 Name on Record AssessorUpdated May 2026

26 Main St

3,420 sqft · built 1935 · 0.048 acres

Last Sale Tax Bill Prior Sale Owner Records
$140,000Feb 2024 $8,0062024 Amount on Record Oct 1996 1 Name on Record Assessor + 1 DocumentUpdated May 2026

29 Main St, #33

3,696 sqft · built 1940 · 0.044 acres

Last Sale Tax Bill Prior Sale Owner Records
$330,000Mar 2009 $9,9812024 1 Name on Record Assessor + 4 DocumentsUpdated May 2026

32 Main St

4,760 sqft · built 1955 · 0.31 acres

Last Sale Tax Bill Prior Sale Owner Records
$350,000Apr 2021 $7,6102024 Amount on Record Mar 2017 1 Name on Record Assessor + 1 DocumentUpdated May 2026

36 Main St, #38

4,669 sqft · built 1935 · 0.101 acres

Last Sale Tax Bill Prior Sale Owner Records
$200,000Feb 2023 $7,6512024 1 Name on Record Assessor + 2 DocumentsUpdated May 2026

37 Main St

7,308 sqft · built 1935 · 0.054 acres

Last Sale Tax Bill Prior Sale Owner Records
$103,000Feb 2020 $11,8242024 Amount on Record Jan 2013 1 Name on Record Assessor + 3 DocumentsUpdated May 2026

40 Main St

0.114 acres

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

42 Main St, #50

5,022 sqft · built 1980 · 0.43 acres

Last Sale Tax Bill Prior Sale Owner Records
$465,000Jun 2022 $15,2882024 Amount on Record Aug 2007 2 Names on Record Assessor + 1 DocumentUpdated May 2026

45 Main St

3,780 sqft · built 1935 · 0.028 acres

Last Sale Tax Bill Prior Sale Owner Records
$230,500Jan 2020 1 Name on Record AssessorUpdated May 2026

47 Main St

0.611 acres

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

49 Main St

4,320 sqft · built 1940 · 0.033 acres

Last Sale Tax Bill Prior Sale Owner Records
$275,000Mar 2006 $9,9042024 Amount on Record Jul 1997 1 Name on Record Assessor + 1 DocumentUpdated May 2026

52 Main St

4 bd · 3 ba · 2,069 sqft · built 1870 · 0.192 acres

Last Sale Tax Bill Prior Sale Owner Records
$138,000Mar 2023 $5,8632024 1 Name on Record Assessor + 1 DocumentUpdated May 2026

53 Main St

6,120 sqft · built 1940 · 0.046 acres

Last Sale Tax Bill Prior Sale Owner Records
$128,750Dec 1997 $13,6332024 1 Name on Record Assessor + 1 DocumentUpdated May 2026

54 Main St

4 bd · 3 ba · 2,320 sqft · built 2005 · 0.357 acres

Last Sale Tax Bill Prior Sale Owner Records
$395,000Sep 2020 $12,4412024 Amount on Record Jun 2019 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

59 Main St

3 bd · 1 ba · 2,632 sqft · built 1870 · 0.68 acres

Last Sale Tax Bill Prior Sale Owner Records
$80,000Sep 2004 $5,3112024 —Dec 1997 1 Name on Record Owner Occupied AssessorUpdated May 2026

62 Main St

5 bd · 3 ba · 9,916 sqft · built 1900 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$330,000Oct 2010 $3752024 2 Names on Record AssessorUpdated May 2026

63 Main St

4 bd · 3 ba · 3,182 sqft · built 1900 · 0.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$305,000Jan 2023 $11,3442024 Amount on Record Mar 2009 1 Name on Record Assessor + 2 DocumentsUpdated May 2026

65 Main St

4 bd · 3 ba · 2,390 sqft · built 1873 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$310,000Sep 2021 $8,8592024 Amount on Record Feb 2008 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

66 Main St

4 bd · 1.5 ba · 2,129 sqft · built 1890 · 0.276 acres

Last Sale Tax Bill Prior Sale Owner Records
$145,000Nov 1998 $8,9142024 2 Names on Record Owner Occupied AssessorUpdated May 2026

67 Main St

4 bd · 2 ba · 1,376 sqft · built 1900 · 0.194 acres

Last Sale Tax Bill Prior Sale Owner Records
$300,000Sep 2004 $10,0112024 Amount on Record Jan 2004 1 Name on Record Owner Occupied AssessorUpdated May 2026

68 Main St

4 bd · 1 ba · 1,888 sqft · built 1870 · 0.459 acres

Last Sale Tax Bill Prior Sale Owner Records
$122,500Aug 2017 $8,5952024 Amount on Record Sep 2015 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

70 Main St

3 bd · 2 ba · 1,357 sqft · built 1870 · 0.76 acres

Last Sale Tax Bill Prior Sale Owner Records
$237,500Jan 2006 $10,3592024 Amount on Record Nov 1995 1 Name on Record Assessor + 1 DocumentUpdated May 2026

74 Main St

2.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$425,000Jan 2026 $4,2432024 1 Name on Record Assessor + 1 DocumentUpdated May 2026

77 Main St

5 bd · 2 ba · 2,385 sqft · built 1900 · 0.45 acres

Last Sale Tax Bill Prior Sale Owner Records
$140,000May 2012 $9,2502024 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

81 Main St

12,442 sqft · built 1962 · 1.7 acres

Last Sale Tax Bill Prior Sale Owner Records
1 Name on Record Assessor + 2 DocumentsUpdated May 2026

92 Main St

5,156 sqft · built 1981 · 0.396 acres

Last Sale Tax Bill Prior Sale Owner Records
$340,000Feb 2022 $17,3892024 1 Name on Record Assessor + 1 DocumentUpdated May 2026

93 Main St

2 bd · 1 ba · 1,506 sqft · built 1932 · 0.199 acres

Last Sale Tax Bill Prior Sale Owner Records
$135,500Oct 1998 $9,5062024 Amount on Record Oct 1998 2 Names on Record Owner Occupied AssessorUpdated May 2026

94 Main St, #96

1.2 acres

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

95 Main St

3 bd · 1 ba · 1,552 sqft · built 1930 · 0.199 acres

Last Sale Tax Bill Prior Sale Owner Records
$124,000Jul 2001 $8,7712024 2 Names on Record AssessorUpdated May 2026

97 Main St

4 bd · 1 ba · 1,558 sqft · built 1900 · 0.211 acres

Last Sale Tax Bill Prior Sale Owner Records
$171,000Feb 2021 $6,7372024 Amount on Record Mar 1999 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

98 Main St

4 bd · 1.5 ba · 1,858 sqft · built 1900 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,4672024 1 Name on Record AssessorUpdated Jun 2026

99 Main St

3 bd · 1.5 ba · 1,582 sqft · built 1910 · 0.199 acres

Last Sale Tax Bill Prior Sale Owner Records
$412,000Dec 2024 $8,7202024 Amount on Record Aug 1995 1 Name on Record AssessorUpdated May 2026

100 Main St

4 bd · 2.5 ba · 3,654 sqft · built 1755 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$12,5102024 1 Name on Record AssessorUpdated May 2026

101 Main St

2,371 sqft · built 1900 · 0.228 acres

Last Sale Tax Bill Prior Sale Owner Records
$117,000Feb 1994 1 Name on Record AssessorUpdated May 2026

102 Main St

0.181 acres

Last Sale Tax Bill Prior Sale Owner Records
$8622024 1 Name on Record AssessorUpdated May 2026

103 Main St

4 bd · 1.5 ba · 2,060 sqft · built 1890 · 0.35 acres

Last Sale Tax Bill Prior Sale Owner Records
$10,4172024 1 Name on Record Owner Occupied AssessorUpdated May 2026

104 Main St

7,482 sqft · built 1930 · 0.119 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,1692024 1 Name on Record AssessorUpdated May 2026

105 Main St

3 bd · 2.5 ba · 2,264 sqft · built 1900 · 0.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$257,500May 2019 $11,4642024 Amount on Record Oct 1998 1 Name on Record Assessor + 3 DocumentsUpdated May 2026

106 Main St

3,730 sqft · built 1940 · 0.099 acres

Last Sale Tax Bill Prior Sale Owner Records
$480,000Oct 2024 $8,0202024 Amount on Record Jun 2023 1 Name on Record Assessor + 3 DocumentsUpdated May 2026

107 Main St

4 bd · 2.5 ba · 2,210 sqft · built 1890 · 0.249 acres

Last Sale Tax Bill Prior Sale Owner Records
—Mar 1996 $10,0902024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

109 Main St

4 bd · 2 ba · 2,202 sqft · built 1890 · 0.53 acres

Last Sale Tax Bill Prior Sale Owner Records
$568,000Oct 2023 $10,8232024 Amount on Record Nov 1998 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

111 Main St

4,644 sqft · built 1960 · 0.901 acres

Last Sale Tax Bill Prior Sale Owner Records
$470,000May 2023 $18,3272024 1 Name on Record Assessor + 1 DocumentUpdated May 2026

112 Main St

2,739 sqft · built 1940 · 0.071 acres

Last Sale Tax Bill Prior Sale Owner Records
$300,000Mar 2024 $6,9552024 Amount on Record Jul 2001 1 Name on Record Assessor + 3 DocumentsUpdated May 2026

115 Main St

7,813 sqft · built 1940 · 0.366 acres

Last Sale Tax Bill Prior Sale Owner Records
$843,000Jan 2022 $22,7162024 1 Name on Record Assessor + 3 DocumentsUpdated May 2026

118 Main St

3,650 sqft · built 1940 · 0.135 acres

Last Sale Tax Bill Prior Sale Owner Records
$490,000Aug 2024 $11,0662024 Amount on Record Apr 2012 1 Name on Record Assessor + 1 DocumentUpdated May 2026

126 Main St, #128

4 bd · 3.5 ba · 3,324 sqft · built 1834 · 0.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$310,000Nov 2008 $12,7442024 Amount on Record Dec 2005 2 Names on Record Owner Occupied AssessorUpdated May 2026

129 Main St

1,252 sqft · built 1974 · 0.079 acres

Last Sale Tax Bill Prior Sale Owner Records
$175,000Jun 2008 $7,2132024 Amount on Record Jan 2005 1 Name on Record Assessor + 1 DocumentUpdated May 2026

130 Main St

3 bd · 1 ba · 1,122 sqft · built 1870 · 0.073 acres

Last Sale Tax Bill Prior Sale Owner Records
$115,000Jun 2013 $5,3322024 Amount on Record Apr 2009 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

131 Main St

2,520 sqft · built 1950 · 0.051 acres

Last Sale Tax Bill Prior Sale Owner Records
$228,000Aug 2011 $7,5542024 Amount on Record Aug 2005 1 Name on Record AssessorUpdated May 2026

132 Main St

1 bd · 1.5 ba · 1,297 sqft · built 1996 · 0.078 acres

Last Sale Tax Bill Prior Sale Owner Records
$40,000Nov 2022 $3,3992024 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

134 Main St

2 bd · 1 ba · 1,658 sqft · built 1921 · 0.117 acres

Last Sale Tax Bill Prior Sale Owner Records
$275,000Nov 2022 $9,2852024 1 Name on Record Assessor + 1 DocumentUpdated May 2026

136 Main St

6 bd · 3 ba · 3,088 sqft · built 1840 · 0.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$170,000Sep 1996 $13,1802024 2 Names on Record AssessorUpdated May 2026

139 Main St

3,720 sqft · built 1940 · 0.051 acres

Last Sale Tax Bill Prior Sale Owner Records
$510,000Jul 2022 $8,3742024 1 Name on Record Assessor + 2 DocumentsUpdated May 2026

140 Main St

5 bd · 2 ba · 2,248 sqft · built 1870 · 0.202 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,4212024 1 Name on Record Owner Occupied AssessorUpdated May 2026

141 Main St

3,528 sqft · built 1930 · 0.029 acres

Last Sale Tax Bill Prior Sale Owner Records
$95,000Mar 2003 $6,3092024 Amount on Record Sep 2001 1 Name on Record AssessorUpdated May 2026

142 Main St

3 bd · 1.5 ba · 1,512 sqft · built 1830 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$185,000Sep 2016 $8,3372024 Amount on Record Jan 2007 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

143 Main St

5,708 sqft · built 1950 · 0.81 acres

Last Sale Tax Bill Prior Sale Owner Records
$540,000Sep 2017 $17,0552024 1 Name on Record Assessor + 3 DocumentsUpdated May 2026

144 Main St

4 bd · 1.5 ba · 1,974 sqft · built 1910 · 0.387 acres

Last Sale Tax Bill Prior Sale Owner Records
$85,500Aug 1994 $10,3122024 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

145 Main St

3 bd · 2.5 ba · 3,324 sqft · built 1851 · 0.092 acres

Last Sale Tax Bill Prior Sale Owner Records
$450,000Oct 2024 $10,7882024 1 Name on Record AssessorUpdated Aug 2026

147 Main St

5 bd · 2.5 ba · 2,824 sqft · built 1800 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$148,300Apr 1999 $10,7412024 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

148 Main St

4 bd · 1.5 ba · 34,514 sqft · built 1860 · 3.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$61,2532024 1 Name on Record AssessorUpdated May 2026

149 Main St

4 bd · 2.5 ba · 3,306 sqft · built 1800 · 0.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$522,000Mar 2024 $12,3972024 Amount on Record Nov 2002 2 Names on Record Assessor + 2 DocumentsUpdated May 2026

151 Main St

4 bd · 1 ba · 1,504 sqft · built 1882 · 0.084 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,4672024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

152 Main St

4 bd · 2 ba · 1,914 sqft · built 1860 · 0.181 acres

Last Sale Tax Bill Prior Sale Owner Records
$239,900Oct 2018 $9,5722024 Amount on Record Dec 1998 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

153 Main St

4 bd · 2 ba · 1,560 sqft · built 1885 · 0.344 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,8812024 2 Names on Record AssessorUpdated May 2026

154 Main St

3 bd · 1.5 ba · 1,176 sqft · built 1830 · 0.25 acres

Last Sale Tax Bill Prior Sale Owner Records
$207,000Jul 2009 $8,0802024 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

155 Main St

3 bd · 1.5 ba · 1,732 sqft · built 1855 · 0.157 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,0262024 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

156 Main St

2 bd · 1 ba · 1,256 sqft · built 2006 · 0.096 acres

Last Sale Tax Bill Prior Sale Owner Records
$120,000May 2006 $5,6692024 Amount on Record Feb 2002 1 Name on Record Assessor + 1 DocumentUpdated May 2026

157 Main St

3 bd · 2 ba · 1,572 sqft · built 1870 · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$74,000Mar 2017 $9,9022024 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

159 Main St

3 bd · 1 ba · 1,740 sqft · built 1870 · 0.504 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,6912024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

161 Main St

2 bd · 2 ba · 1,152 sqft · built 1870 · 0.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$172,500Mar 2020 $7,5652024 Amount on Record Feb 2020 1 Name on Record Assessor + 4 DocumentsUpdated May 2026

163 Main St

4 bd · 1 ba · 1,384 sqft · built 1800 · 0.208 acres

Last Sale Tax Bill Prior Sale Owner Records
$189,900Oct 2018 $8,0032024 Amount on Record Apr 2014 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

165 Main St

3 bd · 1 ba · 1,536 sqft · built 1870 · 0.236 acres

Last Sale Tax Bill Prior Sale Owner Records
$75,000Mar 2019 $8,9772024 Amount on Record Jun 1995 1 Name on Record Assessor + 1 DocumentUpdated May 2026

167B Main St

4 bd · 3 ba · 2,288 sqft · built 1892 · 0.528 acres

Last Sale Tax Bill Prior Sale Owner Records
$390,000Sep 2024 $9,8812024 1 Name on Record AssessorUpdated May 2026

171 Main St

3 bd · 2.5 ba · 2,799 sqft · built 1860 · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$405,000Sep 2020 $9,8552024 Amount on Record Mar 2020 1 Name on Record Assessor + 4 DocumentsUpdated May 2026

173 Main St

4 bd · 1 ba · 1,816 sqft · built 1910 · 0.231 acres

Last Sale Tax Bill Prior Sale Owner Records
$77,000Sep 2000 $8,5532024 Amount on Record Mar 2000 1 Name on Record Owner Occupied AssessorUpdated May 2026

Wildfire Risk on Main St

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

Wildfire RiskLow
this street's cells rank above 20% of the US · above 55% of New York
Wildfire LikelihoodAbout 1 in 7,692 per year
ExposureDirect
4 of 12 cells directly exposed · 11 adjoin burnable vegetation

Property Records in Nearby Streets