Old Rte 55, Pawling, NY Property Records

Dutchess County, Pawling Town and Beekman Town property records for 69 addresses on Old Rte 55, Pawling, NY · Last verified October 2026

Old Rte 55 Highlights

Properties 69
Median Sale Price $430,000
Deeds and Mortgages on File 76
Median Price per Sqft $232
Owner Occupied 59%
Median Annual Tax Bill $8,185
Median Year Built 1940
Median Ownership Tenure 9 years

Properties on Old Rte 55

Owner names and exact recorded amounts are on file and can be viewed instantly on this page with a free 10-day trial.

1 Old Rte 55

3 bd · 2 ba · 1,035 sqft · built 1940 · 1.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$190,000Sep 2002 $7,6202025 Amount on File Feb 1995 2 Owners on File Owner Occupied Assessor + 4 DocumentsUpdated Oct 2026

3 Old Rte 55

3 bd · 2 ba · 2,440 sqft · built 1968 · 0.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$385,000Mar 2023 $8,5682025 2 Owners on File Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

5 Old Rte 55

3 bd · 1 ba · 1,440 sqft · built 1955 · 0.55 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,1582025 2 Owners on File Owner Occupied Assessor + 1 DocumentUpdated May 2026

9 Old Rte 55

3 bd · 1.5 ba · 1,444 sqft · built 1968 · 2.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,7642025 Owner on File Owner Occupied Assessor + 1 DocumentUpdated May 2026

14 Old Rte 55

3 bd · 1 ba · 1,018 sqft · built 1900 · 0.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$211,000Aug 2025 $5,5832025 Owner on File Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

15 Old Rte 55

11 bd · 8.5 ba · 10,769 sqft · built 1968 · 46.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$430,000Mar 1998 $61,9072025 Owner on File Owner Occupied Assessor + 2 DocumentsUpdated May 2026

18 Old Rte 55

4 bd · 2 ba · 2,132 sqft · built 1846 · 24.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$14,5022025 Owner on File Assessor + 1 DocumentUpdated May 2026

20 Old Rte 55

3 bd · 1 ba · 1,424 sqft · built 1930 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,5762025 2 Owners on File Owner Occupied AssessorUpdated May 2026

23 Old Rte 55

2 bd · 1 ba · 1,150 sqft · built 1975 · 3.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,2992025 2 Owners on File Owner Occupied Assessor + 1 DocumentUpdated May 2026

25 Old Rte 55

3 bd · 2 ba · 1,616 sqft · built 1900 · 5.06 acres

Last Sale Tax Bill Prior Sale Owner Records
$300,000Mar 2017 $9,7342025 Owner on File Assessor + 1 DocumentUpdated Oct 2026

29 Old Rte 55

3 bd · 1.5 ba · 1,524 sqft · built 1900 · 0.26 acres

Last Sale Tax Bill Prior Sale Owner Records
$375,000Dec 2022 $6,2112025 Amount on File Nov 2016 2 Owners on File Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

31 Old Rte 55

3 bd · 1.5 ba · 1,092 sqft · built 1918 · 0.589 acres

Last Sale Tax Bill Prior Sale Owner Records
$235,000Jan 2010 $5,1702025 2 Owners on File Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

32 Old Rte 55

3 bd · 1.5 ba · 1,249 sqft · built 1920 · 0.53 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,7272025 Owner on File Owner Occupied AssessorUpdated May 2026

34 Old Rte 55

5 bd · 4 ba · 3,200 sqft · built 2011 · 1.6 acres

Last Sale Tax Bill Prior Sale Owner Records
$214,000Jul 2017 $11,0702025 Amount on File Feb 2016 2 Owners on File Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

36 Old Rte 55

2 bd · 2 ba · 1,716 sqft · built 1840 · 1.73 acres

Last Sale Tax Bill Prior Sale Owner Records
$95,000Jan 2017 $7,8232025 Owner on File Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

37 Old Rte 55

3 bd · 2 ba · 1,392 sqft · built 1940 · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$390,000Sep 2022 $5,9112025 Amount on File Aug 2009 Owner on File Assessor + 1 DocumentUpdated Oct 2026

38 Old Rte 55

4 bd · 2.5 ba · 2,088 sqft · built 1900 · 0.969 acres

Last Sale Tax Bill Prior Sale Owner Records
$430,000Aug 2025 $12,8502025 Owner on File Assessor + 2 DocumentsUpdated Jul 2026

39 Old Rte 55

1,840 sqft · built 1940 · 0.339 acres

Last Sale Tax Bill Prior Sale Owner Records
$81,000Aug 2009 $2,2142025 Owner on File Assessor + 1 DocumentUpdated May 2026

40 Old Rte 55

3 bd · 1.5 ba · 1,648 sqft · built 1974 · 5 acres

Last Sale Tax Bill Prior Sale Owner Records
$247,000Feb 2013 $7,5102025 Amount on File May 1996 Owner on File Owner Occupied AssessorUpdated Oct 2026

42 Old Rte 55

1 bd · 1 ba · 2,176 sqft · built 2011 · 59.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$630,000May 2012 $24,8262025 Owner on File Owner Occupied Assessor + 1 DocumentUpdated May 2026

46 Old Rte 55

2 bd · 2 ba · 2,205 sqft · built 1967 · 12.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$12,6242025 2 Owners on File Owner Occupied Assessor + 1 DocumentUpdated May 2026

47 Old Rte 55

4 bd · 1 ba · 1,376 sqft · built 1930 · 0.739 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,8382025 2 Owners on File Owner Occupied AssessorUpdated May 2026

48 Old Rte 55

4 bd · 2.5 ba · 2,940 sqft · built 1778 · 5.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$12,5322025 2 Owners on File Owner Occupied AssessorUpdated May 2026

51 Old Rte 55

4 bd · 2.5 ba · 2,256 sqft · built 1969 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$470,000Feb 2006 $10,0372025 Owner on File Owner Occupied AssessorUpdated May 2026

52 Old Rte 55

3 bd · 2 ba · 1,280 sqft · built 1958 · 0.76 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,4832025 2 Owners on File Owner Occupied AssessorUpdated May 2026

54 Old Rte 55

4 bd · 3 ba · 2,854 sqft · built 1950 · 12.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$662,500Dec 2024 $17,1892025 Amount on File Dec 2010 Owner on File Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

56 Old Rte 55

3 bd · 2 ba · 1,348 sqft · built 1934 · 0.45 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,8772025 2 Owners on File Owner Occupied AssessorUpdated Sep 2026

60 Old Rte 55

3 bd · 1.5 ba · 2,576 sqft · built 1908 · 0.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,9892025 2 Owners on File Assessor + 2 DocumentsUpdated Aug 2026

63 Old Rte 55

1,714 sqft · built 1920 · 0.319 acres

Last Sale Tax Bill Prior Sale Owner Records
$80,000Aug 2003 $5,4312025 2 Owners on File AssessorUpdated May 2026

64 Old Rte 55

2 bd · 1.5 ba · 1,428 sqft · built 1950 · 4.26 acres

Last Sale Tax Bill Prior Sale Owner Records
$230,000Jun 2013 $9,9782025 Amount on File Mar 2005 Owner on File Owner Occupied AssessorUpdated Oct 2026

67 Old Rte 55

3 bd · 1 ba · 1,290 sqft · built 1900 · 0.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$119,995Nov 2016 $4,4422025 Amount on File Aug 1995 2 Owners on File Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

68 Old Rte 55

3 bd · 2 ba · 3,252 sqft · built 1950 · 6.08 acres

Last Sale Tax Bill Prior Sale Owner Records
$317,500Sep 2019 $13,9342025 Amount on File Jul 2018 Owner on File Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

69 Old Rte 55

3 bd · 3 ba · 7,612 sqft · built 2005 · 17.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$32,4722025 Owner on File Assessor + 2 DocumentsUpdated May 2026

73 Old Rte 55

4 bd · 3.5 ba · 3,259 sqft · built 1999 · 4.95 acres

Last Sale Tax Bill Prior Sale Owner Records
$316,860Jan 2000 $15,6462025 Owner on File Owner Occupied Assessor + 2 DocumentsUpdated May 2026

75 Old Rte 55

3 bd · 4.5 ba · 3,005 sqft · built 1999 · 9.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$240,000May 2017 $21,7062025 Amount on File Dec 2016 Owner on File Owner Occupied Assessor + 4 DocumentsUpdated Oct 2026

86 Old Rte 55

3 bd · 2 ba · 3,236 sqft · built 1950 · 11.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$600,000Jul 2024 $12,5832025 Amount on File Nov 2021 Owner on File Assessor + 2 DocumentsUpdated Oct 2026

92 Old Rte 55

2 bd · 1 ba · 956 sqft · built 1950 · 2.48 acres

Last Sale Tax Bill Prior Sale Owner Records
$290,000Apr 2021 $7,1142025 Owner on File Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

110 Old Rte 55

4 bd · 2 ba · 2,054 sqft · built 1957 · 1.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$10,0342025 2 Owners on File Assessor + 2 DocumentsUpdated May 2026

120 Old Rte 55

6 bd · 3.5 ba · 3,616 sqft · built 1870 · 9.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$14,2582025 Owner on File AssessorUpdated May 2026

124 Old Rte 55

3 bd · 3.5 ba · 3,641 sqft · built 2024 · 25.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$21,5832025 Owner on File Assessor + 1 DocumentUpdated May 2026

126 Old Rte 55

4 bd · 4.5 ba · 2,361 sqft · built 1930 · 5 acres

Last Sale Tax Bill Prior Sale Owner Records
$436,000Jan 2022 $12,3242025 Amount on File Jun 2017 Owner on File Assessor + 1 DocumentUpdated Sep 2026

128 Old Rte 55

2 bd · 1 ba · 1,072 sqft · built 1920 · 1.45 acres

Last Sale Tax Bill Prior Sale Owner Records
$139,050Sep 2001 $5,4522025 2 Owners on File Owner Occupied AssessorUpdated May 2026

129 Old Rte 55

2 bd · 1.5 ba · 1,474 sqft · built 1940 · 1.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$220,000Jun 2015 $6,8782025 Owner on File Owner Occupied AssessorUpdated Oct 2026

130 Old Rte 55

4 bd · 2.5 ba · 2,552 sqft · built 1975 · 10.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$495,000Jun 2025 $11,5272025 Owner on File Assessor + 1 DocumentUpdated May 2026

132 Old Rte 55

3 bd · 2 ba · 1,798 sqft · built 1974 · 8.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$379,900Dec 2003 $7,7752025 Amount on File Jul 1998 2 Owners on File Owner Occupied AssessorUpdated Oct 2026

133 Old Rte 55

3 bd · 2 ba · 2,505 sqft · built 1945 · 0.719 acres

Last Sale Tax Bill Prior Sale Owner Records
$118,000Sep 1995 $8,7572025 Owner on File Owner Occupied AssessorUpdated May 2026

134 Old Rte 55

2 bd · 1 ba · 1,522 sqft · built 1936 · 2.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$125,000Dec 2012 $4,5572025 2 Owners on File Owner Occupied AssessorUpdated May 2026

136 Old Rte 55

2 bd · 1 ba · 1,232 sqft · built 1911 · 2.6 acres

Last Sale Tax Bill Prior Sale Owner Records
$317,500Oct 2015 $11,9112025 Amount on File Apr 2010 Owner on File Owner Occupied AssessorUpdated Oct 2026

144 Old Rte 55

4 bd · 1.5 ba · 1,727 sqft · built 1930 · 4.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,1852025 Owner on File Owner Occupied Assessor + 1 DocumentUpdated May 2026

150 Old Rte 55

7 bd · 6 ba · 3,111 sqft · built 1905 · 15 acres

Last Sale Tax Bill Prior Sale Owner Records
$260,000Sep 2014 $14,2032025 Owner on File Assessor + 3 DocumentsUpdated May 2026

156 Old Rte 55

2 bd · 1 ba · 1,532 sqft · built 1956 · 349 acres

Last Sale Tax Bill Prior Sale Owner Records
Owner on File AssessorUpdated May 2026

158 Old Rte 55

4.65 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,2692025 Owner on File AssessorUpdated May 2026

163 Old Rte 55

2 bd · 1 ba · 1,272 sqft · built 1900 · 0.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$35,000Jun 2017 $9,8522025 Owner on File Assessor + 1 DocumentUpdated Sep 2026

167 Old Rte 55

3 bd · 2 ba · 1,240 sqft · built 1940 · 0.919 acres

Last Sale Tax Bill Prior Sale Owner Records
$163,000Oct 2001 $6,3782025 2 Owners on File Owner Occupied AssessorUpdated May 2026

168 Old Rte 55

2 bd · 2 ba · 1,428 sqft · built 1776 · 2.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$565,000Aug 2026 $11,4942025 Amount on File Jun 2013 2 Owners on File Owner Occupied Assessor + 5 DocumentsUpdated Sep 2026

170 Old Rte 55

1 acres

Last Sale Tax Bill Prior Sale Owner Records
$120,000Jul 2015 $5,7252025 Owner on File AssessorUpdated May 2026

178 Old Rte 55

160 sqft · 5.91 acres

Last Sale Tax Bill Prior Sale Owner Records
$13,000Jun 2011 $19,6022025 Owner on File AssessorUpdated May 2026

179 Old Rte 55

1.41 acres

Last Sale Tax Bill Prior Sale Owner Records
Owner on File AssessorUpdated May 2026

207 Old Rte 55

2 bd · 1 ba · 1,032 sqft · built 1940 · 1.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$185,000Feb 2019 $7,6492025 Owner on File Assessor + 1 DocumentUpdated Sep 2026

213 Old Rte 55

1 bd · 1 ba · 1,183 sqft · built 1942 · 3.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$145,000Feb 2018 $7,8182025 2 Owners on File Assessor + 1 DocumentUpdated May 2026

220 Old Rte 55

3 bd · 2 ba · 1,764 sqft · built 1952 · 2.86 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,3722025 2 Owners on File Owner Occupied AssessorUpdated May 2026

230 Old Rte 55

3.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,000Mar 2018 $7,3542025 Amount on File May 2016 Owner on File Assessor + 1 DocumentUpdated Sep 2026

243 Old Rte 55

2 bd · 2 ba · 1,298 sqft · built 1972 · 11.7 acres

Last Sale Tax Bill Prior Sale Owner Records
$429,000Jan 2019 $11,9782025 2 Owners on File Owner Occupied Assessor + 3 DocumentsUpdated May 2026

255 Old Rte 55

3 bd · 1.5 ba · 1,800 sqft · built 1930 · 1.7 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,4662025 2 Owners on File AssessorUpdated May 2026

300 Old Rte 55

5,180 sqft · built 1950 · 0.219 acres

Last Sale Tax Bill Prior Sale Owner Records
$536,500Oct 2019 $23,1352025 Owner on File Assessor + 3 DocumentsUpdated Jun 2026

304 Old Rte 55

1 bd · 1 ba · 750 sqft · built 1938 · 0.319 acres

Last Sale Tax Bill Prior Sale Owner Records
$292,000Oct 2021 $7,9662025 Amount on File Sep 2011 Owner on File Assessor + 1 DocumentUpdated Oct 2026

309 Old Rte 55

3 bd · 2.5 ba · 1,600 sqft · built 1872 · 0.919 acres

Last Sale Tax Bill Prior Sale Owner Records
$270,000Nov 2018 $8,7902025 Amount on File Mar 2018 2 Owners on File Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

315 Old Rte 55

1 bd · 1 ba · 1,208 sqft · built 1890 · 1.6 acres

Last Sale Tax Bill Prior Sale Owner Records
$72,500Feb 2002 $6,5782025 2 Owners on File AssessorUpdated May 2026

378 Old Rte 55

6 bd · 3 ba · 2,101 sqft · built 1840 · 0.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$190,000Apr 1996 $7,9222025 Owner on File Owner Occupied AssessorUpdated Jun 2026

Property Records in Nearby Streets