Middletown Ave, Old Saybrook, CT Property Records

Old Saybrook Town property records for 76 addresses on Middletown Ave, Old Saybrook, CT · Last verified August 2026

Middletown Ave Highlights

Properties 76
Median Sale Price $430,000
Deeds and Mortgages on File 63
Median Price per Sqft $501
Owner Occupied 50%
Median Annual Tax Bill $5,086
Median Year Built 1939
Median Ownership Tenure 13 years

Properties on Middletown Ave

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

7 Middletown Ave

4 bd · 2.5 ba · 2,022 sqft · built 1987 · 0.469 acres

Last Sale Tax Bill Prior Sale Owner Records
$240,000Dec 1988 $7,4572025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

11 Middletown Ave

4 bd · 2.5 ba · 1,891 sqft · built 1990 · 0.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$452,500Apr 2011 $7,5132025 Amount on Record Mar 2007 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

12 Middletown Ave

2 bd · 1 ba · 1,194 sqft · built 1960 · 0.194 acres

Last Sale Tax Bill Prior Sale Owner Records
$240,000Oct 2017 $5,4782025 Amount on Record Jun 2015 2 Owners on Record Assessor + 3 DocumentsUpdated Jul 2026

17 Middletown Ave

2 bd · 1 ba · 794 sqft · built 1944 · 0.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,1962025 Owner on Record AssessorUpdated Jul 2026

18 Middletown Ave

2 bd · 1 ba · 832 sqft · built 1940 · 0.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,3262025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

19 Middletown Ave

3 bd · 1 ba · 1,135 sqft · built 1944 · 0.13 acres

Last Sale Tax Bill Prior Sale Owner Records
—Sep 2012 $5,1602025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

20 Middletown Ave

3 bd · 1.5 ba · 896 sqft · built 1962 · 0.189 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,1552025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

21 Middletown Ave

3 bd · 1.5 ba · 1,060 sqft · built 1964 · 0.219 acres

Last Sale Tax Bill Prior Sale Owner Records
$548,000Oct 2023 $5,0392025 Amount on Record Dec 2019 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

22 Middletown Ave

3 bd · 1 ba · 1,696 sqft · built 1960 · 0.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$230,000Dec 2015 $5,5862025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

24 Middletown Ave

3 bd · 1.5 ba · 1,016 sqft · built 1967 · 0.169 acres

Last Sale Tax Bill Prior Sale Owner Records
$640,000Nov 2024 $5,1602025 Amount on Record Aug 2021 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

25 Middletown Ave

3 bd · 1.5 ba · 1,194 sqft · built 1940 · 0.169 acres

Last Sale Tax Bill Prior Sale Owner Records
$311,580Sep 2017 $5,6192025 2 Owners on Record Assessor + 2 DocumentsUpdated Jul 2026

27 Middletown Ave

3 bd · 1 ba · 1,162 sqft · built 1900 · 0.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$312,000May 2016 $5,3772025 Amount on Record Dec 2006 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

30 Middletown Ave

3 bd · 1 ba · 857 sqft · built 1938 · 0.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,0862025 2 Owners on Record AssessorUpdated Jul 2026

31 Middletown Ave

3 bd · 2.5 ba · 1,706 sqft · built 1900 · 0.189 acres

Last Sale Tax Bill Prior Sale Owner Records
$70,000Apr 1997 $6,3322025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

34 Middletown Ave

4 bd · 2 ba · 1,888 sqft · built 1953 · 0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$160,000Jun 1996 $5,5742025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

35 Middletown Ave

3 bd · 1 ba · 943 sqft · built 1938 · 0.13 acres

Last Sale Tax Bill Prior Sale Owner Records
$277,500Oct 2007 $4,8482025 Amount on Record Oct 2002 Owner on Record AssessorUpdated Jul 2026

37 Middletown Ave

2 bd · 1 ba · 1,127 sqft · built 1958 · 0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$73,000Mar 1995 $4,4272025 Owner on Record AssessorUpdated Jul 2026

38 Middletown Ave

2 bd · 1 ba · 1,157 sqft · built 1948 · 0.26 acres

Last Sale Tax Bill Prior Sale Owner Records
$299,000Aug 2006 $4,8842025 Amount on Record Mar 2006 2 Owners on Record Assessor + 2 DocumentsUpdated Jul 2026

39 Middletown Ave

4 bd · 1 ba · 640 sqft · built 1908 · 0.08 acres

Last Sale Tax Bill Prior Sale Owner Records
$385,000Jul 2026 $3,6952025 Amount on Record Sep 2021 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

40 Middletown Ave

2 bd · 1.5 ba · 733 sqft · built 1950 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
—Apr 1978 $4,2902025 Owner on Record AssessorUpdated Jul 2026

41 Middletown Ave

1 bd · 1 ba · 570 sqft · built 1930 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$140,000Mar 2008 $3,6472025 2 Owners on Record Assessor + 1 DocumentUpdated Jul 2026

43 Middletown Ave

2 bd · 1 ba · 764 sqft · built 1935 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$75,500May 1998 $3,8982025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

44 Middletown Ave

3 bd · 1 ba · 1,352 sqft · built 1958 · 0.38 acres

Last Sale Tax Bill Prior Sale Owner Records
$348,000Aug 2007 $5,2862025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

45 Middletown Ave

2 bd · 1 ba · 720 sqft · built 1929 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$612,000Jul 2024 $4,9012025 Amount on Record Jul 2010 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

47 Middletown Ave

4 bd · 1 ba · 1,240 sqft · built 1935 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,7902025 2 Owners on Record AssessorUpdated Jul 2026

47A Middletown Ave

2 bd · 1 ba · 640 sqft · built 1935 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$124,900Jun 1999 $3,8182025 Amount on Record Aug 1993 Owner on Record AssessorUpdated Jul 2026

49 Middletown Ave

2 bd · 1 ba · 986 sqft · built 1935 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,3072025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

50 Middletown Ave

2 bd · 2 ba · 1,247 sqft · built 1949 · 0.239 acres

Last Sale Tax Bill Prior Sale Owner Records
$300,000Jul 2017 $5,6872025 Amount on Record Sep 2006 Owner on Record Assessor + 1 DocumentUpdated Jul 2026

51 Middletown Ave

3 bd · 1 ba · 1,092 sqft · built 1958 · 0.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,5902025 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

52 Middletown Ave

2 bd · 1 ba · 888 sqft · built 1965 · 0.119 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,6242025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

55 Middletown Ave

4 bd · 1 ba · 976 sqft · built 1940 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$230,000Nov 2013 $4,4242025 Amount on Record Apr 2005 Owner on Record AssessorUpdated Jul 2026

57 Middletown Ave

3 bd · 1.5 ba · 1,020 sqft · built 1940 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$205,000Jul 2013 $4,5432025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

58 Middletown Ave

3 bd · 1 ba · 854 sqft · built 1950 · 0.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,8872025 2 Owners on Record Assessor + 2 DocumentsUpdated Jul 2026

59 Middletown Ave

2 bd · 1 ba · 640 sqft · built 1935 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$100,000Mar 2023 $3,8322025 Owner on Record Assessor + 2 DocumentsUpdated Aug 2026

61 Middletown Ave

2 bd · 1.5 ba · 1,092 sqft · built 1936 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$430,000Aug 2021 $5,2652025 Amount on Record Jul 2016 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

62 Middletown Ave

3 bd · 1 ba · 704 sqft · built 1953 · 0.069 acres

Last Sale Tax Bill Prior Sale Owner Records
$118,000Aug 1994 $4,0332025 Amount on Record Sep 1988 Owner on Record AssessorUpdated Jul 2026

63 Middletown Ave

2 bd · 1 ba · 576 sqft · built 1937 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,9452025 Owner on Record AssessorUpdated Jul 2026

67 Middletown Ave

3 bd · 1 ba · 815 sqft · built 1940 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$520,000Apr 2026 $4,2592025 —Jun 2011 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

69 Middletown Ave

2 bd · 1 ba · 756 sqft · built 1918 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$430,000Jun 2022 $4,2322025 Amount on Record Oct 2020 2 Owners on Record Assessor + 2 DocumentsUpdated Jul 2026

70 Middletown Ave

3 bd · 1.5 ba · 996 sqft · built 1971 · 0.139 acres

Last Sale Tax Bill Prior Sale Owner Records
$315,000Jun 2012 $5,1942025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

71 Middletown Ave

3 bd · 1 ba · 941 sqft · built 1939 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,4472025 2 Owners on Record AssessorUpdated Jul 2026

72 Middletown Ave

2 bd · 2.5 ba · 495 sqft · built 1924 · 0.069 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,5532025 2 Owners on Record AssessorUpdated Jul 2026

73 Middletown Ave

3 bd · 1 ba · 1,097 sqft · built 1900 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$217,100Aug 2020 $4,5342025 2 Owners on Record Assessor + 1 DocumentUpdated Jul 2026

75 Middletown Ave

3 bd · 1 ba · 888 sqft · built 1902 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$248,500Apr 2020 $4,6902025 Amount on Record Apr 2017 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

76 Middletown Ave

3 bd · 2.5 ba · 1,972 sqft · built 2011 · 2.09 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 2009 $8,9712025 Amount on Record Oct 2006 Owner on Record Owner Occupied AssessorUpdated Jul 2026

77 Middletown Ave

2 bd · 2 ba · 1,364 sqft · built 1940 · 0.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,2002025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

78 Middletown Ave

2 bd · 1 ba · 640 sqft · built 1924 · 0.069 acres

Last Sale Tax Bill Prior Sale Owner Records
$200,000Jun 2008 $4,2162025 Amount on Record Jul 2002 2 Owners on Record AssessorUpdated Jul 2026

79 Middletown Ave

3 bd · 1.5 ba · 1,220 sqft · built 1929 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$285,000Nov 2009 $5,7162025 2 Owners on Record AssessorUpdated Jul 2026

80 Middletown Ave

3 bd · 1.5 ba · 956 sqft · built 1948 · 0.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,0652025 Owner on Record AssessorUpdated Jul 2026

81 Middletown Ave

3 bd · 1 ba · 1,387 sqft · built 1930 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$320,000Sep 2020 $6,1122025 Amount on Record Jul 2004 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

82 Middletown Ave

3 bd · 1 ba · 935 sqft · built 1928 · 0.069 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,9522025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

83 Middletown Ave

3 bd · 1 ba · 915 sqft · built 1935 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,4582025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

84 Middletown Ave

4 bd · 1 ba · 966 sqft · built 1930 · 0.069 acres

Last Sale Tax Bill Prior Sale Owner Records
$165,000Jun 2015 $4,8342025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

85 Middletown Ave

2 bd · 2 ba · 920 sqft · built 1930 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,7662025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

86 Middletown Ave

3 bd · 1.5 ba · 1,146 sqft · built 1930 · 0.069 acres

Last Sale Tax Bill Prior Sale Owner Records
$107,255Jul 1998 $4,8652025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

87 Middletown Ave

3 bd · 1.5 ba · 1,540 sqft · built 1940 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$317,000Sep 2018 $5,9352025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

88 Middletown Ave

4 bd · 1 ba · 977 sqft · built 1924 · 0.069 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,9722025 Owner on Record AssessorUpdated Jul 2026

89 Middletown Ave

3 bd · 1.5 ba · 2,004 sqft · built 1950 · 0.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,7272025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

91 Middletown Ave

3 bd · 1 ba · 851 sqft · built 1956 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,8072025 Owner on Record AssessorUpdated Jul 2026

93 Middletown Ave

3 bd · 2 ba · 1,516 sqft · built 1908 · 0.138 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,6592025 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

94 Middletown Ave

2 bd · 1 ba · 768 sqft · built 1943 · 0.139 acres

Last Sale Tax Bill Prior Sale Owner Records
$91,000Dec 2009 $4,8272025 Amount on Record Jun 2008 2 Owners on Record Assessor + 2 DocumentsUpdated Jul 2026

95 Middletown Ave

4 bd · 2 ba · 1,416 sqft · built 1926 · 0.149 acres

Last Sale Tax Bill Prior Sale Owner Records
$400,000Oct 2020 $6,2572025 Amount on Record Oct 2009 Owner on Record Assessor + 3 DocumentsUpdated Aug 2026

96 Middletown Ave

3 bd · 2 ba · 1,300 sqft · built 1950 · 0.069 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,1062025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

97 Middletown Ave

3 bd · 1.5 ba · 1,216 sqft · built 1910 · 0.089 acres

Last Sale Tax Bill Prior Sale Owner Records
$610,000Oct 2025 $6,0362025 Owner on Record Assessor + 1 DocumentUpdated Jul 2026

98 Middletown Ave

3 bd · 1 ba · 770 sqft · built 1950 · 0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,0132025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

99 Middletown Ave

4 bd · 1.5 ba · 1,467 sqft · built 1903 · 0.189 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,4062025 2 Owners on Record AssessorUpdated Jul 2026

100 Middletown Ave

4 bd · 1.5 ba · 1,105 sqft · built 1928 · 0.069 acres

Last Sale Tax Bill Prior Sale Owner Records
$295,000Dec 2015 $5,3602025 Owner on Record Assessor + 2 DocumentsUpdated Jul 2026

102 Middletown Ave

2 bd · 1 ba · 704 sqft · built 1958 · 0.069 acres

Last Sale Tax Bill Prior Sale Owner Records
$340,000Dec 2017 $5,3242025 Owner on Record Assessor + 1 DocumentUpdated Jul 2026

103 Middletown Ave

3 bd · 2 ba · 1,190 sqft · built 1930 · 0.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$350,000Oct 2006 $6,9392025 Amount on Record May 1999 Owner on Record AssessorUpdated Jul 2026

104 Middletown Ave

3 bd · 1 ba · 768 sqft · built 1958 · 0.069 acres

Last Sale Tax Bill Prior Sale Owner Records
$155,000Aug 1998 $6,1432025 2 Owners on Record AssessorUpdated Jul 2026

105 Middletown Ave

3 bd · 1 ba · 1,197 sqft · built 1930 · 0.089 acres

Last Sale Tax Bill Prior Sale Owner Records
$125,000Feb 1995 $7,1042025 Owner on Record AssessorUpdated Jul 2026

107 Middletown Ave

2 bd · 1.5 ba · 988 sqft · built 1928 · 0.069 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,7722025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

108 Middletown Ave

3 bd · 1 ba · 864 sqft · built 1956 · 0.139 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,9022025 Owner on Record AssessorUpdated Jul 2026

109 Middletown Ave

2 bd · 1 ba · 620 sqft · built 1925 · 0.089 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,8002025 2 Owners on Record AssessorUpdated Jul 2026

111 Middletown Ave

2 bd · 1 ba · 640 sqft · built 1920 · 0.08 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,9522025 Owner on Record AssessorUpdated Jul 2026

115 Middletown Ave

3 bd · 1 ba · 880 sqft · built 1930 · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$425,000Dec 2015 $7,9612025 Amount on Record Apr 2010 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

Property Records in Nearby Streets