Roosevelt Ave, Middletown, NY Property Records

Orange County and Middletown City property records for 43 addresses on Roosevelt Ave, Middletown, NY · Last verified August 2026

Roosevelt Ave Highlights

Properties 43
Median Sale Price $242,740
Deeds and Mortgages on File 59
Median Price per Sqft $198
Owner Occupied 63%
Median Annual Tax Bill $7,247
Median Year Built 1930
Median Ownership Tenure 6 years

Properties on Roosevelt Ave

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

9 Roosevelt Ave, #11

3 bd · 1 ba · 1,190 sqft · built 1951 · 0.208 acres

Last Sale Tax Bill Prior Sale Owner Records
$200,000Dec 2022 $7,2472024 Amount on Record Mar 2022 Owner on Record Assessor + 4 DocumentsUpdated Jun 2026

12 Roosevelt Ave

3 bd · 1 ba · 960 sqft · built 1963 · 0.116 acres

Last Sale Tax Bill Prior Sale Owner Records
$183,000Mar 2007 $6,5812024 Amount on Record Sep 2002 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

13 Roosevelt Ave

3 bd · 2.5 ba · 2,044 sqft · built 1960 · 0.342 acres

Last Sale Tax Bill Prior Sale Owner Records
$242,740May 2020 $9,9132024 Amount on Record Sep 2008 Owner on Record Assessor + 4 DocumentsUpdated May 2026

14 Roosevelt Ave

3 bd · 1.5 ba · 1,810 sqft · built 1959 · 0.168 acres

Last Sale Tax Bill Prior Sale Owner Records
$243,000Dec 2005 $8,4972024 Amount on Record Sep 2002 Owner on Record Owner Occupied AssessorUpdated May 2026

20 Roosevelt Ave

4 bd · 1 ba · 1,296 sqft · built 1930 · 0.444 acres

Last Sale Tax Bill Prior Sale Owner Records
$285,000May 2021 $6,6092024 Amount on Record Oct 2020 Owner on Record Owner Occupied Assessor + 6 DocumentsUpdated May 2026

22 Roosevelt Ave

3 bd · 1 ba · 946 sqft · built 1930 · 0.443 acres

Last Sale Tax Bill Prior Sale Owner Records
$200,000May 2024 $6,1092024 Amount on Record Jan 2020 Owner on Record Assessor + 1 DocumentUpdated May 2026

23 Roosevelt Ave, #25

4 bd · 2 ba · 1,539 sqft · built 1930 · 0.397 acres

Last Sale Tax Bill Prior Sale Owner Records
$210,000Sep 2018 $8,1922024 Amount on Record Oct 2003 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

24 Roosevelt Ave

3 bd · 1 ba · 1,041 sqft · built 1926 · 0.441 acres

Last Sale Tax Bill Prior Sale Owner Records
$245,000Jan 2023 $6,3592024 Amount on Record Jan 2012 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

26 Roosevelt Ave, #28

5 bd · 1.5 ba · 1,811 sqft · built 1900 · 0.883 acres

Last Sale Tax Bill Prior Sale Owner Records
$394,000Aug 2024 $8,3032024 Amount on Record Sep 2021 Owner on Record Assessor + 1 DocumentUpdated May 2026

27 Roosevelt Ave

3 bd · 1 ba · 1,417 sqft · built 1920 · 0.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,7202024 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

29 Roosevelt Ave, #31

3 bd · 1 ba · 1,204 sqft · built 1900 · 0.401 acres

Last Sale Tax Bill Prior Sale Owner Records
$130,000May 2002 $7,1362024 Amount on Record Aug 1996 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

30 Roosevelt Ave

4 bd · 1.5 ba · 1,666 sqft · built 1930 · 0.439 acres

Last Sale Tax Bill Prior Sale Owner Records
$265,000Jan 2021 $7,7752024 Amount on Record Nov 2012 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

32 Roosevelt Ave

3 bd · 1.5 ba · 1,945 sqft · built 1940 · 0.438 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,1082024 2 Owners on Record Owner Occupied AssessorUpdated May 2026

33 Roosevelt Ave

2 bd · 1 ba · 848 sqft · built 1930 · 0.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$62,500May 2012 $4,9982024 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

34 Roosevelt Ave, #36

4 bd · 1.5 ba · 1,708 sqft · built 1914 · 0.874 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,0802024 Owner on Record Owner Occupied AssessorUpdated May 2026

35 Roosevelt Ave, #37

3 bd · 1.5 ba · 1,648 sqft · built 1912 · 0.321 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,0812024 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

38 Roosevelt Ave, #40

3 bd · 1 ba · 1,196 sqft · built 1909 · 0.824 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,9142024 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

39 Roosevelt Ave, #41

3 bd · 1 ba · 1,104 sqft · built 1900 · 0.345 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,5812024 2 Owners on Record AssessorUpdated May 2026

42 Roosevelt Ave

2 bd · 1 ba · 1,302 sqft · built 1922 · 0.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$120,000May 2010 $5,1652024 Amount on Record Dec 1999 Owner on Record Owner Occupied AssessorUpdated May 2026

43 Roosevelt Ave

3 bd · 2 ba · 1,864 sqft · built 1950 · 0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$370,000Apr 2022 $11,8572024 Amount on Record Apr 2021 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

44 Roosevelt Ave

4 bd · 1 ba · 1,875 sqft · built 1937 · 0.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$108,000Jun 2000 $5,6652024 2 Owners on Record Owner Occupied AssessorUpdated May 2026

45 Roosevelt Ave

5 bd · 2.5 ba · 2,154 sqft · built 1939 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$170,000Nov 2011 $7,7752024 Owner on Record Owner Occupied AssessorUpdated May 2026

46 Roosevelt Ave

3 bd · 2.5 ba · 2,308 sqft · built 1920 · 0.43 acres

Last Sale Tax Bill Prior Sale Owner Records
$230,000Jun 2016 $7,2472024 Amount on Record Dec 1998 2 Owners on Record Owner Occupied AssessorUpdated May 2026

47 Roosevelt Ave

3 bd · 1 ba · 1,104 sqft · built 1920 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$191,000Dec 2020 $5,6922024 Amount on Record Jul 2007 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

48 Roosevelt Ave

45.9 acres

Last Sale Tax Bill Prior Sale Owner Records
Owner on Record Assessor + 1 DocumentUpdated May 2026

49 Roosevelt Ave

6 bd · 2 ba · 1,954 sqft · built 1920 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,000Feb 2024 $6,0372024 2 Owners on Record Assessor + 4 DocumentsUpdated May 2026

50 Roosevelt Ave

0.43 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,7222024 Owner on Record AssessorUpdated May 2026

51 Roosevelt Ave

2 bd · 1 ba · 838 sqft · built 1910 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$168,000Mar 2020 $5,1652024 Amount on Record May 2019 Owner on Record Assessor + 5 DocumentsUpdated May 2026

52 Roosevelt Ave

3 bd · 1.5 ba · 1,272 sqft · built 1925 · 0.43 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,0572024 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

53 Roosevelt Ave

4 bd · 2 ba · 1,754 sqft · built 1910 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$188,305Mar 2023 $5,9982024 Amount on Record Dec 2019 Owner on Record Assessor + 3 DocumentsUpdated Jun 2026

54 Roosevelt Ave, #58

3 bd · 1 ba · 1,408 sqft · built 1930 · 1.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,3302024 Owner on Record Owner Occupied AssessorUpdated May 2026

55 Roosevelt Ave, #57

3 bd · 1.5 ba · 1,400 sqft · built 1928 · 0.835 acres

Last Sale Tax Bill Prior Sale Owner Records
$100,000Jan 2023 $8,0532024 2 Owners on Record Assessor + 2 DocumentsUpdated May 2026

57 Roosevelt Ave

3 bd · 2.5 ba · 1,867 sqft · built 1950 · 0.405 acres

Last Sale Tax Bill Prior Sale Owner Records
$442,900Dec 2025 $10,8302024 Amount on Record Sep 2022 2 Owners on Record Assessor + 5 DocumentsUpdated Jul 2026

59 Roosevelt Ave

2 bd · 1 ba · 869 sqft · built 1910 · 0.179 acres

Last Sale Tax Bill Prior Sale Owner Records
$170,000Oct 2023 $3,7212024 Amount on Record Jan 2023 Owner on Record Assessor + 5 DocumentsUpdated Aug 2026

61 Roosevelt Ave, #65

3 bd · 1 ba · 1,064 sqft · built 1920 · 1.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,4142024 Owner on Record Owner Occupied AssessorUpdated May 2026

62 Roosevelt Ave

0.058 acres

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

64 Roosevelt Ave

3 bd · 1 ba · 1,638 sqft · built 1928 · 0.312 acres

Last Sale Tax Bill Prior Sale Owner Records
$334,999Dec 2022 $8,6362024 Amount on Record Oct 2016 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

66 Roosevelt Ave, #68

4 bd · 2.5 ba · 2,286 sqft · built 2003 · 0.319 acres

Last Sale Tax Bill Prior Sale Owner Records
$270,000Nov 2016 $11,5502024 Amount on Record Nov 2003 Owner on Record Owner Occupied AssessorUpdated May 2026

67 Roosevelt Ave

6 bd · 4 ba · 4,255 sqft · built 2003 · 1.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$245,000Sep 2019 $9,7192024 Amount on Record May 2000 Owner on Record Assessor + 1 DocumentUpdated May 2026

68 Roosevelt Ave

2 bd · 1 ba · 1,140 sqft · built 1950 · 0.151 acres

Last Sale Tax Bill Prior Sale Owner Records
$55,000May 1995 $5,9152024 Owner on Record Owner Occupied AssessorUpdated May 2026

69 Roosevelt Ave, #73

2 bd · 2 ba · 1,184 sqft · built 1950 · 0.503 acres

Last Sale Tax Bill Prior Sale Owner Records
$93,000Dec 1998 $7,4142024 Amount on Record Jun 1998 2 Owners on Record Owner Occupied AssessorUpdated May 2026

70 Roosevelt Ave

0.086 acres

Last Sale Tax Bill Prior Sale Owner Records
$5832024 Owner on Record AssessorUpdated May 2026

72 Roosevelt Ave

4 bd · 2 ba · 1,899 sqft · built 1930 · 0.727 acres

Last Sale Tax Bill Prior Sale Owner Records
$138,000Jan 2001 $9,9132024 Owner on Record Owner Occupied AssessorUpdated May 2026

Property Records in Nearby Streets