Lakeside Dr, New Windsor, NY Property Records

Orange County, New Windsor Town and Greenville Town property records for 41 addresses on Lakeside Dr, New Windsor, NY · Last verified August 2026

Lakeside Dr Highlights

Properties 41
Median Sale Price $370,000
Deeds and Mortgages on File 44
Median Price per Sqft $228
Owner Occupied 73%
Median Annual Tax Bill $10,050
Median Year Built 1962
Median Ownership Tenure 7 years

Properties on Lakeside Dr

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

2 Lakeside Dr

3 bd · 2.5 ba · 1,444 sqft · built 1986 · 0.648 acres

Last Sale Tax Bill Prior Sale Owner Records
$168,000Sep 2000 $10,2662024 Amount on Record Oct 1998 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

9 Lakeside Dr

3 bd · 2 ba · 1,236 sqft · built 1987 · 0.554 acres

Last Sale Tax Bill Prior Sale Owner Records
$150,000Mar 2000 $10,4162024 2 Names on Record Owner Occupied AssessorUpdated May 2026

10 Lakeside Dr

3 bd · 2.5 ba · 2,250 sqft · built 1980 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$343,131Sep 2006 $10,4192024 Amount on Record Aug 1997 1 Name on Record Owner Occupied AssessorUpdated May 2026

12 Lakeside Dr

2 bd · 1 ba · 1,475 sqft · built 1950 · 2.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$88,900Nov 1997 $7,8302024 2 Names on Record Owner Occupied AssessorUpdated May 2026

13 Lakeside Dr

3 bd · 2 ba · 2,288 sqft · built 1988 · 0.39 acres

Last Sale Tax Bill Prior Sale Owner Records
$187,000Dec 2016 $9,8472024 Amount on Record Sep 2001 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

16 Lakeside Dr

3 bd · 3 ba · 1,392 sqft · built 1986 · 2.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$10,8162024 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

19 Lakeside Dr

4 bd · 2 ba · 1,508 sqft · built 1954 · 0.702 acres

Last Sale Tax Bill Prior Sale Owner Records
$185,000Aug 2000 $8,8662024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

20 Lakeside Dr

3 bd · 2 ba · 1,944 sqft · built 1957 · 2.7 acres

Last Sale Tax Bill Prior Sale Owner Records
$345,000Dec 2020 $10,6832024 Amount on Record Dec 2016 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

23 Lakeside Dr

1 acres

Last Sale Tax Bill Prior Sale Owner Records
$83,000Apr 2021 $4,5912024 Amount on Record Feb 2004 1 Name on Record Assessor + 1 DocumentUpdated May 2026

24 Lakeside Dr

3 bd · 2.5 ba · 2,716 sqft · built 2004 · 2.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$325,000Nov 2015 $14,0392024 Amount on Record Aug 2004 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

28 Lakeside Dr

3 bd · 2 ba · 2,029 sqft · built 1965 · 2.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$237,000Feb 2019 $11,4042024 Amount on Record Jun 2017 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

29 Lakeside Dr

3 bd · 3 ba · 1,631 sqft · built 1950 · 0.853 acres

Last Sale Tax Bill Prior Sale Owner Records
$39,780Feb 2018 Amount on Record Nov 2016 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Feb 2024

31 Lakeside Dr

3 bd · 3 ba · 1,518 sqft · built 1953 · 0.576 acres

Last Sale Tax Bill Prior Sale Owner Records
$550,000Mar 2023 $9,0342024 Amount on Record Nov 2022 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

33 Lakeside Dr

3 bd · 1.5 ba · 1,284 sqft · built 1955 · 1.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$127,000Jan 2000 $7,9082024 1 Name on Record Owner Occupied AssessorUpdated May 2026

34 Lakeside Dr

4 bd · 1.5 ba · 3,500 sqft · built 1968 · 5.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$232,000Sep 2001 $12,9202024 1 Name on Record Owner Occupied AssessorUpdated May 2026

37 Lakeside Dr

4 bd · 2.5 ba · 982 sqft · built 1950 · 0.62 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,0902024 1 Name on Record Owner Occupied AssessorUpdated May 2026

39 Lakeside Dr

3 bd · 2 ba · 1,944 sqft · built 2020 · 0.509 acres

Last Sale Tax Bill Prior Sale Owner Records
$370,000May 2021 $9,1442024 Amount on Record Jan 2006 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

40 Lakeside Dr

3 bd · 1 ba · 1,254 sqft · built 1950 · 2.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$287,000Apr 2022 $9,1442024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

41 Lakeside Dr

2 bd · 3.5 ba · 1,648 sqft · built 2022 · 0.63 acres

Last Sale Tax Bill Prior Sale Owner Records
$80,000Apr 2021 $10,3722024 Amount on Record Jan 2006 1 Name on Record Owner Occupied AssessorUpdated May 2026

42 Lakeside Dr

3 bd · 2.5 ba · 2,851 sqft · built 2001 · 2.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$19,0612024 2 Names on Record Owner Occupied AssessorUpdated May 2026

43 Lakeside Dr

2 bd · 1 ba · 892 sqft · built 1950 · 0.661 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,2522024 1 Name on Record Owner Occupied AssessorUpdated May 2026

44 Lakeside Dr

3 bd · 1.5 ba · 1,704 sqft · built 1969 · 0.382 acres

Last Sale Tax Bill Prior Sale Owner Records
$477,500Dec 2024 $8,4582024 Amount on Record May 2019 2 Names on Record Assessor + 2 DocumentsUpdated May 2026

45 Lakeside Dr

3 bd · 2.5 ba · 1,350 sqft · built 1962 · 0.706 acres

Last Sale Tax Bill Prior Sale Owner Records
$182,500Jan 2019 $9,0482024 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

46 Lakeside Dr

3 bd · 2 ba · 2,464 sqft · built 1972 · 1.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$22,540May 2021 $11,7382024 Amount on Record Jan 2010 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

47 Lakeside Dr

3 bd · 2 ba · 1,164 sqft · built 1951 · 0.057 acres

Last Sale Tax Bill Prior Sale Owner Records
$226,000Oct 2017 $6,6652024 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

48 Lakeside Dr

3 bd · 1 ba · 876 sqft · built 1945 · 0.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,4392024 1 Name on Record AssessorUpdated May 2026

49 Lakeside Dr

3 bd · 1 ba · 970 sqft · built 1950 · 1.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$374,500Jul 2025 $7,3672024 Amount on Record Jun 2001 1 Name on Record Assessor + 2 DocumentsUpdated May 2026

52 Lakeside Dr

5 bd · 3 ba · 3,014 sqft · built 1972 · 0.515 acres

Last Sale Tax Bill Prior Sale Owner Records
$11,2202024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

53 Lakeside Dr

3 bd · 1 ba · 1,036 sqft · built 1957 · 0.553 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,8162024 1 Name on Record AssessorUpdated May 2026

55 Lakeside Dr

4 bd · 3.5 ba · 2,796 sqft · built 1995 · 0.176 acres

Last Sale Tax Bill Prior Sale Owner Records
$583,000Nov 2023 $13,4472024 Amount on Record Apr 2002 2 Names on Record Assessor + 2 DocumentsUpdated Aug 2026

57 Lakeside Dr

3 bd · 1 ba · 1,066 sqft · built 1965 · 0.389 acres

Last Sale Tax Bill Prior Sale Owner Records
$300,000Aug 2022 $10,0502024 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

59 Lakeside Dr

4 bd · 3.5 ba · 3,002 sqft · built 2001 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$445,000Sep 2013 $15,6222024 Amount on Record Jul 1998 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

60 Lakeside Dr

6 bd · 2 ba · 3,400 sqft · built 1956 · 0.395 acres

Last Sale Tax Bill Prior Sale Owner Records
$410,000Jan 2022 $13,5792024 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

62 Lakeside Dr

4 bd · 2.5 ba · 1,687 sqft · built 1956 · 0.778 acres

Last Sale Tax Bill Prior Sale Owner Records
$432,000Jan 2026 $7,4332024 1 Name on Record Assessor + 1 DocumentUpdated May 2026

65 Lakeside Dr

3 bd · 1 ba · 1,390 sqft · built 1960 · 0.422 acres

Last Sale Tax Bill Prior Sale Owner Records
$246,000Aug 2011 $7,9712024 Amount on Record Oct 2002 1 Name on Record Assessor + 1 DocumentUpdated May 2026

67 Lakeside Dr

0.639 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,2202024 1 Name on Record AssessorUpdated May 2026

68 Lakeside Dr

5 bd · 2.5 ba · 1,358 sqft · built 1952 · 1.05 acres

Last Sale Tax Bill Prior Sale Owner Records
$149,900Dec 1999 $8,3482024 Amount on Record Jul 1996 2 Names on Record Owner Occupied AssessorUpdated May 2026

74 Lakeside Dr

4 bd · 2.5 ba · 1,722 sqft · built 1987 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$255,000Apr 2019 $11,1982024 Amount on Record Jun 2018 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

75 Lakeside Dr

4 bd · 1.5 ba · 1,954 sqft · built 1955 · 2.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$255,000Jan 2023 $10,8882024 2 Names on Record Assessor + 1 DocumentUpdated May 2026

82 Lakeside Dr

4 bd · 2 ba · 2,094 sqft · built 1948 · 1.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$575,000Jan 2024 $12,0102024 Amount on Record Aug 2008 1 Name on Record Assessor + 1 DocumentUpdated May 2026

90 Lakeside Dr

3 bd · 2.5 ba · 2,134 sqft · built 1969 · 0.68 acres

Last Sale Tax Bill Prior Sale Owner Records
$277,500Dec 2010 $10,1572024 1 Name on Record Owner Occupied AssessorUpdated May 2026

Wildfire Risk on Lakeside Dr

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

Wildfire RiskLow
this street's cells rank above 18% of the US · above 48% of New York
Wildfire LikelihoodAbout 1 in 5,185 per year
ExposureDirect
6 of 7 cells directly exposed · 7 adjoin burnable vegetation

Property Records in Nearby Streets