Smiley Dr, New Windsor, MD Property Records

Carroll County property records for 13 addresses on Smiley Dr, New Windsor, MD · Last verified August 2026

Smiley Dr Highlights

Properties 13
Median Sale Price $319,000
Deeds and Mortgages on File 23
Median Price per Sqft $281
Owner Occupied 100%
Median Annual Tax Bill $3,035
Median Year Built 1985
Median Ownership Tenure 22 years

Properties on Smiley Dr

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

1586 Smiley Dr

1 ba · 820 sqft · 1.01 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$106,500Sep 1993 $2,6412025 Amount on Record Jan 1986 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

1587 Smiley Dr

2.5 ba · 1,672 sqft · 1.41 acres

Last Sale Tax Bill Prior Sale Owner Records
$308,000Jul 2007 $3,0942025 Amount on Record Dec 2005 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

1588 Smiley Dr

1 ba · 924 sqft · 1.01 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$67,300Nov 1985 $2,8382025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

1589 Smiley Dr

3 ba · 1,584 sqft · 1.51 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$549,000Apr 2026 $3,2452025 Amount on Record Aug 2023 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

1590 Smiley Dr

1.5 ba · 1,628 sqft · 1.06 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$155,500Aug 1997 $3,3512025 Amount on Record Nov 1993 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

1591 Smiley Dr

3 ba · 1,152 sqft · 2.36 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$500,000Nov 2022 $3,6642025 Amount on Record Sep 2007 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

1592 Smiley Dr

1 ba · 822 sqft · 1.08 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$160,000Jul 2001 $2,8042025 Amount on Record Aug 1989 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

1593 Smiley Dr

1 ba · 976 sqft · 2.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$141,500Nov 1998 $2,8922025 Amount on Record May 1990 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

1594 Smiley Dr

2 ba · 976 sqft · 0.997 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$275,000Jan 2004 $3,0322025 Amount on Record May 1999 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

1595 Smiley Dr

2 ba · 976 sqft · 1.49 acres

Last Sale Tax Bill Prior Sale Owner Records
$425,000Feb 2023 $3,3762025 Amount on Record Nov 2021 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

1596 Smiley Dr

2 ba · 924 sqft · 0.921 acres

Last Sale Tax Bill Prior Sale Owner Records
$230,000May 2017 $2,9852025 Amount on Record Dec 2014 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

1597 Smiley Dr

3 ba · 1,964 sqft · 2.09 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$319,000May 2013 $4,2072025 Amount on Record Jun 2001 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

1598 Smiley Dr

2 ba · 1,384 sqft · 1.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$286,000Aug 2004 $3,0352025 Amount on Record Aug 2001 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

Wildfire Risk on Smiley Dr

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

Wildfire Risk to HomesLow
this street's cells rank at the 10th percentile of exposed land nationally · 21st in Maryland
Wildfire LikelihoodLow — less than 1 in 10,000 per year
ExposureDirect
4 of 4 cells directly exposed · 4 adjoin burnable vegetation

Property Records in Nearby Streets