Main St, Hillsboro, MD Property Records

Caroline County property records for 41 addresses on Main St, Hillsboro, MD · Last verified October 2026

Main St Highlights

Properties 41
Median Sale Price $263,500
Deeds and Mortgages on File 39
Median Price per Sqft $130
Owner Occupied 56%
Median Annual Tax Bill $2,418
Median Year Built 1900
Median Ownership Tenure 9 years

Properties on Main St

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

21908 Main St

2.5 ba · 3,244 sqft · built 1800 · 2.61 acres

Last Sale Tax Bill Prior Sale Owner Records
$195,000Aug 2016 $4,4602026 2 Owners on File Owner Occupied AssessorUpdated Oct 2026

21914 Main St

1 ba · 1,735 sqft · built 1920 · 0.389 acres

Last Sale Tax Bill Prior Sale Owner Records
$95,000Jul 2014 $2,5142026 Amount on File Jun 2014 2 Owners on File Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

21936 Main St

2 ba · 1,400 sqft · built 1950 · 0.275 acres

Last Sale Tax Bill Prior Sale Owner Records
$245,000Jun 2021 $2,8872026 Amount on File Jan 2018 Owner on File Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

21948 Main St

2 ba · 1,904 sqft · built 1910 · 0.33 acres

Last Sale Tax Bill Prior Sale Owner Records
$79,400Dec 1989 $2,4082026 Amount on File Dec 1984 Owner on File AssessorUpdated Oct 2026

21954 Main St

1.5 ba · 1,996 sqft · built 1900 · 0.418 acres

Last Sale Tax Bill Prior Sale Owner Records
$298,000May 2025 $2,3112025 Amount on File May 2001 2 Owners on File Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

21959 Main St

2 ba · 2,168 sqft · built 1885 · 1.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$285,000May 2025 $3,0192025 Amount on File Oct 2017 2 Owners on File Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

21968 Main St

2 ba · 2,488 sqft · built 1900 · 0.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$325,000Aug 2025 $3,4242026 Amount on File Jul 2008 2 Owners on File Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

21969 Main St

3 ba · 2,233 sqft · built 1890 · 0.233 acres

Last Sale Tax Bill Prior Sale Owner Records
$25,250May 2016 $1,4042025 Amount on File Feb 2015 Owner on File AssessorUpdated Aug 2026

21974 Main St

3,112 sqft · built 1900 · 0.454 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,4832026 2 Owners on File Assessor + 1 DocumentUpdated Oct 2026

21979 Main St

4,680 sqft · built 1880 · 0.278 acres

Last Sale Tax Bill Prior Sale Owner Records
$43,000Aug 1996 $2,5722026 Amount on File May 1987 Owner on File AssessorUpdated Oct 2026

21984 Main St

2.5 ba · 2,784 sqft · built 1900 · 0.589 acres

Last Sale Tax Bill Prior Sale Owner Records
$80,000Sep 2017 $1,7182026 Amount on File Jun 2000 2 Owners on File Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

21991 Main St

4,596 sqft · built 1900 · 0.468 acres

Last Sale Tax Bill Prior Sale Owner Records
$602025 Owner on File Owner Occupied AssessorUpdated Aug 2026

21994 Main St

3 ba · 4,880 sqft · built 1800 · 0.371 acres

Last Sale Tax Bill Prior Sale Owner Records
$234,900Dec 2024 $5,5462026 Amount on File Mar 2024 2 Owners on File Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

22004 Main St

1,040 sqft · built 1909 · 0.024 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,000Dec 2003 Owner on File Owner Occupied AssessorUpdated Aug 2026

22005 Main St

2.5 ba · 3,088 sqft · built 1794 · 0.655 acres

Last Sale Tax Bill Prior Sale Owner Records
$330,000Apr 2009 $5,0282026 Amount on File Nov 2003 Owner on File Owner Occupied AssessorUpdated Oct 2026

22008 Main St

2 ba · 2,974 sqft · built 1905 · 0.375 acres

Last Sale Tax Bill Prior Sale Owner Records
$75,000Jun 2011 $2,4132026 2 Owners on File AssessorUpdated Oct 2026

22013 Main St

2 ba · 2,064 sqft · built 1900 · 0.387 acres

Last Sale Tax Bill Prior Sale Owner Records
$263,500Nov 2021 $3,6432026 Amount on File Feb 2009 Owner on File Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

22016 Main St

2 ba · 2,660 sqft · built 1900 · 0.277 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,100Jun 1980 $2,4192026 2 Owners on File AssessorUpdated Oct 2026

22017 Main St

2 ba · 1,952 sqft · built 1900 · 0.207 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,000Apr 1997 $2,4252026 Amount on File Jun 1993 2 Owners on File Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

22020 Main St

3 ba · 2,856 sqft · built 1900 · 0.272 acres

Last Sale Tax Bill Prior Sale Owner Records
$23,000May 1986 $3,0022026 2 Owners on File AssessorUpdated Oct 2026

22023 Main St

1 ba · 1,670 sqft · built 1800 · 0.328 acres

Last Sale Tax Bill Prior Sale Owner Records
$36,000Mar 2017 $1,9012026 —Sep 1994 2 Owners on File Assessor + 1 DocumentUpdated Oct 2026

22027 Main St

288 sqft · built 1900 · 0.217 acres

Last Sale Tax Bill Prior Sale Owner Records
$36,000Mar 2017 $7032026 2 Owners on File Assessor + 1 DocumentUpdated Oct 2026

22028 Main St

2 ba · 2,392 sqft · built 1900 · 0.275 acres

Last Sale Tax Bill Prior Sale Owner Records
$230,000Jun 2020 $3,1372026 Amount on File Mar 2018 Owner on File Owner Occupied Assessor + 4 DocumentsUpdated Oct 2026

22033 Main St

2,320 sqft · built 1900 · 0.099 acres

Last Sale Tax Bill Prior Sale Owner Records
$85,000Sep 2020 $1,9322026 Amount on File Sep 2015 2 Owners on File Assessor + 2 DocumentsUpdated Oct 2026

22037 Main St

1 ba · 1,008 sqft · built 1890 · 0.023 acres

Last Sale Tax Bill Prior Sale Owner Records
$305,000Dec 2019 $9002026 Owner on File Assessor + 1 DocumentUpdated Oct 2026

22040 Main St

1.5 ba · 2,276 sqft · built 1900 · 0.776 acres

Last Sale Tax Bill Prior Sale Owner Records
$365,000Sep 2026 $3,2722026 Amount on File Feb 2025 Owner on File Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

22043 Main St

2,668 sqft · built 1890 · 0.17 acres

Last Sale Tax Bill Prior Sale Owner Records
$305,000Dec 2019 $2,3182026 —Jul 1999 Owner on File Assessor + 1 DocumentUpdated Oct 2026

22047 Main St

1.5 ba · 1,356 sqft · built 1890 · 0.119 acres

Last Sale Tax Bill Prior Sale Owner Records
$96,900Dec 2001 $1,8492026 Amount on File Apr 1994 Owner on File Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

22052 Main St

1 ba · 1,856 sqft · built 1910 · 0.318 acres

Last Sale Tax Bill Prior Sale Owner Records
$75,000Aug 2005 $2,0582026 2 Owners on File Owner Occupied AssessorUpdated Oct 2026

22057 Main St

1.5 ba · 3,393 sqft · built 1900 · 0.53 acres

Last Sale Tax Bill Prior Sale Owner Records
$292,000Feb 2007 $6972026 Amount on File Jun 2001 Owner on File AssessorUpdated Oct 2026

22060 Main St

1.5 ba · 2,817 sqft · built 1900 · 0.489 acres

Last Sale Tax Bill Prior Sale Owner Records
$175,000May 2026 $4,0362026 Amount on File Nov 2025 Owner on File Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

22067 Main St

1 ba · 1,802 sqft · built 1900 · 0.457 acres

Last Sale Tax Bill Prior Sale Owner Records
$150,000Oct 2007 $2,2942026 —Oct 1998 Owner on File AssessorUpdated Oct 2026

22070 Main St

2 ba · 1,716 sqft · built 1900 · 0.332 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,7632026 2 Owners on File Owner Occupied AssessorUpdated Oct 2026

22077 Main St

2 ba · 1,464 sqft · built 1960 · 0.484 acres

Last Sale Tax Bill Prior Sale Owner Records
$140,000Apr 2023 $2,0592026 Amount on File Nov 1990 2 Owners on File Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

22087 Main St

2 ba · 1,474 sqft · built 1900 · 0.355 acres

Last Sale Tax Bill Prior Sale Owner Records
$195,000Oct 2005 $2,3552026 Amount on File Feb 2004 Owner on File Owner Occupied AssessorUpdated Oct 2026

22090 Main St

1 ba · 3,443 sqft · built 1880 · 1.13 acres

Last Sale Tax Bill Prior Sale Owner Records
$85,556Jul 2019 $2,3722026 Amount on File Jul 2018 Owner on File Assessor + 2 DocumentsUpdated Oct 2026

22093 Main St

1 ba · 1,784 sqft · built 1900 · 0.303 acres

Last Sale Tax Bill Prior Sale Owner Records
$98,000Aug 1999 $2,3232026 Amount on File Oct 1984 Owner on File Assessor + 2 DocumentsUpdated Oct 2026

22098 Main St

1.5 ba · 2,224 sqft · built 1900 · 0.276 acres

Last Sale Tax Bill Prior Sale Owner Records
$295,000Dec 2005 $2,8802026 Amount on File Dec 1986 2 Owners on File Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

22101 Main St

1.5 ba · 1,980 sqft · built 1928 · 0.596 acres

Last Sale Tax Bill Prior Sale Owner Records
$174,000Nov 2019 $2,6402026 Amount on File Apr 1989 2 Owners on File Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

22104 Main St

2 ba · 1,568 sqft · built 1900 · 0.275 acres

Last Sale Tax Bill Prior Sale Owner Records
$359,000Jun 2023 $2,1572026 Amount on File Sep 2016 Owner on File Assessor + 1 DocumentUpdated Oct 2026

22108 Main St

2 ba · 1,608 sqft · built 1972 · 0.862 acres

Last Sale Tax Bill Prior Sale Owner Records
—Apr 2006 $6302026 Amount on File Jul 2001 2 Owners on File Assessor + 1 DocumentUpdated Oct 2026

Property Records in Nearby Streets