Hilltop Dr, Madison, CT Property Records

Madison Town property records for 16 addresses on Hilltop Dr, Madison, CT · Last verified August 2026

Hilltop Dr Highlights

Properties 16
Median Sale Price $1,060,000
Deeds and Mortgages on File 24
Median Price per Sqft $446
Owner Occupied 75%
Median Annual Tax Bill $19,664
Median Year Built 1957
Median Ownership Tenure 8 years

Properties on Hilltop Dr

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

5 Hilltop Dr

4 bd · 2.5 ba · 2,890 sqft · built 1953 · 0.93 acres

Last Sale Tax Bill Prior Sale Owner Records
$76,000Jul 2020 $20,1982025 Amount on Record May 1997 2 Owners on Record Owner Occupied Assessor + 5 DocumentsUpdated Jul 2026

9 Hilltop Dr

3 bd · 1 ba · 836 sqft · built 1952 · 0.239 acres

Last Sale Tax Bill Prior Sale Owner Records
$415,000Sep 2021 $14,5412025 Owner on Record Assessor + 3 DocumentsUpdated Aug 2026

10 Hilltop Dr

3 bd · 3 ba · 1,818 sqft · built 1952 · 0.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$17,8072025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

14 Hilltop Dr

3 bd · 4.5 ba · 1,975 sqft · built 1951 · 0.85 acres

Last Sale Tax Bill Prior Sale Owner Records
$510,000Apr 2017 $19,6642025 Amount on Record Jul 1996 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

17 Hilltop Dr

5 bd · 4 ba · 3,510 sqft · built 1950 · 0.819 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,720,000Jun 2024 $22,3872025 Amount on Record Aug 2013 Owner on Record Assessor + 5 DocumentsUpdated Jul 2026

20 Hilltop Dr

3 bd · 3.5 ba · 2,724 sqft · built 2006 · 0.589 acres

Last Sale Tax Bill Prior Sale Owner Records
$650,000Nov 2015 $20,0412025 Amount on Record Jul 1994 Owner on Record Owner Occupied AssessorUpdated Jul 2026

22 Hilltop Dr

3 bd · 3 ba · 2,372 sqft · built 1996 · 0.439 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,060,000Jan 2018 $27,4832025 Amount on Record Mar 1995 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

26 Hilltop Dr

3 bd · 3 ba · 2,272 sqft · built 2008 · 0.369 acres

Last Sale Tax Bill Prior Sale Owner Records
$980,000Oct 2013 $21,9812025 Amount on Record Aug 2003 2 Owners on Record AssessorUpdated Jul 2026

27 Hilltop Dr

4 bd · 2 ba · 2,225 sqft · built 1956 · 0.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$518,000May 2012 $17,8482025 Amount on Record Jun 2006 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

32 Hilltop Dr

4 bd · 3.5 ba · 2,933 sqft · built 1957 · 0.539 acres

Last Sale Tax Bill Prior Sale Owner Records
$850,000Nov 2013 $27,6182025 Amount on Record Jul 2007 2 Owners on Record Assessor + 2 DocumentsUpdated Jul 2026

35 Hilltop Dr

3 bd · 3 ba · 2,107 sqft · built 2001 · 0.25 acres

Last Sale Tax Bill Prior Sale Owner Records
$230,000May 2001 $18,4602025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

36 Hilltop Dr

2 bd · 2 ba · 1,236 sqft · built 1956 · 0.53 acres

Last Sale Tax Bill Prior Sale Owner Records
$16,4052025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

42 Hilltop Dr

3 bd · 2 ba · 1,994 sqft · built 1945 · 1.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$606,000Nov 2020 $18,5092025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

45 Hilltop Dr

2 bd · 2.5 ba · 1,972 sqft · built 2003 · 0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$690,000Sep 2014 $16,1452025 —Apr 2008 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

46 Hilltop Dr

3 bd · 2.5 ba · 1,870 sqft · built 1960 · 0.7 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,200,000Jul 2025 $17,9622025 Amount on Record Jun 2015 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

54 Hilltop Dr

4 bd · 4.5 ba · 3,626 sqft · built 2011 · 0.76 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,300,000Jun 2018 $27,3562025 Amount on Record Oct 2008 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

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