Deepwood Dr, Madison, CT Property Records

Madison Town property records for 36 addresses on Deepwood Dr, Madison, CT · Last verified August 2026

Deepwood Dr Highlights

Properties 36
Median Sale Price $439,900
Deeds and Mortgages on File 62
Median Price per Sqft $345
Owner Occupied 94%
Median Annual Tax Bill $6,258
Median Year Built 1964
Median Ownership Tenure 9 years

Properties on Deepwood Dr

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

12 Deepwood Dr

3 bd · 3 ba · 2,162 sqft · 0.939 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$336,900Jun 2018 $7,6872025 Amount on Record Nov 2006 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

15 Deepwood Dr

3 bd · 2 ba · 1,504 sqft · 0.939 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$232,500Apr 2002 $6,4102025 Amount on Record Jul 1994 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

18 Deepwood Dr

3 bd · 1.5 ba · 1,202 sqft · 0.939 acres

Last Sale Tax Bill Prior Sale Owner Records
$440,000Dec 2025 $6,1012025 Amount on Record May 2002 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

21 Deepwood Dr

3 bd · 2.5 ba · 1,500 sqft · 0.95 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,8342025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

24 Deepwood Dr

3 bd · 1.5 ba · 1,200 sqft · 0.98 acres

Last Sale Tax Bill Prior Sale Owner Records
$475,000Sep 2025 $5,7622025 Amount on Record Jan 2019 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

27 Deepwood Dr

4 bd · 2.5 ba · 1,692 sqft · 0.93 acres

Last Sale Tax Bill Prior Sale Owner Records
$264,710Dec 2017 $6,7452025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

32 Deepwood Dr

4 bd · 1.5 ba · 1,464 sqft · 1.01 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$265,000Mar 2008 $5,9872025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

33 Deepwood Dr

3 bd · 2.5 ba · 1,200 sqft · 0.93 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$439,900May 2023 $6,4712025 Amount on Record Nov 2020 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

38 Deepwood Dr

3 bd · 1.5 ba · 1,200 sqft · 0.939 acres

Last Sale Tax Bill Prior Sale Owner Records
$291,000Jul 2014 $6,0132025 Amount on Record Aug 1994 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

39 Deepwood Dr

3 bd · 1.5 ba · 1,224 sqft · 0.939 acres

Last Sale Tax Bill Prior Sale Owner Records
$267,000Jul 2015 $5,6322025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

46 Deepwood Dr

3 bd · 2.5 ba · 1,655 sqft · 0.98 acres

Last Sale Tax Bill Prior Sale Owner Records
$300,000Mar 2015 $7,2432025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

47 Deepwood Dr

3 bd · 1.5 ba · 1,586 sqft · 0.969 acres

Last Sale Tax Bill Prior Sale Owner Records
$329,000Jun 2019 $6,9352025 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

51 Deepwood Dr

4 bd · 2 ba · 2,156 sqft · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,0952025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

52 Deepwood Dr

3 bd · 2.5 ba · 1,888 sqft · 1.01 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$297,000Aug 2003 $7,4092025 Amount on Record Jun 1997 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

57 Deepwood Dr

4 bd · 1.5 ba · 1,392 sqft · 1.03 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$186,000Apr 2000 $6,3972025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

58 Deepwood Dr

3 bd · 1.5 ba · 1,296 sqft · 1.03 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$143,000Apr 1991 $6,0882025 2 Names on Record Assessor + 1 DocumentUpdated Jul 2026

62 Deepwood Dr

3 bd · 1 ba · 1,344 sqft · 1.08 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,1212025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

65 Deepwood Dr

3 bd · 2.5 ba · 1,632 sqft · 1.08 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$328,000Nov 2017 $6,5562025 Amount on Record Jun 1997 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

71 Deepwood Dr

4 bd · 1.5 ba · 1,236 sqft · 1.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$475,000Oct 2025 $6,0162025 Amount on Record Jun 1993 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

72 Deepwood Dr

3 bd · 1.5 ba · 1,248 sqft · 1.15 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$165,000Jun 1999 $5,9302025 Amount on Record May 1987 2 Names on Record Owner Occupied Assessor + 6 DocumentsUpdated Aug 2026

77 Deepwood Dr

4 bd · 3 ba · 1,430 sqft · 1.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$299,900May 2008 $6,2582025 Amount on Record May 2002 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

78 Deepwood Dr

4 bd · 2.5 ba · 1,671 sqft · 1.1 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$210,000Jun 1997 $6,9222025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

80 Deepwood Dr

3 bd · 2.5 ba · 1,458 sqft · 1.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$362,000Aug 2005 $6,5832025 Amount on Record May 2004 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

81 Deepwood Dr

4 bd · 1.5 ba · 1,236 sqft · 1.13 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$320,000May 2022 $6,1822025 Amount on Record Dec 2016 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

89 Deepwood Dr

3 bd · 1.5 ba · 1,236 sqft · 1.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$263,500Jul 2017 $6,2202025 Amount on Record May 2010 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

90 Deepwood Dr

4 bd · 1.5 ba · 1,872 sqft · 1.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$117,000May 2016 $6,5002025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

93 Deepwood Dr

3 bd · 1 ba · 1,116 sqft · 1.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$350,000Dec 2025 $5,7402025 Amount on Record Sep 2021 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

96 Deepwood Dr

3 bd · 1.5 ba · 1,250 sqft · 1.26 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$162,100Aug 1999 $5,7622025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

99 Deepwood Dr

3 bd · 1.5 ba · 1,432 sqft · 1.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$405,000May 2023 $6,1592025 Amount on Record Aug 2022 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

100 Deepwood Dr

3 bd · 2.5 ba · 1,806 sqft · 1.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$333,000Jun 2019 $6,8162025 Amount on Record Jun 2017 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

105 Deepwood Dr

3 bd · 2.5 ba · 1,332 sqft · 1.25 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$460,000Jun 2024 $6,1932025 Amount on Record Aug 1998 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

106 Deepwood Dr

3 bd · 1.5 ba · 1,300 sqft · 1.33 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$5,9222025 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

112 Deepwood Dr

3 bd · 2.5 ba · 1,516 sqft · 1.36 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$330,000Sep 2020 $6,9292025 Amount on Record Jul 2014 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

115 Deepwood Dr

3 bd · 1.5 ba · 1,236 sqft · 1.28 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$295,000Nov 2003 $6,1702025 Amount on Record Sep 2000 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

123 Deepwood Dr

3 bd · 1.5 ba · 1,380 sqft · 1.2 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$375,000Mar 2024 $5,9332025 —Jun 2016 2 Names on Record Assessor + 1 DocumentUpdated Jul 2026

126 Deepwood Dr

2 bd · 2.5 ba · 1,716 sqft · 2.28 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$10,2482025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

Wildfire Risk on Deepwood Dr

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

Wildfire RiskLow
this street's cells rank at the 20th percentile of exposed land nationally · 55th in Connecticut
Wildfire LikelihoodLow — about 1 in 5,172 per year
ExposureDirect
6 of 6 cells directly exposed · 6 adjoin burnable vegetation

Property Records in Nearby Streets