Contentment Island Rd, Darien, CT Property Records

Darien Town property records for 29 addresses on Contentment Island Rd, Darien, CT · Last verified October 2026

Contentment Island Rd Highlights

Properties 29
Median Sale Price $3,875,000
Deeds and Mortgages on File 35
Median Price per Sqft $786
Owner Occupied 66%
Median Annual Tax Bill $62,228
Median Year Built 1955
Median Ownership Tenure 12 years

Properties on Contentment Island Rd

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

2 Contentment Island Rd

3 bd · 3.5 ba · 3,936 sqft · built 1925 · 1.08 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,900,000May 2021 $38,3202025 Amount on Record Aug 2005 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

3 Contentment Island Rd

5 bd · 4.5 ba · 4,924 sqft · built 1970 · 1.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,875,000Apr 2025 $47,1422025 Amount on Record Dec 1997 2 Owners on Record Assessor + 1 DocumentUpdated Jul 2026

6 Contentment Island Rd

3 bd · 5 ba · 5,940 sqft · built 1960 · 0.807 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,135,000Dec 2018 $49,5572025 Amount on Record May 2010 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

7 Contentment Island Rd

4 bd · 3.5 ba · 5,245 sqft · built 1929 · 1.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,050,000Apr 1996 $43,6652025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

8 Contentment Island Rd

5 bd · 5.5 ba · 6,497 sqft · built 2008 · 1.49 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,350,600Dec 2010 $59,4002025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

9 Contentment Island Rd

6 bd · 5.5 ba · 5,576 sqft · built 1914 · 1.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,965,000Feb 2015 $55,2602025 Amount on Record May 2007 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

11 Contentment Island Rd

4 bd · 4 ba · 4,521 sqft · built 1926 · 1.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,591,000Nov 2019 $39,1812025 Amount on Record Sep 1992 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

12 Contentment Island Rd

2 bd · 4 ba · 3,986 sqft · built 1959 · 1.41 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,000,000Jun 2015 $74,9402025 —Sep 2002 2 Owners on Record AssessorUpdated Jul 2026

14 Contentment Island Rd

6 bd · 5 ba · 5,010 sqft · built 1956 · 7.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$111,1762025 Owner on Record Assessor + 1 DocumentUpdated Jul 2026

15 Contentment Island Rd

2 bd · 1 ba · 1,401 sqft · built 1909 · 1.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$27,1902025 Owner on Record AssessorUpdated Jul 2026

17 Contentment Island Rd

6 bd · 4.5 ba · 7,174 sqft · built 1909 · 2.45 acres

Last Sale Tax Bill Prior Sale Owner Records
$109,0032025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

19 Contentment Island Rd

4 bd · 4 ba · 9,117 sqft · built 1963 · 1.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,425,000Jun 1995 $81,2032025 Amount on Record Dec 1989 Owner on Record AssessorUpdated Jul 2026

22 Contentment Island Rd

4 bd · 4 ba · 4,394 sqft · built 1950 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,600,000Oct 2004 $33,8232025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

23 Contentment Island Rd

4 bd · 7 ba · 5,577 sqft · built 1929 · 3.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,500,000Jul 2013 $119,1092025 Amount on Record — Owner on Record AssessorUpdated Jul 2026

25 Contentment Island Rd

5 bd · 5.5 ba · 4,918 sqft · built 1916 · 2.88 acres

Last Sale Tax Bill Prior Sale Owner Records
$109,8852025 Owner on Record Assessor + 2 DocumentsUpdated Jul 2026

26 Contentment Island Rd

3 bd · 3.5 ba · 3,514 sqft · built 1950 · 1.44 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,150,000Apr 1996 $35,0082025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

27 Contentment Island Rd

5 bd · 7 ba · 9,023 sqft · built 2003 · 3.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,600,000Nov 1998 $164,1362025 Amount on Record Jan 1996 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

29 Contentment Island Rd

4 bd · 4.5 ba · 4,477 sqft · built 1950 · 0.935 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,500,000Jul 2019 $48,5902025 Amount on Record Dec 1997 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

31 Contentment Island Rd

6 bd · 4 ba · 4,805 sqft · built 1916 · 2 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,000,000Aug 2025 $62,2282025 Amount on Record Sep 1998 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

35 Contentment Island Rd

5 bd · 3 ba · 3,628 sqft · built 1955 · 2.33 acres

Last Sale Tax Bill Prior Sale Owner Records
$47,5302025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

37 Contentment Island Rd

5 bd · 5.5 ba · 3,697 sqft · built 2016 · 2.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,200,000Nov 2014 $52,4332025 Amount on Record Jun 1997 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

39 Contentment Island Rd

3 bd · 2 ba · 1,958 sqft · built 1955 · 2.38 acres

Last Sale Tax Bill Prior Sale Owner Records
$118,2442024 Owner on Record AssessorUpdated Jul 2026

40 Contentment Island Rd

5 bd · 6.5 ba · 6,194 sqft · built 2022 · 1.02 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,900,000Nov 1995 $101,5462025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

42 Contentment Island Rd

6 bd · 5 ba · 6,555 sqft · built 1900 · 3.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,950,000May 1993 $81,1052025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

43 Contentment Island Rd

4 bd · 3.5 ba · 6,454 sqft · built 1962 · 1.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,250,000Dec 2023 $54,0262025 Amount on Record Aug 2015 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

44 Contentment Island Rd

6 bd · 6 ba · 9,014 sqft · built 2006 · 2.86 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,200,000Feb 2004 $146,6972025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

45 Contentment Island Rd

5 bd · 4.5 ba · 6,226 sqft · built 1930 · 1.76 acres

Last Sale Tax Bill Prior Sale Owner Records
$102,0972025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

50 Contentment Island Rd

5 bd · 5.5 ba · 6,555 sqft · built 1958 · 2.95 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,500,000Jan 2004 $124,7772025 2 Owners on Record AssessorUpdated Jul 2026

53 Contentment Island Rd

4 bd · 7 ba · 11,627 sqft · built 2020 · 2.98 acres

Last Sale Tax Bill Prior Sale Owner Records
$11,850,000Jul 2015 $256,7992025 Owner on Record Assessor + 2 DocumentsUpdated Jul 2026

Property Records in Nearby Streets