Sold
Last Sold Price
5 beds6,555 sqft$534/sqft
50 Contentment Island Rd, Darien, CT 06820
Single FamilyProperty Type
1.55 acresLot Size
1958Year Built
$534/sq ftPrice per sq ft
Listing closed: 01/27/2004 12:00 AM

Recent comparable sales

Median sold price

$3,706,313

Avg days on market

19

Sale-to-list ratio

102.5%

Darien, CT

9 comparable properties found

$3,615,000 | 25 Patricia Lane, Darien, CT 06820
1

$3,615,000

Sold 06/10/26

5
Bedrooms
5,735
Square Feet
0.3
Acres
$3,850,000 | 107 Raymond Street, Darien, CT 06820
2

$3,850,000

Sold 07/30/26

5
Bedrooms
6,764
Square Feet
2.74
Acres
a front view of a house with a garden
3

$4,350,000

Sold 05/04/26

5
Bedrooms
6,517
Square Feet
1.14
Acres
$4,000,000 | 14 Wilson Ridge Road, Darien, CT 06820
4

$4,000,000

Sold 03/25/25

5
Bedrooms
6,341
Square Feet
0.5
Acres
$3,706,313 | 74 Brookside Road, Darien, CT 06820
5

$3,706,313

Sold 09/12/25

5
Bedrooms
6,069
Square Feet
0.53
Acres
a view of a house with a backyard
6

$2,999,999

Sold 08/20/26

5
Bedrooms
5,777
Square Feet
1.4
Acres
$3,750,000 | 16 Morley Lane, Darien, CT 06820
7

$3,750,000

Sold 08/01/25

5
Bedrooms
5,475
Square Feet
1.02
Acres
$3,616,000 | 10 Prospect Avenue, Darien, CT 06820
8

$3,616,000

Sold 01/06/26

5
Bedrooms
5,338
Square Feet
0.79
Acres
$3,250,000 | 93 Mansfield Avenue, Darien, CT 06820
9

$3,250,000

Sold 12/12/25

5
Bedrooms
5,220
Square Feet
0.53
Acres

Location

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Payment Calculator

$28,188 per month

30 year fixed, 6.55% Interest

Principal and Interest

$17,790

Property Taxes

$10,398

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 50 Contentment Island Road

Property Details
Building Information
  • Stories: 2
  • Year Built: 1958
  • Lot Size: 1.55 AC / 67,518 SF

Property History for 50 Contentment Island Road

DateEvent & SourcePriceAppreciation
Jan 27, 2004

Closed (Public Record)

Public Record #131237425

$3,500,000
DateEvent & SourcePrice
01/27/2004

Closed (Public Record)

Public Record #131237425

$3,500,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 50 Contentment Island Road

Taxable ValueLand$6,968,500Additions$1,092,000Total$8,060,500
Tax Record2025$124,777 ($10,398 / month)
Home Facts
Beds5Baths5.5Total Finished SqFt6,555 SqFtAbove Grade Finished SqFt6,555 SqFtStories2Lot Size128,654 SqFtStyleSingle Family ResidenceYear Built1958Year Renovated2006ZoningR-1CountyWESTERN CONNECTICUTAPNDARI M:68 B:22-23

Schools near 50 Contentment Island Road

This home is within Darien School District.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - 6 to 8
Public - 9 to 12
Rating
School
Distance
Tokeneke Elementary School
PublicPK to 5

Middlesex Middle School
Public6 to 8

Darien High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 50 Contentment Island Road, Darien, CT 06820
$3,500,000
5
6,555
67,518
$11,850,000
3
2,889
479,160
$5,250,000
4
6,454
54,014
5
4.5
6,226
76,666
$3,200,000
5
2,910
88,862
2
1,958
104,108

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.