Google street view image for 8 Contentment Island Rd, Darien, CT 06820

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Sold

$10,323,230

Est. refi paymentEst. refi $43,303/mo

•

5.5 ba

•

6,497

sq ft

8 Contentment Island Rd, Darien, CT 06820

About this home

Located In The Private Enclave Of The Tokeneke Association On Contentment Island, This Stunning State-Of-The-Art Five Bedroom, Five And One Half Bath Shingle-Style Was Designed By Bartels-Pagliaro And Built B Y Brindisi & Yaroscak.

Single-familyProperty Type

2008Year Built

1.49 acresLot Size

$1,589Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$10,323,230

$4.0M since sold in December 2010$182K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 105% higher than the average sale price ($5.03M) of 6 comparable homes.

SOLD FEB 6, 2026
$4,425,000
A
5 beds4.5 baths5,500 sq ft
13 Farm Creek Rd, Norwalk, CT 06853
SOLD AUG 20, 2026
$2,999,999
B
5 beds4.5 baths5,777 sq ft
12 Settlers Trl, Darien, CT 06820
SOLD SEP 1, 2026
$4,725,000
C
5 beds5 baths6,151 sq ft
13 Sunswyck Rd, Darien, CT 06820
SOLD MAY 4, 2026
$4,350,000
D
5 beds5 baths6,517 sq ft
44 Andrews Dr, Darien, CT 06820
SOLD MAY 18, 2026
$7,200,000
E
5 beds7 baths7,941 sq ft
76 Arrowhead Way, Darien, CT 06820
SOLD JUL 20, 2026
$6,510,000
F
5 beds7.5 baths8,370 sq ft
28 Old Farm Rd, Darien, CT 06820

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Earn from this home

Sell

$9,728,592

Est. take-home

List your home with Redfin and save $103,232

Refinance

Est. cash available

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Rent

$7,368/mo

Redfin rental estimate

List your home for rent

Market trends in 06820, CT

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

109.1%

1.1% MoM

Median sale price

$3.0M

$24K MoM

Avg. days on market

13d

0 days MoM

Recently sold homes

110

7 MoM

New listings for sale

NEW 1 HR AGO
$1,850,000
4 beds3 baths3,414 sq ft
101 Hoyt St, Darien, CT 06820
OPEN SAT, 1PM TO 3PM
$1,649,000
3 beds3 baths2,007 sq ft
27 Lakeside Ave, Darien, CT 06820
COMING SOON
$4,725,000
6 beds6 baths6,459 sq ft
12 Seagate Rd, Darien, CT 06820
OPEN SAT, 1PM TO 3PM
$2,699,000
5 beds4.5 baths4,084 sq ft
53 Country Club Rd, Darien, CT 06820
$7,995,000
5 beds6.5 baths5,172 sq ft
3 Coves End Rd, Darien, CT 06820
$1,895,000
4 beds2.5 baths2,456 sq ft
9 Wilson Ridge Rd E, Darien, CT 06820
$3,795,000
4 beds4 baths4,361 sq ft
5 Cross Rd, Darien, CT 06820
OPEN SUN, 12PM TO 3PM
$1,795,000
4 beds2 baths2,091 sq ft
150 Holmes Ave, Darien, CT 06820
FOR SALE BY OWNER
$2,200,000
5 beds4 baths4,600 sq ft
13 Silver Lakes Dr, Darien, CT 06820
See all

Provided by Redfin

Sale history for 8 Contentment Island Rd

Date

Event

Price

Public Records

Dec 2, 2010

Sold

$6,350,600

$977/sq ft

Smart MLS #98426982

Jun 25, 2009

Listed

$6,600,000

$1,016/sq ft

Smart MLS #98318792

Feb 7, 2007

Listed

$3,200,000

$493/sq ft

Smart MLS #98282291

Oct 26, 2006

Listing Removed

—

May 5, 2006

Listed

$3,495,000

$538/sq ft

GMLS #63398

May 30, 2006

Listed

$3,495,000

$538/sq ft

Smart MLS #98257906

Apr 18, 2006

Listing Removed

—

Oct 20, 2005

Listed

$3,495,000

$538/sq ft

GMLS #61478

Oct 27, 2005

Listed

$3,495,000

$538/sq ft

GMLS #46458

Oct 16, 2001

Sold

—

Dec 6, 2000

Listed

$3,950,000

$608/sq ft

Smart MLS #98074860

Aug 19, 2000

Listing Removed

—

Jun 12, 2000

Listed

$4,250,000

$654/sq ft

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Year

Property tax

Land + Additions

Assessment*

2023

$65,214 (+2.2%)

$1,960,560 + $1,742,650

$3,703,210

2022

$63,806 (+2.3%)

$1,960,560 + $1,742,650

$3,703,210

2021

$62,362 (+3.1%)

$1,960,560 + $1,742,650

$3,703,210

2020

$60,473 (−0.9%)

$1,960,560 + $1,742,650

$3,703,210

2019

$60,992 (+4.4%)

$1,960,560 + $1,742,650

$3,703,210

2018

$58,406 (−0.5%)

$1,522,430 + $2,109,800

$3,632,230

2017

$58,697 (−7.1%)

$1,522,430 + $2,109,800

$3,632,230

2016

$63,163 (−4.1%)

$1,538,460 + $2,466,800

$4,005,260

2014

$65,893

$1,923,110 + $2,466,800

$4,389,910

Tax history for 8 Contentment Island Rd

Year

Property tax

Land + Additions

Assessment*

2023

$65,214 (+2.2%)

$1,960,560 + $1,742,650

$3,703,210

2022

$63,806 (+2.3%)

$1,960,560 + $1,742,650

$3,703,210

2021

$62,362 (+3.1%)

$1,960,560 + $1,742,650

$3,703,210

2020

$60,473 (−0.9%)

$1,960,560 + $1,742,650

$3,703,210

2019

$60,992 (+4.4%)

$1,960,560 + $1,742,650

$3,703,210

2018

$58,406 (−0.5%)

$1,522,430 + $2,109,800

$3,632,230

2017

$58,697 (−7.1%)

$1,522,430 + $2,109,800

$3,632,230

2016

$63,163 (−4.1%)

$1,538,460 + $2,466,800

$4,005,260

2014

$65,893

$1,923,110 + $2,466,800

$4,389,910

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

5.5

Stories

Lot width

—

Lot depth

—

Lot size

1.49 Acres

Year renovated

—

Sq. Ft.

6,497

Year built

2008

Style

Single Family Residential

County

Fairfield County

APN

109176

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Around this home

Schools

Tokeneke Elementary School

Public PreK-5 • Assigned • 1.0mi

9/10

Middlesex Middle School

Public 6-8 • Assigned • 2.4mi

10/10

Darien High School

Public 9-12 • Assigned • 2.5mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

10/10 Flood Factor

Estimated 80%+ chance of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 98° expected this year, 16 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

4/10 Air Factor

4 unhealthy days expected this year, 6 days in 30 years

Provided by First Street

Historical weather

Darien, CT • 06820

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.8 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

8.8 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$9.81M – $11.87M

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Nearby similar homes

OPEN SAT, 1PM TO 3PM

$1,649,000

3 beds3 baths2,007 sq ft

27 Lakeside Ave, Darien, CT 06820

$639,000

4 beds2.5 baths1,659 sq ft

41 Baxter Dr, Norwalk, CT 06854

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FOR SALE BY OWNER

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13 Silver Lakes Dr, Darien, CT 06820

New listings for sale in 06820

NEW 1 HR AGO

$1,850,000

4 beds3 baths3,414 sq ft

101 Hoyt St, Darien, CT 06820

OPEN SAT, 1PM TO 3PM

$1,649,000

3 beds3 baths2,007 sq ft

27 Lakeside Ave, Darien, CT 06820

COMING SOON

$4,725,000

6 beds6 baths6,459 sq ft

12 Seagate Rd, Darien, CT 06820

OPEN SAT, 1PM TO 3PM

$2,699,000

5 beds4.5 baths4,084 sq ft

53 Country Club Rd, Darien, CT 06820

$7,995,000

5 beds6.5 baths5,172 sq ft

3 Coves End Rd, Darien, CT 06820

$1,895,000

4 beds2.5 baths2,456 sq ft

9 Wilson Ridge Rd E, Darien, CT 06820

$3,795,000

4 beds4 baths4,361 sq ft

5 Cross Rd, Darien, CT 06820

OPEN SUN, 12PM TO 3PM

$1,795,000

4 beds2 baths2,091 sq ft

150 Holmes Ave, Darien, CT 06820

FOR SALE BY OWNER

$2,200,000

5 beds4 baths4,600 sq ft

13 Silver Lakes Dr, Darien, CT 06820

Home values near 8 Contentment Island Rd

Data from public records.

Address	Redfin Estimate
15 Contentment Island Rd, Darien, CT 2 Beds \| 1 Baths \| 1401 Sq. Ft.	$2,553,184
29 Contentment Island Rd, Darien, CT 5 Beds \| 4.5 Baths \| 4988 Sq. Ft.	$7,286,296

Address	Redfin Estimate
19 Contentment Island Rd, Darien, CT 5 Beds \| 6.5 Baths \| 8274 Sq. Ft.	$10,858,112
7 Contentment Island Rd, Darien, CT 4 Beds \| 3.5 Baths \| 5245 Sq. Ft.	$5,192,993

Address	Redfin Estimate
3 Contentment Island Rd, Darien, CT 5 Beds \| 4.5 Baths \| 4924 Sq. Ft.	$5,309,710
11 Contentment Island Rd, Darien, CT 4 Beds \| 4 Baths \| 4521 Sq. Ft.	$4,702,338

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