Google street view image for 23 Contentment Island Rd, Darien, CT 06820

Off market jul 2013 for $9.5M

$12,133,211

Est. refi paymentEst. refi $65,004/mo

•

7 ba

•

5,577

sq ft

23 Contentment Island Rd, Darien, CT 06820

About this home

23 Contentment Island Rd is a 5,577 square foot house on a 3.17 acre lot with 4 bedrooms and 7 bathrooms. - it last sold on July 19, 2013 for $9,510,000. Based on Redfin's Darien data, we estimate the home's value is $12,133,211.

Single-familyProperty Type

1929Year Built

3.17 acresLot Size

$2,176Est. Price/Sq.Ft.

2 car garageParking

Source:Public Records

Redfin Estimate

$12,133,211

$2.6M since sold in July 2013$1.7M since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 97.8% higher than the average sale price ($6.13M) of 6 comparable homes.

SOLD AUG 18, 2026
$8,850,000
A
5 beds5.5 baths5,823 sq ft
82 Arrowhead Way, Darien, CT 06820
SOLD SEP 23, 2026
$4,600,000
B
5 beds4.5 baths4,740 sq ft
6 Searles Rd, Darien, CT 06820
SOLD OCT 1, 2026
$3,460,000
C
5 beds5 baths5,307 sq ft
60 Crooked Trail Rd, Norwalk, CT 06853
SOLD AUG 20, 2026
$2,999,999
D
5 beds4.5 baths5,777 sq ft
12 Settlers Trl, Darien, CT 06820
SOLD AUG 14, 2026
$8,195,000
E
5 beds7 baths6,998 sq ft
30 Shipway Rd, Darien, CT 06820
SOLD NOV 21, 2025
$8,695,000
F
5 beds6.5 baths6,108 sq ft
25 Tokeneke Trl, Darien, CT 06820

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Earn from this home

Sell

$6,132,680

Est. take-home

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Refinance

Est. cash available

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Rent

$7,402/mo

Redfin rental estimate

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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 23 Contentment Island Rd

Year

Property tax

Land + Additions

Assessment*

2023

$114,301 (+2.2%)

$4,604,250 + $1,886,430

$6,490,680

2022

$111,834 (+2.3%)

$4,604,250 + $1,886,430

$6,490,680

2021

$109,303 (+3.1%)

$4,604,250 + $1,886,430

$6,490,680

2020

$105,993 (−0.8%)

$4,604,250 + $1,886,430

$6,490,680

2019

$106,901 (+3.5%)

$4,604,250 + $1,886,430

$6,490,680

2018

$103,281 (−0.5%)

$4,779,670 + $1,643,250

$6,422,920

2017

$103,794 (+2.5%)

$4,779,670 + $1,643,250

$6,422,920

2016

$101,289 (+8.4%)

$4,779,670 + $1,643,250

$6,422,920

2014

$93,456

$4,779,670 + $1,446,550

$6,226,220

Tax history for 23 Contentment Island Rd

Year

Property tax

Land + Additions

Assessment*

2023

$114,301 (+2.2%)

$4,604,250 + $1,886,430

$6,490,680

2022

$111,834 (+2.3%)

$4,604,250 + $1,886,430

$6,490,680

2021

$109,303 (+3.1%)

$4,604,250 + $1,886,430

$6,490,680

2020

$105,993 (−0.8%)

$4,604,250 + $1,886,430

$6,490,680

2019

$106,901 (+3.5%)

$4,604,250 + $1,886,430

$6,490,680

2018

$103,281 (−0.5%)

$4,779,670 + $1,643,250

$6,422,920

2017

$103,794 (+2.5%)

$4,779,670 + $1,643,250

$6,422,920

2016

$101,289 (+8.4%)

$4,779,670 + $1,643,250

$6,422,920

2014

$93,456

$4,779,670 + $1,446,550

$6,226,220

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

Property details

Interior

Basement Information
Basement Type: Partial

Bathroom Information
# of Full Baths: 6
# of 1/2 Baths: 2

Heating & Cooling
Heating Type: Central Forced Air

Fireplace Information
# of Fireplaces: 6
Has Fireplace

Room Information
# of Rooms: 10

Exterior

Exterior Information
Physical Condition: Good
Building Style Type: Colonial
Exterior Wall: Stone/Stucco

Pool Information
Has Pool

Property Information
Living Sq. Ft: 5,577
Gross Sq. Ft: 5,577
# of Units: 1
# of Stories: 2

Parking & Garage Information
Parking Type: Attached Garage
Garage / Carport Type: Attached

Lot Information
# of Buildings: 1
Land Sq. Ft: 138,085
Municipality Name: DARIEN
Acres: 3.17
Zoning Code: R-1
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 4
Baths: 7.0
Sq. Ft.: 5,577
Stories: 2.0
Lot Size: 3.17 acres
Style: Single Family Residential
Year Built: 1929
Year Renovated: 2014
County: Fairfield County
APN: 109169

Home facts updated by county records on Jul 13, 2023

Around this home

Schools

Tokeneke Elementary School

Public PreK-5 • Assigned • 1.2mi

9/10

Middlesex Middle School

Public 6-8 • Assigned • 2.5mi

10/10

Darien High School

Public 9-12 • Assigned • 2.7mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

3/10 Flood Factor

Minimal risk 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

$11.53M – $13.95M

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Nearby similar homes

OPEN SAT, 1PM TO 3PM

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3 beds3 baths2,007 sq ft

27 Lakeside Ave, Darien, CT 06820

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FOR SALE BY OWNER

$2,200,000

5 beds4 baths4,600 sq ft

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 23 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
3 Contentment Island Rd, Darien, CT 5 Beds \| 4.5 Baths \| 4924 Sq. Ft.	$5,309,710

Address	Redfin Estimate
19 Contentment Island Rd, Darien, CT 5 Beds \| 6.5 Baths \| 8274 Sq. Ft.	$10,858,112
29 Contentment Island Rd, Darien, CT 5 Beds \| 4.5 Baths \| 4988 Sq. Ft.	$7,286,296

Address	Redfin Estimate
31 Contentment Island Rd, Darien, CT 6 Beds \| 5.5 Baths \| 6586 Sq. Ft.	$7,597,283
14 Contentment Island Rd, Darien, CT 6 Beds \| 5 Baths \| 5009 Sq. Ft.	$6,913,946

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