Google satellite image for 42 Contentment Island Rd, Darien, CT 06820

Off market may 1993 for $1.9M

$10,119,677

Est. refi paymentEst. refi $4,519/mo

•

5 ba

•

6,555

sq ft

42 Contentment Island Rd, Darien, CT 06820

About this home

42 Contentment Island Rd is a 6,555 square foot house on a 3.21 acre lot with 6 bedrooms and 5 bathrooms. - it last sold on May 05, 1993 for $1,950,000. Based on Redfin's Darien data, we estimate the home's value is $10,119,677.

Single-familyProperty Type

1900Year Built

3.21 acresLot Size

$1,544Est. Price/Sq.Ft.

3 car garageParking

Source:Public Records

Redfin Estimate

$10,119,677

$8.2M since sold in May 1993$111K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 78.3% higher than the average sale price ($5.68M) 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 MAR 30, 2026
$9,420,000
B
6 beds4.5 baths7,174 sq ft
17 Contentment Island Rd, Darien, CT 06820
SOLD SEP 23, 2026
$4,600,000
C
5 beds4.5 baths4,740 sq ft
6 Searles Rd, Darien, CT 06820
SOLD AUG 20, 2026
$2,999,999
D
5 beds4.5 baths5,777 sq ft
12 Settlers Trl, Darien, CT 06820
SOLD OCT 1, 2026
$3,460,000
E
5 beds5 baths5,307 sq ft
60 Crooked Trail Rd, Norwalk, CT 06853
SOLD SEP 1, 2026
$4,725,000
F
5 beds5 baths6,151 sq ft
13 Sunswyck Rd, Darien, CT 06820

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Earn from this home

Sell

$9,536,723

Est. take-home

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Refinance

Est. cash available

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Rent

$7,435/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

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 42 Contentment Island Rd

Year

Property tax

Land + Additions

Assessment*

2023

$82,725 (+2.2%)

$3,590,300 + $1,107,330

$4,697,630

2022

$80,940 (+2.3%)

$3,590,300 + $1,107,330

$4,697,630

2021

$79,108 (+3.1%)

$3,590,300 + $1,107,330

$4,697,630

2020

$76,712 (−0.9%)

$3,590,300 + $1,107,330

$4,697,630

2019

$77,370 (−0.6%)

$3,590,300 + $1,107,330

$4,697,630

2018

$77,815 (−0.5%)

$3,846,080 + $993,160

$4,839,240

2017

$78,202 (+2.5%)

$3,846,080 + $993,160

$4,839,240

2016

$76,315 (+5.1%)

$3,846,080 + $993,160

$4,839,240

2014

$72,637

$3,846,080 + $993,160

$4,839,240

Tax history for 42 Contentment Island Rd

Year

Property tax

Land + Additions

Assessment*

2023

$82,725 (+2.2%)

$3,590,300 + $1,107,330

$4,697,630

2022

$80,940 (+2.3%)

$3,590,300 + $1,107,330

$4,697,630

2021

$79,108 (+3.1%)

$3,590,300 + $1,107,330

$4,697,630

2020

$76,712 (−0.9%)

$3,590,300 + $1,107,330

$4,697,630

2019

$77,370 (−0.6%)

$3,590,300 + $1,107,330

$4,697,630

2018

$77,815 (−0.5%)

$3,846,080 + $993,160

$4,839,240

2017

$78,202 (+2.5%)

$3,846,080 + $993,160

$4,839,240

2016

$76,315 (+5.1%)

$3,846,080 + $993,160

$4,839,240

2014

$72,637

$3,846,080 + $993,160

$4,839,240

*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: Crawl-Space

Bathroom Information
# of Full Baths: 4
# of 1/2 Baths: 2

Heating & Cooling
Heating Type: Forced Hot Water

Fireplace Information
# of Fireplaces: 2
Has Fireplace

Room Information
# of Rooms: 11

Exterior

Exterior Information
Physical Condition: Average
Building Style Type: Old
Exterior Wall: Stone/Stucco

Property Information
Living Sq. Ft: 6,555
Gross Sq. Ft: 6,555
# 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: 139,828
Municipality Name: DARIEN
Acres: 3.21
Zoning Code: R-1
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 6
Baths: 5.0
Sq. Ft.: 6,555
Stories: 2.0
Lot Size: 3.21 acres
Style: Single Family Residential
Year Built: 1900
Year Renovated: 2000
County: Fairfield County
APN: 109220

Home facts updated by county records on Jul 13, 2023

Around this home

Schools

Tokeneke Elementary School

Public PreK-5 • Assigned • 1.4mi

9/10

Middlesex Middle School

Public 6-8 • Assigned • 2.3mi

10/10

Darien High School

Public 9-12 • Assigned • 2.6mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

8/10 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

$9.61M – $11.64M

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Nearby similar homes

$10,995,000

3 beds3.5 baths4,225 sq ft

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$16,495,000

10 beds10.5 baths11,944 sq ft

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FOR SALE BY OWNER

$2,200,000

5 beds4 baths4,600 sq ft

13 Silver Lakes Dr, Darien, CT 06820

$1,495,000

3 beds3 baths2,134 sq ft

7 Channel Ave, Norwalk, CT 06854

NEW CONSTRUCTION

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New listings for sale in 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 42 Contentment Island Rd

Data from public records.

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

Address	Redfin Estimate
53 Contentment Island Road, Darien, CT 4 Beds \| 7 Baths \| 11627 Sq. Ft.	$14,431,360
43 Contentment Island Road, Darien, CT 4 Beds \| 5 Baths \| 6454 Sq. Ft.	$7,124,460

Address	Redfin Estimate
29 Contentment Island Road, Darien, CT 5 Beds \| 4.5 Baths \| 4988 Sq. Ft.	$7,286,296
37 Contentment Island Road, Darien, CT 5 Beds \| 3.5 Baths \| 4182 Sq. Ft.	$5,497,683

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