Google satellite image for 44 Contentment Island Rd, Darien, CT 06820

Off market feb 2004 for $7.2M

$14,075,571

Est. refi paymentEst. refi $49,095/mo

•

5,350

sq ft

44 Contentment Island Rd, Darien, CT 06820

About this home

Single-familyProperty Type

1907Year Built

1.86 acresLot Size

$2,631Est. Price/Sq.Ft.

3 car garageParking

Listed by OUT-OF-TOWN BROKER • FOREIGN LISTING

Bought with OUT-OF-TOWN BROKER • FOREIGN LISTING

Redfin checked: a few seconds ago

•Source:GMLS #54919

Redfin Estimate

$14,075,571

$6.9M since sold in February 2004$48K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 151.1% higher than the average sale price ($5.60M) 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 AUG 20, 2026
$2,999,999
C
5 beds4.5 baths5,777 sq ft
12 Settlers Trl, Darien, CT 06820
SOLD JUN 16, 2026
$4,300,000
D
6 beds5.5 baths5,505 sq ft
8 Pasture Ln, Darien, CT 06820
SOLD MAR 30, 2026
$9,420,000
E
6 beds4.5 baths7,174 sq ft
17 Contentment Island Rd, Darien, CT 06820
SOLD OCT 1, 2026
$3,460,000
F
5 beds5 baths5,307 sq ft
60 Crooked Trail Rd, Norwalk, CT 06853

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Earn from this home

Sell

$11,173,548

Est. take-home

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Refinance

Est. cash available

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Rent

$7,730/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 44 Contentment Island Rd

Year

Property tax

Land + Additions

Assessment*

2023

$150,748 (+2.2%)

$5,566,610 + $2,993,760

$8,560,370

2022

$147,495 (+2.3%)

$5,566,610 + $2,993,760

$8,560,370

2021

$144,157 (+3.1%)

$5,566,610 + $2,993,760

$8,560,370

2020

$139,791 (−0.8%)

$5,566,610 + $2,993,760

$8,560,370

2019

$140,989 (−1.5%)

$5,566,610 + $2,993,760

$8,560,370

2018

$143,193 (−0.5%)

$5,594,540 + $3,310,510

$8,905,050

2017

$143,906 (+2.5%)

$5,594,540 + $3,310,510

$8,905,050

2016

$140,433 (−14.3%)

$5,594,540 + $3,310,510

$8,905,050

2014

$163,898

$6,898,640 + $4,020,590

$10,919,230

Tax history for 44 Contentment Island Rd

Year

Property tax

Land + Additions

Assessment*

2023

$150,748 (+2.2%)

$5,566,610 + $2,993,760

$8,560,370

2022

$147,495 (+2.3%)

$5,566,610 + $2,993,760

$8,560,370

2021

$144,157 (+3.1%)

$5,566,610 + $2,993,760

$8,560,370

2020

$139,791 (−0.8%)

$5,566,610 + $2,993,760

$8,560,370

2019

$140,989 (−1.5%)

$5,566,610 + $2,993,760

$8,560,370

2018

$143,193 (−0.5%)

$5,594,540 + $3,310,510

$8,905,050

2017

$143,906 (+2.5%)

$5,594,540 + $3,310,510

$8,905,050

2016

$140,433 (−14.3%)

$5,594,540 + $3,310,510

$8,905,050

2014

$163,898

$6,898,640 + $4,020,590

$10,919,230

*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

Stories

Lot width

—

Lot depth

—

Lot size

2.86 Acres

Year renovated

—

Sq. Ft.

9,014

Year built

2006

Style

Single Family Residential

County

Fairfield County

APN

109219

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Parking

Parking and Garage Information
Has Garage
# of Garage Spaces: 3

Interior

Bathroom Information
# of Full Bathrooms: 5
# of Half Bathrooms: 1
Bathrooms Total Integer: 6
Bathrooms Total Decimal: 5.5

Heating & Cooling
Cooling: None
Has Heating
Heating: Hot Water, Oil

Interior Features
Window Features: Bay Window(s)
Interior Features: Entrance Foyer
Has Fireplace(s)
# of Fireplaces Total: 4
Basement: Partial

Exterior

Exterior Features
Exterior Features: Balcony, Dock
Patio And Porch Features: Screened Porch

Property Information
Property Sub-Type: Single Family Residence
Year Built: 1907
Roof: Slate
Construction Materials: Stucco
Building Area Total: 5350.0
Building Area Source: Taxcard

Lot Information
On Waterfront
Waterfront Features: Deep Water, LI Sound
Lot Size Area: 1.86
Lot Size Units: Acres
Lot Size Square Feet: 81021.6
Lot Size Acres: 1.86

Financial

Tax Information
Tax Annual Amount: $39,633
Tax Assessed Value: $3,538,700

Utilities

Utilities Information
Sewer: Septic Tank
Water Source: Public

Location

School Information
Elementary School: Out of Town
Middle Or Junior School: Out of Town

Public facts

Beds: 6
Baths: 6.0
Sq. Ft.: 9,014
Stories: 2.0
Lot Size: 2.86 acres
Style: Single Family Residential
Year Built: 2006
Year Renovated: —
County: Fairfield County
APN: 109219

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

1/10 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

$13.37M – $16.19M

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New listings for sale in 06820

NEW 1 HR AGO

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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

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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

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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

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5 beds4 baths4,600 sq ft

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Home values near 44 Contentment Island Rd

Data from public records.

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

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

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

Property information provided by GMLS when last listed in 2003. This data may not match . Learn more.

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