Google satellite image for 27 Contentment Island Rd, Darien, CT 06820

Off market nov 1998 for $3.6M

$15,198,161

Est. refi paymentEst. refi $16,996/mo

•

5,815

sq ft

27 Contentment Island Rd, Darien, CT 06820

About this home

DARIEN DIRECT WTRFRNT PROP W/ HISTORIC SIGNIF. BELIEVED TO BE THE CEN- TENNIAL BLDG BLT AS THE NY STATE EXHIBIT AT THE 1876 WORLD'S FAIR. PNLD LIB & DR HAVE ACC TO TERR, LR W/ SLIDRS-LAWN & WTR. MBR BALC OVRLKG WATER. GRNHSE OFF KIT. APPROX 5815 SQ FT. EXTRA FACT SHEET-CALL LB. ONE COMMISSION DUE ONLY IF, AS & WHEN TP. STONE BULKHEAD BTH HSE. SEPARATE RAMP TO WATER. LARGE 3 CAR BARN W/ THREE LEVELS. CALL LB FOR EXCLS.

Single-familyProperty Type

1876Year Built

3.35 acresLot Size

$2,614Est. Price/Sq.Ft.

2 car garageParking

Listed by OUT-OF-TOWN BROKER • FOREIGN LISTING

Bought with OUT-OF-TOWN BROKER • FOREIGN LISTING

Redfin checked: a minute ago

•Source:GMLS #39177

Redfin Estimate

$15,198,161

$11.6M since sold in November 1998$2.1M since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 132.5% higher than the average sale price ($6.54M) of 6 comparable homes.

SOLD MAY 18, 2026
$7,200,000
A
5 beds7 baths7,941 sq ft
76 Arrowhead Way, Darien, CT 06820
SOLD JUL 20, 2026
$6,510,000
B
5 beds7.5 baths8,370 sq ft
28 Old Farm Rd, Darien, CT 06820
SOLD JUL 30, 2026
$3,850,000
C
5 beds5 baths6,764 sq ft
107 Raymond St, Darien, CT 06820
SOLD JUL 8, 2026
$8,745,000
D
5 beds7.5 baths9,396 sq ft
45 Old Farm Rd, Darien, CT 06820
SOLD SEP 1, 2026
$4,725,000
E
5 beds5 baths6,151 sq ft
13 Sunswyck Rd, Darien, CT 06820
SOLD AUG 14, 2026
$8,195,000
F
5 beds7 baths6,998 sq ft
30 Shipway Rd, Darien, CT 06820

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Sell

$13,998,702

Est. take-home

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Est. cash available

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Rent

$7,671/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
$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 27 Contentment Island Rd

Date

Event

Price

Smart MLS #98546927

Jan 10, 2013

Listing Removed

—

Jul 20, 2012

Listed

$22,000,000

$3,783/sq ft

Smart MLS #98536598

Jan 10, 2013

Listing Removed

—

Apr 24, 2012

Listed

$26,000,000

$4,471/sq ft

GMLS #82945

Jul 20, 2012

Listed

$22,000,000

$3,783/sq ft

GMLS #82065

Apr 26, 2012

Listed

$26,000,000

$4,471/sq ft

GMLS #39177

Nov 3, 1998

Sold

$3,600,000

$619/sq ft

Feb 3, 1998

Listed

$3,900,000

$671/sq ft

Public Records

Jan 29, 1996

Sold

$2,850,000

$490/sq ft

Public Records

Jun 2, 1992

Sold

$1,800,000

$310/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$159,625 (+7.1%)

$5,025,300 + $4,039,140

$9,064,440

2022

$149,081 (+2.3%)

$5,025,300 + $3,627,120

$8,652,420

2021

$145,707 (+3.1%)

$5,025,300 + $3,627,120

$8,652,420

2020

$141,294 (−0.8%)

$5,025,300 + $3,627,120

$8,652,420

2019

$142,505 (+0.3%)

$5,025,300 + $3,627,120

$8,652,420

2018

$142,028 (−0.5%)

$5,221,300 + $3,611,300

$8,832,600

2017

$142,735 (+2.5%)

$5,221,300 + $3,611,300

$8,832,600

2016

$139,290 (+5.1%)

$5,221,300 + $3,611,300

$8,832,600

2014

$132,577

$5,221,300 + $3,611,300

$8,832,600

Tax history for 27 Contentment Island Rd

Year

Property tax

Land + Additions

Assessment*

2023

$159,625 (+7.1%)

$5,025,300 + $4,039,140

$9,064,440

2022

$149,081 (+2.3%)

$5,025,300 + $3,627,120

$8,652,420

2021

$145,707 (+3.1%)

$5,025,300 + $3,627,120

$8,652,420

2020

$141,294 (−0.8%)

$5,025,300 + $3,627,120

$8,652,420

2019

$142,505 (+0.3%)

$5,025,300 + $3,627,120

$8,652,420

2018

$142,028 (−0.5%)

$5,221,300 + $3,611,300

$8,832,600

2017

$142,735 (+2.5%)

$5,221,300 + $3,611,300

$8,832,600

2016

$139,290 (+5.1%)

$5,221,300 + $3,611,300

$8,832,600

2014

$132,577

$5,221,300 + $3,611,300

$8,832,600

*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

3.3 Acres

Year renovated

2022

Sq. Ft.

9,023

Year built

2003

Style

Single Family Residential

County

Fairfield County

APN

109216

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: 2

Interior

Bathroom Information
# of Full Bathrooms: 6
Bathrooms Total Integer: 6
Bathrooms Total Decimal: 6

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

Interior Features
Interior Features: Eat-in Kitchen, Back Stairs
Has Fireplace(s)
# of Fireplaces Total: 5
Basement: Partial

Exterior

Exterior Features
Exterior Features: Balcony
Patio And Porch Features: Terrace

Property Information
Property Sub-Type: Single Family Residence
Year Built: 1876
Year Built Effective: 1953
Construction Materials: Clapboard
Other Structures: Barn(s), Gazebo, Greenhouse
Building Area Total: 5815.0
Building Area Source: Taxcard

Lot Information
On Waterfront
Waterfront Features: Deep Water, LI Sound
Lot Size Area: 3.35
Lot Size Units: Acres
Lot Size Square Feet: 145926.0
Lot Size Acres: 3.35
Zoning: RA-C1

Financial

Tax Information
Tax Annual Amount: $26,689
Tax Assessed Value: $1,654,660

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: 5
Baths: 7.0
Sq. Ft.: 9,023
Stories: 2.0
Lot Size: 3.3 acres
Style: Single Family Residential
Year Built: 2003
Year Renovated: 2022
County: Fairfield County
APN: 109216

Home facts updated by county records on Jul 13, 2023

Around this home

Schools

Tokeneke Elementary School

Public PreK-5 • Assigned • 1.3mi

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

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

$14.44M – $17.48M

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New listings for sale in 06820

OPEN SAT, 1PM TO 3PM

$1,649,000

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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

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5 Cross Rd, Darien, CT 06820

$1,795,000

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150 Holmes Ave, Darien, CT 06820

FOR SALE BY OWNER

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Home values near 27 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
14 Contentment Island Rd, Darien, CT 6 Beds \| 5 Baths \| 5009 Sq. Ft.	$6,913,946

Address	Redfin Estimate
31 Contentment Island Rd, Darien, CT 6 Beds \| 5.5 Baths \| 6586 Sq. Ft.	$7,597,283
43 Contentment Island Rd, Darien, CT 4 Beds \| 5 Baths \| 6454 Sq. Ft.	$7,124,460

Property information provided by GMLS when last listed in 1998. This data may not match . Learn more.

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