19 Contentment Island Rd, Darien, CT 06820

Off Market Sep 2013 for $5.6M

$11,152,769

Est. refi paymentEst. refi $9,580/mo

•

8,274

sq ft

19 Contentment Island Rd, Darien, CT 06820

About this home

Single-familyProperty Type

1963Year Built

1.16 acresLot Size

$1,348Est. Price/Sq.Ft.

2 car garageParking

Listed by Jeffrey Kelly • Houlihan Lawrence

Listed by Liz Harnisch • William Pitt Sotheby's Int'l

Bought with Douglas Milne • Houlihan Lawrence

Source:Smart MLS #98541822

Redfin Estimate

$11,152,769

$5.5M since sold in September 2013$76K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 80.4% higher than the average sale price ($6.18M) of 6 comparable homes.

SOLD AUG 20, 2026
$2,999,999
A
5 beds4.5 baths5,777 sq ft
12 Settlers Trl, Darien, CT 06820
SOLD JUL 15, 2026
$3,450,000
B
5 beds4.5 baths3,512 sq ft
15 Queens Ln, Darien, CT 06820
SOLD JUL 20, 2026
$6,510,000
C
5 beds7.5 baths8,370 sq ft
28 Old Farm Rd, Darien, CT 06820
SOLD AUG 14, 2026
$8,195,000
D
5 beds7 baths6,998 sq ft
30 Shipway Rd, 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 8, 2026
$8,745,000
F
5 beds7.5 baths9,396 sq ft
45 Old Farm Rd, Darien, CT 06820

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$7,335,515

Est. take-home

List your home with Redfin and save $111,528

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$7,378/mo

Redfin rental estimate

List your home for rent

Market trends in 06820, CT

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

110.4%

1.4% MoM

Median sale price

$3.0M

$18K MoM

Avg. days on market

13d

1 days MoM

Recently sold homes

105

27 MoM

New listings for sale

COMING SOON
$3,925,000
4 beds3.5 baths4,093 sq ft
20 Lighthouse Way, Darien, CT 06820
COMING SOON
$5,995,000
6 beds7.5 baths8,068 sq ft
67 Peach Hill Rd, Darien, CT 06820
COMING SOON
$1,595,000
3 beds2.5 baths2,021 sq ft
3 Fairfield Ave, Darien, CT 06820
COMING SOON
$1,749,000
4 beds2.5 baths2,106 sq ft
60 Middlesex Rd, Darien, CT 06820
$1,725,000
2 beds2.5 baths1,460 sq ft
10 Hale Ln #10, Darien, CT 06820
$2,495,000
5 beds3.5 baths3,404 sq ft
14 Nolen Ln, Darien, CT 06820
FOR SALE BY OWNER
$1,200,000
3 beds2 baths1,812 sq ft
84 Holmes Ave, Darien, CT 06820
$895,000
2 beds1.5 baths910 sq ft
64 Noroton Ave, Darien, CT 06820
$2,250,000
4 beds3.5 baths3,511 sq ft
1644 Boston Post Rd, Darien, CT 06820
$1,999,000
4 beds2.5 baths3,065 sq ft
2 Stony Brook Rd S, Darien, CT 06820
See all

Provided by Redfin

Sale history for 19 Contentment Island Rd

Date

Event

Price

GMLS #82552

Sep 20, 2013

Sold

$5,635,000

$681/sq ft

Jun 6, 2012

Listed

$6,995,000

$845/sq ft

+14

ONE OF A KIND SECLUDED ARTIST'S DIRECT WTRFRNT RETREAT W/ RARE, PRIV SANDY BEACH & BREATHTKING VIEWS OF LI SOUND PRESENTS A UNIQUE OPPORTUNITY FOR TRULY EXCEPTIONAL LIVING. SURROUNDED BY MAJOR WTRFRNT ESTATES IN AN EXCLUSIVE PRIV ASSOC & LESS THAN 1 HR TO MANHATTAN, THIS SPACIOUS BRICK & SHINGLE RES SET ON A MAGNIFICENT PARK-LIKE ACRE ENHANCED W/ MATURE, SPECIMEN PLANTINGS OFFERS A SPECTACULAR 2 STRY STUDIO, 2 MASTER SUITES W/ ADDTL GUEST SUITE, PROF OFFICE SPACE & 2 BDRM STAFF QUARTERS. AN EXTRAORDINARYILY EQUISITE SETTING SUGGESTING ENDLESS POSSIBILITES TO CREATE ONE'S OWN WTRFRNT SANCTUARY.

Smart MLS #98541822

Sep 20, 2013

Sold

$5,635,000

$681/sq ft

Jun 5, 2012

Listed

$6,995,000

$845/sq ft

Smart MLS #95051345

Sep 1, 1995

Listing Removed

—

Sep 1, 1993

Listed

$2,600,000

$314/sq ft

Public Records

Jun 6, 1995

Sold

$2,425,000

$293/sq ft

Public Records

Dec 15, 1989

Sold

$1,950,000

$236/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$75,175 (+2.2%)

$2,885,750 + $1,383,130

$4,268,880

2022

$73,553 (+2.3%)

$2,885,750 + $1,383,130

$4,268,880

2021

$71,888 (−0.1%)

$2,885,750 + $1,383,130

$4,268,880

2020

$71,964 (−0.9%)

$2,885,750 + $1,521,100

$4,406,850

2019

$72,581 (−1.9%)

$2,885,750 + $1,521,100

$4,406,850

2018

$73,996 (−0.5%)

$2,995,160 + $1,606,570

$4,601,730

2017

$74,364 (+2.5%)

$2,995,160 + $1,606,570

$4,601,730

2016

$72,569 (+5.1%)

$2,995,160 + $1,606,570

$4,601,730

2014

$69,072

$2,995,160 + $1,606,570

$4,601,730

Tax history for 19 Contentment Island Rd

Year

Property tax

Land + Additions

Assessment*

2023

$75,175 (+2.2%)

$2,885,750 + $1,383,130

$4,268,880

2022

$73,553 (+2.3%)

$2,885,750 + $1,383,130

$4,268,880

2021

$71,888 (−0.1%)

$2,885,750 + $1,383,130

$4,268,880

2020

$71,964 (−0.9%)

$2,885,750 + $1,521,100

$4,406,850

2019

$72,581 (−1.9%)

$2,885,750 + $1,521,100

$4,406,850

2018

$73,996 (−0.5%)

$2,995,160 + $1,606,570

$4,601,730

2017

$74,364 (+2.5%)

$2,995,160 + $1,606,570

$4,601,730

2016

$72,569 (+5.1%)

$2,995,160 + $1,606,570

$4,601,730

2014

$69,072

$2,995,160 + $1,606,570

$4,601,730

*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

1.16 Acres

Year renovated

—

Sq. Ft.

8,274

Year built

1963

Style

Single Family Residential

County

Fairfield County

APN

109168

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Parking

Garage Information
Garage & Parking: Attached Garage
Garages Number: 2

Interior

Interior Information
Total Rooms: 16
Laundry Room Location: First
Interior Features: Security System
In-Law Apartment: Yes
Fireplaces Total: 3
Cooling System: Central Air
Appliances Included: Cook Top, Dishwasher, Dryer, Microwave, Refrigerator, Wall Oven, Washer

Bathroom Information
# of Baths (Full): 6
# of Baths (Half): 1

Bedroom Information
Beds Total: 5

Room Information
Rooms Additional: Laundry Room, Staff Quarters
Room Count: 10
Basement Description: Crawl Space, Partial, Unfinished
Has Attic
Attic Description: Walk-up

Exterior

Exterior Features
Roof Information: Slate, Wood Shingle
Exterior Siding: Brick, Shingle, Wood
Exterior Features: Balcony, Patio, Underground Sprinkler

Lot Information
Lot Description: In Flood Zone, Level Lot

Land Information
Encumbrances Restrictions: Easements

Building Information
Foundation Type: Block
Color: Khaki

Property Information
Waterfront Description: Beach, Frontage, L. I. Sound Frontage, View, Direct Waterfront
Property Type: Single Family For Sale
# of Stories: 0
Living Area SQFT Per Public Record: 8274

Financial

Assessments Information
Assessed Value: $5,749,520

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Septic
Heat Type: Hot Air, Radiant
Heat Fuel Type: Oil, Propane

Location

HOA Information
Has Home Owner's Assocation
HOA Fee Amount: $3,737
Association Fee Includes: Security Service

School Information
Middle Jr High School: Middlesex
High School: Darien
Elementary School: Tokeneke

Location Information
State: Connecticut
Directions: Tokeneke Rd. To Old Farm To Searles To Contentment Island Rd
Direct Waterfront
County: Fairfield

Public facts

Beds: 4
Baths: 4.0
Sq. Ft.: 8,274
Stories: 2.0
Lot Size: 1.16 acres
Style: Single Family Residential
Year Built: 1963
Year Renovated: —
County: Fairfield County
APN: 109168

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

9/10 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

$10.60M – $12.83M

Reach more buyers when you sell with Redfin. Save up to $111,528 in fees. 3 minutes to get started.

Get a free, detailed breakdown of how we calculated your estimate.

Nearby similar homes

$639,000

3 beds2 baths1,863 sq ft

49 Baxter Dr, Norwalk, CT 06854

$5,295,000

4 beds5.5 baths4,710 sq ft

34 Nearwater Rd, Norwalk, CT 06853

$3,000,000

3 beds2.5 baths2,442 sq ft

32 Nearwater Rd, Norwalk, CT 06853

$2,795,000

3 beds2.5 baths2,221 sq ft

63 Neptune Ave, Norwalk, CT 06854

$1,495,000

3 beds3 baths2,134 sq ft

7 Channel Ave, Norwalk, CT 06854

$3,950,000

4 beds3.5 baths6,021 sq ft

15 Wildcat Rd, Darien, CT 06820

New listings for sale in 06820

COMING SOON

$3,925,000

4 beds3.5 baths4,093 sq ft

20 Lighthouse Way, Darien, CT 06820

COMING SOON

$5,995,000

6 beds7.5 baths8,068 sq ft

67 Peach Hill Rd, Darien, CT 06820

COMING SOON

$1,595,000

3 beds2.5 baths2,021 sq ft

3 Fairfield Ave, Darien, CT 06820

COMING SOON

$1,749,000

4 beds2.5 baths2,106 sq ft

60 Middlesex Rd, Darien, CT 06820

$1,725,000

2 beds2.5 baths1,460 sq ft

10 Hale Ln #10, Darien, CT 06820

$2,495,000

5 beds3.5 baths3,404 sq ft

14 Nolen Ln, Darien, CT 06820

FOR SALE BY OWNER

$1,200,000

3 beds2 baths1,812 sq ft

84 Holmes Ave, Darien, CT 06820

$895,000

2 beds1.5 baths910 sq ft

64 Noroton Ave, Darien, CT 06820

$2,250,000

4 beds3.5 baths3,511 sq ft

1644 Boston Post Rd, Darien, CT 06820

Home values near 19 Contentment Island Rd

Data from public records.

Address	Redfin Estimate
15 Contentment Island Road, Darien, CT 2 Beds \| 1 Baths \| 1401 Sq. Ft.	$2,234,150
29 Contentment Island Road, Darien, CT 5 Beds \| 4.5 Baths \| 4988 Sq. Ft.	$6,891,902

Address	Redfin Estimate
31 Contentment Island Road, Darien, CT 6 Beds \| 5.5 Baths \| 6586 Sq. Ft.	$8,435,953
14 Contentment Island Road, Darien, CT 6 Beds \| 5 Baths \| 5009 Sq. Ft.	$8,722,895

Address	Redfin Estimate
3 Contentment Island Road, Darien, CT 5 Beds \| 4.5 Baths \| 4924 Sq. Ft.	$5,271,131
7 Contentment Island Road, Darien, CT 4 Beds \| 3.5 Baths \| 5245 Sq. Ft.	$6,299,026

Property information provided by Smart MLS when last listed in 2012. This data may not match . Learn more.

More real estate resources

Cities
Minor Civil Divisions
Zip Codes
Neighborhoods
Popular Searches

Greenwich homes for sale
Darien homes for sale
Stamford homes for sale

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Wilton homes for sale
Weston homes for sale
Monroe homes for sale
Fairfield homes for sale
New Canaan homes for sale

Houses for rent in Tokeneke	Agents near me	Westport, CT homes for sale	Tokeneke Housing Market
Houses for sale near me	Greenwich, CT homes for sale	New Haven, CT homes for sale
Land for sale near me	Stamford, CT homes for sale	Milford, CT homes for sale
Open Houses near me	West Hartford, CT homes for sale	Tokeneke Property Records
Condos for sale near me	Norwalk, CT homes for sale	CT New Listings