31 Contentment Island Rd, Darien, CT 06820

Off Market Aug 2025 for $6M

$8,435,953

Est. refi paymentEst. refi $9,053/mo

•

6,586

sq ft

31 Contentment Island Rd, Darien, CT 06820

About this home

Escape to a world of elegance and serenity at this custom waterfront estate that captures the enchanting essence of New England's coastal charm. Gold Coast Luxury in exclusive Tokeneke Association. Set on a sprawling perched lot, this residence offers an unparalleled living experience with 6 generously sized bedrooms and 5.5 bathrooms. Every room in this meticulously crafted home provides breathtaking water views, ensuring a magical ambience throughout. Designed by a local coveted firm, Brooks & Falotico. The chef's kitchen is perfect for culinary enthusiasts, while the formal dining room and expansive living areas offer exquisite spaces for entertaining all with fireplaces and views to last into the evening. Enjoy the privilege of your own private dock and mooring, perfect for fishing, bird watching and a day on the water. Guests will want to extend their stay! Retreat to the charming cottage, a delightful addition for visitors seeking comfort and privacy. Leisurely afternoons await! The estate also features a gym, mudroom, boat garage, library with speak-easy and a leveled lawn ensuring all your lifestyle needs are met within this exclusive escape. Room to build and even design a pool on one of three locations on the property. Experience the ultimate blend of luxury and coastal beauty, just a stone's throw from the captivating waters of Long Island Sound. Indulge in a lifestyle where elegance meets nature, offering a truly dreamy retreat. Stop daydreaming, start living.

Single-familyProperty Type

1912Year Built

2 acresLot Size

$1,281Est. Price/Sq.Ft.

2 car garageParking

Listed by Nancy Dauk • Compass Connecticut, LLC

Listed by Patricia Schram • Compass Connecticut, LLC

Bought with Keiley Fuller • Compass Connecticut, LLC

Source:Smart MLS #24105934

Redfin Estimate

$8,435,953

$2.4M since sold in August 2025$298K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 27.3% higher than the average sale price ($6.63M) 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 AUG 20, 2026
$2,999,999
C
5 beds4.5 baths5,777 sq ft
12 Settlers Trl, Darien, CT 06820
SOLD AUG 27, 2026
$5,500,000
D
5 beds5 baths3,240 sq ft
13 Edgehill Dr, Darien, CT 06820
SOLD JUN 16, 2026
$4,300,000
E
6 beds5.5 baths5,505 sq ft
8 Pasture Ln, 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

$3,235,645

Est. take-home

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Refinance

Est. cash available

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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 31 Contentment Island Rd

Date

Event

Price

Smart MLS #24105934

Aug 8, 2025

Sold

$6,000,000

$911/sq ft

Jun 27, 2025

Pending

—

Jun 23, 2025

Listed

$6,175,000

$938/sq ft

Smart MLS #24077819

Jun 2, 2025

Listing Removed

—

Mar 7, 2025

Listed

$6,495,000

$986/sq ft

Mar 5, 2025

Coming Soon

Smart MLS #24042518

Jan 6, 2025

Listing Removed

—

Sep 3, 2024

Listed

$6,995,000

$1,062/sq ft

Aug 30, 2024

Coming Soon

Smart MLS #24020994

Jul 31, 2024

Listing Removed

—

Jun 28, 2024

Price Changed

$7,750,000

$1,177/sq ft

Jun 4, 2024

Listed

$8,500,000

$1,291/sq ft

May 31, 2024

Coming Soon

Public Records

Sep 29, 1998

Sold

$2,000,000

$304/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$59,634 (+2.2%)

$2,296,000 + $1,090,390

$3,386,390

2022

$58,347 (+2.3%)

$2,296,000 + $1,090,390

$3,386,390

2021

$57,027 (+3.1%)

$2,296,000 + $1,090,390

$3,386,390

2020

$55,300 (−0.8%)

$2,296,000 + $1,090,390

$3,386,390

2019

$55,774

$2,296,000 + $1,090,390

$3,386,390

2018

$55,789 (−0.5%)

$2,561,370 + $908,110

$3,469,480

2017

$56,067 (+2.5%)

$2,561,370 + $908,110

$3,469,480

2016

$54,714 (+5.1%)

$2,561,370 + $908,110

$3,469,480

2014

$52,077

$2,561,370 + $908,110

$3,469,480

Tax history for 31 Contentment Island Rd

Year

Property tax

Land + Additions

Assessment*

2023

$59,634 (+2.2%)

$2,296,000 + $1,090,390

$3,386,390

2022

$58,347 (+2.3%)

$2,296,000 + $1,090,390

$3,386,390

2021

$57,027 (+3.1%)

$2,296,000 + $1,090,390

$3,386,390

2020

$55,300 (−0.8%)

$2,296,000 + $1,090,390

$3,386,390

2019

$55,774

$2,296,000 + $1,090,390

$3,386,390

2018

$55,789 (−0.5%)

$2,561,370 + $908,110

$3,469,480

2017

$56,067 (+2.5%)

$2,561,370 + $908,110

$3,469,480

2016

$54,714 (+5.1%)

$2,561,370 + $908,110

$3,469,480

2014

$52,077

$2,561,370 + $908,110

$3,469,480

*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 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Other

County

Fairfield County

APN

109209

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Parking

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

Interior

Interior Information
Total Rooms: 20
Laundry Room Location: Large laundry room
Laundry Room Info: Main Level
In-Law Apartment: Yes
In-Law Access: Detached
Fireplaces Total: 7
Cooling System: Central Air
Appliances Included: Gas Cooktop, Electric Range, Microwave, Refrigerator, Subzero, Icemaker, Dishwasher, Instant Hot Water Tap, Washer, Electric Dryer, Wine Chiller

Bathroom Information
# of Baths (Full): 5
# of Baths (Half): 1

Bedroom Information
Beds Total: 6

Room Information
Rooms Additional: Workshop
Basement Description: Full, Unfinished, Storage
Has Attic
Attic Description: Storage Space, Floored, Pull-Down Stairs

Exterior

Exterior Features
Roof Information: Slate
Exterior Siding: Shingle, Clapboard

Lot Information
Lot Description: Level Lot, Professionally Landscaped, Water View, Open Lot

Building Information
Foundation Type: Concrete, Stone
Construction Description: Frame
Color: Light Grey

Property Information
Waterfront Description: L. I. Sound Frontage, Walk to Water, Dock or Mooring, View, Access
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 0

Financial

Assessments Information
Assessed Value: $4,019,890

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Septic
Hot Water Description: Oil, 65 Gallon Tank
Heat Type: Hot Air, Zoned
Heat Fuel Type: Oil
Fuel Tank Location: In Basement

Location

HOA Information
Has Home Owner's Assocation
HOA Fee Frequency: Annually
HOA Fee Amount: $2,500
Association Fee Includes: Security Service, Road Maintenance
Association Amenities: Security Services

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

Location Information
State: Connecticut
Nearby Amenities: Golf Course, Health Club, Library, Park, Playground/Tot Lot, Public Transportation, Tennis Courts
Directions: Old Farm Rd to Searles Rd to Contentment Island. Please Park on UPPER Drive, (stay left up Shennemere) vs continuing down Contentment. You will see cottage. Past cottage to front door.
Direct Waterfront
County: Fairfield

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 2 acres
Style: Other
Year Built: —
Year Renovated: —
County: Fairfield County
APN: 109209

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 2

Around this home

Schools

Tokeneke Elementary School

Public PreK-5 • Assigned • 1.3mi

9/10

Middlesex Middle School

Public 6-8 • Assigned • 2.4mi

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

5/10 Flood Factor

Estimated 27-37% chance of a flood reaching the building in the next 30 years

2/10 Fire Factor

0.00% chance of being 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

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Estimated sale price

$8.02M – $9.70M

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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

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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 31 Contentment Island Rd

Data from public records.

Address	Redfin Estimate
19 Contentment Island Road, Darien, CT 5 Beds \| 6.5 Baths \| 8274 Sq. Ft.	$11,152,769
14 Contentment Island Road, Darien, CT 6 Beds \| 5 Baths \| 5009 Sq. Ft.	$8,722,895

Address	Redfin Estimate
53 Contentment Island Road, Darien, CT 4 Beds \| 7 Baths \| 11627 Sq. Ft.	$13,982,146
43 Contentment Island Road, Darien, CT 4 Beds \| 5 Baths \| 6454 Sq. Ft.	$7,002,135

Address	Redfin Estimate
29 Contentment Island Road, Darien, CT 5 Beds \| 4.5 Baths \| 4988 Sq. Ft.	$6,891,902
37 Contentment Island Road, Darien, CT 5 Beds \| 3.5 Baths \| 4182 Sq. Ft.	$6,435,502

Property information provided by Smart MLS when last listed in 2023. This data may not match . Learn more.

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