Sold on Aug 2026

$4,200,000

•

5,678

sq ft

2 Roland Dr, Darien, CT 06820

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About this home

The moment you step onto the inviting front porch, you'll feel the warmth and charm of this exceptional 5-bedroom, 4.5-bath Colonial perched on a quiet cul-de-sac. Experience sophisticated design, unparalleled comfort, and an unbeatable location. Welcome to your dream home in Darien. The heart of the home is the chef's kitchen, fully renovated and featuring top-of-the-line appliances, a leathered black quartz island, and space for everyone to gather. Flowing through french doors to the spacious family room, adorned with custom built-ins and the sun-drenched playroom that opens to the professionally landscaped backyard and terrace-your private oasis for outdoor living. Upstairs, the luxurious primary suite is a true retreat, boasting a cozy fireplace, an expansive walk-in closet, and a spa-inspired bathroom with a double vanity, oversized shower, and a classic clawfoot tub. The additional 4 bedrooms all gift generous size, oversized closets and 3 more fully renovated bathrooms. The great room wows with size and soaring exposed beams, a striking stone fireplace. A fun, warm and inviting spacee for all to enjoy. Don't forget the basement with finished space, workout area and a hockey shooting room. Situated just minutes from school, the train, parks, downtown shops, and acclaimed restaurants, this property offers luxury living along with convenience and a true sense of community.

Single-familyProperty Type

2004Year Built

0.53 acresLot Size

$740Price/Sq.Ft.

3 car garageParking

Listed by Stephanie Hanford • Compass Connecticut, LLC

Listed by Jennifer Farnum • Compass Connecticut, LLC

Contact: Agent Attribution Contact: (917) 499-5402 | Office Attribution Contact: (203) 423-3100

Bought with Andrew Smith • Houlihan Lawrence

Source:Smart MLS #24165314

Redfin Estimate

$4,274,561

$75K since sold in August 2026$111K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 14.5% higher than the average sale price ($3.73M) of 6 comparable homes.

SOLD JUL 29, 2026
$4,000,000
A
5 beds4.5 baths5,166 sq ft
16 Overbrook Ln, Darien, CT 06820
SOLD AUG 7, 2026
$3,250,000
B
5 beds5.5 baths5,226 sq ft
14 Revere Rd, Darien, CT 06820
SOLD DEC 12, 2025
$3,250,000
C
5 beds5 baths5,220 sq ft
93 Mansfield Ave, Darien, CT 06820
SOLD SEP 1, 2026
$4,725,000
D
5 beds5 baths6,151 sq ft
13 Sunswyck Rd, Darien, CT 06820
SOLD JUL 16, 2026
$3,925,000
E
5 beds4.5 baths4,840 sq ft
8 Sunset Rd, Darien, CT 06820
SOLD SEP 15, 2026
$3,250,000
F
5 beds3.5 baths4,301 sq ft
11 McLaren Rd S, Darien, CT 06820

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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

109.0%

1.3% MoM

Median sale price

$3.0M

$23K MoM

Avg. days on market

13d

0 days MoM

Recently sold homes

112

9 MoM

New listings for sale

NEW 23 HRS AGO
$16,495,000
10 beds10.5 baths11,944 sq ft
155 Long Neck Point Rd, Darien, CT 06820
COMING SOON
$3,600,000
5 beds4.5 baths4,423 sq ft
18 Bates Farm Ln, Darien, CT 06820
FOR SALE BY OWNER
$2,200,000
5 beds4 baths3,033 sq ft
13 Silver Lakes Dr, Darien, CT 06820
$7,500,000
5 beds7 baths10,213 sq ft
460 Middlesex Rd, Darien, CT 06820
$2,895,000
4 beds2.5 baths4,080 sq ft
30 Birch Rd, Darien, CT 06820
$3,825,000
5 beds3.5 baths4,400 sq ft
21 Harbor Rd, Darien, CT 06820
OPEN SEP 28, 2PM TO 4PM
$1,895,000
4 beds3 baths2,303 sq ft
13 Chestnut St, Darien, CT 06820
VIDEO TOUR
$3,595,000
3 beds4.5 baths4,733 sq ft
31 Hancock Ln, Darien, CT 06820
3D WALKTHROUGH
$1,200,000
3 beds2 baths1,974 sq ft
145 West Ave, Darien, CT 06820
$1,749,000
4 beds2.5 baths2,106 sq ft
60 Middlesex Rd, Darien, CT 06820
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Rental estimate

Est. $7,496 per month, based on comparable rentals

Sale and tax history for 2 Roland Dr

Sale History
Tax History

Date

Event

Price

Smart MLS #24165314

Aug 7, 2026

Sold

$4,200,000

$740/sq ft

May 18, 2026

Pending

—

Apr 30, 2026

Listed

$4,250,000

$749/sq ft

Apr 23, 2026

Coming Soon

$4,250,000

$749/sq ft

Smart MLS #170376573

May 6, 2021

Sold

$2,777,500

$489/sq ft

Mar 2, 2021

Listed

$2,695,000

$475/sq ft

Welcome home to this perfect 5 bedroom, 4.5 bath colonial home in the heart of Darien. A picture perfect front porch, and walkable to down town Darien shops and restaurants as well as the Train Station. Three story grand entryway and amazing architectural detail throughout as well as wood beamed great room with stone fire place make this the house you have been waiting for. The kitchen is a chef's dream with top-of-the-line appliances, granite countertops and separate wet bar area with wine refrigerator. An adjacent sun-filled office with French doors and family room with built-ins, all overlooking the backyard and terrace for outdoor enjoyment. Master bedroom suite offers fireplace, walk-in and luxurious master bath with steam shower. Three car garage completes this perfect home.

Public Records

Dec 1, 2017

Sold

$2,280,000

$402/sq ft

Smart MLS #99181185

Dec 1, 2017

Listing Removed

—

Nov 30, 2017

Sold

$2,280,000

$402/sq ft

Apr 12, 2017

Listed

$2,375,000

$418/sq ft

Welcome to this 5 bedroom, 4 full & 1 half bath colonial w/an inviting wrap-around porch to sit & watch the world go by. Boasting a 3 story foyer, architectural detail & an amazing vaulted ceiling, wood beamed great room w/stone fireplace, perfect for relaxing & entertaining. The kitchen is a chef’s dream w/top-of-the-line appliances, granite countertops & separate wet bar area w/wine refrigerator. An adjacent, sun-filled breakfast room & family room w/built-ins, all overlooking the backyard & terrace for outdoor enjoyment. Master bedroom suite offers fireplace, walk-in & luxurious master bath w/steam shower. Everything you need & more including a 3-car garage, plenty of storage plus walk to all the wonderful amenities Darien has to offer.

Public Records

Jul 5, 2012

Sold

$2,650,000

$467/sq ft

Smart MLS #98486780

Sep 1, 2011

Listing Removed

—

Jan 6, 2011

Listed

$2,695,000

$475/sq ft

Smart MLS #98425219

Sep 1, 2009

Listing Removed

—

Jun 10, 2009

Listed

$2,995,000

$527/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$27,695 (+2.2%)

$541,170 + $1,031,520

$1,572,690

2022

$27,097 (+2.3%)

$541,170 + $1,031,520

$1,572,690

2021

$26,484 (+3.1%)

$541,170 + $1,031,520

$1,572,690

2020

$25,682 (−0.8%)

$541,170 + $1,031,520

$1,572,690

2019

$25,902 (−13.1%)

$541,170 + $1,031,520

$1,572,690

2018

$29,821 (−0.4%)

$749,700 + $1,104,810

$1,854,510

2017

$29,928 (+2.5%)

$749,700 + $1,102,290

$1,851,990

2016

$29,206 (+5.1%)

$749,700 + $1,102,290

$1,851,990

2014

$27,798

$749,700 + $1,102,290

$1,851,990

Public record

Beds

Baths

4.5

Stories

Lot width

—

Lot depth

—

Lot size

0.53 Acres

Year renovated

—

Sq. Ft.

5,678

Year built

2004

Style

Single Family Residential

County

Fairfield County

APN

104231

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: 3

Interior

Interior Information
Total Rooms: 11
Laundry Room Info: Main Level
Interior Features: Audio System, Auto Garage Door Opener, Central Vacuum, Security System
Built In Audio, Lighting, Security System, Thermostat(s)
Fireplaces Total: 3
Cooling System: Central Air
Appliances Included: Gas Range, Microwave, Range Hood, Refrigerator, Freezer, Subzero, Dishwasher, Disposal, Washer, Dryer, Wine Chiller

Bathroom Information
# of Baths (Full): 4
# of Baths (Half): 1

Bedroom Information
Beds Total: 5

Room Information
Rooms Additional: Exercise Room, Foyer, Laundry Room, Mud Room
Basement Description: Full, Partially Finished
Has Attic
Attic Description: Storage Space, Walk-up

Exterior

Exterior Features
Roof Information: Wood Shingle
Exterior Siding: Shake, Wood
Exterior Features: Sidewalk, Porch, Lighting, Stone Wall, French Doors, Underground Sprinkler, Patio

Lot Information
Lot Description: Level Lot, On Cul-De-Sac, Professionally Landscaped

Building Information
Foundation Type: Block
Construction Description: Frame
Color: White

Property Information
Waterfront Description: Beach Rights, Water Community
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 5678

Financial

Assessments Information
Assessed Value: $2,012,430

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Public Sewer Connected
Hot Water Description: Oil, 80 Gallon Tank
Heat Type: Hot Air
Heat Fuel Type: Oil
Fuel Tank Location: In Basement
Energy Features: Generator

Location

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

Location Information
State: Connecticut
Directions: Mansfield to Roland
County: Fairfield

Public facts

Beds: 5
Baths: 4.5
Sq. Ft.: 5,678
Stories: 2.0
Lot Size: 0.53 acres
Style: Single Family Residential
Year Built: 2004
Year Renovated: —
County: Fairfield County
APN: 104231

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 5

Around this home

Schools

Royle Elementary School

Public PreK-5 • Assigned • 0.2mi

9/10

Middlesex Middle School

Public 6-8 • Assigned • 1.5mi

10/10

Darien High School

Public 9-12 • Assigned • 1.0mi

10/10

Provided by GreatSchools

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 99° expected this year, 16 days in 30 years

6/10 Wind Factor

77% 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

82/ 100

Very good sunlight

Sunscore

This home receives average direct sun exposure in Darien. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

8.6 hrs

5.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$4.06M – $4.92M

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New listings for sale in 06820

NEW 23 HRS AGO

$16,495,000

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155 Long Neck Point Rd, Darien, CT 06820

COMING SOON

$3,600,000

5 beds4.5 baths4,423 sq ft

18 Bates Farm Ln, Darien, CT 06820

FOR SALE BY OWNER

$2,200,000

5 beds4 baths3,033 sq ft

13 Silver Lakes Dr, Darien, CT 06820

$7,500,000

5 beds7 baths10,213 sq ft

460 Middlesex Rd, Darien, CT 06820

$2,895,000

4 beds2.5 baths4,080 sq ft

30 Birch Rd, Darien, CT 06820

$3,825,000

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21 Harbor Rd, Darien, CT 06820

OPEN SEP 28, 2PM TO 4PM

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VIDEO TOUR

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3D WALKTHROUGH

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Home values near 2 Roland Dr

Data from public records.

Address	Redfin Estimate
3 Roland Drive, Darien, CT 4 Beds \| 3.5 Baths \| 3980 Sq. Ft.	$2,882,766
9 Roland Drive, Darien, CT 4 Beds \| 2.5 Baths \| 2024 Sq. Ft.	$2,187,647

Address	Redfin Estimate
12 Roland Drive, Darien, CT 4 Beds \| 2.5 Baths \| 3076 Sq. Ft.	$2,515,127
4 Roland Drive, Darien, CT 5 Beds \| 5.5 Baths \| 5502 Sq. Ft.	$4,495,859

Address	Redfin Estimate
10 Roland Drive, Darien, CT 5 Beds \| 3.5 Baths \| 2900 Sq. Ft.	$3,043,784
15 Roland Drive, Darien, CT 5 Beds \| 3.5 Baths \| 2474 Sq. Ft.	$2,572,565

Property information provided by Smart MLS when last listed in 2026. This data may not match . Learn more.

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About this home

Redfin Estimate

Market trends in 06820, CT

Homeowner tools

Sale and tax history for 2 Roland Dr

Public record

Property details

Around this home

Schools

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06820

Home values near 2 Roland Dr

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