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2 Roland Drive

Darien, Connecticut 06820

PENDING$4,250,000
Beds
5
Baths
4 | 1
SqFt
5,678
Acres
0.53
Year Built
2004
Matt Caiola

Matt Caiola

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3-Car Garage3 Fireplaces

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.

Key Facts

City/Town
Darien
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
2004
Days on Market
95 days
Beds
5
Baths
4 full · 1 half
Living Area
5,678 sq ft
Lot Size
0.53 acres
Garage / Parking
3 garage
Property Taxes
$31,152 / Annually

Market Snapshot

The Darien Market

Single Family · trailing 12 months

Median Days on Market

51

25 active listings

Median $ / Sq Ft

$733

25 active listings

Sale-to-List Ratio

106.3%

211 sales

How this home compares

List Price

$4.25M

vs $3.80M median

11.8% above median

Price / Sq Ft

$749

vs $733 median

In line with median

Days on Market

95 days

vs 51 days median

44 days longer than median

Based on 25 active and 211 closed sales (trailing 12 mo) of single family in Darien. Source: SmartMLS · As of July 27, 2026.

Location

2 Roland Drive, Darien, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$25,683

per month

  • Principal & Interest$21,670
  • Property Taxes$2,596
  • Insurance$1,417
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Darien
Neighborhood
N/A
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
2004
New Construction
No/Resale
Living Area
5,678 sq ft

Schools

Elementary
Royle
High
Darien

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
3
Laundry
Main Level
Appliances
Gas RangeMicrowaveRange HoodRefrigeratorFreezerSubzeroDishwasherDisposalWasherDryerWine Chiller
Basement
FullPartially Finished
Interior Features
Audio SystemAuto Garage Door OpenerCentral VacuumSecurity System
Additional Rooms
Exercise RoomFoyerLaundry RoomMud Room

Exterior & Lot

Lot Size
0.53 acres
Zoning
R12
Garage / Parking
3 garage spacesAttached Garage
Waterfront Details
Beach RightsWater Community
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
ShakeWood
Color
White
Roof
Wood Shingle
Foundation
Block
Exterior Features
SidewalkPorchLightingStone WallFrench DoorsUnderground SprinklerPatio
Lot Description
Level LotOn Cul-De-SacProfessionally Landscaped

Listing & Financials

Property Taxes
$31,152 / Annually
Days on Market
95
MLS #
24165314
MLS Status
Under Contract

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Stephanie Hanford

(917) 499-5402

Compass Connecticut, LLC

(203) 423-3100

Co-Listed By

Jennifer Farnum

Compass Connecticut, LLC

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/27/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 7/27/2026 at 1:20 PM UTC.