2 Roland Drive, Darien, CT 06820
SOLD
AUG 7, 2026

$4,213,700

Trulia Estimate
  • 5 Beds
  • 4.5 Baths
  • 5,678 sqft (on 0.53 acres)

2 Roland Drive, Darien, CT 06820

Est. Refi. Payment $28,617/mo*
Refinance Your Home
Currently Off Market - Sold Aug 7, 2026 for $4,200,000 (1% below list price)

Home Value

Trulia Estimate
$4.21M
Since last month
Decreased$119K (-2.7%)
Since last year
Increased$232K (+5.8%)
Since last sale
Increased$23K (+0.5%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +49% in the last 10 years
MonthEstimated value
2026
September 2026$4.22M
August 2026$4.22M
July 2026$4.34M
June 2026$4.32M
May 2026$4.27M
April 2026$4.02M
March 2026$4.25M
February 2026$4.06M
January 2026$3.99M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
93 Mansfield Avenue, Darien, CT
0.08
Single-Family Home
$3,250,000
12/12/25
5
5
5,220
8 Sunset Road, Darien, CT
0.15
Single-Family Home
$3,925,000
07/16/26
5
4.5
4,840
10 Prospect Avenue, Darien, CT
0.13
Single-Family Home
$3,616,000
01/06/26
5
5
5,338
11 McLaren Road South, Darien, CT
0.13
Single-Family Home
$3,250,000
09/15/26
5
3.5
4,301
12 Sunset Road, Darien, CT
0.17
Single-Family Home
$3,912,000
06/15/26
4
4.5
4,306
16 Overbrook Lane, Darien, CT
0.38
Single-Family Home
$4,000,000
07/29/26
5
4.5
5,166
174 Leroy Avenue, Darien, CT
0.36
Single-Family Home
$4,475,000
08/17/26
5
4.5
5,506
6 Priscilla Lane, Darien, CT
0.49
Single-Family Home
$4,800,000
12/18/25
5
4.5
6,192
33 Fairview Avenue, Darien, CT
0.24
Single-Family Home
$3,300,000
06/12/26
4
2.5
3,102

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
10 McLaren Road South, Darien, CT 06820
0.09
$2,879,800
4
4.5
3,183
Off Market
93 Mansfield Avenue, Darien, CT 06820
0.08
$3,250,000
5
5
5,220
Recently Sold
84 Mansfield Avenue, Darien, CT 06820
0.09
$4,645,100
5
5.5
6,000
Off Market
17 McLaren Road, Darien, CT 06820
0.13
$2,029,800
3
2.5
1,926
Off Market
11 McLaren Road South, Darien, CT 06820
0.13
$3,250,000
5
3.5
4,301
Recently Sold
17 Oak Crest Road, Darien, CT 06820
0.14
$1,133,500
3
2
1,523
Off Market
8 Sunset Road, Darien, CT 06820
0.15
$3,925,000
5
4.5
4,840
Recently Sold
8 Prospect Avenue, Darien, CT 06820
0.13
$2,765,500
5
3
3,036
Off Market
19 Oak Crest, Darien, CT 06820
0.15
$2,388,100
4
2.5
2,343
Off Market
10 Prospect Avenue, Darien, CT 06820
0.13
$3,616,000
5
5
5,338
Recently Sold
14 Partridge Lane, Darien, CT 06820
0.15
$2,986,500
5
4.5
3,917
Off Market

Local Information

  • Map ViewExplore the area around 2 Roland Drive.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2004
0.53 acre lot
5,678 sqft
$740/sqft
3 Car Garage

About this House

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.
2 Roland Drive, Darien, CT 06820 is a 5 bedroom, 5 bathroom, 5,678 sqft single-family home built in 2004. It last sold for $4,200,000 on Aug 7, 2026 (1% below the $4,250,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,213,700.
Last check for updates: about 8 hours ago
Listed by Stephanie Hanford, (917) 499-5402
Compass Connecticut, LLC, (203) 423-3100
Co-Listing Agent: Jennifer Farnum, (917) 658-7982
Compass Connecticut, LLC, (203) 423-3100
Bought with: Andrew F. Smith, (203) 524-8652, Houlihan Lawrence, (203) 869-0700
Source: Smart MLS, MLS#24165314

Home Details for 2 Roland Drive

Interior Features

Interior Details
Basement: Full,Partially FinishedNumber of Rooms: 11Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Great Room, Kitchen, Living Room, Rec Play Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 5678 Square Feet
Appliances & Utilities
Appliances: Gas Range, Microwave, Range Hood, Refrigerator, Freezer, Subzero, Dishwasher, Disposal, Washer, Dryer, Wine Cooler, Water HeaterDishwasherDisposalDryerLaundry: Main Level,Mud RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 3Has a Fireplace
Windows, Doors, Floors & Walls
Door: French Doors
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: WoodPatio / Porch: Porch, PatioExterior: Sidewalk, Lighting, Stone Wall, Underground SprinklerFoundation: BlockNo Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageParking Spaces: 3Parking: Attached,Garage Door Opener
Frontage
Waterfront: Beach Access, Water CommunityNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 5678 Square Feet

Property Information

Year Built
Year Built: 2004
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Shake Siding, Wood SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 104231

Price & Status

Price
List Price: $4,250,000Price Per Sqft: $740/sqft
Status Change & Dates
Off Market Date: Mon May 18 2026Possession Timing: 8/10/2026

Active Status

MLS Status: Closed

Location

Direction & Address
City: Darien
School Information
Elementary School: RoyleJr High / Middle School: MiddlesexHigh School: Darien

Building

Building Area
Building Area: 5678 Square Feet

HOA

No HOA

Lot Information

Lot Area: 0.53 acres

Miscellaneous

BasementMls Number: 24165314Attic: Storage, Walk-upAttribution Contact: (917) 499-5402Above Grade Unfinished Area: 5678Activation Date: Thu Apr 30 2026

Price and Tax history

DateEventPrice
Aug 7, 2026
Source: Smart MLS #24165314
Sold
$4,200,000
May 18, 2026
Source: Smart MLS #24165314
Pending
$4,250,000
Apr 30, 2026
Source: Smart MLS #24165314
Listed For Sale
$4,250,000
May 6, 2021
Source: Smart MLS #170376573
Sold
$2,777,500
Mar 10, 2021
Source: Smart MLS #170376573
Contingent
$2,695,000

Market trends in Darien

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.82M
$155KMoM
Sale-to-List Price
110.3%
1.4%MoM
Price per sq ft
$821
$21MoM
Available listings
29
7MoM

Around this home

What Locals Say about Darien

At least 147 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 89 % Say yards are well-kept

  • 88 % Say parking is easy

  • 87 % Say car is needed

  • 84 % Say there's holiday spirit

  • 82 % Say people would walk alone at night

  • 80 % Say kids play outside

  • 73 % Say there's wildlife

  • 71 % Say it's quiet

  • 70 % Say they plan to stay for at least 5 years

  • 58 % Say neighbors are friendly

  • 58 % Say there are community events

  • 58 % Say there are sidewalks

  • 55 % Say it's walkable to restaurants

  • 48 % Say it's walkable to grocery stores

  • 44 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Kimrichardnyc
    "Happy, safe and friendly place to live and raise children. Need more diversification like in wesport CT though. "
    0
    Flag
  • Trulia User
    "This is the best town to raise kids and build friendships. The beaches, parks, restaurants, nature and proximity to NYC also makes a great place to live. We have found the people generally friendly and welcoming. "
    0
    Flag
  • Trulia User
    "great place to raise kids, we have lived here for about a decade. fantastic schools, great neighbors"
    0
    Flag
  • Jessica_hatch7
    "NA commute to the city is an easy 65 minute train ride. We have two stations in Darien, both easily accessible. "
    3
    Flag
  • Peter S.
    "Holidays and school events. Dining and activities such as sports, the arts and many many social events"
    0
    Flag
  • Mzengo8
    "My neighborhood plays kid lacrosse/ basketball or football games. And we have parties on almost every holiday. Which is very fun for all of the kids on the block "
    0
    Flag
  • Bill T.
    "Dead end but on a hill and has a loop so kids can run around, play and explore. Lots of trees and woods surround the neighborhood."
    3
    Flag
  • Tad
    "My commute is five minutes to the train station, five minute walk from parking lot to the tracks, then an hour on the train to grand central each work day. "
    1
    Flag
  • Allison w.
    "They would love it, such a friendly area. Dogs are everywhere and appreciated. I have 2 dogs and I am so glad there are a ton of dogs around. "
    0
    Flag
  • Chad W.
    "Darien is as family friendly as it gets. There is a lot of money here. Some are kind, but many are snobby. It's a bit of a bubble, which is why many families move here."
    0
    Flag
  • Jessica_hatch7
    "The people are amazing and the schools are fantastic. We are only 60 minutes from the city and the trains run very frequently. "
    2
    Flag
  • Victoria_belluscio
    "Great place to raise children- excellent schools- everything is 5-10 min away so good for busy schedules! 2 train stations for easy commuting, beaches, parks and more!"
    0
    Flag
  • Kathrynquirk445
    "Beautiful area. Gorgeous homes. Lovely neighbors. Lived here many years and love it. Great privacy and incredibly convenient."
    0
    Flag
  • Bill T.
    "Big circle where no cars or trucks visit unless they live here or have business in the neighborhood... great place for kids"
    1
    Flag
  • dwenger
    "Spectacular location: Walk to beaches, shops, Train to NYC, convenient to I-95 and more "
    0
    Flag

LGBTQ Local Legal Protections

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Frequently asked questions about 2 Roland Drive

  • What is 2 Roland Drive estimated to be worth?
    Trulia's estimated value for 2 Roland Drive in Darien, CT is $4,213,700.
  • What is the price history for 2 Roland Drive?
    2 Roland Drive in Darien, CT last sold for $4,200,000 in August 2026.
  • Is Darien a buyer's or seller's market?
    Darien is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Darien?
    The median sale price in Darien is $2.82M. That is down $155K from the prior month.
  • Does 2 Roland Drive have air conditioning?
    Yes, 2 Roland Drive in Darien, CT has air conditioning.
  • Does 2 Roland Drive have laundry facilities?
    Yes, 2 Roland Drive in Darien, CT has in-unit laundry.

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