Is Darien, CT dog-friendly?

As of early 2026, 92% of users say it's dog friendly

Are yards well-kept in Darien, CT?

As of early 2026, 89% of users say yards are well-kept

Is parking easy in Darien, CT?

As of early 2026, 88% of users say parking is easy

Is a car needed in Darien, CT?

As of early 2026, 87% of users say car is needed

Does Darien, CT show holiday spirit?

As of early 2026, 84% of users say there's holiday spirit

Would people walk alone at night in Darien, CT?

As of early 2026, 81% of users say people would walk alone at night

Do kids play outside in Darien, CT?

As of early 2026, 80% of users say kids play outside

Is there wildlife in Darien, CT?

As of early 2026, 73% of users say there's wildlife

As of early 2026, 71% of users say it's quiet

Do residents of Darien, CT plan to stay at least 5 years?

As of early 2026, 70% of users say they plan to stay for at least 5 years

Are neighbors friendly in Darien, CT?

As of early 2026, 58% of users say neighbors are friendly

Are there community events in Darien, CT?

As of early 2026, 58% of users say there are community events

Does Darien, CT have sidewalks?

As of early 2026, 58% of users say there are sidewalks

Is Darien, CT walkable to restaurants?

As of early 2026, 55% of users say it's walkable to restaurants

Is Darien, CT walkable to grocery stores?

As of early 2026, 48% of users say it's walkable to grocery stores

Are the streets well-lit in Darien, CT?

As of early 2026, 44% of users say streets are well-lit

FOR SALE

0.53 ACRES

2 Roland Drive
Darien, CT 06820

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

$4,250,000

Est. Mortgage $27,172/mo*

Get Pre-Qualified

$4,250,000

Est. Mortgage $27,172/mo*

Get Pre-Qualified

5 Beds

4.5 Baths

5,678 sqft

(on 0.53 acres)

We estimate this home will sell faster than 86% nearby.

Local Information

-- mins to

Commute Destination

Description

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.

We estimate this home will sell faster than 86% nearby.

Home Highlights

Parking

3 Car Garage

Outdoor

Porch, Patio

A/C

Heating & Cooling

HOA

None

Price/Sqft

$749

Listed

13 days ago

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

Days on Market
Days on Market: 13

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: $749
Status Change & Dates Possession Timing: 8/10/2026

Active Status
MLS Status: Active

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

Agent Information
Listing Agent Listing ID: 24165314

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

Last check for updates: about 8 hours ago

Listing courtesy of Stephanie Hanford, (917) 499-5402

Compass Connecticut, LLC, (917) 499-5402

Co-Listing Agent: Jennifer Farnum, (917) 658-7982

Compass Connecticut, LLC, (203) 423-3100

Source: Smart MLS, MLS#24165314

Also Listed on Smart MLS.

Price History for 2 Roland Drive

Date	Price	Event	Source
04/30/2026	$4,250,000	Listed For Sale	Smart MLS #24165314

05/06/2021	$2,777,500	Sold	Smart MLS #170376573
Recording Date 05/06/2021 County Transfer Tax N/A Total Transfer Tax N/A
03/10/2021	$2,695,000	Contingent	Smart MLS #170376573

03/02/2021	$2,695,000	Listed For Sale	Smart MLS #170376573

11/30/2017	$2,280,000	Sold	Smart MLS #99181185
Recording Date 11/30/2017 County Transfer Tax N/A Total Transfer Tax N/A
10/06/2017	$2,375,000	PriceChange	Agent Provided
Price Change $175,000 (-7%)
07/06/2017	$2,550,000	PriceChange	Agent Provided
Price Change $145,000 (-5%)
05/09/2017	$2,695,000	PriceChange	Agent Provided
Price Change $54,000 (-2%)
04/12/2017	$2,749,000	Listed For Sale	Agent Provided

07/05/2012	$2,650,000	Sold	N/A
Recording Date 07/05/2012 County Transfer Tax N/A Total Transfer Tax $247
05/03/2012	$2,695,000	Pending	Agent Provided

04/26/2012	$2,695,000	Listed For Sale	Agent Provided

05/01/2011	$2,695,000	ListingRemoved	Agent Provided

03/30/2011	$2,695,000	PriceChange	Agent Provided
Price Change $155,000 (-5%)
03/17/2011	$2,850,000	PriceChange	Agent Provided
Price Change $145,000 (-5%)
01/08/2011	$2,995,000	Listed For Sale	Agent Provided

04/19/2005	$2,795,000	Sold	N/A
Recording Date 04/19/2005 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$31,152
Assessment	$2,012,430

Home facts updated by county records

Comparable Sales for 2 Roland Drive

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
50 Mansfield Avenue, Darien, CT	0.22	Single-Family Home	$3,000,750	06/30/25	5	3.5	4,376
10 Prospect Avenue, Darien, CT	0.13	Single-Family Home	$3,616,000	01/06/26	5	5	5,338
74 Brookside Road, Darien, CT	0.33	Single-Family Home	$3,706,313	09/12/25	5	5	6,069
2 Knollwood Lane, Darien, CT	0.32	Single-Family Home	$2,300,000	08/19/25	4	3.5	3,678
2 Tanglewood Trail, Darien, CT	0.39	Single-Family Home	$4,500,000	07/16/25	5	4.5	5,338
45 Brookside Road, Darien, CT	0.29	Single-Family Home	$2,440,000	06/25/25	4	4.5	3,618
9 Sunset Road, Darien, CT	0.18	Single-Family Home	$3,400,000	06/23/25	4	3.5	3,417
162 Leroy Avenue, Darien, CT	0.28	Single-Family Home	$3,825,000	07/15/25	5	5	4,295

Assigned Schools

These are the assigned schools for 2 Roland Drive.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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
81 % 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

Learn more about our methodology.

Kimrichardnyc
Resident
1y ago
"Happy, safe and friendly place to live and raise children. Need more diversification like in wesport CT though. "
0
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Trulia User
Resident
1y ago
"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
Resident
2y ago
"great place to raise kids, we have lived here for about a decade. fantastic schools, great neighbors"
0
Flag
Jessica_hatch7
Resident
6y ago
"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.
Resident
6y ago
"Holidays and school events. Dining and activities such as sports, the arts and many many social events"
0
Flag
Mzengo8
Resident
7y ago
"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.
Prev. Resident
7y ago
"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
Resident
7y ago
"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.
Resident
7y ago
"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
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Chad W.
Resident
7y ago
"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
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Jessica_hatch7
Resident
7y ago
"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
Resident
7y ago
"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
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Kathrynquirk445
Resident
8y ago
"Beautiful area. Gorgeous homes. Lovely neighbors. Lived here many years and love it. Great privacy and incredibly convenient."
0
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Bill T.
Prev. Resident
8y ago
"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
11y ago
"Spectacular location: Walk to beaches, shops, Train to NYC, convenient to I-95 and more "
0
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LGBTQ Local Legal Protections

Additional Cost

Stephanie Hanford, Compass Connecticut, LLC, (917) 499-5402

Agent Phone: (917) 499-5402

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

2 Roland Drive, Darien, CT 06820 is a 5 bedroom, 5 bathroom, 5,678 sqft single-family home built in 2004. This property is currently available for sale and was listed by Smart MLS on Apr 23, 2026. The MLS # for this home is MLS# 24165314.

2 Roland Drive
Darien, CT 06820

$4,250,000

$4,250,000

Local Information