256 Brookside Rd, Darien, CT 06820
OFF MARKET

256 Brookside Rd
Darien, CT 06820

  • 6 Beds
  • 6.5 Baths
  • 4,876 sqft (on 2.11 acres)

$5,590,600

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $36,041/mo*
Refinance Your Home

$5,590,600

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $36,041/mo*
Refinance Your Home
6 Beds
6.5 Baths
4,876 sqft
(on 2.11 acres)

Local Information

  • Map ViewExplore the area around 256 Brookside Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Originally designed by Ed Wallace, this remarkable Connecticut colonial has been tastefully renovated and expanded, boasting every amenity and 2.1 acres of meticulously landscaped grounds in a desirable, private location. The main house includes six bedrooms plus four full and two half baths. A gourmet eat-in kitchen opens onto a light-filled family room with wood burning fireplace and views of the private backyard. Nestled among the lovely land and gardens are a guest house and stunning pool with pool house offering a spacious living area with a half bath and outdoor shower. The separate guest house includes a generous entertaining space, potting room, separate bedroom, and full bath. This is an opportunity to own a very special property.
256 Brookside Rd, Darien, CT 06820 is a 6 bedroom, 8 bathroom, 4,876 sqft single-family home built in 1948. It last sold for $3,790,000 on Sep 3, 2017. It is currently off market. The Trulia Estimate is $5,590,600, with a rent estimate of $25,688/month.

Home Highlights

Parking
Garage
Outdoor
Patio, Deck, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 256 Brookside Rd

Interior Features

Interior Details
BasementNumber of Rooms: 12
Heating & Cooling
Heating: Other, OilAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: OtherGardenLawnPatio
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1948Year Updated: 2006
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 2.11 acres

Additional Information

Greenhouse

Price History for 256 Brookside Rd

DatePriceEventSource
09/03/2017$3,790,000Sold
Smart MLS #99174218
06/16/2017$3,950,000PriceChange
Agent Provided
03/30/2017$4,095,000PriceChange
Agent Provided
09/07/2016$4,250,000PriceChange
Agent Provided
05/06/2016$4,395,000PriceChange
Agent Provided
03/17/2016$4,595,000Listed For SaleAgent Provided
07/20/2004$2,100,256Sold
Smart MLS #98197224
08/18/1998$925,000Sold
N/A

Market trends in Darien

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.73M
Sale-to-List Price
105.6%
Price per sq ft
$787
Available listings
54
11MoM
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Property Tax and Assessment

Year2025
Tax$40,996
Assessment$2,648,310
Home facts updated by county records

Comparable Sales for 256 Brookside Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
225 Brookside Rd, Darien, CT
0.16
Single-Family Home
$4,650,000
06/09/26
6
6
8,000
15 Marianne Road, Darien, CT
0.26
Single-Family Home
$4,600,000
05/08/26
5
5
6,325
74 Salisbury Road, Darien, CT
0.24
Single-Family Home
$4,795,000
06/23/26
5
5
6,798
304 Brookside Road, Darien, CT
0.23
Single-Family Home
$6,095,000
07/16/26
6
6.5
7,344
267 Brookside Road, Darien, CT
0.07
Single-Family Home
$2,850,000
05/29/26
4
3.5
3,416
20 Shady Acres Road, Darien, CT
0.25
Single-Family Home
$2,460,000
08/20/25
5
4
3,322
49 Salisbury Rd, Darien, CT
0.33
Single-Family Home
$2,865,000
04/20/26
5
4.5
4,000
146 Ridge Acres Road, Darien, CT
0.30
Single-Family Home
$3,300,000
02/25/26
4
5
3,422
50 Buttonwood Lane, Darien, CT
0.61
Single-Family Home
$4,500,000
12/03/25
7
6.5
7,200
48 Dorchester Road, Darien, CT
0.56
Single-Family Home
$5,295,000
07/22/25
5
6
6,242

Nearby homes

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Assigned Schools

These are the assigned schools for 256 Brookside Rd.
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

  • 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. "
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  • 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. "
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  • Trulia User
    "great place to raise kids, we have lived here for about a decade. fantastic schools, great neighbors"
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  • 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
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  • 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 "
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  • 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
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  • 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
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  • 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."
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  • 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
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  • 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
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  • Kathrynquirk445
    "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.
    "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
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17 rentals with a garage in Darien, CT

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Homes for sale near 256 Brookside Rd

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Off Market Homes Near 256 Brookside Rd

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