285 Brookside Rd, Darien, CT 06820
OFF MARKET

$2,977,700

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 3,600 sqft (on 2 acres)

285 Brookside Rd, Darien, CT 06820

Est. Refi. Payment $20,374/mo*
Refinance Your Home
Currently Off Market - Sold Nov 1, 2002 for $1,575,000

Home Value

Trulia Estimate
$2.98M
Since last month
Decreased$45K (-1.5%)
Since last year
Increased$282K (+10.4%)
Since last sale
Increased$1M (+89.3%)
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 +70% in the last 10 years
MonthEstimated value
2026
October 2026$2.98M
September 2026$3.03M
August 2026$3.02M
July 2026$3M
June 2026$3.07M
May 2026$2.98M
April 2026$2.88M
March 2026$2.94M
February 2026$2.81M
January 2026$2.73M
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
267 Brookside Road, Darien, CT
0.12
Single-Family Home
$2,850,000
05/29/26
4
3.5
3,416
49 Salisbury Rd, Darien, CT
0.16
Single-Family Home
$2,865,000
04/20/26
5
4.5
4,000
74 Salisbury Road, Darien, CT
0.10
Single-Family Home
$4,795,000
06/23/26
5
5
6,798
63 Dorchester Road, Darien, CT
0.48
Single-Family Home
$3,500,000
05/12/26
4
4.5
3,470
23 Maplewood Drive, Darien, CT
0.67
Single-Family Home
$2,710,000
12/08/25
5
3.5
3,506
115 Maywood Road, Norwalk, CT
0.64
Single-Family Home
$1,130,000
12/03/25
4
4
2,375
15 Marianne Road, Darien, CT
0.25
Single-Family Home
$4,600,000
05/08/26
5
5
6,325
132 W Norwalk Rd, Norwalk, CT
0.86
Single-Family Home
$1,650,000
07/22/26
4
2.5
3,744
196 W Norwalk Rd, Norwalk, CT
0.69
Single-Family Home
$1,675,000
07/01/26
3
2.5
3,960
146 Ridge Acres Road, Darien, CT
0.48
Single-Family Home
$3,300,000
02/25/26
4
5
3,422

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
283 Brookside Rd, Darien, CT 06820
0.02
$2,629,600
4
4
3,575
Off Market
291 Brookside Rd, Darien, CT 06820
0.03
$2,833,600
3
3
4,005
Off Market
297 Brookside Rd, Darien, CT 06820
0.06
$2,977,400
4
3
3,443
Off Market
275 Brookside Rd, Darien, CT 06820
0.06
$3,204,900
4
3
3,046
Off Market
1 Gracie Ln, Darien, CT 06820
0.09
$4,696,000
4
4.5
5,284
Off Market
62 Salisbury Rd, Darien, CT 06820
0.10
$2,360,900
4
3
2,370
Off Market
74 Salisbury Road, Darien, CT 06820
0.10
$4,795,000
5
5
6,798
Recently Sold
48 Salisbury Rd, Darien, CT 06820
0.11
$4,474,900
4
4
5,608
Off Market
300 Brookside Rd, Darien, CT 06820
0.11
$6,024,800
6
9
9,076
Off Market
267 Brookside Rd #R, Darien, CT 06820
0.12
$1,997,800
5
3.5
3,256
Off Market
267 Brookside Road, Darien, CT 06820
0.12
$2,850,000
4
3.5
3,416
Recently Sold
3 Gracie Ln, Darien, CT 06820
0.13
$2,351,400
4
3
3,598
Off Market
2 Gracie Ln, Darien, CT 06820
0.13
$3,624,700
5
6
7,723
Off Market
42 Salisbury Rd, Darien, CT 06820
0.14
$4,466,800
5
6
6,172
Off Market
268 Brookside Rd, Darien, CT 06820
0.14
$4,546,100
5
6
6,517
Off Market
37 Salisbury Road, Darien, CT 06820
0.14
$2,978,500
4
3.5
3,261
Off Market
304 Brookside Road, Darien, CT 06820
0.15
$6,095,000
6
6.5
7,344
Recently Sold
83 Salisbury Rd, Darien, CT 06820
0.15
$2,105,800
4
3
2,590
Off Market
49 Salisbury Rd, Darien, CT 06820
0.16
$2,865,000
5
4.5
4,000
Recently Sold
267R Brookside Ave, Darien, CT 06820
0.17
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 285 Brookside Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1955
2 acre lot
3,600 sqft
$827/sqft
Garage

About this House

This single-family home is located at 285 Brookside Rd, Darien, CT. 285 Brookside Rd is in Darien, CT and in ZIP code 06820. This property has 4 bedrooms, 4 bathrooms and approximately 3,600 sqft of floor space. This property has a lot size of 2.00 acres and was built in 1955.
285 Brookside Rd, Darien, CT 06820 is a 4 bedroom, 4 bathroom, 3,600 sqft single-family home built in 1955. It last sold for $1,575,000 on Nov 1, 2002. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,977,700, with a rent estimate of $10,101/month.

Home Details for 285 Brookside Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 10Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Office, Recreation Room
Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: CompositionDeckExterior: WoodGardenLawnPatioPorch
Parking & Garage
GarageParking Spaces: 4Parking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1955Year Updated: 2002
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 2.00 acres

Price and Tax history

DateEventPrice
Nov 1, 2002
Source: Smart MLS #98138936
Sold
$1,575,000
Aug 28, 1992
Source: N/A
Sold
$375,000

Market trends in Darien

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
34
5MoM
Sourced by Trulia Market Trends

Around this home

What Locals Say about Darien

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.
  • 84% say there's holiday spirit
  • 58% say neighbors are friendly
  • 58% say there are community events
Trulia Trick or TreatStart Ghost Hunt
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.
  • David Holst-grubbe
    "The city is entirely safe and heavily patrolled by town cops. The school system is second to none anywhere. The city spends a great deal of money to keep everything clean and well maintained."
    0
    Flag
  • 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

LGBTQ Local Legal Protections

Frequently asked questions about 285 Brookside Rd

  • What is 285 Brookside Rd estimated to be worth?
    Trulia's estimated value for 285 Brookside Rd in Darien, CT is $2,977,700.
  • What is the price history for 285 Brookside Rd?
    285 Brookside Rd in Darien, CT last sold for $1,575,000 in November 2002.
  • Is Darien a buyer's or seller's market?
    Darien is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Darien?
    Residents describe Darien, CT as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See recently sold homes in Darien, CT.
  • Does 285 Brookside Rd have air conditioning?
    Yes, 285 Brookside Rd in Darien, CT has air conditioning.
  • Does 285 Brookside Rd have laundry facilities?
    Yes, 285 Brookside Rd in Darien, CT has in-unit laundry.

Explore by feature - Pet Friendly

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Off Market Homes Near 285 Brookside Rd

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