104 Brookside Rd, Darien, CT 06820
OFF MARKET

$3,848,500

Trulia Estimate
  • 5 Beds
  • 6 Baths
  • 4,982 sqft (on 1.06 acres)

104 Brookside Rd, Darien, CT 06820

Est. Refi. Payment $25,875/mo*
Refinance Your Home
Currently Off Market - Sold Mar 16, 2012 for $2,237,500

Home Value

Trulia Estimate
$3.85M
Since last month
Increased$17K (+0.5%)
Since last year
Increased$388K (+11.3%)
Since last sale
Increased$2M (+71%)
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 +50% in the last 10 years
MonthEstimated value
2026
November 2026$3.83M
October 2026$3.84M
September 2026$3.81M
August 2026$3.87M
July 2026$3.75M
June 2026$3.81M
May 2026$3.75M
April 2026$3.67M
March 2026$3.66M
February 2026$3.53M
January 2026$3.5M
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
16 Overbrook Ln, Darien, CT
0.22
Single-Family Home
$4,000,000
07/29/26
5
4.5
5,166
12 Sunset Road, Darien, CT
0.25
Single-Family Home
$3,912,000
06/15/26
4
4.5
4,306
9 Point O Woods Road South, Darien, CT
0.37
Single-Family Home
$2,950,000
05/28/26
6
5
4,848
8 Sunset Road, Darien, CT
0.28
Single-Family Home
$3,925,000
07/16/26
5
4.5
4,840
10 Prospect Avenue, Darien, CT
0.44
Single-Family Home
$3,616,000
01/06/26
5
5
5,338
32 Birch Road, Darien, CT
0.31
Single-Family Home
$4,000,000
10/09/26
4
4.5
4,695
12 Dellwood Road, Darien, CT
0.69
Single-Family Home
$2,300,000
04/16/26
5
5
4,672
26 Birch Road, Darien, CT
0.28
Single-Family Home
$3,012,000
11/18/25
4
3.5
4,155
5 Birch Road, Darien, CT
0.29
Single-Family Home
$3,300,000
08/21/26
5
2.5
3,316
93 Mansfield Avenue, Darien, CT
0.48
Single-Family Home
$3,250,000
12/12/25
5
5
5,220

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
5 Meadowbrook Rd, Darien, CT 06820
0.04
$3,454,200
5
5.5
4,408
Off Market
102 Brookside Rd, Darien, CT 06820
0.04
$2,356,800
4
3
3,044
Off Market
1 Meadowbrook Rd, Darien, CT 06820
0.05
$2,819,100
3
3
2,703
Off Market
101 Brookside Rd, Darien, CT 06820
0.06
$3,175,100
6
4
3,783
Off Market
95 Brookside Rd, Darien, CT 06820
0.06
$3,258,300
5
5
4,790
Off Market
105 Brookside Rd, Darien, CT 06820
0.06
$2,660,200
4
3
2,788
Off Market
7 Meadowbrook Rd, Darien, CT 06820
0.07
$5,032,600
5
6
6,258
Off Market
11 Meadowbrook Rd, Darien, CT 06820
0.09
$3,996,000
5
4
4,974
Off Market
3 Overbrook Ln, Darien, CT 06820
0.09
$2,904,800
6
4.5
3,929
Off Market
2 Meadowbrook Rd, Darien, CT 06820
0.09
$3,606,600
5
5
4,540
Off Market
6 Meadowbrook Rd, Darien, CT 06820
0.10
$3,456,100
6
6
4,730
Off Market
90 Brookside Rd, Darien, CT 06820
0.10
$2,720,900
5
5.5
3,906
Off Market
8 Meadowbrook Rd, Darien, CT 06820
0.11
$3,604,700
5
5
3,438
Off Market
36 Sunset Rd, Darien, CT 06820
0.11
$3,619,900
5
5
4,621
Off Market
111 Brookside Rd, Darien, CT 06820
0.11
$4,668,100
8
6
6,372
Off Market
51 Sunset Rd, Darien, CT 06820
0.12
-
-
-
-
Off Market
3 Rabbit Ln, Darien, CT 06820
0.12
$3,354,700
6
6
5,726
Off Market
10 Meadowbrook Rd, Darien, CT 06820
0.12
$4,052,400
5
5.5
4,502
Off Market
9 Appletree Ln, Darien, CT 06820
0.13
$5,267,500
6
5.5
6,300
Off Market
26 Sunset Rd, Darien, CT 06820
0.13
$3,277,900
4
3
3,245
Off Market

Local Information

  • Map ViewExplore the area around 104 Brookside Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1916
1.06 acre lot
4,982 sqft
$772/sqft
Garage

About this House

BROOKSIDE RD View full listing information on Halstead.com RECENTLY REDESIGNED THIS HOME IS READY FOR TODAY'S LIFESTYLE. PERFECTLY SITED ON A PROFESSIONALLY LANDSCAPED LEVEL ACRE. HIGH CEILINGS, LARGE EAT- IN KITCHEN. CENTRALLY LOCATED TO TOWN. CLASSIC NEW ENGLAND HOME.
104 Brookside Rd, Darien, CT 06820 is a 5 bedroom, 6 bathroom, 4,982 sqft single-family home built in 1916. It last sold for $2,237,500 on Mar 16, 2012. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,848,500.

Home Details for 104 Brookside Rd

Interior Features

Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 11
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1916Year Updated: 2010
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Wood
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 1.06 acres

Price and Tax history

DateEventPrice
Mar 16, 2012
Source: Smart MLS #98520295
Sold
$2,237,500
Nov 13, 2011
Source: Agent Provided
Listed For Sale
$2,485,000
Jul 21, 2004
Source: N/A
Sold
$2,375,000
Jul 21, 1994
Source: N/A
Sold
$780,000
Oct 17, 1991
Source: N/A
Sold
$650,000

Market trends in Darien

Last updated October 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
36
2MoM
Sourced by Trulia Market Trends

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.
  • 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 104 Brookside Rd

  • What is 104 Brookside Rd estimated to be worth?
    Trulia's estimated value for 104 Brookside Rd in Darien, CT is $3,848,500.
  • What is the price history for 104 Brookside Rd?
    104 Brookside Rd in Darien, CT last sold for $2,237,500 in March 2012.
  • 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 104 Brookside Rd have a pool?
    Yes, 104 Brookside Rd in Darien, CT has a pool.
  • How big is the lot at 104 Brookside Rd?
    The lot at 104 Brookside Rd in Darien, CT is about 1.1 acres.

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Off Market Homes Near 104 Brookside Rd

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