44 Brookside Road, Darien, CT 06820
OFF MARKET

$2,550,200

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 3,730 sqft (on 0.87 acres)

44 Brookside Road, Darien, CT 06820

Est. Refi. Payment $17,793/mo*
Refinance Your Home
Currently Off Market - Sold Dec 8, 2023 for $1,740,000

Home Value

Trulia Estimate
$2.55M
Since last month
Decreased$24K (-1%)
Since last year
Increased$198K (+8.5%)
Since last sale
Increased$787K (+45.2%)
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 +69% in the last 10 years
MonthEstimated value
2026
October 2026$2.53M
September 2026$2.55M
August 2026$2.55M
July 2026$2.54M
June 2026$2.56M
May 2026$2.49M
April 2026$2.43M
March 2026$2.47M
February 2026$2.37M
January 2026$2.37M
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
5 Birch Road, Darien, CT
0.34
Single-Family Home
$3,300,000
08/21/26
5
2.5
3,316
33 Fairview Avenue, Darien, CT
0.17
Single-Family Home
$3,300,000
06/12/26
4
2.5
3,102
28 East Lane, Darien, CT
0.38
Single-Family Home
$1,600,000
09/29/26
4
3.5
3,260
12 Sunset Road, Darien, CT
0.31
Single-Family Home
$3,912,000
06/15/26
4
4.5
4,306
115 Tokeneke Road, Darien, CT
0.62
Single-Family Home
$1,880,000
10/01/26
4
2.5
2,408
10 Prospect Avenue, Darien, CT
0.24
Single-Family Home
$3,616,000
01/06/26
5
5
5,338
29 Richmond Drive, Darien, CT
0.70
Single-Family Home
$2,060,000
05/12/26
4
3
3,512
26 Birch Road, Darien, CT
0.50
Single-Family Home
$3,012,000
11/18/25
4
3.5
4,155
27 Point O Woods Road South, Darien, CT
0.52
Single-Family Home
$2,900,000
06/15/26
4
2.5
3,384
17 Richmond Drive, Darien, CT
0.64
Single-Family Home
$2,700,000
08/17/26
4
3
2,894

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 Bates Farm Ln, Darien, CT 06820
0.02
$3,870,600
5
5.5
5,477
Off Market
40 Brookside Rd, Darien, CT 06820
0.02
$2,684,100
4
2
2,932
Off Market
14 Bates Farm Ln, Darien, CT 06820
0.03
$2,975,100
5
6.5
5,150
Off Market
45 Brookside Road, Darien, CT 06820
0.03
$2,624,300
4
4.5
3,618
Off Market
54 Brookside Rd, Darien, CT 06820
0.05
$3,685,900
8
5.5
5,528
Off Market
33 Brookside Rd, Darien, CT 06820
0.05
$1,465,400
3
1.5
1,782
Off Market
567 Boston Post Rd, Darien, CT 06820
0.06
$1,710,900
3
2
2,032
Off Market
567 Boston Post Rd #1, Darien, CT 06820
0.06
$1,334,200
2
1
2,032
Off Market
537 Post Rd, Darien, CT 06820
0.06
-
Studio
1
700
Off Market
537 Boston Post Rd, Darien, CT 06820
0.06
-
-
-
-
Off Market
45 Granaston Ln, Darien, CT 06820
0.06
$3,225,500
4
3.5
4,900
Off Market
31 Brookside Road, Darien, CT 06820
0.06
$1,769,700
3
2.5
2,362
Off Market
22 Bates Farm Ln, Darien, CT 06820
0.07
$3,585,300
5
6
6,107
Off Market
599 Post Rd #1, Darien, CT 06820
0.07
-
1
1
-
Off Market
57 Brookside Rd, Darien, CT 06820
0.07
$1,795,700
4
3
2,450
Off Market
40 Granaston Ln, Darien, CT 06820
0.08
$2,667,500
3
3
2,605
Off Market
551 Post Rd, Darien, CT 06820
0.08
$770,200
1
1
850
Off Market
33 Granaston Ln, Darien, CT 06820
0.08
$2,784,600
5
3.5
4,132
Off Market
33 Prospect Ave, Darien, CT 06820
0.08
$2,675,800
3
2
2,934
Off Market
551 Post Rd #3R, Darien, CT 06820
0.08
-
1
1
850
Off Market

Local Information

  • Map ViewExplore the area around 44 Brookside Road.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1866
0.87 acre lot
3,730 sqft
$684/sqft
Garage

About this House

Welcome to 44 Brookside, where timeless elegance and modern convenience merge seamlessly. A meticulously maintained colonial residence showcasing quintessential New England architecture, nestled in the heart of Darien. As you approach, you'll be greeted by charming stone pillars, a sprawling flat lawn and an inviting front porch. Upon entering, you'll be captivated by abundant natural light that fills each room. The main level boasts a spacious floor plan and lofty ceilings that make an ideal atmosphere for both entertaining and everyday living. The heart of this home is the kitchen family room, complete with quartz countertops, stainless steel appliances and a cozy fireplace flowing to a screened-in porch, creating an ideal space for year-round enjoyment. The adjacent living room offers a comfortable retreat for relaxation. On the second level, you'll discover four generously sized bedrooms, including a luxurious primary suite that is an oasis of comfort with a walk-in closet and beautiful bath. Convenience is at your doorstep, with a short stroll to the train station, downtown, Cherry Lawn Park and Royle Elementary School. Do not let this opportunity pass you by to make 44 Brookside your forever home!
44 Brookside Road, Darien, CT 06820 is a 4 bedroom, 3 bathroom, 3,730 sqft single-family home built in 1866. It last sold for $1,740,000 on Dec 8, 2023 (3% below the $1,795,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,550,200, with a rent estimate of $8,390/month.
Last check for updates: about 9 hours ago
Listed by Peter Stuart, (203) 219-5427
Houlihan Lawrence, (203) 655-8238
Bought with: Keiley Fuller, (203) 858-4609, Compass Connecticut, LLC, (203) 423-3100
Source: Smart MLS, MLS#170600478

Home Details for 44 Brookside Road

Interior Features

Interior Details
Basement: Partial,Concrete,Storage Space,Sump PumpNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3730 Square Feet
Appliances & Utilities
Appliances: Gas Range, Oven/Range, Microwave, Refrigerator, Freezer, Subzero, Dishwasher, Disposal, Washer, Dryer, Water HeaterDishwasherDisposalDryerLaundry: Mud RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Radiator,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 2Has a Fireplace
Windows, Doors, Floors & Walls
Window: Storm Window(s)Door: Storm Door(s)
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: AsphaltFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 2Parking: Detached,Garage Door Opener,Private,Paved
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 3730 Square Feet

Property Information

Year Built
Year Built: 1866
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial,Farm House
Building
Construction Materials: Wood SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 104140

Price & Status

Price
List Price: $1,795,000
Status Change & Dates
Off Market Date: Sat Oct 21 2023Possession Timing: Negotiable

Active Status

MLS Status: Closed

Media

Location

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

Building

Building Area
Building Area: 3730 Square Feet

Community

Community Features: Park, Playground, Near Public Transport, Tennis Court(s)
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 0.87 acres

Energy

Energy Efficiency Features: Doors, Windows

Miscellaneous

BasementMls Number: 170600478Attic: Pull Down StairsAbove Grade Unfinished Area: 3730

Additional Information

ParkPlaygroundNear Public TransportTennis Court(s)

Price and Tax history

DateEventPrice
Dec 8, 2023
Source: Smart MLS #170600478
Sold
$1,740,000
Oct 21, 2023
Source: Smart MLS #170600478
Pending
$1,795,000
Sep 27, 2023
Source: Smart MLS #170600478
Listed For Sale
$1,795,000
Oct 15, 2019
Source: Agent Provided
ListingRemoved
$1,399,000
Apr 4, 2019
Source: Agent Provided
PriceChange
$1,399,000
Price decreased by 6%

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

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Frequently asked questions about 44 Brookside Road

  • What is 44 Brookside Road estimated to be worth?
    Trulia's estimated value for 44 Brookside Road in Darien, CT is $2,550,200.
  • What is the price history for 44 Brookside Road?
    44 Brookside Road in Darien, CT last sold for $1,740,000 in December 2023.
  • 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 44 Brookside Road have air conditioning?
    Yes, 44 Brookside Road in Darien, CT has air conditioning.
  • Does 44 Brookside Road have laundry facilities?
    Yes, 44 Brookside Road in Darien, CT has in-unit laundry.

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Off Market Homes Near 44 Brookside Road

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