44 Brookside Road, Darien, CT 06820
OFF MARKET

44 Brookside Road
Darien, CT 06820

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

$2,540,300

Trulia Estimate
as of Jul 2, 2026
Est. Refi. Payment $16,431/mo*
Refinance Your Home

$2,540,300

Trulia Estimate
as of Jul 2, 2026
Est. Refi. Payment $16,431/mo*
Refinance Your Home
4 Beds
2.5 Baths
3,730 sqft
(on 0.87 acres)

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

Description

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). It is currently off market. The Trulia Estimate is $2,540,300, with a rent estimate of $7,852/month.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

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)
Last check for updates: about 14 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

Price History for 44 Brookside Road

DatePriceEventSource
12/08/2023$1,740,000Sold
Smart MLS #170600478
10/21/2023$1,795,000PendingSmart MLS #170600478
09/27/2023$1,795,000Listed For SaleSmart MLS #170600478
10/15/2019$1,399,000ListingRemovedAgent Provided
04/04/2019$1,399,000PriceChange
Agent Provided
11/05/2018$1,495,000PriceChange
Agent Provided
08/13/2018$1,550,000PriceChange
Agent Provided
06/14/2018$1,650,000Listed For SaleAgent Provided
08/03/2012$1,595,000Sold
Smart MLS #98537416
05/02/2012$1,595,000Listed For SaleAgent Provided
07/01/1992$535,000Sold
N/A

Market trends in Darien

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
64
1MoM
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Property Tax and Assessment

Year2025
Tax$19,433
Assessment$1,255,380
Home facts updated by county records

Comparable Sales for 44 Brookside Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
33 Fairview Avenue, Darien, CT
0.17
Single-Family Home
$3,300,000
06/12/26
4
2.5
3,102
7 Circle Road, Darien, CT
0.51
Single-Family Home
$2,130,000
07/17/25
4
3.5
3,512
12 Sunset Road, Darien, CT
0.31
Single-Family Home
$3,912,000
06/15/26
4
4.5
4,306
4 Rabbit Lane, Darien, CT
0.46
Single-Family Home
$2,675,000
08/11/25
5
3.5
3,690
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
2 Knollwood Lane, Darien, CT
0.53
Single-Family Home
$2,300,000
08/19/25
4
3.5
3,678

Nearby homes

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Assigned Schools

These are the assigned schools for 44 Brookside Road.
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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

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. "
    0
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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. "
    0
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  • Trulia User
    "great place to raise kids, we have lived here for about a decade. fantastic schools, great neighbors"
    0
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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 "
    0
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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
    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
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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."
    0
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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
    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
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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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Apartments for Rent

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Homes for sale near 44 Brookside Road

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Off Market Homes Near 44 Brookside Road

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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.