376 Brookside Rd, Darien, CT 06820
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Property image
OFF MARKET

376 Brookside Rd
Darien, CT 06820

  • 5 Beds
  • 5 Baths
  • 4,568 sqft (on 2.72 acres)

$5,108,500

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $32,939/mo*
Refinance Your Home

$5,108,500

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $32,939/mo*
Refinance Your Home
5 Beds
5 Baths
4,568 sqft
(on 2.72 acres)

Local Information

  • Map ViewExplore the area around 376 Brookside Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Style, quality, and beautiful landscaping-- This Connecticut-style farmhouse includes many of the unique characteristics of the original early 20th century structure. Front&back porches & floor-to-ceiling bay windows. Enter the welcoming foyer to the formal living and dining rooms and the open kitchen/family room with window walls. French doors lead to a large walled terrace overlooking 2.7 FLAT, USABLE, breathtaking acres. Sparkling 55x25 poolw/ spa & waterfall and wisteria covered pergola surrounded by finely manicured lawns. In addition to the main house, designed by George Van Gelderin, there is a red barn, adding more personality to this wonderful compound. Beauty, timeless design and character, convenient to all Darien has to offer.
376 Brookside Rd, Darien, CT 06820 is a 5 bedroom, 5 bathroom, 4,568 sqft single-family home built in 1998. It last sold for $3,250,000 on Jul 15, 2013. It is currently off market. The Trulia Estimate is $5,108,500, with a rent estimate of $24,237/month.

Home Highlights

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

Home Details for 376 Brookside Rd

Interior Features

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

Property Information

Year Built
Year Built: 1998
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: 2.72 acres

Price History for 376 Brookside Rd

DatePriceEventSource
07/15/2013$3,250,000Sold
Smart MLS #98540730
09/07/2012$3,600,000PriceChange
Agent Provided
05/29/2012$3,850,000Listed For SaleAgent Provided

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$41,877
Assessment$2,705,220
Home facts updated by county records

Comparable Sales for 376 Brookside Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
63 Dorchester Road, Darien, CT
0.18
Single-Family Home
$3,500,000
05/12/26
4
4.5
3,470
48 Dorchester Road, Darien, CT
0.25
Single-Family Home
$5,295,000
07/22/25
5
6
6,242
15 Marianne Road, Darien, CT
0.33
Single-Family Home
$4,600,000
05/08/26
5
5
6,325
469 Brookside Road, New Canaan, CT
0.42
Single-Family Home
$3,850,000
12/16/25
6
5
5,275
49 Salisbury Rd, Darien, CT
0.36
Single-Family Home
$2,865,000
04/20/26
5
4.5
4,000
217 West Norwalk Road, Norwalk, CT
0.37
Single-Family Home
$2,325,000
07/28/25
4
4.5
4,448
109 Stephen Mather Road, Darien, CT
0.54
Single-Family Home
$3,000,000
03/02/26
5
3.5
4,817
74 Salisbury Road, Darien, CT
0.35
Single-Family Home
$4,795,000
06/23/26
5
5
6,798
23 Maplewood Drive, Darien, CT
0.55
Single-Family Home
$2,710,000
12/08/25
5
3.5
3,506
37 Salisbury Road, Darien, CT
0.33
Single-Family Home
$2,795,000
08/11/25
4
3.5
3,261

Nearby homes

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Assigned Schools

These are the assigned schools for 376 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. "
    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 "
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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."
    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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Explore by feature - Pet Friendly

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17 rentals with a garage in Darien, CT

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23 rentals with a washer/dryer in Darien, CT

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Homes for sale near 376 Brookside Rd

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Off Market Homes Near 376 Brookside Rd

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