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

298 Brookside Rd
Darien, CT 06820

  • 5 Beds
  • 4 Baths
  • 5,423 sqft (on 2.85 acres)

$5,284,800

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $34,074/mo*
Refinance Your Home

$5,284,800

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $34,074/mo*
Refinance Your Home
5 Beds
4 Baths
5,423 sqft
(on 2.85 acres)

Local Information

  • Map ViewExplore the area around 298 Brookside Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

CALM...TRANQUIL...PEACEFUL....A WELCOMING & MAGICAL LUXURY...A SENSE OF LIFE'S TRUE QUALITY.
Down a lovely private drive lined by beautiful stone walls and specimen trees this exceptional home comes in to view. Strategically sited on over 2 acres of Connecticut Landscape, it is hard not to feel relief... away from today's crazy world.
From the moment you enter... the natural light is as evident as the free-flowing open spaces that have been thoughtfully expanded and renovated. The heart of this special home is the stunning and very spacious kitchen with a two center islands (one for prep and one for seating), top of the line appliances, adjoining butlers bar with full pantry and a beautifully designed octagonal cathedral casual dining/breakfast area with great views of the property and pool.
The kitchen also is accessed from a complete mudroom entrance with half bath and opens to an exemplary family room, with vaulted ceilings and space galore. Perfect for many family activities...be it TV or movie watching, game or play space, or to simply just relax and enjoy.
A separate office/homework room adjoins the kitchen as well as a spacious dining room, and living room... both with wonderful wood burning fireplaces and French doors which open to the magnificent property... perfect for entertaining and for family gatherings.
An additional large adjoining bonus room, is perfect for a gym, playroom creative space or a spare fifth bedroom for when guests visit!
A first-floor dual desk office, was custom designed (amazing cabinetry) and built for function and productivity. It offers a wonderful work area for those who desire working from home while taking in views and privacy!
The lovely private and spacious Master Bedroom and Bath is located on the second level.... complete with double walk-in closets and outstanding wrap around views of this majestic property. The Master Bath is complete with a spa shower, soaking tub and his and her vanities. This Master Bedroom Suite will check off all the boxes!
Three additional, well-appointed bedrooms, all bright, with views and... bath access are outfitted with California Closets, and a full-size laundry room complete the second floor. Above the garage is another of this property's gems! A fully finished 500 sq. ft., private entrance bonus space. (teenage heaven? media room? game room? it offers a private space to work, a children's play area, gym, you name it!
Outdoors, the pool area is divine! Heated (of course) with separate spa, surrounded by a large patio and landscaping for entertaining. All within sight of the built-in outdoor cooking area off the kitchen.
Plenty of space if you wanted your own tennis courts too !

This home is conveniently located close to both Darien and New Canaan... offering the wonderful ability to enjoy both towns and all the shopping and dining options you will ever need! Also... Cherry Lawn Park is right down the street... filled with children's play areas, the wonderful Nature Center offering after school programs... There are tennis courts...community gardens and dog park., and... it's always fun to watch the town children play some team baseball! This home is the complete package and ready for your enjoyment this summer!
298 Brookside Rd, Darien, CT 06820 is a 5 bedroom, 5 bathroom, 5,423 sqft single-family home built in 1960. It last sold for $2,500,000 on Nov 18, 2020. It is currently off market. The Trulia Estimate is $5,284,800, with a rent estimate of $22,912/month.

Home Highlights

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

Home Details for 298 Brookside Rd

Interior Features

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

Exterior Features

Exterior Home Features
Roof: OtherExterior: OtherPatio
Pool
Pool

Property Information

Year Built
Year Built: 1960Year Updated: 2021
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 2.85 acres

Price History for 298 Brookside Rd

DatePriceEventSource
11/18/2020$2,500,000Sold
Smart MLS #170309131
10/14/2020$2,479,000PendingAgent Provided
08/21/2020$2,479,000PriceChange
Agent Provided
06/27/2020$2,595,000Listed For SaleAgent Provided
06/01/1995$905,200Sold
N/A
05/31/1989$595,000Sold
N/A

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$48,174
Assessment$3,111,990
Home facts updated by county records

Comparable Sales for 298 Brookside Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
20 Shady Acres Road, Darien, CT
0.24
Single-Family Home
$2,460,000
08/20/25
5
4
3,322
15 Marianne Road, Darien, CT
0.09
Single-Family Home
$4,600,000
05/08/26
5
5
6,325
267 Brookside Road, Darien, CT
0.18
Single-Family Home
$2,850,000
05/29/26
4
3.5
3,416
74 Salisbury Road, Darien, CT
0.14
Single-Family Home
$4,795,000
06/23/26
5
5
6,798
37 Salisbury Road, Darien, CT
0.22
Single-Family Home
$2,795,000
08/11/25
4
3.5
3,261
49 Salisbury Rd, Darien, CT
0.26
Single-Family Home
$2,865,000
04/20/26
5
4.5
4,000
304 Brookside Road, Darien, CT
0.08
Single-Family Home
$6,095,000
07/16/26
6
6.5
7,344
63 Dorchester Road, Darien, CT
0.48
Single-Family Home
$3,500,000
05/12/26
4
4.5
3,470
48 Dorchester Road, Darien, CT
0.44
Single-Family Home
$5,295,000
07/22/25
5
6
6,242
225 Brookside Rd, Darien, CT
0.33
Single-Family Home
$4,650,000
06/09/26
6
6
8,000

Nearby homes

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Assigned Schools

These are the assigned schools for 298 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. "
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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. "
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  • Trulia User
    "great place to raise kids, we have lived here for about a decade. fantastic schools, great neighbors"
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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
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  • 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
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  • 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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Homes for sale near 298 Brookside Rd

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Off Market Homes Near 298 Brookside Rd

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