246 Brookside Road, Darien, CT 06820
Property image
Property image
FOR SALE
4.12 ACRES

246 Brookside Road
Darien, CT 06820

  • 7 Beds
  • 8 Baths
  • 8,100 sqft (on 4.12 acres)

$7,900,000

Est. Mortgage $51,564/mo*
Get Pre-Qualified

$7,900,000

Est. Mortgage $51,564/mo*
Get Pre-Qualified
7 Beds
8 Baths
8,100 sqft
(on 4.12 acres)

Home Highlights

Parking
6 Car Garage
Outdoor
Patio, Pool
Price/Sqft
$975
Listed
134 days ago
Climate Control
Forced Air, Oil & Central Air

Local Information

  • Map ViewExplore the area around 246 Brookside Road.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Introducing a one-of-a-kind gem in Darien: the historic Eliaseph Whitney House, originally built in 1770, nestled on an expansive 4.12-acre parcel- one of the largest of its kind in town. This iconic property effortlessly blends centuries-old charm with modern-day functionality. Step inside to discover timeless details like wood-beamed ceilings and floors, multiple fireplaces, a cozy den and library, all complemented by bright, open living spaces with a kitchen family room space built for today's lifestyle. Two garage spaces offer room for six cars and incredible storage. The surprises don't stop indoors-step outside into meticulously maintained grounds showcasing a gorgeous pool, landscaping, split rail fences, and charming stone walls that evoke a sense of storybook elegance. A sprawling, incredible field offers endless opportunities for recreation or relaxation, and the potential to divide the property into two lots opens the door to even more possibilities. Adding to the allure is a stunning barn-style guest house, built in 2008, offering two bedrooms and endless possibilities. Whether it's a private retreat for guests, a party barn, or a multi-generational living space, this addition enhances the property's versatility. This is more than a home - it's a rare opportunity to own a piece of Darien's history, surrounded by natural beauty, modern comforts, and limitless potential. A true treasure, this iconic home is a generational opportunity awaiting you!
Last check for updates: 19 minutes ago
Listing courtesy of Keiley Fuller, (203) 858-4609
Compass Connecticut, LLC, (203) 858-4609
Source: Smart MLS, MLS#24165104
Also Listed on Smart MLS.

Home Details for 246 Brookside Road

Interior Features

Interior Details
Basement: Full,Unfinished,Sump PumpNumber of Rooms: 25Types of Rooms: Master Bedroom, Bedroom, Den, Dining Room, Family Room, Kitchen, Living Room, Office, Rec Play Room
Beds & Baths
Number of Bedrooms: 7Number of Bathrooms: 9Number of Bathrooms (full): 7Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 8100 Square Feet
Appliances & Utilities
Appliances: Cooktop, Oven, Microwave, Refrigerator, Ice Maker, Dishwasher, Disposal, Washer, Dryer, Wine Cooler, Water HeaterDishwasherDisposalDryerLaundry: Upper Level,Mud RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 7Has a Fireplace

Exterior Features

Exterior Home Features
Roof: WoodPatio / Porch: PatioFencing: Partial, FencedOther Structures: Barn(s), Guest House, Shed(s)Exterior: Lighting, Outdoor Grill, Garden, Stone Wall, Underground SprinklerFoundation: Masonry, StoneGardenHas a Private Pool
Parking & Garage
Number of Garage Spaces: 6Number of Covered Spaces: 6No CarportHas a GarageHas an Attached GarageParking Spaces: 6Parking: Attached,Detached
Pool
Pool: Gunite, In GroundPool
Frontage
Waterfront: Beach AccessNot on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 8100 Square Feet

Days on Market

Days on Market: 134

Property Information

Year Built
Year Built: 1770
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: ClapboardNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 103025

Price & Status

Price
List Price: $7,900,000Price Per Sqft: $975
Status Change & Dates
Possession Timing: Negotiable

Active Status

MLS Status: Active

Location

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

Agent Information

Listing Agent
Listing ID: 24165104

Building

Building Area
Building Area: 8100 Square Feet

Community

Community Features: Library, Park, Playground
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 4.12 Acres

Miscellaneous

BasementMls Number: 24165104Attic: Storage, Pull Down StairsAttribution Contact: (203) 858-4609Above Grade Unfinished Area: 8100

Additional Information

LibraryParkPlayground

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.
  • 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
  • dwenger
    "Spectacular location: Walk to beaches, shops, Train to NYC, convenient to I-95 and more "
    0
    Flag

Market trends in Darien

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.98M
$246KMoM
Sale-to-List Price
108.9%
3.3%MoM
Price per sq ft
$800
$12MoM
Available listings
36
18MoM

Home Value

Trulia Estimate
$7.14M
Since last month
Decreased$72K (-1%)
Since last year
Increased$1M (+18.9%)
Since last sale
Increased$4M (+98.6%)
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 +57% in the last 10 years
MonthEstimated value
2026
August 2026$7.15M
June 2026$7.22M
May 2026$7.33M
April 2026$7.67M
March 2026$6.66M
February 2026$6.42M
January 2026$6.21M
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
234 Brookside Road, Darien, CT
0.07
Single-Family Home
$4,750,000
08/14/26
6
6.5
6,829
304 Brookside Road, Darien, CT
0.29
Single-Family Home
$6,095,000
07/16/26
6
6.5
7,344
15 Marianne Road, Darien, CT
0.33
Single-Family Home
$4,600,000
05/08/26
5
5
6,325
74 Salisbury Road, Darien, CT
0.30
Single-Family Home
$4,795,000
06/23/26
5
5
6,798
7 Buttonwood Lane, Darien, CT
0.48
Single-Family Home
$5,200,000
07/10/26
5
7
8,502
50 Buttonwood Lane, Darien, CT
0.55
Single-Family Home
$4,500,000
12/03/25
7
6.5
7,200
267 Brookside Road, Darien, CT
0.10
Single-Family Home
$2,850,000
05/29/26
4
3.5
3,416
316 Mansfield Avenue, Darien, CT
0.56
Single-Family Home
$5,625,000
07/24/26
5
6
9,039

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
234 Brookside Road, Darien, CT 06820
0.07
$4,750,000
6
6.5
6,829
Recently Sold
267 Brookside Road, Darien, CT 06820
0.10
$2,850,000
4
3.5
3,416
Recently Sold
222 Brookside Road, Darien, CT 06820
0.18
$3,900,000
5
5.5
10,000
For Sale
25 Three Wells Road, Darien, CT 06820
0.21
$3,014,300
5
5
6,061
Off Market
22 Shady Acres Road, Darien, CT 06820
0.20
$5,789,300
5
8.5
8,277
Off Market
146 Ridge Acres Road, Darien, CT 06820
0.26
$3,300,000
4
5
3,422
Recently Sold
20 Shady Acres Road, Darien, CT 06820
0.28
$3,352,400
5
4
3,322
Off Market
9 Shady Acres Road, Darien, CT 06820
0.27
$3,111,600
5
4
4,676
Off Market
304 Brookside Road, Darien, CT 06820
0.29
$6,095,000
6
6.5
7,344
Recently Sold
74 Salisbury Road, Darien, CT 06820
0.30
$4,795,000
5
5
6,798
Recently Sold
175 Brookside Road, Darien, CT 06820
0.35
$9,250,000
6
8.5
11,314
For Sale

Price and Tax history

DateEventPrice
Apr 8, 2026
Source: Smart MLS #24165104
Listed For Sale
$7,900,000
Nov 25, 2002
Source: N/A
Sold
$3,600,000

LGBTQ Local Legal Protections

Keiley Fuller, Compass Connecticut, LLC, (203) 858-4609
Agent Phone: (203) 858-4609
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.

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Frequently asked questions about 246 Brookside Road

  • What is the estimated monthly payment for 246 Brookside Road?
    Based on a $7,900,000 list price with 20% down at today's rates, the estimated monthly payment for 246 Brookside Road in Darien, CT is approximately $52,436 (about $41,235 principal & interest, $11,126 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 246 Brookside Road compare to homes in Darien?
    246 Brookside Road in Darien, CT is listed at $7,900,000, about 166% above the $2.98M median sale price in Darien.
  • 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 homes for sale in Darien, CT.
  • What are the closest schools to 246 Brookside Road?
    The closest schools to 246 Brookside Road in Darien, CT are Darien High School (rated 10/10), Middlesex Middle School (rated 10/10), Ox Ridge Elementary School (Pre-K, rated 10/10).
  • Does 246 Brookside Road have air conditioning?
    Yes, 246 Brookside Road in Darien, CT has air conditioning.
  • Does 246 Brookside Road have a pool?
    Yes, 246 Brookside Road in Darien, CT has a pool.
246 Brookside Road, Darien, CT 06820 is a 7 bedroom, 9 bathroom, 8,100 sqft single-family home built in 1770. This property is currently available for sale and was listed by Smart MLS on Apr 8, 2026. The MLS # for this home is MLS# 24165104.