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246 Brookside Road

Darien, Connecticut 06820

ACTIVE$7,900,000
Beds
7
Baths
7 | 2
SqFt
8,100
Acres
4.12
Year Built
1770
Matt Caiola

Matt Caiola

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Guest HousePool6-Car Garage7 Fireplaces

About This Home

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!

Key Facts

City/Town
Darien
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1770
Days on Market
110 days
Beds
7
Baths
7 full · 2 half
Living Area
8,100 sq ft
Lot Size
4.12 acres
Garage / Parking
6 garage
Property Taxes
$55,531 / Annually

Market Snapshot

The Darien Market

Single Family · trailing 12 months

Median Days on Market

51

25 active listings

Median $ / Sq Ft

$733

25 active listings

Sale-to-List Ratio

106.3%

211 sales

How this home compares

List Price

$7.90M

vs $3.80M median

2.1× the median

Price / Sq Ft

$975

vs $733 median

33.0% above median

Days on Market

110 days

vs 51 days median

59 days longer than median

Based on 25 active and 211 closed sales (trailing 12 mo) of single family in Darien. Source: SmartMLS · As of July 27, 2026.

Location

246 Brookside Road, Darien, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$47,541

per month

  • Principal & Interest$40,280
  • Property Taxes$4,628
  • Insurance$2,633
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Darien
Neighborhood
N/A
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1770
New Construction
No/Resale
Living Area
8,100 sq ft

Schools

Elementary
Ox Ridge
High
Darien

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
7
Laundry
Upper Level
Appliances
Cook TopWall OvenMicrowaveRefrigeratorIcemakerDishwasherDisposalWasherDryerWine Chiller
Basement
FullUnfinishedSump Pump
Additional Rooms
Bonus RoomExercise RoomLaundry RoomMud RoomSitting Room

Exterior & Lot

Lot Size
4.12 acres
Zoning
R2
Garage / Parking
6 garage spacesAttached GarageDetached Garage
Waterfront Details
Beach Rights
Water Source
Private Well
Sewer
Septic
Flood Zone
No
Pool
GuniteIn Ground Pool
Construction
Clapboard
Color
Beige
Roof
Wood Shingle
Foundation
MasonryStone
Exterior Features
BarnLightingGuest HousePatioGrillShedGarden AreaStone WallUnderground Sprinkler
Lot Description
Fence - PartialFence - RailSecludedDryLevel LotProfessionally LandscapedOpen Lot

Listing & Financials

Property Taxes
$55,531 / Annually
Days on Market
110
MLS #
24165104
MLS Status
Active

Similar Properties

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Listed By

Keiley Fuller

(203) 858-4609

Compass Connecticut, LLC

(203) 423-3100

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/27/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 7/27/2026 at 6:35 AM UTC.