246 Brookside Road
Darien, Connecticut 06820
- Beds
- 7
- Baths
- 7 | 2
- SqFt
- 8,100
- Acres
- 4.12
- Year Built
- 1770
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
25
54 under contract
Median List Price
$3.80M
25 active listings
Median Closed Price
$2.71M
211 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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.