Darien, CT / 164 DAYS ON MARKET

246 Brookside RoadDarien, CT 06820

Asking price$7,900,000Active

Our Take

246 Brookside Road is home to the Eliaseph Whitney House, originally built in 1770 on 4.12 acres. Historic features include wood-beamed ceilings and floors, multiple fireplaces, a den, and a library, alongside open living spaces with a kitchen-family-room area. Outside are a pool, landscaped grounds, split-rail fences, stone walls, and a broad field. The property also includes two garage spaces accommodating six cars and a barn-style guest house built in 2008 with two bedrooms.

Estimated buyer rebate

Buy with Cress and Save at least$118,500 on brokerage fees*

When you buy with Cress, we give you back a portion of the brokerage commission we receive. For purchases of $5 million and above, we rebate 60% or more of the buyer-agent commission we receive. Contact Cress for your tailored rebate. At this asking price, the base estimate is $118,500.

See how the commission rebate works ↗

*Base estimate assumes a 2.5% buyer-agent commission and a 60% rebate. Any rebate above 60% for a $5M+ purchase is determined with Cress. Actual savings depend on final purchase price and commission received.

At a glance

Active · MLS #24165104
Bedrooms
7
BathroomsBaths
7 full / 2 half
Square feet
8,100
Year built
1770
Acres
4.12
Property taxes
$55,531

July 2025-June 2026

What stands out

  • Historic Eliaseph Whitney House, originally built in 1770
  • Wood-beamed ceilings, floors, and multiple fireplaces
  • Pool, landscaped grounds, and stone walls
  • Broad field for recreation or relaxation
  • Two garage spaces with room for six cars
  • Barn-style guest house built in 2008
  • Guest house with two bedrooms
Read the full listing description

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!

Schools

Elementary
Ox Ridge
Middle
Middlesex
High
Darien

Schools as reported by SmartMLS. Confirm attendance assignments with the district.

A closer look at the location

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246 Brookside Road, Darien, CT 06820

Price history

DateEventPrice
Originally listed$7,900,000

Intermediate price changes and previous listings may not be included.

Could this be your next home?

Let’s talk about the property—and what working with Cress could save you.

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*Base estimate: $7,900,000 asking price × assumed 2.5% buyer-agent commission × 60% rebate = $118,500. For the $5M+ tier, we offer a 60% rebate or more; contact Cress to determine any additional rebate. Actual savings depend on the final purchase price and commission Cress receives. The assumed commission is not a representation of this listing's offered compensation.

Listed by Compass Connecticut, LLC · (203) 423-3100

Keiley Fuller

SmartMLS · Listing #24165104 · Active

Listing data checked: Sep 17, 2026, 7:00 PM EDT.

Listing information is deemed reliable but not guaranteed. Cress commentary is separate from the MLS listing description. Contact Cress about a correction.

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