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246 Brookside RoadDarien, CT 06820

For Sale

$7,900,000

Smart Buyer Rebate $79,000

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!

Listed by Keiley Fuller

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Compass Connecticut, LLC

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(203) 858-4609

Last updated April 29, 2026

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Source: SmartMLS #24165104

Listing Facts

  • TypeSingle-family
  • NeighborhoodDarien
  • Bedrooms7
  • Bathrooms9
  • Days on Prevu25
  • Taxes$55,531/year
  • Size8,100 sqft
  • Price per sqft$975

Location

Mortgage Calculator

Listing History

04/06/2026
Listed by Compass Connecticut, LLC
$7,900,000

Property Details for 246 Brookside Road

Exterior

Construction

  • New Construction: No/Resale
  • Roof: Wood Shingle
  • Year Built: 1770
  • Architectural Style: Colonial
  • Construction Materials: Frame, Stone
  • Exterior Features: Barn, Lighting, Guest House, Patio, Grill, Shed, Garden Area, Stone Wall, Underground Sprinkler

Features

  • Pool Features: Gunite, In Ground Pool
  • Pool Private: Yes
  • Waterfront Features: Beach Rights

Measurements

  • Lot Features: Fence - Partial, Fence - Rail, Secluded, Dry, Level Lot, Professionally Landscaped, Open Lot
  • Lot Size Acres: 4.12

Financial

Taxes

  • Parcel Number: 103025
  • Tax Annual Amount: $55,531.00
  • Tax Year: 25

Interior

Features

  • Appliances: Cook Top, Wall Oven, Microwave, Refrigerator, Icemaker, Dishwasher, Disposal, Washer, Dryer, Wine Chiller
  • Fireplaces Total: 7

Measurements

  • Living Area: 6,948

Rooms

  • Basement: Full, Unfinished, Sump Pump
  • Bathrooms Full: 7
  • Bathrooms Half: 2
  • Bathrooms Total Integer: 9
  • Bedrooms Total: 7
  • Rooms Total: 25

Parking

Parking

  • Attached Garage: Attached Garage, Detached Garage
  • Garage Spaces: 6

Schools

Elementary School

  • Elementary School: Ox Ridge

High School

  • High School: Darien

Middle or Junior School

  • Middle Or Junior School: Middlesex

Utilities

Equipment

  • Cooling: Central Air
  • Heating: Hot Air
  • Laundry Features: Upper Level
  • Sewer: Septic
  • Water Source: Private Well

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 7 bedrooms and 9 bathrooms in this single-family home at 246 Brookside Road.

What schools are nearby to 246 Brookside Road?

Nearby schools include the Ox Ridge Elementary School, Middlesex Middle School, and Darien High School.

Does this single-family home have parking?

Yes, there are 6 parking spaces available for 246 Brookside Road.

What are the annual taxes for 246 Brookside Road?

Annual taxes for this single-family home are estimated at $55,531.

How does 246 Brookside Road compare to other single-family homes in Darien?

This single-family home is listed 7% above the average price for single-family homes in Darien and has been on the market for 26 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 8,100 sqft.

246 Brookside Road is a 7-bedroom, 9-bath single-family home for sale in Darien CT 06820. Available on Prevu for 25 days at $7,900,000. This property features 8,100 square feet of living space, located in Darien. The median listing price for single-family homes in this area is $4,447,500. Nearby schools include Ox Ridge Elementary School, Middlesex Middle School, and Darien High School. View other single-family home listings in Fairfield County.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.