246 Brookside RoadDarien, CT 06820

Single Family · 7 Beds · 7 Full Baths · 2 Half Baths · 8,100 Sq. ft. | 4.12 Acres
$7,900,000 Active

246 Brookside Road Overview

Time on Site:
82 days

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!

Love this property?
Create a profile so you can receive updates on this property as soon as they happen!
View Map

246 Brookside Road Facts & Features

  • Type Single Family
  • Sq. ft. 8,100
  • Price/Sq.ft. $975
  • Lot 4.12 Acres

Details

General

Association/HOA

  • Association: No

School Information

  • Elementary School: Ox Ridge
  • Middle Or Junior School: Middlesex
  • High School: Darien

Listing Information

  • Bank Owned Property: No
  • Potential Short Sale: No

Building Information

  • Year Built: 1770

Location/Region

  • County Or Parish: Fairfield
  • Neighborhood: N/A

Building Exterior/Construction

  • New Construction Type: No/Resale

Community/Development

  • Community Features: Library, Park, Playground/Tot Lot

Tax Information

  • Tax Annual Amount: $55,531.00
  • Tax Year: July 2025-June 2026

General Information

  • Flood Zone: No
  • Parcel Number: 103025
  • Property Type: Single Family For Sale
  • Zoning: R2

Interior

Parking Information

  • Garage Spaces: 6

Beds/Baths

  • Bathrooms Full: 7
  • Bathrooms Half: 2
  • Bathrooms Total: 9
  • Bedrooms Total: 7

Building Interior

  • Attic Description: Unfinished, Storage Space, Pull-Down Stairs
  • Attic: Yes
  • Energy Features: Built Green Certification, Active Solar, Generator
  • Fuel Tank Location: In Basement
  • Heat Fuel Type: Oil
  • Hot Water Description: Domestic
  • Laundry Room Info: Upper Level
  • Rooms Additional: Bonus Room, Exercise Room, Laundry Room, Mud Room, Sitting Room

General Information

  • Appliances: Cook Top, Wall Oven, Microwave, Refrigerator, Icemaker, Dishwasher, Disposal, Washer, Dryer, Wine Chiller
  • Basement: Full, Unfinished, Sump Pump
  • Cooling: Central Air
  • Fireplaces Total: 7
  • Foundation Details: Masonry, Stone
  • Heating: Hot Air
  • Living Area: 8100

Exterior

Parking Information

  • Parking Features: Attached Garage, Detached Garage

Lot Information

  • Lot Features: Fence - Partial, Fence - Rail, Secluded, Dry, Level Lot, Professionally Landscaped, Open Lot
  • Lot Size Acres: 4.12
  • Lot Size Source: Public Records
  • Water Source: Private Well

Waterfront/View

  • Waterfront Features: Beach Rights
  • Waterfront: No

Building Exterior/Construction

  • Architectural Style: Colonial
  • Color: Beige
  • Construction Materials: Clapboard
  • Roof: Wood Shingle

General Information

  • Exterior Features: Barn, Lighting, Guest House, Patio, Grill, Shed, Garden Area, Stone Wall, Underground Sprinkler
  • Pool Features: Gunite, In Ground Pool
  • Pool Private: Yes
  • Sewer: Septic

Room Information

Room: Den

  • Level: Main
  • Length: 14
  • Width: 11

Room: Dining Room

  • Level: Main
  • Length: 13
  • Width: 20
  • Description: Hardwood Floor

Room: Eat-In Kitchen

  • Level: Main
  • Length: 13
  • Width: 31
  • Description: Remodeled,Dining Area,Island

Room: Family Room

  • Level: Main
  • Length: 29
  • Width: 18

Room: Living Room

  • Level: Main
  • Length: 18
  • Width: 24
  • Description: Bay/Bow Window,Beams,Book Shelves,Fireplace,Hardwood Floor

Room: Office

  • Level: Main
  • Length: 10
  • Width: 14

Room: Primary BR Suite

  • Level: Main
  • Length: 18
  • Width: 20
  • Description: Bedroom Suite,Full Bath,Walk-In Closet

Room: Bedroom

  • Level: Other
  • Length: 13
  • Width: 16
  • Description: Full Bath,Walk-In Closet,Hardwood Floor

Room: Bedroom

  • Level: Other
  • Length: 12
  • Width: 12
  • Description: Full Bath,Hardwood Floor

Room: Bedroom

  • Level: Upper
  • Length: 11
  • Width: 18
  • Description: Full Bath

Room: Bedroom

  • Level: Upper
  • Length: 18
  • Width: 10
  • Description: Full Bath

Room: Bedroom

  • Level: Upper
  • Length: 13
  • Width: 17
  • Description: Full Bath

Room: Bedroom

  • Level: Upper
  • Length: 13
  • Width: 18
  • Description: Full Bath,Walk-In Closet

Room: Rec/Play Room

  • Level: Upper
  • Length: 20
  • Width: 20

246 Brookside Road Monthly Cost

$
$ %
%
$
$
* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

246 Brookside Road Market Data

Based on the last 30 days in this zip code

$4,422,954
Average List Price
$946
Average Price per Square Foot
32
Properties Sold
66
Average Days on Market
111
Properties for Sale
Calculations provided by Reliance Network

246 Brookside Road History

Date Event Value Agent
4/8/2026Source: Smart MLS Added to Database
April 08, 2026
Listing provided courtesy of Compass Connecticut, LLC- MLS# 24165104MLS ProviderContact Information: (203) 858-4609