246 Brookside Rd

Darien, CT 06820

$7,900,000
Price
7
Beds
8,100 Sq. Ft.
$975 / Sq. Ft.
8,100
Sq. Ft.
$975
per Sq. Ft.
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Listed By Compass
Listed By Compass

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...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!

Listing Agent

  1. Keiley Fuller

    Keiley Fuller

    Listing Agent

    Compass

    keiley.fuller@compass.com

    P: (203)-858-4609

    CallTextEmail

Property Details for 246 Brookside Road

Basement Description
Full, Unfinished, Sump Pump
Direct Waterfront
No
Garages Number
6
Neighborhood
N/A
Style
Colonial
Garage Parking Info
Attached Garage, Detached Garage
Swimming Pool
Yes
LISTING UPDATED: 04/08/2026 03:45 PM

Property Details for 246 Brookside Road

StatusActive
MLS #24165104
Days on Market2
Taxes$55,531 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1770
Lot Size4.12 AC / 179,467 SF
CountyFairfield County
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Location

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Building Information for 246 Brookside Road

Stories-Year Built1770Building Size-Lot Size4.12 AC / 179,467 SF

Payment Calculator

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$44,408 per month

30 year fixed, 6.46% Interest

Principal and Interest

$39,781

Property Taxes

$4,628

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 246 Brookside Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Post Road to Brookside Road.
  • Elementary School: Ox Ridge
  • Flood Zone: No
  • High School: Darien
  • Latitude: 41.101261
  • Longitude: -73.470268
  • Middle Jr High School: Middlesex
  • Neighborhood Amenities: Library, Park, Playground/Tot Lot
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $55,531
Interior and Exterior Features
Exterior Features
  • Exterior Features: Barn, Lighting, Guest House, Patio, Grill, Shed, Garden Area, Stone Wall, Underground Sprinkler
  • Pool Description: Gunite, In Ground Pool
  • Waterfront Description: Beach Rights
Interior Features
  • Appliances Included: Cook Top, Wall Oven, Microwave, Refrigerator, Icemaker, Dishwasher, Disposal, Washer, Dryer, Wine Chiller
  • Attic Description: Unfinished, Storage Space, Pull-Down Stairs
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 7
  • Laundry Room Info: Upper Level
  • Rooms Additional: Bonus Room, Exercise Room, Laundry Room, Mud Room, Sitting Room
  • Rooms Total: 25
Room 1
  • Room Entry Order: 1
  • Room Features: Bay/Bow Window,Beams,Book Shelves,Fireplace,Hardwood Floor
  • Room Length: 18.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 24.0
Room 2
  • Room Entry Order: 10
  • Room Features: Full Bath
  • Room Length: 13.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 17.0
Room 3
  • Room Entry Order: 11
  • Room Features: Full Bath
  • Room Length: 18.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 10.0
Room 4
  • Room Entry Order: 12
  • Room Features: Full Bath
  • Room Length: 11.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 18.0
Room 5
  • Listing Key: 4ED24C248DD25220E063E201100AF01E
  • Room Entry Order: 13
  • Room Features: Full Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 13.0
  • Room Level: Other
  • Room Type: Bedroom
  • Room Width: 16.0
Room 6
  • Room Entry Order: 14
  • Room Features: Full Bath,Hardwood Floor
  • Room Length: 12.0
  • Room Level: Other
  • Room Type: Bedroom
  • Room Width: 12.0
Room 7
  • Room Entry Order: 2
  • Room Features: Hardwood Floor
  • Room Length: 13.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 20.0
Room 8
  • Room Entry Order: 3
  • Room Features: Remodeled,Dining Area,Island
  • Room Length: 13.0
  • Room Level: Main
  • Room Type: Eat-In Kitchen
  • Room Width: 31.0
Room 9
  • Listing Key: 4ED24C248DD25220E063E201100AF01E
  • Room Entry Order: 4
  • Room Length: 29.0
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 18.0
Room 10
  • Room Entry Order: 5
  • Room Length: 14.0
  • Room Level: Main
  • Room Type: Den
  • Room Width: 11.0
Room 11
  • Room Entry Order: 6
  • Room Length: 10.0
  • Room Level: Main
  • Room Type: Office
  • Room Width: 14.0
Room 12
  • Room Entry Order: 7
  • Room Length: 20.0
  • Room Level: Upper
  • Room Type: Rec/Play Room
  • Room Width: 20.0
Room 13
  • Room Entry Order: 8
  • Room Features: Bedroom Suite,Full Bath,Walk-In Closet
  • Room Length: 18.0
  • Room Level: Main
  • Room Type: Primary BR Suite
  • Room Width: 20.0
Room 14
  • Room Entry Order: 9
  • Room Features: Full Bath,Walk-In Closet
  • Room Length: 13.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 18.0
Property
Property and Assessments
  • Color: Beige
  • Construction Description: Frame, Stone
  • Exterior Siding: Clapboard
  • Foundation Type: Masonry, Stone
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Wood Shingle
  • Year Built: 1770
  • Year Built Source: Owner
  • Bank Owned Property: No
  • Sq Ft Description: Square footage calculated via photographer.
  • Living Area SQFT Per Public Records: 6948
Lot Information
  • Lot Description: Fence - Partial, Fence - Rail, Secluded, Dry, Level Lot, Professionally Landscaped, Open Lot
  • Parcel Number: 103025
  • Sq Ft Est Heated Above Grade: 8100.0
  • Sq Ft Total: 8100.0
  • Zoning: R2
Utilities
  • Energy Features: Built Green Certification, Active Solar, Generator
  • Heat Fuel Type: Oil
  • Hot Water Description: Domestic
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 246 Brookside Road

DateEvent & SourcePriceAppreciation
Nov 25, 2002

Closed (Public Record)

Public Record #107831218

$3,600,000—
DateEvent & SourcePrice
11/25/2002

Closed (Public Record)

Public Record #107831218

$3,600,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 246 Brookside Road

Taxable ValueLand$1,534,680Additions$2,052,610Total$3,587,290
Tax Record2024$55,531 ($4,628 / month)
Home Facts
Beds6Baths4.5Total Finished SqFt6,948 SqFtAbove Grade Finished SqFt6,948 SqFtStories2Lot Size179,467 SqFtStyleSingle Family ResidenceYear Built1929Year Renovated2007ZoningR2CountyFAIRFIELDAPNDARI M:04 B:28AFireplace TypeHas Fireplace

Schools near 246 Brookside Road

This home is within Darien School District.
Rating
School
Type
Grades
Distance
Ox Ridge Elementary School
Public - PK to 5
Middlesex Middle School
Public - 6 to 8
Darien High School
Public - 9 to 12
Rating
School
Distance
Ox Ridge Elementary School
PublicPK to 5

Middlesex Middle School
Public6 to 8

Darien High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 246 Brookside Road, Darien, CT 06820

246 Brookside Road is a single family home for sale in Darien, CT 06820. This property was listed for sale on April 6, 2026 by Compass, it's currently listed at $7,900,000. It has been on the market for a total of 2 days and was last sold on November 25, 2002. This listing's school district is Darien School District. Nearby schools include Ox Ridge Elementary School, Middlesex Middle School and Darien High School. 246 Brookside Road is a 7-bed, 9-bath, 8,100 sqft single family home built in 1770.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.