Is Darien, CT dog-friendly?

As of early 2026, 92% of users say it's dog friendly

Are yards well-kept in Darien, CT?

As of early 2026, 89% of users say yards are well-kept

Is parking easy in Darien, CT?

As of early 2026, 88% of users say parking is easy

Is a car needed in Darien, CT?

As of early 2026, 87% of users say car is needed

Does Darien, CT show holiday spirit?

As of early 2026, 84% of users say there's holiday spirit

Would people walk alone at night in Darien, CT?

As of early 2026, 81% of users say people would walk alone at night

Do kids play outside in Darien, CT?

As of early 2026, 80% of users say kids play outside

Is there wildlife in Darien, CT?

As of early 2026, 73% of users say there's wildlife

As of early 2026, 71% of users say it's quiet

Do residents of Darien, CT plan to stay at least 5 years?

As of early 2026, 70% of users say they plan to stay for at least 5 years

Are neighbors friendly in Darien, CT?

As of early 2026, 58% of users say neighbors are friendly

Are there community events in Darien, CT?

As of early 2026, 58% of users say there are community events

Does Darien, CT have sidewalks?

As of early 2026, 58% of users say there are sidewalks

Is Darien, CT walkable to restaurants?

As of early 2026, 55% of users say it's walkable to restaurants

Is Darien, CT walkable to grocery stores?

As of early 2026, 48% of users say it's walkable to grocery stores

Are the streets well-lit in Darien, CT?

As of early 2026, 44% of users say streets are well-lit

FOR SALE

4.12 ACRES

246 Brookside Road
Darien, CT 06820

7 Beds
8 Baths
8,100 sqft (on 4.12 acres)

$7,900,000

Est. Mortgage $40,123/mo*

Get Pre-Qualified

$7,900,000

Est. Mortgage $40,123/mo*

Get Pre-Qualified

7 Beds

8 Baths

8,100 sqft

(on 4.12 acres)

Local Information

-- mins to

Commute Destination

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!

Home Highlights

Parking

6 Car Garage

Outdoor

Patio, Pool

A/C

Heating & Cooling

HOA

None

Price/Sqft

$975

Listed

30 days ago

Home Details for 246 Brookside Road

Interior Features
Interior Details Basement: Full,Unfinished,Sump PumpNumber of Rooms: 25Types of Rooms: Master Bedroom, Bedroom, Den, Dining Room, Family Room, Kitchen, Living Room, Office, Rec Play Room
Beds & Baths Number of Bedrooms: 7Number of Bathrooms: 9Number of Bathrooms (full): 7Number of Bathrooms (half): 2
Dimensions and Layout Living Area: 8100 Square Feet
Appliances & Utilities Appliances: Cooktop, Oven, Microwave, Refrigerator, Ice Maker, Dishwasher, Disposal, Washer, Dryer, Wine Cooler, Water HeaterDishwasherDisposalDryerLaundry: Upper Level,Mud RoomMicrowaveRefrigeratorWasher
Heating & Cooling Heating: Forced Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa Number of Fireplaces: 7Has a Fireplace

Exterior Features
Exterior Home Features Roof: WoodPatio / Porch: PatioFencing: Partial, FencedOther Structures: Barn(s), Guest House, Shed(s)Exterior: Lighting, Outdoor Grill, Garden, Stone Wall, Underground SprinklerFoundation: Masonry, StoneGardenHas a Private Pool
Parking & Garage Number of Garage Spaces: 6Number of Covered Spaces: 6No CarportHas a GarageHas an Attached GarageParking Spaces: 6Parking: Attached,Detached
Pool Pool: Gunite, In GroundPool
Frontage Waterfront: Beach AccessNot on Waterfront
Water & Sewer Sewer: Septic Tank
Finished Area Finished Area (above surface): 8100 Square Feet

Days on Market
Days on Market: 30

Property Information
Year Built Year Built: 1770
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building Construction Materials: ClapboardNot a New ConstructionDoes Not Include Home Warranty
Property Information Parcel Number: 103025

Price & Status
Price List Price: $7,900,000Price Per Sqft: $975
Status Change & Dates Possession Timing: Negotiable

Active Status
MLS Status: Active

Location
Direction & Address City: Darien
School Information Elementary School: Ox RidgeJr High / Middle School: MiddlesexHigh School: Darien

Agent Information
Listing Agent Listing ID: 24165104

Building
Building Area Building Area: 8100 Square Feet

Community
Community Features: Library, Park, Playground
Other Playground

HOA
No HOA

Lot Information
Lot Area: 4.12 Acres

Miscellaneous
BasementMls Number: 24165104Attic: Storage, Pull Down StairsAttribution Contact: (203) 858-4609Above Grade Unfinished Area: 8100

Additional Information
LibraryParkPlayground

Last check for updates: about 7 hours ago

Listing courtesy of Keiley Fuller, (203) 858-4609

Compass Connecticut, LLC, (203) 858-4609

Source: Smart MLS, MLS#24165104

Also Listed on Smart MLS.

Price History for 246 Brookside Road

Date	Price	Event	Source
04/08/2026	$7,900,000	Listed For Sale	Smart MLS #24165104

11/25/2002	$3,600,000	Sold	N/A
Recording Date 11/25/2002 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$55,531
Assessment	$3,587,290

Home facts updated by county records

Comparable Sales for 246 Brookside Road

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
50 Buttonwood Lane, Darien, CT	0.55	Single-Family Home	$4,500,000	12/03/25	7	6.5	7,200
48 Dorchester Road, Darien, CT	0.62	Single-Family Home	$5,295,000	07/22/25	5	6	6,242
276 Mansfield Avenue, Darien, CT	0.57	Single-Family Home	$4,800,000	07/08/25	6	6	8,972
26 Peach Hill Road, Darien, CT	0.84	Single-Family Home	$6,125,000	07/01/25	6	7	8,454
20 Shady Acres Road, Darien, CT	0.28	Single-Family Home	$2,460,000	08/20/25	5	4	3,322
146 Ridge Acres Road, Darien, CT	0.26	Single-Family Home	$3,300,000	02/25/26	4	5	3,422
49 Salisbury Rd, Darien, CT	0.38	Single-Family Home	$2,865,000	04/20/26	5	4.5	4,000
202 Mansfield Ave, Darien, CT	0.74	Single-Family Home	$2,795,000	08/21/25	6	6	6,058
37 Salisbury Road, Darien, CT	0.36	Single-Family Home	$2,795,000	08/11/25	4	3.5	3,261

Assigned Schools

These are the assigned schools for 246 Brookside Road.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Darien

At least 147 Trulia users voted on each feature.

92 % Say it's dog friendly
89 % Say yards are well-kept
88 % Say parking is easy
87 % Say car is needed
84 % Say there's holiday spirit
81 % Say people would walk alone at night
80 % Say kids play outside
73 % Say there's wildlife
71 % Say it's quiet
70 % Say they plan to stay for at least 5 years
58 % Say neighbors are friendly
58 % Say there are community events
58 % Say there are sidewalks
55 % Say it's walkable to restaurants
48 % Say it's walkable to grocery stores
44 % Say streets are well-lit

Learn more about our methodology.

Kimrichardnyc
Resident
1y ago
"Happy, safe and friendly place to live and raise children. Need more diversification like in wesport CT though. "
0
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Trulia User
Resident
1y ago
"This is the best town to raise kids and build friendships. The beaches, parks, restaurants, nature and proximity to NYC also makes a great place to live. We have found the people generally friendly and welcoming. "
0
Flag
Trulia User
Resident
2y ago
"great place to raise kids, we have lived here for about a decade. fantastic schools, great neighbors"
0
Flag
Jessica_hatch7
Resident
6y ago
"NA commute to the city is an easy 65 minute train ride. We have two stations in Darien, both easily accessible. "
3
Flag
Peter S.
Resident
6y ago
"Holidays and school events. Dining and activities such as sports, the arts and many many social events"
0
Flag
Mzengo8
Resident
7y ago
"My neighborhood plays kid lacrosse/ basketball or football games. And we have parties on almost every holiday. Which is very fun for all of the kids on the block "
0
Flag
Bill T.
Prev. Resident
7y ago
"Dead end but on a hill and has a loop so kids can run around, play and explore. Lots of trees and woods surround the neighborhood."
3
Flag
Tad
Resident
7y ago
"My commute is five minutes to the train station, five minute walk from parking lot to the tracks, then an hour on the train to grand central each work day. "
1
Flag
Allison w.
Resident
7y ago
"They would love it, such a friendly area. Dogs are everywhere and appreciated. I have 2 dogs and I am so glad there are a ton of dogs around. "
0
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Chad W.
Resident
7y ago
"Darien is as family friendly as it gets. There is a lot of money here. Some are kind, but many are snobby. It's a bit of a bubble, which is why many families move here."
0
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Jessica_hatch7
Resident
7y ago
"The people are amazing and the schools are fantastic. We are only 60 minutes from the city and the trains run very frequently. "
2
Flag
Victoria_belluscio
Resident
7y ago
"Great place to raise children- excellent schools- everything is 5-10 min away so good for busy schedules! 2 train stations for easy commuting, beaches, parks and more!"
0
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Kathrynquirk445
Resident
8y ago
"Beautiful area. Gorgeous homes. Lovely neighbors. Lived here many years and love it. Great privacy and incredibly convenient."
0
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Bill T.
Prev. Resident
8y ago
"Big circle where no cars or trucks visit unless they live here or have business in the neighborhood... great place for kids"
1
Flag
dwenger
11y ago
"Spectacular location: Walk to beaches, shops, Train to NYC, convenient to I-95 and more "
0
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LGBTQ Local Legal Protections

Additional Cost

Keiley Fuller, Compass Connecticut, LLC, (203) 858-4609

Agent Phone: (203) 858-4609

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

246 Brookside Road, Darien, CT 06820 is a 7 bedroom, 9 bathroom, 8,100 sqft single-family home built in 1770. This property is currently available for sale and was listed by Smart MLS on Apr 8, 2026. The MLS # for this home is MLS# 24165104.

246 Brookside Road
Darien, CT 06820

$7,900,000

$7,900,000

Local Information