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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!

Highlights

  • Residential
  • Single Family Residence
  • Built in 1770
  • 4.12 Acre Lot
  • 6 Car Garage
  • 219 days on Market

  • Bedrooms
    7
  • Bathrooms
    7 full · 2 half
  • Year Built
    1770
  • Architectural Style
    Colonial
  • Construction Materials
    Frame, Stone, Clapboard
  • Foundation
    Stone
  • Garage Spaces
    6.0
  • Parking Features
    Attached
  • Living Area
    8100.0
  • Appliances
    Dryer, Dishwasher, Microwave, Refrigerator, Washer, Disposal, Cooktop, Oven, Wine Cooler, Ice Maker
  • Exterior Features
    Barbecue, Garden
  • Patio And Porch
    Patio
  • Pool Features
    Gunite, In Ground, Outdoor Pool
  • Cooling
    Central Air
  • Heating
    Forced Air, Oil, Active Solar
  • Basement
    Full, Unfinished, Sump Pump

  • Acres
    4.12
  • Lot Features
    Level
  • Water Front Features
    Beach Access
  • Water
    Well


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Frequently Asked Questions

How do I schedule a tour of 246 Brookside Rd?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 246 Brookside Rd.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 246 Brookside Rd?

Click Ask a Question to talk with our team. You already know it is a 7 bed, 7 bath, listed for $7,900,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Darien, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 246 Brookside Rd?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 246 Brookside Rd at around $49,584. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 246 Brookside Rd?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Fairfield County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 246 Brookside Rd?

In most cases, yes. Whether 246 Brookside Rd is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Darien's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 246 Brookside Rd?

We can handle that for you. Our preferred local agent specializes in residentials in Darien and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

What is the price per square foot for this home?

This home is listed at $7,900,000 with 8,100 sqft of space—that comes out to approximately $975 per square foot.

How long has this property been on the market?

246 Brookside Rd was listed on April 08, 2026, which means it's been on the market for 219 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 1770, making it approximately 256 years old.

What is the lot size of this property?

246 Brookside Rd sits on a 4.12-acre lot, which is 179,467 square feet.

What schools are assigned to this property?

Based on MLS info, this home is zoned for:

  • Elementary: Ox Ridge
  • Middle: Middlesex
  • High: Darien

Want to see how these schools compare? Check out our Fairfield County School Guide to see ratings, reviews, and more for the schools in the area.

What are the property taxes for 246 Brookside Rd?

The most recent public record shows annual property taxes for 246 Brookside Rd were approximately $55,531. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is 246 Brookside Rd still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.

Source: ez Home Search, MLS Data

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Listing information provided exclusively for consumers' 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 deemed reliable but not guaranteed by the MLS. Copyright 2026, SmartMLS. All rights reserved.

Last Updated: November 13, 2026 at 03:23PM | Source: SmartMLS | MLS#: 24165104