About 246 Brookside Road
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!
Features of 246 Brookside Road
| MLS® # | 24165104 |
|---|---|
| Price | $7,900,000 |
| Bedrooms | 7 |
| Bathrooms | 9.00 |
| Full Baths | 7 |
| Half Baths | 2 |
| Square Footage | 8,100 |
| Acres | 4.12 |
| Type | Single Family For Sale |
| Style | Colonial |
| Status | Active |
Community Information
| Address | 246 Brookside Road |
|---|---|
| Area | N/A |
| City | Darien |
| County | Fairfield |
| State | Connecticut |
| Zip Code | 06820 |
Amenities
| Features | Built Green Certification, Active Solar, Generator |
|---|---|
| Parking | Attached Garage, Detached Garage |
| # of Garages | 6 |
| Is Waterfront | No |
| Waterfront | Beach Rights |
| Has Pool | Yes |
| Pool | Gunite, In Ground Pool |
Interior
| Appliances | Cook Top, Wall Oven, Microwave, Refrigerator, Icemaker, Dishwasher, Disposal, Washer, Dryer, Wine Chiller |
|---|---|
| Heating | Hot Air, Oil |
| Cooling | Central Air |
| Fireplace | Yes |
| # of Fireplaces | 7 |
| Has Basement | Yes |
| Basement | Full, Unfinished, Sump Pump |
Exterior
| Exterior | Clapboard |
|---|---|
| Exterior Features | Barn, Lighting, Guest House, Patio, Grill, Shed, Garden Area, Stone Wall, Underground Sprinkler |
| Lot Description | Fence - Partial, Fence - Rail, Secluded, Dry, Level Lot, Professionally Landscaped, Open Lot |
| Roof | Wood Shingle |
| Foundation | Masonry, Stone |
School Information
| Elementary | Ox Ridge |
|---|---|
| Middle | Middlesex |
| High | Darien |
Additional Information
| Date Listed | April 8th, 2026 |
|---|---|
| Days on Market | 154 |
| Zoning | R2 |
| RE / Bank Owned | No |
Listing Details
| Office | Compass Connecticut, LLC |
|---|