About 149 Dudley Road
Originally built in 1726 and extensively remodeled, reimagined and re-engineered in 2007, 149 Dudley Road is a rare country estate where nearly three centuries of history meet sophisticated modern living. Set behind gates on more than five magnificent level acres, this exceptional property combines timeless New England character, beautifully considered interiors and extraordinary amenities in an idyllic, park-like setting. The main residence is warm, elegant and filled with natural light, with wide-board floors, handsome millwork, dramatic stone fireplaces, original architectural details and inviting covered and wraparound porches that honor the home's remarkable heritage. Generously scaled rooms and an open, effortless flow are complemented by a stunning kitchen and beautifully appointed baths featuring luxurious finishes that are both classic and timeless. Designed equally for intimate everyday living and memorable entertaining, the home extends seamlessly outdoors. An exceptional outdoor living room with fireplace and pergola, expansive tiered terraces, heated pool and spa create a private resort-like setting surrounded by mature landscaping, sweeping lawns and a picturesque freshwater pond. Adding another dimension to the property is the extraordinary three-story carriage barn-a destination unto itself. With expansive entertaining and recreation spaces, offices, a spectacular secret "Speak Easy" and extensive garage and storage capacity for car collections, boats
Features of 149 Dudley Road
| MLS® # | 24207078 |
|---|---|
| Price | $2,995,000 |
| Bedrooms | 5 |
| Bathrooms | 5/1 |
| Full Baths | 5 |
| Half Baths | 1 |
| Square Footage | 5,940 |
| Acres | 5.34 |
| Type | Single Family For Sale |
| Style | Colonial |
Community Information
| Address | 149 Dudley Road |
|---|---|
| Area | N/A |
| City | Wilton |
| County | Fairfield |
| State | Connecticut |
| Zip Code | 06897 |
Amenities
| Parking Spaces | 8 |
|---|---|
| Parking | Detached Garage, Barn, Other |
| Garage Spaces | 8 |
| Is Waterfront | Yes |
| Waterfront | Pond, View, Access |
| Has Pool | Yes |
| Pool | Gunite, Heated, Spa, Safety Fence, In Ground Pool |
Interior
| Appliances | Cook Top, Wall Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer |
|---|---|
| Heating | Hot Water, Oil |
| Cooling | Central Air |
| Fireplace | Yes |
| # of Fireplaces | 3 |
Exterior
| Exterior | Clapboard, Stone |
|---|---|
| Exterior Features | Porch-Wrap Around, Balcony, Shed, Porch, Barn, Guest House, French Doors, Underground Sprinkler, Patio |
| Lot Description | Fence - Full, Some Wetlands, Dry, Level Lot, Professionally Landscaped |
| Roof | Wood Shingle |
| Foundation | Concrete |
School Information
| Elementary | Miller-Driscoll |
|---|---|
| Middle | Middlebrook |
| High | Wilton |
Additional Information
| Date Listed | September 16th, 2026 |
|---|---|
| Days on Market | 4 |
| Zoning | R-2 |
| RE / Bank Owned | No |
Listing Details
| Office | William Raveis Real Estate |
|---|
