149 Dudley Road, Wilton, Connecticut

$2,995,000

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5

Beds

6

Baths

5,940

Square feet

5.34

Acres

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 6.00
Full Baths 5
Half Baths 1
Square Footage 5,940
Acres 5.34
Type Single Family For Sale
Style Colonial
Status Active

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
# of Garages 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
Has Basement Yes
Basement Partial, Unfinished

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 20
Zoning R-2
RE / Bank Owned No

Listing Details

OfficeWilliam Raveis Real Estate

Listing Map

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Listing information last updated on October 7th, 2026 at 4:45pm EDT.