149 Dudley Road, Wilton, CT 06897

• 5 beds |
• 6 baths |
• 5,940 sqft

Property Description

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

Listing Status:

Active

Date Added:

September 16, 2026

Data Last Updated:

October 5, 2026 at 4:50AM

Listing Office:

William Raveis Real Estate : (203) 966-3555

Listing Agent:

Melissa Rwambuya : (917) 670-5053

MLS ID:

24207078

Interior

• Rooms: Bonus RoomFoyerLaundry RoomMud RoomWine Cellar
• Appliances: Cook TopWall OvenMicrowaveRefrigeratorDishwasherWasherDryer
• Laundry: Upper Level
• Basement: PartialUnfinished
• A/C: Central Air
• Heating: Hot WaterOil
• Fireplace: Fireplaces: 3

Exterior

• General: Porch-Wrap AroundBalconyShedPorchBarnGuest HouseFrench DoorsUnderground SprinklerPatio
• Style: Colonial
• Pool: GuniteHeatedSpaSafety FenceIn Ground Pool
• Parking: Parking spaces: 8

Construction

• Roofing: Wood Shingle

Location

• County: Fairfield

Lot

• Zoning: R-21924406

Utilities

• Water: Private Well
• Sewer: Septic

Financial

• Exclusions: See Inclusion/Exclusion List