149 Dudley Rd Wilton, CT, 06897

single family home
$ 2,995,000 For Sale Active Sep 16, 2026
  • 5 beds
  • 6 baths
  • 5,940 sq ft
  • 5.34 acres
  • 1726 year built
  • in ground pool
  • 8 cars garage
  • waterfront
Open House

About the Home

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

Rooms & Interior

5 bedrooms beds
5 full + 1 half baths
5,940 square feet sq ft

Room Details

  • Bedroom (Main Level)
  • Bedroom (Upper Level)
  • Primary Bedroom (Upper Level)
  • Bedroom (Upper Level)
  • Living Room (Main Level)
  • Bedroom (Upper Level)
  • Dining Room (Main Level)
  • Other Rooms Bonus room, Foyer, Laundry room, Mud room, Wine cellar

Home Features

Heating

  • Fireplaces: 3
  • Heating: hot water
  • Heat fuel type: oil
  • Fuel tank: in basement

Cooling

  • Central air

Appliances

  • Cook top
  • Wall oven
  • Microwave
  • Refrigerator
  • Dishwasher
  • Washer
  • Dryer

Attic

  • Heated
  • Finished
  • Walk-up

Basement

  • Partial
  • Unfinished

Laundry

  • Upper level

Exterior Features

  • Porch-wrap around
  • Balcony
  • Shed
  • Porch
  • Barn
  • Guest house
  • French doors
  • Underground sprinkler
  • Patio

Property Details

Parking

  • Garage spaces: 8
  • Detached garage
  • Barn
  • Other

Swimming Pool

  • Gunite
  • Heated
  • Spa
  • Safety fence
  • In ground pool

Waterfront

  • Direct waterfront
  • Pond
  • View
  • Access

Lot Details

  • Lot surface: 5.34 acres
  • Fence - full
  • Some wetlands
  • Dry
  • Level lot
  • Professionally landscaped

Utilities

  • Water: private well
  • Sewage: septic

Construction Details

Style
colonial

Construction year
1726

Exterior Siding
clapboard, stone

Foundation
concrete

Roof
wood shingle


Open Houses

There are 2 scheduled open houses for 149 Dudley Road, Wilton, CT.
September 18, 2026 Sep 18, 2026 11:00 - 13:00 (broker)
September 20, 2026 Sep 20, 2026 14:00 - 16:00 (public)

Area & Town

This home is located in South Wilton neighborhood, in the town of Wilton.

Wilton Connecticut

Natural beauty, great community, best education

  • $1.35M med. price
  • 51 homes for sale

Finance & Listing Info

Status Active
Listing date September 16, 2026
List price $ 2,995,000
Current price $ 2,995,000
Tax amount $ 55,479
Tax year july 2026-june 2027
MLS ID #24207078
List Agent Melissa Rwambuya
List Office William Raveis Real Estate

149 Dudley Road Home Photos

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