Wilton, CT / 1 DAY ON MARKET

149 Dudley RoadWilton, CT 06897

Asking price$2,995,000Active

Open house

  • Sunday, September 20, 20262:00 pm – 4:00 pm ET

Our Take

149 Dudley Road in Wilton is a 1726 country estate remodeled and re-engineered in 2007, set behind gates on more than five level acres. The main residence features wide-board floors, millwork, stone fireplaces, original architectural details, covered and wraparound porches, a kitchen, and appointed baths. Outdoor amenities include a fireplace-and-pergola living room, tiered terraces, a heated pool and spa, mature landscaping, lawns, and a freshwater pond. A three-story carriage barn adds offices, recreation and entertaining spaces, a speak-easy, and garage and storage capacity.

Estimated buyer rebate

Buy with Cress and Save $37,438 on brokerage fees*

When you buy with Cress, we give you back a portion of the brokerage commission we receive.

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*Estimate assumes a 2.5% buyer-agent commission and a 50% rebate. Actual savings depend on final purchase price and commission received.

At a glance

Active · MLS #24207078
Bedrooms
5
BathroomsBaths
5 full / 1 half
Square feet
5,940
Year built
1726
Acres
5.34
Property taxes
$55,479

July 2026-June 2027

What stands out

  • Built in 1726 and remodeled in 2007
  • Wide-board floors and original architectural details
  • Covered and wraparound porches
  • Kitchen and baths with classic finishes
  • Outdoor living room with fireplace and pergola
  • Heated pool, spa, and tiered terraces
  • Three-story carriage barn with offices and recreation spaces
  • Garage and storage capacity for car collections and boats
Read the full listing 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

Schools

Elementary
Miller-Driscoll
Middle
Middlebrook
High
Wilton

Schools as reported by SmartMLS. Confirm attendance assignments with the district.

A closer look at the location

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149 Dudley Road, Wilton, CT 06897

Price history

DateEventPrice
Originally listed$2,995,000

Intermediate price changes and previous listings may not be included.

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*Estimate: $2,995,000 asking price × assumed 2.5% buyer-agent commission × 50% rebate = $37,438. Actual savings depend on the final purchase price and commission Cress receives. The assumed commission is not a representation of this listing's offered compensation.

Listed by William Raveis Real Estate · (203) 966-3555

Melissa Rwambuya

SmartMLS · Listing #24207078 · Active

Listing data checked: Sep 17, 2026, 7:11 PM EDT.

Listing information is deemed reliable but not guaranteed. Cress commentary is separate from the MLS listing description. Contact Cress about a correction.

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