About this 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 and recreation spaces, offices, a spectacular secret "Speak Easy" and extensive garage and storage capacity for car collections, boats and recreational vehicles, the barn offers remarkable flexibility for a wide range of pursuits. A high-capacity generator provides additional peace of mind. Throughout the property, thoughtful details reveal themselves at every turn-from stained glass and original wood, stone and metalwork to shiplap, tucked-away spaces and compelling views across the grounds. Historic yet thoroughly modern, grand yet welcoming, 149 Dudley Road is more than a beautiful country home. It is a truly magical estate-one that has evolved gracefully through the centuries and is ready for its next chapter.

Facts and features

Schools

• Miller-Driscoll School

  elementary · K-2 · 1.7 mi

• Middlebrook School

  middle · 6-8 · 2.0 mi

  10

• Wilton High School

  high · 9-12 · 2.2 mi

  10

• Our Lady of Fatima Catholic School

  elementary · K-8 · 1.1 mi

• Cider Mill School

  elementary · 3-5 · 1.8 mi

  9

• Our Lady of Fatima School

  elementary · K-8 · 1.1 mi

Price history

• Sep 16, 2026 · Listed$2,995,000
• Feb 11, 2017 · Listing Removed$2,395,000
• Jan 25, 2017 · Listing Removed$2,395,000
• Jan 24, 2017 · Relisted$2,395,000
• Dec 3, 2016 · Listing Removed$2,395,000
• Jun 28, 2016 · Listed$2,395,000
• Jun 23, 2016 · Listed$2,395,000
• May 9, 2011 · Sold$2,150,000

Tax history

• 2026$55,479 tax · $2,213,680 assessed
• 2023$41,642 tax · $1,423,170 assessed
• 2022$39,856 tax · $1,411,830 assessed
• 2021$39,348 tax · $1,411,830 assessed
• 2020$38,769 tax · $1,411,830 assessed
• 2019$39,201 tax · $1,373,540 assessed
• 2018$38,012 tax · $1,348,410 assessed
• 2017$36,118 tax · $1,300,600 assessed

Home value

$2,965,000

• Collateral Analytics$2,965,000
• Cotality$2,899,400
• Quantarium$3,092,338

Where it is