For Sale

Listed by Melissa Rwambuya from William Raveis Real Estate

Source: SmartMLS Connecticut #24207078

149 Dudley Rd, Fairfield County, CT, 06897

$2,995,000

5
6
8
5940 sq. ft.
5.34 ac.

SingleFam

•

1 day on the market

What's around 149 Dudley Rd

About this property

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.

Looking for more information on 149 Dudley Rd?

Explore comparables, sales history and growth for this property.
Learn more

Similar properties for sale nearby

For Sale
$2,395,000
249 Chestnut Hill Road
Wilton CT 06897
5
7
3
Single-Family
Listing courtesy of William Raveis Real Estate
For Sale
$1,795,000
122 Millstone Rd
Fairfield County CT 06897
5
5
5
Single-Family
Listing courtesy of Compass Connecticut, LLC
For Sale
$1,569,000
132 Signal Hill Road
Wilton CT 06897
5
5
6
Single-Family
Listing courtesy of William Raveis Real Estate

Other properties for sale by William Raveis Real Estate

For Sale
$1,699,000
761 New Norwalk Rd
Fairfield County CT 06840
5
4
2
Single-Family
Listing courtesy of William Raveis Real Estate
For Sale
$2,999,999
2141 Ponus Ridge
Fairfield County CT 06840
5
4
2
Single-Family
Listing courtesy of William Raveis Real Estate
For Sale
$1,395,000
8 Rising Road
Norwalk CT 06850
6
4
12
Single-Family
Listing courtesy of William Raveis Real Estate

Browse properties sold in nearby areas

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the "DMCA") provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under MLS GRID IDX Rules Updated September 16, 2024 7 U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to: dmca@ratemyagent.com

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner's behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Email
© 2026 RateMyAgent