- Overview
- Description
- Property Details
- Location
- HOA Management
- Facts & Features
- Getting Around
- Nearby Homes
Street View
$2,995,000
Monthly Est:$14,907
5 Beds
- 6 Baths
5 full baths + 1 half bath
5,940sqft
149 Dudley Rd, Wilton, CT 06897
$2,995,000
$14,907/moEst:
Get Pre-Approved
Single Family Residence
Built in 1726
$-- HOA
5.34 acres lot
$504/sq.ft
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
- Houzeo last checked: 45 minutes ago
- Listing updated: October 6, 2026 at 3:52 pm
- Listing Provided by: Melissa Rwambuya | William Raveis Real Estate
- Source: SMART MLS-CT | MLS#: 24207078

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1726
HOA Fees
-
Finished Area
5,940 sqft
Lot Size
5.34 acres lot
Basement Area
- sqft
MLS Name
SMART MLS
MLS Number
24207078
MLS Status
Active
Days on Market
21

Continue Your Journey in App
Find your dream home, receive real-time updates, and many more!
Download App
Continue Your Journey in App
Find your dream home, receive real-time updates, and many more!
Location
HOA Management
0
HOA Fees
$-/
Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 5
Bathrooms: 6
Interior
Appliances
Cook Top, Wall Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer
Heating
Hot Water, Oil
Cooling
Central Air
Exterior Features
Porch Wrap Around, Balcony, Shed, Porch, Barn, Guest House, French Doors, Underground Sprinkler, Patio
Sewer
Septic
Construction
Year Built
Year Built: 1726
Home type
Single Family Residence
Architectural Style
Colonial
Roof
Wood Shingle
Foundation Details
Concrete
Utilities & Energy
Pool Features
Gunite, Heated, Spa, Safety Fence, In Ground Pool
Water Source
Private Well
Basement
Partial, Unfinished
Laundry Features
Upper Level
Parking Features
Detached Garage, Barn, Other
Other Features
Subdivision Name
N/a
Lot Features
Fence Full, Some Wetlands, Dry, Level Lot, Professionally Landscaped
Price History
| Date | Event | Price |
|---|---|---|
09/16/2026 Source: | Listed for Sale | $2,995,000 +49.75% $504/sqft |
02/11/2017 Source: | Price Decreased | $2,000,000 -8.05% $337/sqft |
05/11/2011 Source: | Sold | $2,175,000 +21869.70% $366/sqft |
02/01/2011 Source: #98477512 | Listing Removed | $9,900 +11.24% $2/sqft |
10/15/2009 Source: #98436536 | Price Decreased | $8,900 -99.40% $1/sqft |
Show more
Nearby Homes
Find Homes by Property Features in Wilton, CT
Based on information provided to and compiled by the SMART MLS, Inc. through Oct 08, 2026, 09:00AM. IDX information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. ©2026 SMART MLS, Inc. All Rights Reserved.
Advertising Broker: Derek Greene | The Greene Realty Group