$2,995,000
- 5
- beds
- 5 full · 1 half
- baths
- 5,940
- sqft
- 1726
- year built
- 5
- beds
- 5 full · 1 half
- baths
- 5,940
- sqft
- 1726
- year built
- Status:
- Active
- MLS #:
- 24207078
- County:
- Fairfield
- Listed By:
- Melissa Rwambuya - William Raveis Real Estate
- Agent Email:
- melissa.rwambuya@raveis.com
Sponsoring Broker: Derek Eisenberg, Continental Real Estate Group, Inc
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.
Highlights
- Residential
- Single Family Residence
- Built in 1726
- 5.34 Acre Lot
- Waterfront
- 8 Car Garage
- 59 days on Market
-
- Bedrooms
- 5
-
- Bathrooms
- 5 full · 1 half
-
- Year Built
- 1726
-
- Architectural Style
- Colonial
-
- Construction Materials
- Frame, Stone, Concrete, Clapboard
-
- Foundation
- Concrete Perimeter
-
- Garage Spaces
- 8.0
-
- Parking Features
- Other
-
- Living Area
- 5940.0
-
- Interior Features
- In-Law Floorplan, Entrance Foyer
-
- Appliances
- Dryer, Dishwasher, Microwave, Refrigerator, Washer, Cooktop, Oven
-
- Exterior Features
- Balcony
-
- Patio And Porch
- Patio, Porch
-
- Pool Features
- Gunite, Heated, In Ground, Outdoor Pool
-
- Cooling
- Central Air
-
- Heating
- Hot Water, Oil
-
- Basement
- Partial, Unfinished
-
- Acres
- 5.34
-
- Lot Features
- Level, Waterfront
-
- Water Front Features
- Pond
-
- Water Front
- Yes
-
- View
- Water
-
- Water
- Well
-
- County
- Fairfield
-
- City
- Wilton
-
- Zip Code
- 06897
-
- High School
- Wilton
-
- Middle School
- Middlebrook
-
- Elementary School
- Miller-Driscoll
-
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Estimated Value
$3,324,114
Estimated Sales Price Range:
$2,725,773 - $3,922,454
Source: Constellation Data Labs
Price History
| 09/16/2026 | Listed | $2,995,000 |
| Source: SmartMLS #24207078 | ||
| 02/10/2017 | Sold | $2,000,000 |
| Source: SmartMLS #99150493 | ||
| 06/23/2016 | Listed | $2,395,000 |
| Source: SmartMLS #99150493 | ||
Source: MLS Data
Deed History
| 02/13/2017 | Warranty Deed | $0 |
| 05/09/2011 | Warranty Deed | $2,150,000 |
| 04/20/2006 | Warranty Deed | $1,320,000 |
Source: Public records via Constellation Data Labs
Mortgage History
| 04/19/2018 | Unknown | $392,500 |
| 02/13/2017 | Unknown | $1,350,000 |
| 02/13/2017 | Credit Line (Revolving) / HELOC | $250,000 |
| 12/29/2015 | Credit Line (Revolving) / HELOC | $470,000 |
| 03/30/2012 | ARM (Adjustable Rate Mortgage as of August, 2009) | $1,612,500 |
| 05/09/2011 | $1,612,500 | |
| 01/24/2008 | $321,000 | |
| 04/20/2006 | $1,650,000 | |
| 07/26/2002 | $569,000 | |
| 05/03/1999 | $650,000 |
Source: Public records via Constellation Data Labs
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There are currently 60 properties available in Wilton, with 11 under contract to close soon. Properties in the city have an average sale price of $1,638,948 and typically spend 66 days on the market before being sold.
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Source: ez Home Search, MLS Data
Frequently Asked Questions
How do I schedule a tour of 149 Dudley Rd?
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How do I get more information about 149 Dudley Rd?
Click Ask a Question to talk with our team. You already know it is a 5 bed, 5 bath, listed for $2,995,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Wilton, and can even get you in to see the property quickly.
How do I get a virtual tour of 149 Dudley Rd?
Yes! A virtual tour is available for 149 Dudley Rd. Click here to view the full walkthrough and explore every room at your own pace. If you would like a guided virtual showing or have questions along the way, we can connect you with our local expert to walk you through it live.
How much is the monthly mortgage payment for 149 Dudley Rd?
With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 149 Dudley Rd at around $21,667. This includes estimated property taxes and insurance.
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How do I get pre-approved to buy 149 Dudley Rd?
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Can I negotiate the asking price for 149 Dudley Rd?
In most cases, yes. Whether 149 Dudley Rd is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Wilton's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.
How do I make an offer on 149 Dudley Rd?
We can handle that for you. Our preferred local agent specializes in residentials in Wilton and can guide you through every step of the offer process.
You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.
What is the price per square foot for this home?
This home is listed at $2,995,000 with 5,940 sqft of space—that comes out to approximately $504 per square foot.
How long has this property been on the market?
149 Dudley Rd was listed on September 16, 2026, which means it's been on the market for 59 days.
Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.
When was this house built?
This home was built in 1726, making it approximately 300 years old.
What is the lot size of this property?
149 Dudley Rd sits on a 5.34-acre lot, which is 232,610 square feet.
What schools are assigned to this property?
Based on MLS info, this home is zoned for:
- Elementary: Miller-Driscoll
- Middle: Middlebrook
- High: Wilton
Want to see how these schools compare? Check out our Fairfield County School Guide to see ratings, reviews, and more for the schools in the area.
What are the property taxes for 149 Dudley Rd?
The most recent public record shows annual property taxes for 149 Dudley Rd were approximately $55,479. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.
Is 149 Dudley Rd still available for sale?
Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.
Source: ez Home Search, MLS Data
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Listing information provided exclusively for consumers' 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 deemed reliable but not guaranteed by the MLS. Copyright 2026, SmartMLS. All rights reserved.
Last Updated: November 14, 2026 at 04:17AM | Source: SmartMLS | MLS#: 24207078
