149 Dudley Road

Open: 9/27 01:00PM - 03:00PM
Open: 9/27 01:00PM - 03:00PM
Curb Appeal! Wonderful Wrap Around Porch.
Gated Entry
Foyer
Dining Room with Fireplace
Original Restored Fireplace
Eat in Kitchen with Doors to Outdoor Eating Area
Open Concept Kitchen
High End Appliances
High End Appliances
Butlers Pantry
Family Room with Doors to Patio and Pool, Gazebo and Spa
Family Room with Fireplace
First Floor Guest Room
First Floor Guest Full Bath
Mudroom Access to Back Door
Second Floor Bedroom/Office with Balcony
Primary Suite
Primary suite with Balcony Overlooking Backyard and Pool
Primary Spa Bath
Double Vanities, Vaulted Ceiling
Ensuite Bedroom Second Floor
Ensuite Bathroom
Bedroom Second Floor
Second Floor Bathroom
Third Floor Game Room
Third Floor Game Room with Wet Bar
Third Floor Bedroom
Third Floor Full Bath
Entertainment Barn
Speak Easy with Large Wine Room
Speak Easy Bar with Multiple Kegerators
Barn Apartment with Kitchen, Bedroom, Bathroom and Laundry
Car Lovers Garage
Car Lovers Garage
Gym and Bathroom in Barn
Heated Gunite Pool, Spa and Pergola
View to the back of the home
Large Flat Yard
Pond with Aerator Fountain
Five Meticulous Acres to Enjoy!
Active
$2,995,000
5 beds5,940 sqft
149 Dudley Rd, Wilton, CT 06897
Est: $20,100/moGet pre-approved
Single FamilyProperty Type
5.34 acresLot Size
1726Year Built
$504/sq ftPrice per sq ft
8 carsParking Spaces

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...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
6 days on Market
  • Listed by: Melissa Rwambuya 203.966.3555 melissa.rwambuya@raveis.com • William Raveis Real Estate
Last updated: 09/22/2026 11:30 AM • Source: SMARTMLS, MLS#: 24207078

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Listing Courtesy of William Raveis Real Estate, Melissa Rwambuya
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Property Taxes

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Property Information for 149 Dudley Road

Property Details
  • Taxes: $55,479 / year
  • MLS Type: Residential
  • County: Fairfield County
  • Basement Description: Partial, Unfinished
  • Direct Waterfront: Yes
  • Garages Number: 8
  • Style: Colonial
  • Garage Parking Info: Detached Garage, Barn, Other
  • Swimming Pool: Yes
Building Information
  • Year Built: 1726
  • Lot Size: 5.34 AC / 232,610 SF
Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Use GPS
  • Elementary School: Miller-Driscoll
  • Flood Zone: No
  • High School: Wilton
  • Intermediate School: Cider Mill
  • Latitude: 41.187572
  • Longitude: -73.405979
  • Middle Jr High School: Middlebrook
  • State: Connecticut
Parking
  • Parking Total Spaces: 8
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2026-June 2027
  • Property Tax: $55,479
Interior and Exterior Features
Exterior Features
  • Exterior Features: Porch-Wrap Around, Balcony, Shed, Porch, Barn, Guest House, French Doors, Underground Sprinkler, Patio
  • Pool Description: Gunite, Heated, Spa, Safety Fence, In Ground Pool
  • Waterfront Description: Pond, View, Access
Interior Features
  • Appliances Included: Cook Top, Wall Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer
  • Attic Description: Heated, Finished, Walk-up
  • Cooling System: Central Air
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 3
  • Laundry Room Info: Upper Level
  • Rooms Additional: Bonus Room, Foyer, Laundry Room, Mud Room, Wine Cellar
  • Rooms Total: 11
Room 1
  • Room Entry Order: 1
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 2
  • Room Level: Main
  • Room Type: Dining Room
Room 3
  • Room Entry Order: 3
  • Room Level: Upper
  • Room Type: Primary Bedroom
Room 4
  • Room Entry Order: 4
  • Room Level: Main
  • Room Type: Bedroom
Room 5
  • Listing Key: 5B7790DB44FBEB27E063E201100AB796
  • Room Entry Order: 5
  • Room Level: Upper
  • Room Type: Bedroom
Room 6
  • Room Entry Order: 6
  • Room Level: Upper
  • Room Type: Bedroom
Room 7
  • Room Entry Order: 7
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Color: White
  • Construction Description: Frame, Concrete, Masonry
  • Exclusions: See Inclusion/Exclusion List
  • Exterior Siding: Clapboard, Stone
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Wood Shingle
  • Year Built: 1726
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Over Garage
  • In Law Apartment: Yes
  • Sq Ft Description: Total Finished Space Above Grade including Building 2. Extensively Renovated in 2007.
  • Living Area SQFT Per Public Records: 4966
Lot Information
  • Lot Description: Fence - Full, Some Wetlands, Dry, Level Lot, Professionally Landscaped
  • Parcel Number: 1924406
  • Sq Ft Est Heated Above Grade: 5940.0
  • Sq Ft Total: 5940.0
  • Zoning: R-2
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, Domestic
  • Radon Mitigation Air: Yes
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 149 Dudley Road

DateEvent & SourcePriceAppreciation
May 9, 2011

Closed (Public Record)

Public Record #310435428

$2,150,000

+10.1% / yr

Apr 20, 2006

Closed (Public Record)

Public Record #195014074

$1,320,000—
Apr 20, 2006

Closed (Public Record)

Public Record #695014074

$1,320,000—
DateEvent & SourcePrice
05/09/2011

Closed (Public Record)

Public Record #310435428

$2,150,000

+10.1% / yr

04/20/2006

Closed (Public Record)

Public Record #195014074

$1,320,000
04/20/2006

Closed (Public Record)

Public Record #695014074

$1,320,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 149 Dudley Road

Taxable ValueLand$395,710Additions$1,817,970Total$2,213,680
Tax Record2025$54,036 ($4,503 / month)
Home Facts
Beds0Lot Size232,610 SqFtStyleSingle Family ResidenceZoningR-2CountyWESTERN CONNECTICUTAPNWILT M:0043 B:002 L:00

Schools near 149 Dudley Road

This home is within Wilton School District.
Rating
School
Type
Grades
Distance
Miller-Driscoll School
Public - PK to 2
Cider Mill School
Public - 3 to 5
Middlebrook School
Public - 6 to 8
Wilton High School
Public - 9 to 12
Rating
School
Distance
Miller-Driscoll School
PublicPK to 2

Cider Mill School
Public3 to 5

Middlebrook School
Public6 to 8

Wilton High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Wilton
Wilton
Indulge in away-from-it-all serenity. Once a small farming town, today's Wilton is a charming residential community spanning 27 square miles in Fairfield County, north of Merritt Parkway. Here, 18,500 residents enjoy a peaceful, community-focused lifestyle alongside bountiful outdoor space and the...
Wilton Guide

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More information about 149 Dudley Road, Wilton, CT 06897

149 Dudley Road is a single family home for sale in Wilton, CT 06897. This property was listed for sale on September 16, 2026 by William Raveis Real Estate, it's currently listed at $2,995,000. It has been on the market for a total of 6 days and was last sold on May 9, 2011. This listing's school district is Wilton School District. Nearby schools include Miller-Driscoll School, Cider Mill School and Middlebrook School. 149 Dudley Road is a 5-bed, 6-bath, 5,940 sqft single family home built in 1726.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Raveis Real Estate, Melissa Rwambuya

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.