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$2,995,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 5 Full Baths
  • 1 Partial Bath
  • 5,940 Sq. Ft.
  • 8 Car Garage
  • Updated 23 hours ago

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Open House: 2:00 PM - 4:00 PM

Sunday 9/20 2:00 PM - 4:00 PM

149 Dudley Road,Wilton, CT 06897

149 Dudley RoadWiltonCT06897

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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

Full Property Details for 149 Dudley Rd

General

  • Price: $2,995,000
  • Taxes: (July 2026-June 2027)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24207078
  • Updated: 9/16/2026
  • Added to Site: 1 day(s) ago

Interior

  • Number of Rooms: 11
  • Rooms/Areas: Bonus Room, Foyer, Laundry Room, Mud Room, Wine Cellar
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Cook Top, Wall Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 6
  • Full Bathrooms: 5
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Primary Bedroom, Upper
  • Bedroom 1: Bedroom, Main
  • Bedroom 2: Bedroom, Upper
  • Bedroom 3: Bedroom, Upper
  • Bedroom 4: Bedroom, Upper

Other Rooms

  • Living Room: Living Room, Main
  • Dining Room: Dining Room, Main
  • Laundry: Upper Level
  • In-Law/Au Pair Suite: Yes

Additional Information

  • Pool: Yes
  • Pool Description: Gunite, Heated, Spa, Safety Fence, In Ground Pool

Exterior

  • Exterior Features: Porch-Wrap Around, Balcony, Shed, Porch, Barn, Guest House, French Doors, Underground Sprinkler, Patio
  • Color: White

Parking

  • Garage: Yes
  • Garage Spaces: 8
  • Total Spaces: 8
  • Parking: Detached Garage, Barn, Other

Location

  • County: Fairfield
  • Driving Directions: Use GPS

School Information

  • Elementary School: Miller-Driscoll
  • Middle School: Middlebrook
  • Intermediate School: Cider Mill
  • High School: Wilton

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, Domestic

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard, Stone
  • Basement Desc.: Partial, Unfinished
  • Roof: Wood Shingle
  • Attic: Yes
  • Square Feet: 5,940
  • Above Ground: 5,940 Sq. Ft.
  • Year Built: 1726

Lot Features

  • Lot Size (Acres): 5.34
  • Zoning: R-2
  • Lot Description: Fence - Full, Some Wetlands, Dry, Level Lot, Professionally Landscaped

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Pond, View, Access

Financial Considerations

  • Assessment Amount: $2,213,680
  • Tax Year: July 2026-June 2027

Disclosures and Reports

  • Exclusions: See Inclusion/Exclusion List
  • Property ID: 1924406

Listed by William Raveis Real Estate, Melissa Rwambuya

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Listing agent

— 149 Dudley Rd —

  • Melissa Rwambuya

    William Raveis Real Estate

Agent Contact: (917) 670-5053 Office Contact: (203) 966-3555

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 149 Dudley Rd

School District:Wilton School District
NameGradesDistance
Miller-Driscoll School
217 Wolfpit Road, Wilton, CT 06897
PK-21.8 mi
Cider Mill School
240 School Road, Wilton, CT 06897
3-51.9 mi
Middlebrook School, Wilton, CT
131 School Road, Wilton, CT 06897
6-82 mi
Wilton High School
395 Danbury Road, Wilton, CT 06897
9-122.2 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 149 Dudley Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/16/2026
Listed
$2,995,000
77.48%
MLS
2/13/2017
Sold
$1,687,500
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 149 Dudley Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$54,036
2%
$2,213,680
—
2023
$52,995
27%
$2,213,680
56%
2023
$41,642
4%
$1,423,170
1%
2022
$39,856
1%
$1,411,830
—
2021
$39,348
1%
$1,411,830
—
2020
$38,769
-1%
$1,411,830
3%
2019
$39,201
3%
$1,373,540
2%
2018
$38,012
5%
$1,348,410
4%
2017
$36,118
2%
$1,300,600
—
2016
$35,558
2%
$1,300,600
—
2015
$34,895
1%
$1,300,600
—
2014
$34,479
2%
$1,300,600
—
2011
$33,803
—
$1,300,600
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by William Raveis Real Estate, Melissa Rwambuya

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149 Dudley Road, Wilton, CT 06897 (MLS# 24207078) is a Single Family property with 5 bedrooms, 5 full bathrooms and 1 partial bathroom. 149 Dudley Road is currently listed for $2,995,000 and was received on September 16, 2026. Want to learn more about 149 Dudley Road? Do you have questions about finding other Single Family real estate for sale in Wilton? You can browse all Wilton real estate or contact a Coldwell Banker agent to request more information.

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