149 Dudley Road
Wilton, Connecticut 06897
- Beds
- 5
- Baths
- 5 | 1
- SqFt
- 5,940
- Acres
- 5.34
- Year Built
- 1726
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
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
Key Facts
- City/Town
- Wilton
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1726
- Days on Market
- 0 days
- Beds
- 5
- Baths
- 5 full · 1 half
- Living Area
- 5,940 sq ft
- Lot Size
- 5.34 acres
- Garage / Parking
- 8 garage · 8 total
- Property Taxes
- $55,479 / Annually
Market Snapshot
The Wilton Market
Single Family · trailing 12 months
Active Listings
31
19 under contract
Median List Price
$1.79M
31 active listings
Median Closed Price
$1.42M
211 sales
Median Days on Market
33
31 active listings
Median $ / Sq Ft
$417
31 active listings
Sale-to-List Ratio
105.5%
211 sales
How this home compares
List Price
$3.00M
vs $1.79M median
66.9% above median
Price / Sq Ft
$504
vs $417 median
20.9% above median
Days on Market
0 days
vs 33 days median
33 days fresher than median
Based on 31 active and 211 closed sales (trailing 12 mo) of single family in Wilton. Source: SmartMLS · As of September 17, 2026.
Location
149 Dudley Road, Wilton, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$15,556
- Property Taxes$4,623
- Insurance$998
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Wilton
- Neighborhood
- N/A
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1726
- New Construction
- No/Resale
- Living Area
- 5,940 sq ft
Schools
- Elementary
- Miller-Driscoll
- Middle
- Cider Mill
- High
- Wilton
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 3
- Laundry
- Upper Level
- Appliances
- Cook TopWall OvenMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- PartialUnfinished
- In-Law Apartment
- YesOver Garage
- Additional Rooms
- Bonus RoomFoyerLaundry RoomMud RoomWine Cellar
Exterior & Lot
- Lot Size
- 5.34 acres
- Zoning
- R-2
- Garage / Parking
- 8 garage spaces8 total parking spacesDetached GarageBarnOther
- Waterfront
- Direct waterfront
- Waterfront Details
- PondViewAccess
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- No
- Pool
- GuniteHeatedSpaSafety FenceIn Ground Pool
- Construction
- ClapboardStone
- Color
- White
- Roof
- Wood Shingle
- Foundation
- Concrete
- Exterior Features
- Porch-Wrap AroundBalconyShedPorchBarnGuest HouseFrench DoorsUnderground SprinklerPatio
- Lot Description
- Fence - FullSome WetlandsDryLevel LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $55,479 / Annually
- Days on Market
- 0
- MLS #
- 24207078
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/17/2026. This information is provided 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 or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 9/17/2026 at 12:05 AM UTC.