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149 Dudley Road

Wilton, Connecticut 06897

ACTIVE - NEW$2,995,000
Beds
5
Baths
5 | 1
SqFt
5,940
Acres
5.34
Year Built
1726
Matt Caiola

Matt Caiola

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WaterfrontGuest HouseWine CellarPool8-Car Garage3 FireplacesVirtual Tour

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$21,177

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Melissa Rwambuya

(917) 670-5053

William Raveis Real Estate

(203) 966-3555

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.