149 Dudley Road, Wilton, CT 06897
Property image
Property image
FOR SALE
NEW
OPEN SUN, 2-4PM
3D VIEW
5.34 ACRES

$2,995,000

  • 5 Beds
  • 5.5 Baths
  • 5,940 sqft (on 5.34 acres)

149 Dudley Road, Wilton, CT 06897

Est. Mortgage $20,363/mo*
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Home Highlights

Single-Family Home
Built in 1726
5.34 acre lot
$504/sqft
Garage

Local Information

  • Map ViewExplore the area around 149 Dudley Road.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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.
Last check for updates: about 9 hours ago
Listing courtesy of Melissa Rwambuya, (917) 670-5053
William Raveis Real Estate, (917) 670-5053
Source: Smart MLS, MLS#24207078
Also Listed on Smart MLS.

Open House

Sunday, September 20
2:00 PM to 4:00 PM

Home Details for 149 Dudley Road

Interior Features

Interior Details
Basement: Partial,UnfinishedNumber of Rooms: 11Types of Rooms: Master Bedroom, Bedroom, Dining Room, Living Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 5940 Square Feet
Appliances & Utilities
Appliances: Cooktop, Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Upper Level,Mud RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 3Has a Fireplace
Windows, Doors, Floors & Walls
Door: French Doors
View
Has a ViewView: Water

Exterior Features

Exterior Home Features
Roof: WoodPatio / Porch: Wrap Around, Porch, PatioFencing: FullOther Structures: Shed(s), Barn(s), Guest HouseExterior: Balcony, Underground SprinklerFoundation: Concrete PerimeterHas a Private Pool
Parking & Garage
Number of Garage Spaces: 8Number of Covered Spaces: 8No CarportHas a GarageNo Attached GarageParking Spaces: 8Parking: Detached,Barn,Other
Pool
Pool: Gunite, Heated, Pool/Spa Combo, Fenced, In GroundPool
Frontage
WaterfrontWaterfront: Waterfront, Pond, AccessOn Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 5940 Square Feet

Days on Market

Days on Market: <1 day on Trulia

Property Information

Year Built
Year Built: 1726
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Clapboard, StoneNot a New ConstructionDoes Not Include Home Warranty
Property Information
Not Included in Sale: See Inclusion/Exclusion ListParcel Number: 1924406

Price & Status

Price
List Price: $2,995,000Price Per Sqft: $504
Status Change & Dates
Possession Timing: Negotiable

Active Status

MLS Status: Active

Media

Location

Direction & Address
City: Wilton
School Information
Elementary School: Miller-DriscollJr High / Middle School: Middlebrook, Cider MillHigh School: Wilton

Agent Information

Listing Agent
Listing ID: 24207078

Building

Building Area
Building Area: 5940 Square Feet

HOA

No HOA

Lot Information

Lot Area: 5.34 Acres

Miscellaneous

BasementMls Number: 24207078Attic: Heated, Finished, Walk-upWater ViewWater View: WaterAttribution Contact: (917) 670-5053Above Grade Unfinished Area: 5940

Around this home

What Locals Say about Wilton

At least 67 Trulia users voted on each feature.

  • 94 % Say car is needed

  • 88 % Say parking is easy

  • 86 % Say there's holiday spirit

  • 84 % Say it's quiet

  • 81 % Say yards are well-kept

  • 81 % Say it's dog friendly

  • 80 % Say there's wildlife

  • 68 % Say people would walk alone at night

  • 66 % Say neighbors are friendly

  • 57 % Say they plan to stay for at least 5 years

  • 56 % Say kids play outside

  • 43 % Say there are community events

  • 24 % Say it's walkable to restaurants

  • 21 % Say streets are well-lit

  • 19 % Say it's walkable to grocery stores

  • 17 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Jelani37
    "It’s a small town, and traffic can be bad during rush hours on the Merritt "
    0
    Flag
  • Aimee Calandria
    "Christmas caroling, Memorial parade, farmers market, garden sale, Halloween parade, summer outside sale"
    0
    Flag
  • Kim Biltoft
    "Family oriented, very neighborly, help is there when you ask for it. Lots of ways to get involved in the community. "
    0
    Flag
  • Avdi R.
    "Very nice and friendly town! Very quiet and peaceful. Well kept neighborhoods and town. I spend a lot of time walking trails and enjoying the local town plazas"
    2
    Flag
  • Geneveaninevanstaden
    "Wilton is a lovely town to live in and the community is kind, friendly & welcoming. The public & communal areas are well kept and the parks & recreation facilities are well maintained. Wilton has great schools & is a great town for families."
    2
    Flag
  • Kelly H.
    "Best area to raise a family! The people are great! The schools are great! The public areas are great!"
    0
    Flag
  • Geneveaninevanstaden
    "Recently moved to Wilton and absolutely love it. We love going for family walks in the nature trails, or just taking a walk to the local restaurants or cafes. The parks are clean and well maintained, the rivers and lakes are clear and looked after. The Wilton community is friendly and welcoming, it’s a great place to call home."
    3
    Flag
  • Annie O.
    "This is a small city located in Fairfield Co Connecticut, known locally as “the country” and for being a little over an hour commute outside of NYC. Getting to a major highway requires driving through neighborhoods. "
    1
    Flag
  • Ygibney
    "Great schools close to ymca close to supermarket and close to train. Convenient location to neighboring towns ."
    0
    Flag
  • Barbara S.
    "Wilton is a caring, active, and beautiful community. A terrific library and many interest groups expand the reach of the educational resources. "
    0
    Flag
  • Azlouko
    "Fun family events in town Friendly neighbors Good school system Halloween parade Memorial Day parade"
    1
    Flag
  • Nya
    "Great schools, safe to live. We don’t have a great downtown but near by towns have. We have few good restaurants, great library and a farmers market. "
    0
    Flag
  • Samwals
    "No , there is no public transportation here. Everything is done by car. The city is spread out and there is no way they could supply public transportation except for the elderly "
    1
    Flag
  • BlessedOne
    "Lived in Wilton for 11 years. Plus is Low crime rate. Negative is expensive rent for old houses that are not update and built in 1900’s."
    1
    Flag
  • Trulia User
    "Great fairs, library events, parades! Super fun place to live. Outdoor activities too including hiking and biking. "
    0
    Flag
  • Pookie368
    "Most parts near me are not good to walk a dog. Not a lot of sidewalks and a lot of traffic. There are however a few parks to walk with your dog scattered around town."
    0
    Flag
  • Samwals
    "It doesn’t feel unique . There is nothing special about the town nor the neighborhood. The people are hoodwinked by the propaganda about how great the schools are. Scores have declined each year. "
    2
    Flag
  • Elizabethalleva
    "Wilton is amazing! Great schools. Great people. Beautiful homes!! This is a wonderful place to raise a family"
    4
    Flag
  • Samwals
    "Beautiful neighborhood, over rated schools. High taxes, high debt, Low turnout on budget issues. Poor road maintenance, wasted money on new school, with declining school age population. Retail outlets closing, with no incentives to stay. No plan to attract new businesses. A pompous attitude prevails by a community who time past by"
    0
    Flag
  • nrbattista
    "Outstanding area for raising children and commuting to NYC."
    0
    Flag
  • Liz C.
    "We live here and it is the best place we have ever lived! We thought when we bought it that we would move in a couple of years, but now we know this has everything we need and is safe, walkable, pet friendly, conveniently located and the neighborhood community is awesome. Having 4 bedrooms and a detached house with plenty of parking for our family and guests makes living easy. Our resident board and the management company are proactive and approachable. The grounds and upkeep through every season have been outstanding, nothing to complain about! These houses rarely come on the market and when they do there are always multiple bids. This has proven to be an amazing investment. Grumman Village possesses a desirable and stable mixed neighborhood of families, singles, couples and retirees."
    0
    Flag

Market trends in Wilton

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.47M
$46.67KMoM
Sale-to-List Price
105.1%
0.7%MoM
Price per sq ft
$427
$4MoM
Available listings
49
15MoM

Home Value

Trulia Estimate
$3.73M
Since last month
Increased$16K (+0.4%)
Since last year
Increased$205K (+5.9%)
Since last sale
Increased$2M (+84.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +63% in the last 10 years
MonthEstimated value
2026
September 2026$3.69M
August 2026$3.69M
July 2026$3.67M
June 2026$3.71M
May 2026$3.64M
April 2026$3.66M
March 2026$3.67M
February 2026$3.54M
January 2026$3.51M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
146 Dudley Road, Wilton, CT
0.05
Single-Family Home
$1,585,000
06/02/26
4
3
2,660
66 Little Brook Road, Wilton, CT
0.42
Single-Family Home
$1,850,000
10/24/25
4
3.5
4,023
57 Little Brook Road, Wilton, CT
0.33
Single-Family Home
$1,150,000
10/16/25
4
3.5
2,724
25 Cherry Lane, Wilton, CT
0.20
Single-Family Home
$1,105,000
06/01/26
3
2.5
2,331
109 Westport Road, Wilton, CT
0.64
Single-Family Home
$1,225,000
09/25/25
4
2.5
3,889
304 Chestnut Hill Road, Wilton, CT
0.69
Single-Family Home
$1,660,000
11/07/25
4
3
4,162
89 Chestnut Hill Road, Wilton, CT
0.98
Single-Family Home
$2,206,020
05/12/26
6
5
5,576
2 Deerfield Road, Wilton, CT
0.87
Single-Family Home
$2,075,000
08/18/26
6
5
5,289
74 Raymond Lane, Wilton, CT
0.29
Single-Family Home
$805,000
06/29/26
3
3
2,092

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
146 Dudley Road, Wilton, CT 06897
0.05
$1,585,000
4
3
2,660
Recently Sold
126 Dudley Road, Wilton, CT 06897
0.11
$1,755,200
5
5
5,497
Off Market
110 Dudley Road, Wilton, CT 06897
0.14
$695,000
3
1
1,522
Recently Sold
15 Little Brook Road, Wilton, CT 06897
0.19
$1,473,500
4
3.5
3,660
Off Market
25 Cherry Lane, Wilton, CT 06897
0.20
$1,105,000
3
2.5
2,331
Recently Sold
8 Little Brook Road, Wilton, CT 06897
0.22
$1,485,600
5
3.5
3,782
Off Market
15 Morand Lane, Wilton, CT 06897
0.19
$1,426,600
5
3.5
2,604
Off Market
18 Little Brook Road, Wilton, CT 06897
0.24
$2,294,600
5
4.5
6,670
Off Market
41 Cherry Lane, Wilton, CT 06897
0.26
$1,477,700
4
3.5
3,654
Off Market
41 Little Brook Road, Wilton, CT 06897
0.28
$1,940,900
5
3.5
4,453
Off Market
153 Spoonwood Road, Wilton, CT 06897
0.26
$1,645,400
4
4.5
4,133
Off Market

Price and Tax history

DateEventPrice
Sep 16, 2026
Source: Smart MLS #24207078
Listed For Sale
$2,995,000
Feb 10, 2017
Source: Smart MLS #99150493
Sold
$2,000,000
May 9, 2011
Source: Smart MLS #98460531
Sold
$2,175,000
Feb 5, 2011
Source: Agent Provided
ListingRemoved
$9,900
Jan 28, 2011
Source: Agent Provided
Listed For Rent
$9,900

LGBTQ Local Legal Protections

Melissa Rwambuya, William Raveis Real Estate, (917) 670-5053
Agent Phone: (917) 670-5053
IDX information is provided exclusively for 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 is deemed reliable but not guaranteed.

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Frequently asked questions about 149 Dudley Road

  • What is the estimated monthly payment for 149 Dudley Road?
    Based on a $2,995,000 list price with 20% down at today's rates, the estimated monthly payment for 149 Dudley Road in Wilton, CT is approximately $20,701 (about $16,408 principal & interest, $4,218 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 149 Dudley Road compare to homes in Wilton?
    149 Dudley Road in Wilton, CT is listed at $2,995,000, about 104% above the $1.47M median sale price in Wilton.
  • What do residents say about Wilton?
    Residents describe Wilton, CT as easy to park in, quiet, and well-kept. Most residents say you need a car. See homes for sale in Wilton, CT.
  • What are the closest schools to 149 Dudley Road?
    The closest schools to 149 Dudley Road in Wilton, CT are Cider Mill School (Elementary, rated 9/10), Middlebrook School (Middle, rated 10/10), Miller-Driscoll School (Pre-K/Elementary).
  • Does 149 Dudley Road have air conditioning?
    Yes, 149 Dudley Road in Wilton, CT has air conditioning.
  • Does 149 Dudley Road have a pool?
    Yes, 149 Dudley Road in Wilton, CT has a pool.
149 Dudley Road, Wilton, CT 06897 is a 5 bedroom, 6 bathroom, 5,940 sqft single-family home built in 1726. This property is currently available for sale and was listed by Smart MLS on Sep 16, 2026. The MLS # for this home is MLS# 24207078.