149 Dudley Rd, Wilton, CT 06897
OFF MARKET

149 Dudley Rd
Wilton, CT 06897

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

$3,655,100

Trulia Estimate
as of Jun 12, 2026
Est. Refi. Payment $23,513/mo*
Refinance Your Home

$3,655,100

Trulia Estimate
as of Jun 12, 2026
Est. Refi. Payment $23,513/mo*
Refinance Your Home
6 Beds
5.5 Baths
5,940 sqft
(on 5.34 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

PICTURESQUE WILTON CT RETREAT
CALL LISTING AGENT HANNELORE 914-450-3880 TO TOUR
In the bucolic neighborhoods of Fairchester ( Fairfield County, CT and Westchester County, NY) pride of home is ubiquitous. You see it in the well-kept houses, the gated gardens and the glistening pools. Many homes are lovely. Only a few, however, are magical. 149 Dudley Road is one of them. Time is suspended here. The casually elegant country home is, at once, both old and new. Wide board flooring, handsome millwork, stone fireplaces, covered and wrap-around porches bring the character and quality of yesteryear into today. Light-filled rooms and state-of-the-art amenities combine today’s casual lifestyle with the home’s timeless grace. There is history to this home. Originally built in 1790 and extensively remodeled, reimagined and re-engineered in 2007, 149 Dudley Road has always been a home brimming with life. People loved one another here. Children chased each other around the property - more than five level acres of lawn and leafy trees. Fabulous dinners were conjured up in the kitchen. Dreams were spun in the bedrooms. Birthdays, anniversaries, successes were celebrated in the living and dining rooms. This is a home where happiness lived and still does.
Happiness is as embedded in 149 Dudley Road as are the nails that support the framing from the cellar beams to the roof rafters. You can feel this magical quality as soon as the gates to the property open wide to embrace you. The terraces, the outdoor dining and living areas, the pool and spa compete for your attention with the expansive acreage and pretty pond. And, then, there’s the carriage barn! Three stories of charmed living space and garages for both cars & boats. The barn has endless potential for a home business, artist barn or collectors space. There are 3 office spaces and a bathroom on the main floor of the barn; a huge double height storage area and garage. The second floor of the barn features a guest apartment with full size kitchen, living room, dining room, laundry room, bedroom and full bath. See for yourself. Appreciate the stunning kitchen and baths appointed with today’s most desired finishes, all classic in sensibility and design. Walk through the welcoming rooms. Discover tucked-away closets, stained glass windows, original wood and stone and metal features, shiplap and more. Let the compelling views from the park-like grounds draw you to the windows. Sit by the pool. Feel the magic. Imagine happiness - yours and your family’s - in this remarkable home.
In a very real sense, home is everything. Make yours magical. Come home to 149 Dudley Road.
Remarkable Compound. 5+ Gated Acres Rebuilt 6000 SF main house in pristine show condition. Casual Country lifestyle- 11 Room, 3 Story historically significant rebuilt antique with top of the line amenities. Completely rebuilt and expanded home blending all of today's amenities with a casual modern living. Three story-4000 SF carriage barn. Outdoor amenities include a large level lawn, heated pool, spa, pergola, stone fireplace, patios, storage shed, box gardens,grill station & automatic full house generator. Scenic pond with fountain. Incredibly private yet conveniently located in South Wilton. Easy commute to NYC
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Porch, Patio, Deck, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 149 Dudley Rd

Interior Features

Interior Details
BasementAtticIn-law unitNumber of Rooms: 18Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Library, Master Bath, Mud Room, Office, Pantry, Recreation Room, WorkshopWet BarCeiling Fan
Heating & Cooling
Heating: Forced Air, Other, Radiant, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Tile, Hardwood, SlateGated Entry
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or SpaJetted Bath Tub
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: Stone, WoodGardenLawnPatioPorchSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Detached

Property Information

Year Built
Year Built: 2007Year Updated: 2007
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 5.34 acres

Additional Information

Intercom

Price History for 149 Dudley Rd

DatePriceEventSource
02/10/2017$2,000,000Sold
Smart MLS #99150493
05/09/2011$2,175,000Sold
Smart MLS #98460531
02/05/2011$9,900ListingRemovedAgent Provided
01/28/2011$9,900Listed For RentAgent Provided
09/23/2010$2,499,000PriceChange
Agent Provided
04/30/2010$2,550,000Listed For SaleAgent Provided
04/20/2006$1,320,000Sold
N/A

Market trends in Wilton

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
59
2MoM
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$54,036
Assessment$2,213,680
Home facts updated by county records

Homeowner tools

Estimated monthly rent$17,038/mo
List your home for rent

Homes for rent near 149 Dudley Rd

See what comparable homes in the neighborhood are renting for.
Skip to last item
Skip to first item

Comparable Sales for 149 Dudley Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
41 Little Brook Road, Wilton, CT
0.32
Single-Family Home
$1,800,000
07/11/25
5
3.5
4,453
104 Cherry Lane, Wilton, CT
0.57
Single-Family Home
$2,050,000
07/02/25
5
5
5,032
37 Topfield Road, Wilton, CT
0.39
Single-Family Home
$1,420,000
08/28/25
4
3.5
4,728
146 Dudley Road, Wilton, CT
0.10
Single-Family Home
$1,585,000
06/02/26
4
3
2,660
66 Little Brook Road, Wilton, CT
0.47
Single-Family Home
$1,850,000
10/24/25
4
3.5
4,023
109 Westport Road, Wilton, CT
0.60
Single-Family Home
$1,225,000
09/25/25
4
2.5
3,889
57 Little Brook Road, Wilton, CT
0.37
Single-Family Home
$1,150,000
10/16/25
4
3.5
2,724
25 Cherry Lane, Wilton, CT
0.23
Single-Family Home
$1,105,000
06/01/26
3
2.5
2,331
89 Chestnut Hill Road, Wilton, CT
0.94
Single-Family Home
$2,206,020
05/12/26
6
5
5,576
304 Chestnut Hill Road, Wilton, CT
0.71
Single-Family Home
$1,660,000
11/07/25
4
3
4,162

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 149 Dudley Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

  • 18 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • 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

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

Explore by feature - Garage

Explore by feature - Air Conditioning

Explore by feature - Pool

Explore by feature - Washer/dryer

Homes for sale near 149 Dudley Rd

Skip to last item
Skip to first item

Off Market Homes Near 149 Dudley Rd

Skip to last item
Skip to first item
149 Dudley Rd, Wilton, CT 06897 is a 6 bedroom, 6 bathroom, 5,940 sqft single-family home built in 2007. This property is not currently available for sale. 149 Dudley Rd was last sold on Feb 10, 2017 for $2,000,000. The current Trulia Estimate for 149 Dudley Rd is $3,655,100.