65 Dudley Rd, Wilton, CT 06897
OFF MARKET

65 Dudley Rd
Wilton, CT 06897

  • 4 Beds
  • 6 Baths
  • 5,476 sqft (on 2.69 acres)

$2,602,100

Trulia Estimate
as of Jun 12, 2026
Est. Refi. Payment $16,761/mo*
Refinance Your Home

$2,602,100

Trulia Estimate
as of Jun 12, 2026
Est. Refi. Payment $16,761/mo*
Refinance Your Home
4 Beds
6 Baths
5,476 sqft
(on 2.69 acres)

Local Information

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

Description

Majestically crowning a gentle, tree studded knoll, this rare jewel of a home heralds life spent happily ever after. Past its rustic stone walls and lamp-lit entry pillars, the graceful driveway leads to a bounty of luxury, quality and detail both inside and out. You’ll follow the walkway to the pillared portico and into the two story foyer. There the combination of gleaming hardwood floors, exquisite millwork and flood of natural light sets the tone for what you’ll see throughout this fine home.
You’ll find yourself drawn to the living room where you can sit by the fireplace and perhaps envision having a drink from the beautifully crafted wet bar room that’s adjacent. You might see yourself afterward crossing the hall to enjoy dinner in the formal dining room. . . a meal prepared in the home’s dream kitchen which is outfitted with top-of-the line appliances including a Viking Professional cooktop and Sub-Zero refrigerator. The large windows and French doors in both the kitchen and the adjoining family room offer tremendous views of the grounds. It’s a real delight to take in those views while sitting around the kitchen table for a snack or meal, or relaxing in the family room in front of the floor-to-ceiling stone fireplace. If you need a private refuge, a place to gather your thoughts or focus on work, the library/study is the perfect venue. From there you can step outside and experience all the natural grace of New England, enhanced with exquisite planting designs and impeccable landscape elements including an in-ground pool with waterfall and an expansive wooden deck. You’ll find you escape into a lush private retreat every time you step into the yard.
Back inside, you can take one of two staircases from the kitchen and family room areas, or the beautiful front staircase, up to the second floor. A stunning master bedroom awaits with its double entry doors, fireplace, tray ceiling, his and hers fitted walk-in closets and large, luxurious master bath. You’ll also find three other spacious bedrooms, all with en suite baths, plus a wonderful second family room perfect for play, study or as a media room.
The lower level of the home offers additional space for entertainment or hobbies, including a dark room and a potential wine cellar. Then, if you’re still looking to expand the square footage, take a look at the third floor, where 970 square feet of space is ready to finish.
Importantly, this enchanting property is located about 2 miles from Wilton’s town center and top-rated schools, within easy commuting distance of New York City. The home is truly a rare find and the perfect place to call home.

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

Home Details for 65 Dudley Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 10Wet BarCeiling Fan
Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or SpaJetted Bath Tub
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodGardenLawnPatioSprinkler System
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1999
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 2.69 acres

Price History for 65 Dudley Rd

DatePriceEventSource
05/12/2011$1,622,000Sold
Smart MLS #98481290
07/19/2004$1,604,000Sold
Smart MLS #98196279
01/20/1999$1,130,000Sold
Smart MLS #98016880

Market trends in Wilton

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
57
18MoM
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Property Tax and Assessment

Year2025
Tax$34,157
Assessment$1,399,300
Home facts updated by county records

Homeowner tools

Estimated monthly rent$16,995/mo
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Homes for rent near 65 Dudley Rd

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Comparable Sales for 65 Dudley Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
41 Little Brook Road, Wilton, CT
0.56
Single-Family Home
$1,800,000
07/11/25
5
3.5
4,453
37 Topfield Road, Wilton, CT
0.65
Single-Family Home
$1,420,000
08/28/25
4
3.5
4,728
146 Dudley Road, Wilton, CT
0.34
Single-Family Home
$1,585,000
06/02/26
4
3
2,660
104 Cherry Lane, Wilton, CT
0.71
Single-Family Home
$2,050,000
07/02/25
5
5
5,032
109 Westport Road, Wilton, CT
0.43
Single-Family Home
$1,225,000
09/25/25
4
2.5
3,889
25 Cherry Lane, Wilton, CT
0.31
Single-Family Home
$1,105,000
06/01/26
3
2.5
2,331
66 Little Brook Road, Wilton, CT
0.70
Single-Family Home
$1,850,000
10/24/25
4
3.5
4,023
57 Little Brook Road, Wilton, CT
0.61
Single-Family Home
$1,150,000
10/16/25
4
3.5
2,724
122 Sharp Hill Rd, Wilton, CT
0.79
Single-Family Home
$1,850,000
12/09/25
4
3
3,679
189 Westport Road, Wilton, CT
0.74
Single-Family Home
$1,585,000
06/12/25
4
2.5
4,602

Nearby homes

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Assigned Schools

These are the assigned schools for 65 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

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Homes for sale near 65 Dudley Rd

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Off Market Homes Near 65 Dudley Rd

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65 Dudley Rd, Wilton, CT 06897 is a 4 bedroom, 6 bathroom, 5,476 sqft single-family home built in 1999. This property is not currently available for sale. 65 Dudley Rd was last sold on May 12, 2011 for $1,622,000. The current Trulia Estimate for 65 Dudley Rd is $2,602,100.