36 Dudley Rd, Litchfield, CT 06759
OFF MARKET

36 Dudley Rd
Litchfield, CT 06759

  • 4 Beds
  • 4.5 Baths
  • 4,315 sqft (on 5.51 acres)

$1,156,600

Trulia Estimate
as of Jul 19, 2026
Est. Refi. Payment $7,633/mo*
Refinance Your Home

$1,156,600

Trulia Estimate
as of Jul 19, 2026
Est. Refi. Payment $7,633/mo*
Refinance Your Home
4 Beds
4.5 Baths
4,315 sqft
(on 5.51 acres)

Local Information

  • Map ViewExplore the area around 36 Dudley Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Surrounded by the Litchfield Land Trust and land under a permanent conservation easement, this striking post-modern, located at the end of a long driveway off a cul-de-sac, offers total privacy and eternal peacefulness. Private, yet close to the amenities of Litchfield and Bantam, the 5 +/- diverse acres include a rushing brook and a perfect site for an in-ground pool with sweeping western views over meadows, forest and beyond. With multiple terraces, patios, hot tub, walls of floor-to-ceiling windows and two-fireplaces, it is perfect for entertaining, yet the first floor master bedroom suite with private terrace and stunning full bath, and three additional bedrooms and two full baths upstairs make it equally suitable for private living. The split-level main floor is comprised of a large family room with wet bar, built-in audio system, wood-burning fireplace, hardwood floors and a terrace. Above is the dramatic living room with vaulted ceiling, wood-burning fireplace, hardwood floors, floor-to-ceiling windows and another terrace. An elegant dining room, an office and an eat-in kitchen with a screened-in porch and access through the mudroom to a three-car garage complete this level. Downstairs, there is a gym with sliders out to the hot tub, a full-bath, cedar closet and a large unfinished basement with abundant storage space. Rare opportunity for privacy, convenience and space.
36 Dudley Rd, Litchfield, CT 06759 is a 4 bedroom, 5 bathroom, 4,315 sqft single-family home built in 1992. It last sold for $645,000 on Mar 12, 2021. It is currently off market. The Trulia Estimate is $1,156,600, with a rent estimate of $6,244/month.

Home Highlights

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

Home Details for 36 Dudley Rd

Interior Features

Heating & Cooling
Heating: Baseboard, Radiant, Electric, OilAir ConditioningHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 9Types of Rooms: Laundry RoomCeiling Fan
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or Spa
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodPatio
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 1992
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 5.51 acres

Building

Community rooms
Fitness Center
Fitness & Sports
Tennis Court

Price History for 36 Dudley Rd

DatePriceEventSource
03/12/2021$645,000Sold
N/A
12/30/2020$699,000ContingentSmart MLS #170279513
12/30/2020$699,000PendingAgent Provided
04/07/2020$699,000Listed For SaleAgent Provided
01/18/2019$799,999ListingRemovedAgent Provided
08/12/2018$799,999PriceChange
Agent Provided
07/21/2018$849,999Listed For SaleAgent Provided

Market trends in Litchfield

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
19
2MoM
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Property Tax and Assessment

Year2025
Tax$12,872
Assessment$643,590
Home facts updated by county records

Comparable Sales for 36 Dudley Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
87 Cathole Road, Litchfield, CT
1.03
Single-Family Home
$1,225,500
09/19/25
4
2.5
2,740
114 Cathole Road, Litchfield, CT
0.88
Single-Family Home
$600,000
08/18/25
3
1.5
1,633
203 Maple Street, Litchfield, CT
0.78
Single-Family Home
$465,000
08/29/25
5
2.5
1,276
67 Cathole Road, Litchfield, CT
1.17
Single-Family Home
$530,000
01/09/26
3
2
1,960
318 Milton Road, Litchfield, CT
1.12
Single-Family Home
$638,000
11/03/25
3
1.5
1,680
213 Brush Hill Road, Litchfield, CT
0.71
Single-Family Home
$325,750
05/29/26
2
2
1,056
469 Milton Road, Litchfield, CT
1.55
Single-Family Home
$1,275,000
06/30/26
4
2.5
3,192
566 Maple Street, Litchfield, CT
1.70
Single-Family Home
$1,300,000
05/04/26
4
4
2,880
143 Goodhouse Road, Litchfield, CT
1.92
Single-Family Home
$654,000
11/24/25
4
2.5
3,087
8 Goodhouse Road, Litchfield, CT
1.24
Single-Family Home
$542,500
10/31/25
3
1.5
1,152

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Assigned Schools

These are the assigned schools for 36 Dudley Rd.
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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 Litchfield

At least 27 Trulia users voted on each feature.

  • 97 % Say car is needed

  • 92 % Say yards are well-kept

  • 91 % Say it's dog friendly

  • 83 % Say parking is easy

  • 76 % Say there's holiday spirit

  • 75 % Say people would walk alone at night

  • 73 % Say it's quiet

  • 71 % Say there's wildlife

  • 70 % Say they plan to stay for at least 5 years

  • 68 % Say neighbors are friendly

  • 56 % Say kids play outside

  • 52 % Say there are community events

  • 45 % Say it's walkable to restaurants

  • 37 % Say there are sidewalks

  • 33 % Say it's walkable to grocery stores

  • 25 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Lucascridland
    "Litchfield hills 10k. Superb restaurants in the area. Wonderful nature walks. Connecticut at its finest."
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  • Rptcl
    "This is a beautiful town. Quaint, southern New England town with great architecture. The people are friendly and helpful. It has been our home for 43 years. I love my town. "
    0
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  • Mackr16
    "Very animal friendly as it is a rural community. Plenty of dog owners throughout the borough. Given the White Memorial Nature Preserve and ample public land, great place to be a dog"
    1
    Flag
  • Alix M.
    "Lots of people have dogs and all the various trails, green spaces, parks and public areas welcome them. Sadly, because a lot of streets are not high traffic, people allow their dogs to poop and don’t pick up (or they think it’s ok because they are walking in front of a farm). There are a couple of funky pet supply stores and almost every store has a dish of water outside. All the FedEx, UPS and USPS carriers have treats and know the dogs. Being an agricultural area, there is an abundance of vets!"
    1
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  • Lindsay.murphy108
    "Walk to town. Lots of kids for mine to run around with. Feels safe and friendly. I would recommend to anyone. "
    2
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  • Natalie M.
    "It’s a great place to live and I definitely highly recommend it for anyone. But a place, grow old in it, do it here. But only if you have the money to afford it because it’s expensive. But lots of history here so do it"
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  • Natalie M.
    "It’s woodsy and quiet. Nobody bother anyone and it’s primarily the safest place you could live. Highly recommend if you can afford it"
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  • Elizabeth C.
    "I have lived in this neighborhood for over a year and i love it! It is well kept, the neighborhood is nice, as well as the neighbors."
    3
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  • Wildirishrose
    "Lots of character—New England charm. A popular spot for tourists and retirees from NYC. Lots of great restaurants and cafes, low key bars. Shopping but it mostly comes at a premium. A great sense of community especially surrounding holidays and school events."
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  • juneglenn
    "Chestnut Hill is a very historic and beautiful location in Litchfield. One hundred year old maple trees line the road, along with beautiful stone walls. Hiking trails to the White Memorial Foundation are accessible from this location."
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  • sagetbarrows
    "Litchfield is a wonderful town full of history, activities and community involvement. There are many top notch restaurants, businesses and places to go. White Memorial, Tops mead State Park, Bantam Lake, skiing..The Warner Theatre are all here or within a 15 minute drive. The schools are rated high and are small enough so the kids all know each other or of each other. People from out of town are willing to pay a lot of money to spend weekends here. There are a lot of weekend homes but we are lucky to be able to live here everyday!"
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  • Ppnthr1
    "Quiet streets, relatively flat, good walking or cycling. Very private and quiet."
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