39 Dudley Rd
Litchfield, CT 06759
- 4 Beds
- 4.5 Baths
- 3,494 sqft (on 7.10 acres)
4 Beds
4.5 Baths
3,494 sqft
(on 7.10 acres)
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1998
Lot Size
7.1 acres
Living Area
3,494 sqft
Price/Sqft
$374
Parking
Garage
About this House
Stylish, warm, welcoming contemporary. Entrancing views, wonderful western outlook to nearby hills, sensational sunsets. Excellent privacy on 7 acres bounded by large tract of land protected with conservation easement. Attractively set swimming pool (coping needs finishing). First floor bedroom offers possibility for living on one level. Nearby Montessori schools and many other exceptional public and private educational institutions. Great combination of features for use as primary residence or second home. All of this within 4 miles of Litchfield Green and 2 miles from Arethusa ice cream!! Finished area of walk-out lower level is in addition to quoted square footage.
39 Dudley Rd, Litchfield, CT 06759 is a 4 bedroom, 5 bathroom, 3,494 sqft single-family home built in 1998. It last sold for $795,000 on Jul 5, 2005. It is currently off market. The Trulia Estimate is $1,307,900, with a rent estimate of $6,786/month.
Home Details for 39 Dudley Rd
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Interior Details BasementNumber of Rooms: 9 |
Heating & Cooling Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 2Floors: Concrete |
Appliances & Utilities DishwasherDisposalDryerWasher |
Fireplace & Spa Fireplace |
Windows, Doors, Floors & Walls Double Paned Windows |
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Exterior Home Features Roof: AsphaltDeckExterior: WoodGardenPatioPorch |
Pool Pool |
Parking & Garage GarageParking Spaces: 2Parking: Garage Attached |
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Year Built Year Built: 1998 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Units in Building: 1 |
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Lot Area: 7.10 acres |
Price History for 39 Dudley Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 03/16/2021 | ListingRemoved | Smart MLS #170338963 | |
| 02/09/2021 | $1,295,000 | Listed For Sale | Smart MLS #170338963 |
| 01/21/2021 | ListingRemoved | Smart MLS #170338963 | |
| 01/13/2021 | $1,295,000 | PriceChange | Smart MLS #170338963 |
| 09/23/2020 | $1,395,000 | Listed For Sale | Agent Provided |
| 07/05/2005 | $795,000 | Sold | N/A |
| 05/18/1998 | $160,000 | Sold | N/A |
Market trends in Litchfield
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
19
2MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $15,648 |
| Assessment | $782,390 |
Home facts updated by county records
Comparable Sales for 39 Dudley Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.93 | Single-Family Home | $1,225,500 | 09/19/25 | 4 | 2.5 | 2,740 | |
0.64 | Single-Family Home | $465,000 | 08/29/25 | 5 | 2.5 | 1,276 | |
0.78 | Single-Family Home | $600,000 | 08/18/25 | 3 | 1.5 | 1,633 | |
1.07 | Single-Family Home | $530,000 | 01/09/26 | 3 | 2 | 1,960 | |
1.22 | Single-Family Home | $638,000 | 11/03/25 | 3 | 1.5 | 1,680 | |
1.69 | Single-Family Home | $1,275,000 | 06/30/26 | 4 | 2.5 | 3,192 | |
1.84 | Single-Family Home | $1,300,000 | 05/04/26 | 4 | 4 | 2,880 | |
0.73 | Single-Family Home | $325,750 | 05/29/26 | 2 | 2 | 1,056 | |
2.03 | Single-Family Home | $654,000 | 11/24/25 | 4 | 2.5 | 3,087 | |
1.08 | Single-Family Home | $433,000 | 06/12/26 | 4 | 1 | 1,352 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 39 Dudley Rd.
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
75 % Say people would walk alone at night
74 % Say there's holiday spirit
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.
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LGBTQ Local Legal Protections