442 Milton Rd, Litchfield, CT 06759
Property image
Property image
OFF MARKET

$716,900

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 2,660 sqft (on 1.85 acres)

442 Milton Rd, Litchfield, CT 06759

Refinance Your Home
Currently Off Market - Sold Oct 20, 2020 for $487,500

Home Value

Trulia Estimate
$717K
Since last month
Decreased$26K (-3.5%)
Since last year
Increased$2K (+0.3%)
Since last sale
Increased$226K (+46.3%)
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 +84% in the last 10 years
MonthEstimated value
2026
September 2026$713K
August 2026$739K
July 2026$743K
June 2026$742K
May 2026$727K
April 2026$714K
March 2026$701K
February 2026$686K
January 2026$675K
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
476 Milton Road, Litchfield, CT
0.25
Single-Family Home
$430,000
08/31/26
3
1.5
1,864
552 Milton Road, Litchfield, CT
0.76
Single-Family Home
$355,000
02/24/26
3
2
2,392
469 Milton Road, Litchfield, CT
0.26
Single-Family Home
$1,275,000
06/30/26
4
2.5
3,192
566 Maple Street, Litchfield, CT
0.30
Single-Family Home
$1,300,000
05/04/26
4
4
2,880
318 Milton Road, Litchfield, CT
0.82
Single-Family Home
$638,000
11/03/25
3
1.5
1,680
204 Goodhouse Road, Litchfield, CT
1.20
Single-Family Home
$422,500
04/09/26
4
1.5
1,794
143 Goodhouse Road, Litchfield, CT
0.93
Single-Family Home
$654,000
11/24/25
4
2.5
3,087
8 Goodhouse Road, Litchfield, CT
1.19
Single-Family Home
$542,500
10/31/25
3
1.5
1,152
10 Maple View Trail, Litchfield, CT
1.23
Single-Family Home
$806,500
12/19/25
3
2.5
2,521
336 Maple Street, Litchfield, CT
1.31
Single-Family Home
$608,000
09/11/26
2
2
1,984

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
476 Milton Road, Litchfield, CT 06759
0.25
$430,000
3
1.5
1,864
Recently Sold
469 Milton Road, Litchfield, CT 06759
0.26
$1,275,000
4
2.5
3,192
Recently Sold
435 Milton Road, Litchfield, CT 06759
0.30
$1,077,900
3
2.5
2,648
Off Market
566 Maple Street, Litchfield, CT 06759
0.30
$1,300,000
4
4
2,880
Recently Sold
Address Not Disclosed, Litchfield, CT 06759
0.52
-
-
-
86,248
Off Market
66 Headquarters Road, Litchfield, CT 06759
0.62
$1,211,500
3
3.5
2,457
Off Market
28 Headquarters Road, Litchfield, CT 06759
0.62
$985,000
3
3
3,225
For Sale
12 Headquarters Road, Litchfield, CT 06759
0.68
$1,147,000
5
3
2,954
Off Market
129 Headquarters Road, Litchfield, CT 06759
0.71
$1,016,300
4
3.5
3,731
Off Market
5 Shear Shop Road, Litchfield, CT 06759
0.70
$545,300
4
2
2,338
Off Market
552 Milton Road, Litchfield, CT 06759
0.75
$355,000
3
2
2,392
Recently Sold
318 Milton Road, Litchfield, CT 06759
0.82
$673,400
3
1.5
1,680
Off Market

Local Information

  • Map ViewExplore the area around 442 Milton Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1966
1.85 acre lot
2,660 sqft
$270/sqft
Garage

About this House

Charming 8-room Gambrel-reproduction Colonial located in the Milton Historic District. Updated kitchen, beautifully appointed living room with fireplace and butternut paneling, large family room with woodstove. Formal dining room with custom paneling, office, three bedrooms, and two full baths & one half bath. Large 1,200 square foot woodworking shop/barn with home occupation status. Additional three-bay garage.
442 Milton Rd, Litchfield, CT 06759 is a 3 bedroom, 3 bathroom, 2,660 sqft single-family home built in 1966. It last sold for $487,500 on Oct 20, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $716,900, with a rent estimate of $4,231/month.

Home Details for 442 Milton Rd

Interior Features

Interior Details
BasementNumber of Rooms: 8
Heating & Cooling
Heating: Forced Air, OilHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodPatioPorch
Parking & Garage
GarageParking: Garage Attached, Garage Detached

Property Information

Year Built
Year Built: 1966
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 1.85 acres

Price and Tax history

DateEventPrice
Oct 20, 2020
Source: Smart MLS #170318655
Sold
$487,500
Aug 29, 2020
Source: Agent Provided
Pending
$495,000
Aug 17, 2020
Source: Agent Provided
PendingToActive
$495,000
Aug 12, 2020
Source: Agent Provided
Pending
$495,000
Jul 21, 2020
Source: Agent Provided
Listed For Sale
$495,000

Market trends in Litchfield

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
26
4MoM

Around this home

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 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.
  • Rptcl
    "People are always walking dogs here it is a wonderful place to live. Quiet and peanut and beautiful. "
    0
    Flag
  • Lucascridland
    "Litchfield hills 10k. Superb restaurants in the area. Wonderful nature walks. Connecticut at its finest."
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • Lindsay.murphy108
    "Walk to town. Lots of kids for mine to run around with. Feels safe and friendly. I would recommend to anyone. "
    2
    Flag
  • 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"
    0
    Flag
  • 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"
    0
    Flag
  • 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
    Flag
  • 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."
    0
    Flag
  • 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."
    0
    Flag
  • 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!"
    0
    Flag
  • Ppnthr1
    "Quiet streets, relatively flat, good walking or cycling. Very private and quiet."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 442 Milton Rd

  • What is 442 Milton Rd estimated to be worth?
    Trulia's estimated value for 442 Milton Rd in Litchfield, CT is $716,900.
  • What is the price history for 442 Milton Rd?
    442 Milton Rd in Litchfield, CT last sold for $487,500 in October 2020.
  • Is Litchfield a buyer's or seller's market?
    Litchfield is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Litchfield?
    Residents describe Litchfield, CT as well-kept, dog-friendly, and easy to park in. Most residents say you need a car. See recently sold homes in Litchfield, CT.
  • Does 442 Milton Rd have laundry facilities?
    Yes, 442 Milton Rd in Litchfield, CT has in-unit laundry.
  • How big is the lot at 442 Milton Rd?
    The lot at 442 Milton Rd in Litchfield, CT is about 1.9 acres.

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