103 Highview Dr, Winsted, CT 06098
OFF MARKET

$385,900

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,592 sqft (on 2.29 acres)

103 Highview Dr, Winsted, CT 06098

Est. Refi. Payment $2,718/mo*
Refinance Your Home

Home Value

Trulia Estimate
$386K
Since last month
Decreased$2K (-0.4%)
Since last year
Increased$9K (+2.5%)
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 +97% in the last 10 years
MonthEstimated value
2026
September 2026$384K
August 2026$384K
July 2026$386K
June 2026$402K
May 2026$397K
April 2026$386K
March 2026$380K
February 2026$367K
January 2026$367K
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
311 Taylor Brook Rd, Winsted, CT
0.25
Single-Family Home
$425,000
03/03/26
3
2
1,653
226 South Rd, Winsted, CT
0.13
Single-Family Home
$225,000
07/08/26
2
1
1,008
118 South Road, Winsted, CT
0.84
Single-Family Home
$433,000
05/29/26
4
3
2,240
117 South Road, Winsted, CT
0.82
Single-Family Home
$375,000
02/05/26
3
3
2,747
1167 Saw Mill Hill Road, Torrington, CT
0.66
Single-Family Home
$540,000
11/04/25
4
3.5
4,000
426 Platt Hill Road, Winsted, CT
1.04
Single-Family Home
$660,000
08/14/26
3
2.5
3,086
195 Reaching Hill Road, Winsted, CT
1.23
Single-Family Home
$400,000
09/11/26
3
2
1,324
440 Platt Hill Road, Winsted, CT
0.80
Single-Family Home
$440,000
02/06/26
4
2.5
3,416
116 Wahnee Rd, Torrington, CT
1.14
Single-Family Home
$63,000
04/28/26
2
1
816
142 Mountain Rd, Winsted, CT
1.63
Single-Family Home
$206,000
12/17/25
3
2
1,734

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
106 Highview Drive, Winsted, CT 06098
0.15
-
-
-
-
Off Market
108 Highview Drive, Winsted, CT 06098
0.17
$457,000
3
2.5
2,780
Off Market
469 Platt Hill Road, Winsted, CT 06098
0.29
$895,000
4
2
3,088
For Sale
317 Taylor Brook Road, Winsted, CT 06098
0.33
$503,900
3
2.5
2,464
Off Market
319 Taylor Brook Road, Winsted, CT 06098
0.36
$558,300
4
2.5
2,969
Off Market
Platt Hill Road, Winsted, CT 06098
0.40
-
-
-
-
Off Market
121 Highview Drive, Winsted, CT 06098
0.37
$412,500
4
3
2,148
Off Market
102 Hollow Hill Road, Winsted, CT 06098
0.40
$678,700
3
2.5
2,692
Off Market
123 Highview Drive, Winsted, CT 06098
0.39
$418,100
3
2
1,882
Off Market
342 Taylor Brook Road, Winsted, CT 06098
0.62
$1,030,900
4
4
3,379
Off Market
233 Ledge Drive, Torrington, CT 06790
0.66
$301,100
4
3.5
2,284
Off Market
1167 Saw Mill Hill Road, Torrington, CT 06790
0.66
$565,700
4
3.5
4,000
Off Market

Local Information

  • Map ViewExplore the area around 103 Highview Dr.
  • Schools1 Preschool School2 Elementary Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1969
2.29 acre lot
1,592 sqft
$242/sqft
Garage

About this House

This single-family home is located at 103 Highview Dr, Winsted, CT. 103 Highview Dr is in Winsted, CT and in ZIP code 06098. This property has 3 bedrooms, 2 bathrooms and approximately 1,592 sqft of floor space. This property has a lot size of 2.29 acres and was built in 1969.
103 Highview Dr, Winsted, CT 06098 is a 3 bedroom, 2 bathroom, 1,592 sqft single-family home built in 1969. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $385,900, with a rent estimate of $3,026/month.

Home Details for 103 Highview Dr

Interior Features

Interior Details
BasementNumber of Rooms: 6
Heating & Cooling
Heating: ElectricHeating Fuel: Electric
Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 1969
Property Type / Style
Property Type: Single Family HomeArchitecture: split level

Community

Units in Building: 1

Lot Information

Lot Area: 2.29 acres

Price and Tax history

YearProperty taxTax assessment
2025
$4,960
$170,030
Home facts updated by county records

Market trends in Winchester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
9
1MoM

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 Winchester

At least 4 Trulia users voted on each feature.

  • 100 % Say people would walk alone at night

  • 89 % Say parking is easy

  • 80 % Say car is needed

  • 78 % Say it's quiet

  • 70 % Say yards are well-kept

  • 67 % Say there's wildlife

  • 64 % Say there's holiday spirit

  • 50 % Say it's dog friendly

  • 40 % Say it's walkable to grocery stores

  • 38 % Say neighbors are friendly

  • 36 % Say kids play outside

  • 33 % Say they plan to stay for at least 5 years

  • 33 % Say streets are well-lit

  • 33 % Say there are community events

  • 29 % Say it's walkable to restaurants

  • 11 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Carrie P.
    "The homes have big, spacious yards, and most people are dog owners. There is not a lot of traffic on the street."
    0
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LGBTQ Local Legal Protections

Frequently asked questions about 103 Highview Dr

  • What is 103 Highview Dr estimated to be worth?
    Trulia's estimated value for 103 Highview Dr in Winsted, CT is $385,900.
  • Is Winsted a buyer's or seller's market?
    Winsted is currently a seller's market, based on recent for-sale activity.
  • What are the closest schools to 103 Highview Dr?
    The closest schools to 103 Highview Dr in Winsted, CT are Mary P. Hinsdale School (Pre-K/Elementary), Pearson Middle School (Elementary, rated 6/10).
  • Does 103 Highview Dr have a pool?
    Yes, 103 Highview Dr in Winsted, CT has a pool.
  • How big is the lot at 103 Highview Dr?
    The lot at 103 Highview Dr in Winsted, CT is about 2.3 acres.
  • Does 103 Highview Dr have a garage?
    Yes, 103 Highview Dr in Winsted, CT has a garage.

Explore by feature - Pet Friendly

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Explore by feature - Washer/dryer

11 rentals with a washer/dryer in Winsted, CT

Apartments for Rent

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Off Market Homes Near 103 Highview Dr

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