110 Highview Dr, Winsted, CT 06098
Property image
Property image
OFF MARKET

110 Highview Dr
Winsted, CT 06098

  • 2 Beds
  • 2 Baths
  • 2,559 sqft (on 2 acres)

$363,200

Trulia Estimate
as of Jul 29, 2026
Est. Refi. Payment $2,481/mo*
Refinance Your Home

$363,200

Trulia Estimate
as of Jul 29, 2026
Est. Refi. Payment $2,481/mo*
Refinance Your Home
2 Beds
2 Baths
2,559 sqft
(on 2 acres)

Local Information

  • Map ViewExplore the area around 110 Highview Dr.
  • Schools1 Preschool School3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1978
Lot Size
2 acres
Living Area
2,559 sqft
Price/Sqft
$142
Parking
Garage

About this House

Privacy at its best. Tucked in the woods off a country lane sits this 2 bedroom multi level Contemporary with a rustic flair. Situated on just over 2 acres this property has its own pond. The main living level consists of an open living area with a combination kitchen/dining room and just a few steps down to the large living room with hearth and wood stove, also there is a modest size bedroom and full bath. The upper level hosts a large master suite with walk-in closet and full bath. There is a large family room and game room in the lower level along with a laundry room, you could easily add a third bedroom in this space and still have room for a modest size family room.
110 Highview Dr, Winsted, CT 06098 is a 2 bedroom, 2 bathroom, 2,559 sqft single-family home built in 1978. It last sold for $189,000 on Feb 7, 2020. It is currently off market. The Trulia Estimate is $363,200, with a rent estimate of $3,521/month.

Home Details for 110 Highview Dr

Interior Features

Interior Details
BasementNumber of Rooms: 4
Heating & Cooling
Heating: Baseboard, OilHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DryerRefrigeratorWasher
Fireplace & Spa
Hot Tub or Spa

Exterior Features

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

Property Information

Year Built
Year Built: 1978
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 2.00 acres

Price History for 110 Highview Dr

DatePriceEventSource
02/07/2020$189,000Sold
Smart MLS #170254495
12/30/2019$219,000PendingAgent Provided
11/23/2019$219,000Listed For SaleAgent Provided

Market trends in Winchester

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
13
2MoM
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Property Tax and Assessment

Year2025
Tax$4,939
Assessment$169,330
Home facts updated by county records

Comparable Sales for 110 Highview Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
226 South Rd, Winsted, CT
0.24
Single-Family Home
$225,000
07/08/26
2
1
1,008
311 Taylor Brook Rd, Winsted, CT
0.34
Single-Family Home
$425,000
03/03/26
3
2
1,653
102 Hollow Hill Road, Winsted, CT
0.60
Single-Family Home
$639,000
07/31/25
3
2.5
2,692
1167 Saw Mill Hill Road, Torrington, CT
0.49
Single-Family Home
$540,000
11/04/25
4
3.5
4,000
117 South Road, Winsted, CT
1.04
Single-Family Home
$375,000
02/05/26
3
3
2,747
118 South Road, Winsted, CT
1.06
Single-Family Home
$433,000
05/29/26
4
3
2,240
208 Cardinal Circle, Torrington, CT
1.32
Single-Family Home
$365,000
08/01/25
3
2.5
2,304
142 Mountain Rd, Winsted, CT
1.51
Single-Family Home
$206,000
12/17/25
3
2
1,734
440 Platt Hill Road, Winsted, CT
0.96
Single-Family Home
$440,000
02/06/26
4
2.5
3,416
195 Reaching Hill Road, Winsted, CT
1.27
Single-Family Home
$101,500
09/22/25
3
2
1,324

Nearby homes

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Assigned Schools

These are the assigned schools for 110 Highview Dr.
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."
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Apartments for Rent

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Explore by feature - Pet Friendly

13 pet-friendly rentals in Winsted, CT

Homes for sale near 110 Highview Dr

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Off Market Homes Near 110 Highview Dr

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