372 E Wakefield Blvd, Winsted, CT 06098
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Property image
OFF MARKET

372 E Wakefield Blvd
Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 780 sqft (on 0.47 acres)

$739,200

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $4,882/mo*
Refinance Your Home

$739,200

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $4,882/mo*
Refinance Your Home
2 Beds
1 Bath
780 sqft
(on 0.47 acres)

Local Information

  • Map ViewExplore the area around 372 E Wakefield Blvd.
  • Schools1 Preschool School3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Perched on a nubble overlooking the expands of 2nd bay at Highland Lake. This property offers much privacy as it is located at the end of a private road with only 3 other homes on it.Plenty of room for guest parking. It appears enough room to tear down the cottage and build one of the most private year round homes on the lake. Property faces due west for stunning sunsets. Abutted by 3 acres of preserved land.
372 E Wakefield Blvd, Winsted, CT 06098 is a 2 bedroom, 1 bathroom, 780 sqft single-family home built in 1952. It last sold for $349,900 on May 9, 2018. It is currently off market. The Trulia Estimate is $739,200, with a rent estimate of $1,931/month.

Home Highlights

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

Home Details for 372 E Wakefield Blvd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 3Types of Rooms: Dining Room, Family Room, Sun RoomWet BarCeiling Fan
Heating & Cooling
Heating: Heat Pump, Stove, Electric, Propane Butane, Wood PelletAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Hardwood
Appliances & Utilities
Cable ReadyDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: Asphalt, Shake ShingleDeckExterior: Other, VinylGardenPatioPorch
Parking & Garage
Parking Spaces: 6Parking: Off Street

Property Information

Year Built
Year Built: 1952
Property Type / Style
Property Type: Single Family HomeArchitecture: Loft

Community

Units in Building: 1

Lot Information

Lot Area: 0.47 acres

Mobile R/V

RV Parking
Rv Parking

Price History for 372 E Wakefield Blvd

DatePriceEventSource
05/09/2018$349,900Sold
Smart MLS #L10187223
03/30/2018$349,900PendingAgent Provided
08/18/2017$349,900PriceChange
Agent Provided
07/06/2016$399,900Listed For SaleAgent Provided
10/08/1998$134,900Sold
N/A

Market trends in Winchester

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
15
4MoM
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Property Tax and Assessment

Year2025
Tax$10,210
Assessment$350,000
Home facts updated by county records

Comparable Sales for 372 E Wakefield Blvd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
343 West Wakefield Boulevard, Winsted, CT
0.24
Single-Family Home
$236,434
08/25/25
2
1
674
409 W Wakefield Blvd, Winsted, CT
0.34
Single-Family Home
$500,000
01/06/26
2
1
712
226 East Wakefield Boulevard, Winsted, CT
0.44
Single-Family Home
$380,000
09/17/25
3
1.5
1,196
621 Wynne Road, Winsted, CT
1.15
Single-Family Home
$320,000
06/26/26
2
1
975
101 Ridge St, Winsted, CT
0.96
Single-Family Home
$280,000
07/28/25
3
1
1,422
266 Perch Rock Trail, Winsted, CT
0.27
Single-Family Home
$800,000
08/04/25
3
2
1,488
375 Platt Hill Rd, Winsted, CT
0.69
Single-Family Home
$370,000
02/11/26
3
1
2,033
230 East Wakefield Boulevard, Winsted, CT
0.43
Single-Family Home
$300,000
05/11/26
3
2
1,536
548 East Wakefield Boulevard, Winsted, CT
0.73
Single-Family Home
$425,000
10/28/25
2
1
512
351 Platt Hill Road, Winsted, CT
0.57
Single-Family Home
$370,000
04/17/26
3
2
1,715

Nearby homes

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Assigned Schools

These are the assigned schools for 372 E Wakefield Blvd.
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

12 pet-friendly rentals in Winsted, CT

Homes for sale near 372 E Wakefield Blvd

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Off Market Homes Near 372 E Wakefield Blvd

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