404 E Wakefield Blvd, Winsted, CT 06098
OFF MARKET

404 E Wakefield Blvd
Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,731 sqft (on 0.60 acres)

$1,124,900

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $7,420/mo*
Refinance Your Home

$1,124,900

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $7,420/mo*
Refinance Your Home
3 Beds
1.5 Baths
1,731 sqft
(on 0.60 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Three season cottage filled with charm and privacy. This 3 bedroom 1.5 bath cottage is all you need to enjoy lake life. Eat in kitchen, living room with propane stove for those chilly nights. The large deck with bench seats is perfect for relaxation, entertaining guests or soaking up the sun while taking in the gorgeous views. Situated on .60 acres. Enjoy summers boating, fishing, swimming, kayaking, paddle boarding and making memories! Approx. 118 ft. of direct waterfront. Detached 2 car garage. Deck 24 X 16. Addition in 2001. Town sewer, private well. Highland Lake is a 444 acre boating lake noted for its crystal clear water, fishing and beauty all four seasons. This lake is Connecticut's hidden gem! Located at the foothills of the Berkshires. Wonderful music venues, restaurants, hiking trails, skiing and shopping all nearby.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 404 E Wakefield Blvd

Interior Features

Heating & Cooling
Heating: OtherAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2Floors: Other
Interior Details
Number of Rooms: 5

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: Other
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1935
Property Type / Style
Property Type: Single Family HomeArchitecture: cottage

Community

Units in Building: 1

Lot Information

Lot Area: 0.60 acres

Price History for 404 E Wakefield Blvd

DatePriceEventSource
10/18/2019$412,500Sold
Smart MLS #170212331
08/14/2019$469,000PendingAgent Provided
08/12/2019$469,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$17,195
Assessment$589,470
Home facts updated by county records

Comparable Sales for 404 E Wakefield Blvd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
323 East Wakefield Boulevard, Winsted, CT
0.39
Single-Family Home
$397,000
06/04/25
3
2.5
1,426
351 Platt Hill Road, Winsted, CT
0.64
Single-Family Home
$370,000
04/17/26
3
2
1,715
126 Forest Avenue, Winsted, CT
0.77
Single-Family Home
$375,000
10/28/25
3
1.5
1,833
226 East Wakefield Boulevard, Winsted, CT
0.57
Single-Family Home
$380,000
09/17/25
3
1.5
1,196
409 W Wakefield Blvd, Winsted, CT
0.21
Single-Family Home
$500,000
01/06/26
2
1
712
343 West Wakefield Boulevard, Winsted, CT
0.17
Single-Family Home
$236,434
08/25/25
2
1
674
421 Unity Place, Winsted, CT
0.41
Single-Family Home
$286,000
06/09/25
3
2
1,440
50 Lakeview Road, Winsted, CT
0.71
Single-Family Home
$425,000
08/13/25
4
2.5
2,086
375 Platt Hill Rd, Winsted, CT
0.68
Single-Family Home
$370,000
02/11/26
3
1
2,033
266 Perch Rock Trail, Winsted, CT
0.41
Single-Family Home
$800,000
08/04/25
3
2
1,488

Nearby homes

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Assigned Schools

These are the assigned schools for 404 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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404 E Wakefield Blvd, Winsted, CT 06098 is a 3 bedroom, 2 bathroom, 1,731 sqft single-family home built in 1935. This property is not currently available for sale. 404 E Wakefield Blvd was last sold on Oct 18, 2019 for $412,500. The current Trulia Estimate for 404 E Wakefield Blvd is $1,124,900.