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

404 E Wakefield Blvd
Winsted, CT 06098

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

$1,111,100

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $7,406/mo*
Refinance Your Home

$1,111,100

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $7,406/mo*
Refinance Your Home
3 Beds
1.5 Baths
1,731 sqft
(on 0.60 acres)

Home Value

Trulia Estimate
$1.11M
Since last month
Decreased$7K (-0.6%)
Since last year
Decreased$91K (-7.6%)
Since last sale
Increased$697K (+169.1%)
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 +142% in the last 10 years
MonthEstimated value
2026
August 2026$1.11M
July 2026$1.12M
June 2026$1.16M
May 2026$1.13M
April 2026$1.09M
March 2026$1.05M
February 2026$1.06M
January 2026$1.05M
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
351 Platt Hill Road, Winsted, CT
0.64
Single-Family Home
$370,000
04/17/26
3
2
1,715
424 East Wakefield Boulevard, Winsted, CT
0.18
Single-Family Home
$1,600,000
06/26/26
5
2
3,693
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
375 Platt Hill Rd, Winsted, CT
0.68
Single-Family Home
$370,000
02/11/26
3
1
2,033
230 East Wakefield Boulevard, Winsted, CT
0.56
Single-Family Home
$300,000
05/11/26
3
2
1,536
538 Wheelers Point, Winchester, CT
0.43
Single-Family Home
$1,500,000
10/14/25
4
3
2,496
258 Perch Rock Trail, Winsted, CT
0.45
Single-Family Home
$925,000
06/04/26
4
2
1,373

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
339 West Wakefield Boulevard, Winsted, CT 06098
0.17
$576,100
3
2
1,322
Off Market
343 West Wakefield Boulevard, Winsted, CT 06098
0.17
$249,500
2
1
674
Off Market
406 A East Wakefield Boulevard, Winsted, CT 06098
0.17
$1,336,300
4
2.5
1,282
Off Market
424 East Wakefield Boulevard, Winsted, CT 06098
0.18
$1,600,000
5
2
3,693
Recently Sold
371 Norwood Road, Winsted, CT 06098
0.23
$193,100
1
1
592
Off Market
306 West Wakefield Boulevard, Winsted, CT 06098
0.35
$1,193,400
4
2.5
2,248
Off Market
325 East Wakefield Boulevard, Winsted, CT 06098
0.38
$290,600
2
1.5
1,192
Off Market
325 Norcross Road, Winsted, CT 06098
0.38
$394,200
1
1
749
Off Market
323 East Wakefield Boulevard, Winsted, CT 06098
0.39
$423,600
3
2.5
1,426
Off Market
315 East Wakefield Boulevard, Winsted, CT 06098
0.40
$311,100
3
1
988
Off Market
322 Norcross Road, Winsted, CT 06098
0.40
$250,500
1
1
598
Off Market
266 Perch Rock Trail, Winsted, CT 06098
0.41
$846,700
3
2
1,488
Off Market

Local Information

  • Map ViewExplore the area around 404 E Wakefield Blvd.
  • Schools1 Preschool School2 Elementary Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1935
Lot Size
0.6 acres
Living Area
1,731 sqft
Price/Sqft
$642
Parking
Garage

About this House

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.
404 E Wakefield Blvd, Winsted, CT 06098 is a 3 bedroom, 2 bathroom, 1,731 sqft single-family home built in 1935. It last sold for $412,500 on Oct 18, 2019. It is currently off market. The Trulia Estimate is $1,111,100, with a rent estimate of $2,707/month.

Home Details for 404 E Wakefield Blvd

Interior Features

Levels, Entrance, & Accessibility
Stories: 2Floors: Other
Interior Details
Number of Rooms: 5
Heating & Cooling
Air Conditioning

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 and Tax history

DateEventPrice
Oct 18, 2019
Source: Smart MLS #170212331
Sold
$412,500
Aug 14, 2019
Source: Agent Provided
Pending
$469,000
Aug 12, 2019
Source: Agent Provided
Listed For Sale
$469,000

Market trends in Winchester

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
10
3MoM

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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Frequently asked questions about 404 E Wakefield Blvd

  • What is 404 E Wakefield Blvd estimated to be worth?
    Trulia's estimated value for 404 E Wakefield Blvd in Winsted, CT is $1,111,100.
  • What is the price history for 404 E Wakefield Blvd?
    404 E Wakefield Blvd in Winsted, CT last sold for $412,500 in October 2019.
  • Is Winsted a buyer's or seller's market?
    Winsted is currently a balanced market, based on recent for-sale activity.
  • What are the closest schools to 404 E Wakefield Blvd?
    The closest schools to 404 E Wakefield Blvd in Winsted, CT are Mary P. Hinsdale School (Pre-K/Elementary), Pearson Middle School (Elementary, rated 6/10).
  • How big is the lot at 404 E Wakefield Blvd?
    The lot at 404 E Wakefield Blvd in Winsted, CT is about 0.60 acres (26,136 sq ft).
  • Does 404 E Wakefield Blvd have a garage?
    Yes, 404 E Wakefield Blvd in Winsted, CT has a garage.

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