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

399 E Wakefield Blvd
Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,632 sqft (on 0.72 acres)

$332,800

Trulia Estimate
as of Jul 14, 2026
Est. Refi. Payment $2,252/mo*
Refinance Your Home

$332,800

Trulia Estimate
as of Jul 14, 2026
Est. Refi. Payment $2,252/mo*
Refinance Your Home
3 Beds
1.5 Baths
1,632 sqft
(on 0.72 acres)

Local Information

  • Map ViewExplore the area around 399 E Wakefield Blvd.
  • Schools1 Preschool School3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Year round living in the Highland Lake community! Swimming, fishing and boating await you. Enjoy living near Highland Lake with access to town beaches and public boat launch. Power boats are allowed. Nearby is Highland Lake Marina offering boat slips and moorings. This 3 bedroom colonial has one full and one half bath. Bedroom on first floor. Great yard to relax or garden. 24 hours notice for all showings please. Masks must be worn at all times. Please do not sit on the furniture. Video surveillance inside. Bring offers
399 E Wakefield Blvd, Winsted, CT 06098 is a 3 bedroom, 2 bathroom, 1,632 sqft single-family home built in 1981. It last sold for $160,000 on Apr 20, 2021. More recently, it was listed as a rental in October 2012 with an asking price of $1,200 per month. That rental listing was removed on April 4, 2013. It is currently off market. The Trulia Estimate is $332,800, with a rent estimate of $3,016/month.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 399 E Wakefield Blvd

Interior Features

Heating & Cooling
Heating: Baseboard, ElectricHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile
Interior Details
Number of Rooms: 5Types of Rooms: Dining Room, Family Room
Appliances & Utilities
DishwasherRefrigerator

Exterior Features

Exterior Home Features
Roof: OtherExterior: Other
Parking & Garage
Parking Spaces: 2Parking: Off Street

Property Information

Year Built
Year Built: 1981
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.72 acres

Price History for 399 E Wakefield Blvd

DatePriceEventSource
04/20/2021$160,000Sold
Smart MLS #170340748
02/22/2021$169,900ContingentSmart MLS #170340748
11/11/2020$169,900PriceChange
Agent Provided
09/25/2020$174,900Listed For SaleAgent Provided
03/02/2019$174,900ListingRemovedAgent Provided
08/31/2018$174,900Listed For SaleAgent Provided
06/01/2015$122,500Sold
N/A
04/04/2013$1,200ListingRemovedAgent Provided
10/15/2012$1,200Listed For RentAgent 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
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$4,453
Assessment$152,670
Home facts updated by county records

Comparable Sales for 399 E Wakefield Blvd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
226 East Wakefield Boulevard, Winsted, CT
0.40
Single-Family Home
$380,000
09/17/25
3
1.5
1,196
230 East Wakefield Boulevard, Winsted, CT
0.39
Single-Family Home
$300,000
05/11/26
3
2
1,536
351 Platt Hill Road, Winsted, CT
0.69
Single-Family Home
$370,000
04/17/26
3
2
1,715
266 Perch Rock Trail, Winsted, CT
0.27
Single-Family Home
$800,000
08/04/25
3
2
1,488
343 West Wakefield Boulevard, Winsted, CT
0.37
Single-Family Home
$236,434
08/25/25
2
1
674
424 East Wakefield Boulevard, Winsted, CT
0.24
Single-Family Home
$1,600,000
06/26/26
5
2
3,693
155 Rockwell Street, Winsted, CT
1.00
Single-Family Home
$151,000
02/20/26
3
1
1,317
101 Ridge St, Winsted, CT
0.86
Single-Family Home
$280,000
07/28/25
3
1
1,422
50 Lakeview Road, Winsted, CT
0.68
Single-Family Home
$425,000
08/13/25
4
2.5
2,086
258 Perch Rock Trail, Winsted, CT
0.31
Single-Family Home
$925,000
06/04/26
4
2
1,373

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 399 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."
    0
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

16 pet-friendly rentals in Winsted, CT

Explore by feature - Washer/dryer

6 rentals with a washer/dryer in Winsted, CT

Homes for sale near 399 E Wakefield Blvd

Skip to last item
Skip to first item

Off Market Homes Near 399 E Wakefield Blvd

Skip to last item
Skip to first item