337 E Wakefield Blvd, Winsted, CT 06098
OFF MARKET

337 E Wakefield Blvd
Winsted, CT 06098

  • 4 Beds
  • 3 Baths
  • 2,000 sqft

$386,200

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $2,623/mo*
Refinance Your Home

$386,200

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $2,623/mo*
Refinance Your Home
4 Beds
3 Baths
2,000 sqft

Home Value

Trulia Estimate
$386K
Since last month
Decreased$12K (-3.1%)
Since last year
Decreased$7K (-1.7%)
Since last sale
Increased$186K (+92.8%)
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 +136% in the last 10 years
MonthEstimated value
2026
August 2026$386K
July 2026$398K
June 2026$398K
May 2026$399K
April 2026$380K
March 2026$374K
February 2026$368K
January 2026$366K
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
230 East Wakefield Boulevard, Winsted, CT
0.20
Single-Family Home
$300,000
05/11/26
3
2
1,536
258 Perch Rock Trail, Winsted, CT
0.14
Single-Family Home
$925,000
06/04/26
4
2
1,373
226 East Wakefield Boulevard, Winsted, CT
0.21
Single-Family Home
$380,000
09/17/25
3
1.5
1,196
216 Perch Rock Trl, Winsted, CT
0.21
Single-Family Home
$1,000,000
01/12/26
4
2
2,557
107 Birdsall Street, Winsted, CT
0.77
Single-Family Home
$210,000
07/02/26
4
2
1,874
43 East Lake Street, Winsted, CT
0.59
Single-Family Home
$920,000
11/17/25
4
3
2,131
156 Shore Drive, Winsted, CT
0.45
Single-Family Home
$691,000
05/21/26
5
1.5
1,258
51 Pratt St, Winsted, CT
0.90
Single-Family Home
$390,000
04/27/26
4
2
2,239
12 Cherry Street, Winsted, CT
0.77
Single-Family Home
$277,000
10/09/25
4
1
1,492
39 Orchard Street, Winsted, CT
0.81
Single-Family Home
$290,000
11/26/25
3
1.5
1,200

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
325 East Wakefield Boulevard, Winsted, CT 06098
0.04
$290,600
2
1.5
1,192
Off Market
323 East Wakefield Boulevard, Winsted, CT 06098
0.05
$423,600
3
2.5
1,426
Off Market
315 East Wakefield Boulevard, Winsted, CT 06098
0.06
$311,100
3
1
988
Off Market
303 East Wakefield Boulevard, Winsted, CT 06098
0.08
$295,300
2
1
960
Off Market
266 Perch Rock Trail, Winsted, CT 06098
0.10
$846,700
3
2
1,488
Off Market
325 Norcross Road, Winsted, CT 06098
0.08
$394,200
1
1
749
Off Market
322 Norcross Road, Winsted, CT 06098
0.09
$250,500
1
1
598
Off Market
258 Perch Rock Trail, Winsted, CT 06098
0.14
$925,000
4
2
1,373
Recently Sold
155 Alpha Avenue, Winsted, CT 06098
0.12
$330,500
2
1
954
Off Market
234 East Wakefield Boulevard, Winsted, CT 06098
0.16
$145,900
2
1
816
Off Market
319 White Oak Trail, Winsted, CT 06098
0.14
$42,900
-
-
-
For Sale
230 East Wakefield Boulevard, Winsted, CT 06098
0.20
$300,000
3
2
1,536
Recently Sold

Local Information

  • Map ViewExplore the area around 337 E Wakefield Blvd.
  • Schools1 Preschool School2 Elementary Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1988
Living Area
2,000 sqft
Price/Sqft
$193
Parking
Garage

About this House

New commanding architecturally designed 16x24 deck with 12x20 sun deck above! This also creates a 16x24 covered shade living area or covered parking. Incredible views of Litchfield Hills and Highland Lake!

Six 10 inch pillars beneath deck with three 8 inch pillars holding sun deck.

Magnificent chalet cape artist home. Three room art studio in first floor basement. Three zone heating. New furnace; new high tech oil tank; and new heat pump heat/air conditioning system. Real time propane hot water system. Professionally landscaped Japanese gardens.
 Dawn Redwoods to Ginko Trees.
337 E Wakefield Blvd, Winsted, CT 06098 is a 4 bedroom, 3 bathroom, 2,000 sqft single-family home built in 1988. It last sold for $200,000 on Sep 9, 2003. It is currently off market. The Trulia Estimate is $386,200, with a rent estimate of $3,186/month.

Home Details for 337 E Wakefield Blvd

Interior Features

Interior Details
BasementAtticIn-law unitNumber of Rooms: 9Types of Rooms: Breakfast Nook, Family Room, Laundry Room, Library, Office, Recreation Room
Heating & Cooling
Heating: Baseboard, Heat Pump, Electric, Oil, Propane ButaneAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 3Floors: Other, Carpet
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Other, VinylGardenPatio
Parking & Garage
GarageParking Spaces: 4Parking: Garage Attached

Property Information

Year Built
Year Built: 1988Year Updated: 2016
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 7841 sqft

Price and Tax history

DateEventPrice
Sep 9, 2003
Source: N/A
Sold
$200,000
Jan 3, 1990
Source: N/A
Sold
$165,000

Market trends in Winsted

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
12
2MoM

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 Winsted

At least 82 Trulia users voted on each feature.

  • 85 % Say car is needed

  • 85 % Say there's wildlife

  • 82 % Say it's dog friendly

  • 67 % Say it's walkable to restaurants

  • 67 % Say there's holiday spirit

  • 67 % Say yards are well-kept

  • 67 % Say parking is easy

  • 62 % Say streets are well-lit

  • 59 % Say kids play outside

  • 58 % Say there are sidewalks

  • 57 % Say neighbors are friendly

  • 52 % Say people would walk alone at night

  • 44 % Say it's quiet

  • 39 % Say they plan to stay for at least 5 years

  • 30 % Say it's walkable to grocery stores

  • 18 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Amber Matarainen
    "Takes forever to get anywhere worthy of being. Traffic gets backed up midday, and people speed through lights all the time"
    0
    Flag
  • Linda Kaiser
    "Small town feel with all of the required amenities. People are friendly and there are several excellent eateries. "
    0
    Flag
  • Nick W.
    " great schools nice tonw friendly people and streets are fimmaly getting repaved though some aren't even tho they need it Really badly "
    2
    Flag
  • Tammy W.
    "I really like it here just really wish that we had a grocery store in walking distance. There is only one in this town and if you don’t have a car you can not get to it."
    0
    Flag
  • Tammy W.
    "It’s not a bad place to live. Most of the people are nice and it is a clean place. I am just looking for a place with a bigger yard and closer to grocery stores. That is the biggest problem with this town. If you don’t have a car it is very hard to live here. If they could fix that problem I would not be looking to move out of town."
    0
    Flag
  • Tammy W.
    "People are always walking their dogs around my neighborhood. Just have to remind a few of them that they need to clean up after their dogs and not leave it there. But it is nice to see that family’s still walk around and enjoy themselves."
    2
    Flag
  • Tammy W.
    "This is a nice place to raise your kids. And it is a very safe place as well. I have lived here my whole life."
    5
    Flag
  • Tammy W.
    "Great. The driver was very nice and helpful when needed. It is not expensive to ride the bus. I would recommend public transit to everybody that needs it. The drivers are very nice about stopping close to your designation."
    1
    Flag
  • Trulia User
    "My neighborhood is close to downtown, close to the Main Street and easily accessible for the public transportation "
    0
    Flag
  • Nick W.
    "I think most of the surrounding areas within Winsted are Gradually getting better, Great schools, Awsome neighbors(Most) small town feel is good for me."
    0
    Flag
  • Shanura G.
    "I've lived here for over 25 yrs and love...very great neighborhood and friendly people...school system is great"
    0
    Flag
  • Ericka A.
    "watch out for walkways they need work and the best parks for kids is the baseball/memorial park and peirson elementary park there enclosed "
    0
    Flag
  • Jennifer M.
    "Winsted is a small working class town. the schools are improving and you g families should definitely consider moving here. "
    0
    Flag
  • Bruinssox1
    "No dog parks to bring your dog too. The parks we do have are no dogs allowed.There is a lot of traffic to watch out for"
    0
    Flag
  • Kaeabalan
    "There are a million dogs on my street and the surrounding streets. I see people out walking dogs frequently, day and night. On the occasion my dog gets loose, the neighbors are a great help in bringing him home. "
    2
    Flag
  • Eric R.
    "Great access to parks and public activities. Close to local community college, private neighbors, easy access to local hospitals."
    1
    Flag
  • Choiniere j.
    "Been here almost a year, and its what you make of it. Could be better her and there, but its a nice town for your family. Not too much in the cost of living, which is a plus!"
    6
    Flag
  • liz
    "Nice and quiet area where neighbors look out for each other's property."
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 337 E Wakefield Blvd

  • What is 337 E Wakefield Blvd estimated to be worth?
    Trulia's estimated value for 337 E Wakefield Blvd in Winsted, CT is $386,200.
  • What is the price history for 337 E Wakefield Blvd?
    337 E Wakefield Blvd in Winsted, CT last sold for $200,000 in September 2003.
  • Is Winsted a buyer's or seller's market?
    Winsted is currently a balanced market, based on recent for-sale activity.
  • What do residents say about Winsted?
    Residents describe Winsted, CT as dog-friendly, walkable to restaurants, and well-kept. See recently sold homes in Winsted, CT.
  • Does 337 E Wakefield Blvd have air conditioning?
    Yes, 337 E Wakefield Blvd in Winsted, CT has air conditioning.
  • Does 337 E Wakefield Blvd have laundry facilities?
    Yes, 337 E Wakefield Blvd in Winsted, CT has in-unit laundry.

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