Would people walk alone at night in Winchester, CT?

As of early 2026, 100% of users say people would walk alone at night

Is parking easy in Winchester, CT?

As of early 2026, 89% of users say parking is easy

Is a car needed in Winchester, CT?

As of early 2026, 80% of users say car is needed

Is Winchester, CT quiet?

As of early 2026, 78% of users say it's quiet

Are yards well-kept in Winchester, CT?

As of early 2026, 70% of users say yards are well-kept

Is there wildlife in Winchester, CT?

As of early 2026, 67% of users say there's wildlife

Does Winchester, CT show holiday spirit?

As of early 2026, 64% of users say there's holiday spirit

Is Winchester, CT dog-friendly?

As of early 2026, 50% of users say it's dog friendly

Is Winchester, CT walkable to grocery stores?

As of early 2026, 40% of users say it's walkable to grocery stores

Are neighbors friendly in Winchester, CT?

As of early 2026, 38% of users say neighbors are friendly

Do kids play outside in Winchester, CT?

As of early 2026, 36% of users say kids play outside

Do residents of Winchester, CT plan to stay at least 5 years?

As of early 2026, 33% of users say they plan to stay for at least 5 years

Are the streets well-lit in Winchester, CT?

As of early 2026, 33% of users say streets are well-lit

Are there community events in Winchester, CT?

As of early 2026, 33% of users say there are community events

Is Winchester, CT walkable to restaurants?

As of early 2026, 29% of users say it's walkable to restaurants

Does Winchester, CT have sidewalks?

As of early 2026, 11% of users say there are sidewalks

What is 665 E Wakefield Blvd estimated to be worth?

Trulia's estimated value for 665 E Wakefield Blvd in Winsted, CT is $405,200 .

Is Winsted a buyer's or seller's market?

Winsted is currently a seller's market, based on recent for-sale activity.

What are the closest schools to 665 E Wakefield Blvd?

The closest schools to 665 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 665 E Wakefield Blvd?

The lot at 665 E Wakefield Blvd in Winsted, CT is about 5.2 acres .

OFF MARKET

$405,200

Trulia Estimate

Studio

665 E Wakefield Blvd, Winsted, CT 06098

Est. Refi. Payment $2,820/mo*

Refinance Your Home

Home Value

Trulia Estimate

$405K

Since last month

$66K (-15.9%)

Since last year

$103K (+41.9%)

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 decreased by -1% in the last 10 years

Month	Estimated value
2026
September 2026	$350K
August 2026	$404K
July 2026	$416K
June 2026	$344K
May 2026	$349K
April 2026	$405K
March 2026	$377K
February 2026	$322K
January 2026	$370K
2025
December 2025	$389K
November 2025	$371K
October 2025	$316K
September 2025	$375K
August 2025	$246K
July 2025	$379K
June 2025	$428K
May 2025	$352K

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
621 Wynne Road, Winsted, CT	0.10	Single-Family Home	$320,000	06/26/26	2	1	975
660 East Wakefield Boulevard, Winchester, CT	0.07	Single-Family Home	$750,000	07/10/26	2	2	1,320
664 E Wakefield Blvd, Winsted, CT	0.08	Single-Family Home	$425,000	06/08/26	3	2	1,528
674 East Wakefield Boulevard, Winsted, CT	0.09	Single-Family Home	$1,050,000	06/18/26	3	3	2,097
722 Lake Drive, Winsted, CT	0.13	Single-Family Home	$1,200,000	05/20/26	3	2.5	1,556
748 Lake Drive, Winsted, CT	0.24	Single-Family Home	$1,250,000	07/09/26	5	4	3,584
740 Lake Dr, Winsted, CT	0.20	Single-Family Home	$880,000	09/17/25	3	3	1,851
142 Mountain Rd, Winsted, CT	0.55	Single-Family Home	$206,000	12/17/25	3	2	1,734
817 East Wakefield Boulevard, Winsted, CT	0.37	Single-Family Home	$231,000	02/20/26	2	1	1,051
614 E Wakefield Blvd, Winsted, CT	0.34	Single-Family Home	$1,900,000	08/11/26	6	2.5	2,200

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
660 East Wakefield Boulevard, Winchester, CT 06098	0.07	$750,000	2	2	1,320	Recently Sold
659 East Wakefield Boulevard, Winsted, CT 06098	0.07	$203,500	1	1	400	Off Market
638 & 640 Jewel Rd, Winsted, CT 06098	0.06	-	-	-	-	Off Market
624 Wynne Road, Winsted, CT 06098	0.09	$75,000	-	-	-	Recently Sold
674 East Wakefield Boulevard, Winsted, CT 06098	0.09	$1,050,000	3	3	2,097	Recently Sold
621 Wynne Road, Winsted, CT 06098	0.10	$320,000	2	1	975	Recently Sold
722 Lake Drive, Winsted, CT 06098	0.13	$1,200,000	3	2.5	1,556	Recently Sold
748 Lake Drive, Winsted, CT 06098	0.24	$1,250,000	5	4	3,584	Recently Sold
630 East Wakefield Boulevard, Winsted, CT 06098	0.25	$1,279,100	3	2	2,320	Off Market
752 Lake Drive, Winsted, CT 06098	0.25	$1,600,000	4	2.5	2,129	For Sale
756 Lake Drive, Winsted, CT 06098	0.25	$615,300	3	1	816	Off Market
600 East Wakefield Boulevard, Winsted, CT 06098	0.27	$649,900	2	1	1,361	For Sale

Local Information

Map ViewExplore the area around 665 E Wakefield Blvd.
Schools1 Preschool School2 Elementary Schools
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

5.18 acre lot

About this House

This single-family home is located at 665 E Wakefield Blvd, Winsted, CT. 665 E Wakefield Blvd is in Winsted, CT and in ZIP code 06098. This property has a lot size of 5.18 acres.

665 E Wakefield Blvd, Winsted, CT 06098 is a studio single-family home. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $405,200, with a rent estimate of $2,504/month.

Home Details for 665 E Wakefield Blvd

Property Information
Property Type / Style Property Type: Single Family Home

Exterior Features
Exterior Home Features Patio

Lot Information
Lot Area: 5.18 acres

Price and Tax history

Year	Property tax	Tax assessment
2025	$7,089	$243,040

Home facts updated by county records

Additional Cost

Market trends in Winchester

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

1MoM

Around this home

Mary P. Hinsdale School
PK-2
Public
263 Students
Winchester School District
NA
GreatSchools Rating
Parent Rating Average
No reviews available for this school.

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.
Resident
7y ago
"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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Frequently asked questions about 665 E Wakefield Blvd

What is 665 E Wakefield Blvd estimated to be worth?
Trulia's estimated value for 665 E Wakefield Blvd in Winsted, CT is $405,200.
Is Winsted a buyer's or seller's market?
Winsted is currently a seller's market, based on recent for-sale activity.
What are the closest schools to 665 E Wakefield Blvd?
The closest schools to 665 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 665 E Wakefield Blvd?
The lot at 665 E Wakefield Blvd in Winsted, CT is about 5.2 acres.

Explore by feature - Pet Friendly

13 pet-friendly rentals in Winsted, CT

SPECIAL OFFER
PET FRIENDLY
$1,150 - $1,350/mo
Fees may apply
Studio-2 bd
1-2 ba
Gilbert Clock Apartments | 13 Wallens St,
Winsted, CT 06098
PET FRIENDLY
$1,500/mo
Total price
1 bd
1 ba
600 sqft
101A Whiting St #1D,
Winsted, CT 06098
PET FRIENDLY
$1,650/mo
Total price
2 bd
1 ba
800 sqft
1013F Whiting St #3F,
Winsted, CT 06098
APPLY INSTANTLY
PET FRIENDLY
$1,400/mo
Total price
1 bd
1 ba
155 Gilbert Ave #9,
Winsted, CT 06098
NEW - 1 DAY AGO
APPLY INSTANTLY
PET FRIENDLY
$1,295/mo
Total price
2 bd
1 ba
21 Greenwoods Ave #4,
Winsted, CT 06098
PET FRIENDLY
$1,625/mo
Total price
2 bd
1 ba
75 Hurlbut St,
Winsted, CT 06098
PET FRIENDLY
$1,650/mo
Total price
2 bd
1 ba
101F4 Whiting St #4F,
Winsted, CT 06098
PET FRIENDLY
$1,025/mo
Total price
1 bd
1 ba
146 Elm St #2,
Winsted, CT 06098
PET FRIENDLY
$1,500/mo
Total price
1 bd
1 ba
700 sqft
A101 Whiting St #1D,
Winsted, CT 06098
PET FRIENDLY
$1,025/mo
Fees may apply
1 bd
1 ba
389 Main St #6790,
Winsted, CT 06098

Explore by feature - Washer/dryer

NEW - 19 HRS AGO
$1,595/mo
Fees may apply
2 bd
1 ba
Litchfield Heights Apartments. LLC | 15 Mountain View Ter,
Winsted, CT 06098
PET FRIENDLY
$1,650/mo
Total price
2 bd
1 ba
800 sqft
1013F Whiting St #3F,
Winsted, CT 06098
PET FRIENDLY
$1,650/mo
Total price
2 bd
1 ba
101F4 Whiting St #4F,
Winsted, CT 06098
PET FRIENDLY
$1,500/mo
Total price
1 bd
1 ba
700 sqft
A101 Whiting St #1D,
Winsted, CT 06098
$1,950/mo
Fees may apply
2 bd
2 ba
1,289 sqft
59 Cook St #7,
Winsted, CT 06098

Apartments for Rent

Skip to last item

PET FRIENDLY
$1,625/mo
Fees may apply
2 bd
1 ba
75-95 Hurlbut St #D,
Winsted, CT 06098
PET FRIENDLY
$1,150 - $1,350/mo
Fees may apply
Studio-2 bd
1-2 ba
Gilbert Clock Apartments | 13 Wallens St,
Winsted, CT 06098
PET FRIENDLY
$1,500/mo
Total price
1 bd
1 ba
101A Whiting St #1D,
Winsted, CT 06098
PET FRIENDLY
$1,650/mo
Total price
2 bd
1 ba
1013F Whiting St #3F,
Winsted, CT 06098
APPLY INSTANTLY
PET FRIENDLY
$1,400/mo
Total price
1 bd
1 ba
155 Gilbert Ave #9,
Winsted, CT 06098
NEW - 1 DAY AGO
APPLY INSTANTLY
PET FRIENDLY
$1,295/mo
Total price
2 bd
1 ba
21 Greenwoods Ave #4,
Winsted, CT 06098
PET FRIENDLY
$1,650/mo
Total price
2 bd
1 ba
101F4 Whiting St #4F,
Winsted, CT 06098
PET FRIENDLY
$1,025/mo
Total price
1 bd
1 ba
146 Elm St #2,
Winsted, CT 06098
PET FRIENDLY
$1,500/mo
Total price
1 bd
1 ba
A101 Whiting St #1D,
Winsted, CT 06098
PET FRIENDLY
$1,025/mo
Fees may apply
1 bd
1 ba
389 Main St #6790,
Winsted, CT 06098
PET FRIENDLY
$1,025/mo
Fees may apply
1 bd
1 ba
389 Main St #6790-5,
Winsted, CT 06098
$1,950/mo
Fees may apply
2 bd
2 ba
59 Cook St #7,
Winsted, CT 06098
PET FRIENDLY
$1,300/mo
Fees may apply
2 bd
1 ba
91 Elm St #1,
Winsted, CT 06098
$1,375/mo
Fees may apply
2 bd
1 ba
398 Main St #11,
Winsted, CT 06098
See more homes for rent in
Winsted
Take a look

Skip to first item

Off Market Homes Near 665 E Wakefield Blvd

Skip to last item

SOLD
SEP 11, 2026
$400,000
3 bd
2 ba
1,324 sqft
195 Reaching Hill Road,
Winsted, CT 06098
eXp Realty
SOLD
SEP 1, 2026
$325,000
4 bd
2 ba
2,103 sqft
120 East Lake Street,
Winsted, CT 06098
Northwest CT Realty
SOLD
SEP 1, 2026
$400,000
3 bd
2.5 ba
2,556 sqft
383 White Pine Road,
Torrington, CT 06790
Coldwell Banker Realty
SOLD
AUG 31, 2026
$310,000
2 bd
1.5 ba
864 sqft
251 Gillette Road,
New Hartford, CT 06057
Tier 1 Real Estate
SOLD
AUG 31, 2026
$259,900
4 bd
1.5 ba
1,110 sqft
150 Marshall Street,
Torrington, CT 06790
Sullivan Real Estate Inc
SOLD
AUG 28, 2026
$225,000
3 bd
2 ba
1,612 sqft
215 Ledge Drive #215,
Torrington, CT 06790
The Washington Agency
SOLD
AUG 28, 2026
$450,000
2 bd
1 ba
2,752 sqft
216 Old North Road,
Barkhamsted, CT 06063
Berkshire Hathaway NE Prop.
SOLD
AUG 26, 2026
$408,200
3 bd
2 ba
1,178 sqft
28 Davis Road,
New Hartford, CT 06057
KW Legacy Partners
SOLD
AUG 26, 2026
$420,000
5 bd
3 ba
2,496 sqft
26 Elm Street,
Winsted, CT 06098
LPT Realty
SOLD
AUG 25, 2026
$450,000
3 bd
2.5 ba
2,236 sqft
172 Wedgewood Drive,
Torrington, CT 06790
Dave Jones Realty, LLC
See more homes for sale in
Winsted
Take a look