535 E Wakefield Blvd, Winchester, CT 06098
OFF MARKET

$708,700

Trulia Estimate
  • 5 Beds
  • 3 Baths
  • 3,395 sqft (on 0.75 acres)

535 E Wakefield Blvd, Winchester, CT 06098

Est. Refi. Payment $4,747/mo*
Refinance Your Home
Currently Off Market - Sold May 8, 2000 for $179,000

Home Value

Trulia Estimate
$709K
Since last month
Increased$800 (+0.1%)
Since last year
Decreased$62K (-8.1%)
Since last sale
Increased$525K (+293.4%)
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 -5% in the last 10 years
MonthEstimated value
2026
August 2026$704K
July 2026$703K
June 2026$727K
May 2026$700K
April 2026$676K
March 2026$671K
February 2026$679K
January 2026$677K
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
538 Wheelers Point, Winchester, CT
0.08
Single-Family Home
$1,500,000
10/14/25
4
3
2,496
424 East Wakefield Boulevard, Winsted, CT
0.30
Single-Family Home
$1,600,000
06/26/26
5
2
3,693
126 Forest Avenue, Winsted, CT
0.64
Single-Family Home
$375,000
10/28/25
3
1.5
1,833
748 Lake Drive, Winsted, CT
0.80
Single-Family Home
$1,250,000
07/09/26
5
4
3,584
435/434 West Wakefield Boulevard, Winsted, CT
0.40
Single-Family Home
$1,215,000
09/10/25
8
4.5
5,231
195 Reaching Hill Road, Winsted, CT
0.84
Single-Family Home
$101,500
09/22/25
3
2
1,324
878 West Wakefield Boulevard, Winsted, CT
0.92
Single-Family Home
$1,200,000
07/07/26
4
3
3,330
621 Wynne Road, Winsted, CT
0.59
Single-Family Home
$320,000
06/26/26
2
1
975
674 East Wakefield Boulevard, Winsted, CT
0.71
Single-Family Home
$1,050,000
06/18/26
3
3
2,097
664 E Wakefield Blvd, Winsted, CT
0.68
Single-Family Home
$425,000
06/08/26
3
2
1,528

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
533 Wheeler Point, Winsted, CT 06098
0.01
$684,800
2
1.5
1,200
Off Market
421 Unity Place, Winsted, CT 06098
0.10
$304,900
3
2
1,440
Off Market
538 Wheelers Point, Winchester, CT 06098
0.08
$1,572,400
4
3
2,496
Off Market
548 East Wakefield Boulevard, Winsted, CT 06098
0.19
$444,700
2
1
512
Off Market
552 East Wakefield Boulevard, Winsted, CT 06098
0.23
$1,339,700
3
3
2,526
Off Market
424 East Wakefield Boulevard, Winsted, CT 06098
0.30
$1,600,000
5
2
3,693
Recently Sold
406 A East Wakefield Boulevard, Winsted, CT 06098
0.32
$1,305,000
4
2.5
1,282
Off Market
508 West Wakefield Boulevard, Winsted, CT 06098
0.39
$1,759,800
7
4
2,687
Off Market
435/434 West Wakefield Boulevard, Winsted, CT 06098
0.40
$1,283,200
8
4.5
5,231
Off Market
600 East Wakefield Boulevard, Winsted, CT 06098
0.42
$649,900
2
1
1,361
For Sale
630 East Wakefield Boulevard, Winsted, CT 06098
0.45
$1,273,900
3
2
2,320
Off Market
371 Norwood Road, Winsted, CT 06098
0.49
$194,200
1
1
592
Off Market

Local Information

  • Map ViewExplore the area around 535 E Wakefield Blvd.
  • Schools1 Preschool School2 Elementary Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1938
Lot Size
0.75 acres
Living Area
3,395 sqft
Price/Sqft
$209
Parking
Garage

About this House

Expanded version of a Storybook Cape overlooking Highland Lake that boasts wood floors throughout, updated kitchen w/granite counters and massive fieldstone fireplace. Less than 10 years ago this home was brought to the next level with a 2,000 square foot addition that includes a large foyer, 3+ car garage, master suite, family room and office. Along with the private setting there is a large deck overlooking the lake with a panoramic sunset view. Across the street there is a waterfront patio area and dock with small shed and a spectacular view as well.
535 E Wakefield Blvd, Winchester, CT 06098 is a 5 bedroom, 3 bathroom, 3,395 sqft single-family home built in 1938. It last sold for $179,000 on May 8, 2000. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $708,700, with a rent estimate of $4,357/month.

Home Details for 535 E Wakefield Blvd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 8
Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

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

Property Information

Year Built
Year Built: 1938
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.75 acres

Price and Tax history

DateEventPrice
Aug 3, 2022
Source: Smart MLS #170509160
ListingRemoved
Jul 15, 2022
Source: Smart MLS #170509160
PriceChange
$699,900
Price decreased by 20%
Jun 26, 2022
Source: Smart MLS #170500368
PriceChange
$869,900
Price decreased by 7%
Jun 17, 2022
Source: Smart MLS #170500368
Listed For Sale
$935,900
Aug 6, 2016
Source: Agent Provided
ListingRemoved
$785,000

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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 535 E Wakefield Blvd

  • What is 535 E Wakefield Blvd estimated to be worth?
    Trulia's estimated value for 535 E Wakefield Blvd in Winchester, CT is $708,700.
  • What is the price history for 535 E Wakefield Blvd?
    535 E Wakefield Blvd in Winchester, CT last sold for $179,000 in May 2000.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a balanced market, based on recent for-sale activity.
  • What are the closest schools to 535 E Wakefield Blvd?
    The closest schools to 535 E Wakefield Blvd in Winchester, CT are Mary P. Hinsdale School (Pre-K/Elementary), Pearson Middle School (Elementary, rated 6/10).
  • How big is the lot at 535 E Wakefield Blvd?
    The lot at 535 E Wakefield Blvd in Winchester, CT is about 0.75 acres (32,670 sq ft).
  • Does 535 E Wakefield Blvd have a garage?
    Yes, 535 E Wakefield Blvd in Winchester, CT has a garage.

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 535 E Wakefield Blvd

Skip to last item
Skip to first item

Homes for sale near 535 E Wakefield Blvd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item