535 E Wakefield Blvd, Winchester, CT 06098
OFF MARKET

535 E Wakefield Blvd
Winchester, CT 06098

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

$702,200

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $4,620/mo*
Refinance Your Home

$702,200

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $4,620/mo*
Refinance Your Home
5 Beds
3 Baths
3,395 sqft
(on 0.75 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 535 E Wakefield Blvd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 8
Heating & Cooling
Heating: Other, OilAir ConditioningHeating Fuel: Other
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 History for 535 E Wakefield Blvd

DatePriceEventSource
08/03/2022ListingRemovedSmart MLS #170509160
07/15/2022$699,900PriceChange
Smart MLS #170509160
06/26/2022$869,900PriceChange
Smart MLS #170500368
06/17/2022$935,900Listed For SaleSmart MLS #170500368
08/06/2016$785,000ListingRemovedAgent Provided
04/18/2016$785,000Listed For SaleAgent Provided
05/08/2000$179,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$14,079
Assessment$482,650
Home facts updated by county records

Comparable Sales for 535 E Wakefield Blvd

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
421 Unity Place, Winsted, CT
0.10
Single-Family Home
$286,000
06/09/25
3
2
1,440
508 West Wakefield Boulevard, Winsted, CT
0.39
Single-Family Home
$1,575,000
06/30/25
7
4
2,687
126 Forest Avenue, Winsted, CT
0.64
Single-Family Home
$375,000
10/28/25
3
1.5
1,833
435/434 West Wakefield Boulevard, Winsted, CT
0.40
Single-Family Home
$1,215,000
09/10/25
8
4.5
5,231
323 East Wakefield Boulevard, Winsted, CT
0.73
Single-Family Home
$397,000
06/04/25
3
2.5
1,426
50 Lakeview Road, Winsted, CT
1.16
Single-Family Home
$425,000
08/13/25
4
2.5
2,086
819 East Wakefield Boulevard, Winsted, CT
1.00
Single-Family Home
$439,900
12/04/25
3
1.5
1,892
279 Pratt Street, Winsted, CT
0.89
Single-Family Home
$290,000
08/28/25
4
1
1,978
740 Lake Dr, Winsted, CT
0.74
Single-Family Home
$880,000
09/17/25
3
3
1,851

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Assigned Schools

These are the assigned schools for 535 E Wakefield Blvd.
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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."
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Apartments for Rent

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Homes for sale near 535 E Wakefield Blvd

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Off Market Homes Near 535 E Wakefield Blvd

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Homes for rent near 535 E Wakefield Blvd

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535 E Wakefield Blvd, Winchester, CT 06098 is a 5 bedroom, 3 bathroom, 3,395 sqft single-family home built in 1938. This property is not currently available for sale. 535 E Wakefield Blvd was last sold on May 8, 2000 for $179,000. The current Trulia Estimate for 535 E Wakefield Blvd is $702,200.