424 East Wakefield Boulevard, Winsted, CT 06098
SOLD
JUN 26, 2026

$1,533,900

Trulia Estimate
  • 5 Beds
  • 2 Baths
  • 3,693 sqft (on 0.59 acres)

424 East Wakefield Boulevard, Winsted, CT 06098

Est. Refi. Payment $10,252/mo*
Refinance Your Home
Currently Off Market - Sold Jun 26, 2026 for $1,600,000 (0% above list price)

Home Value

Trulia Estimate
$1.53M
Since last month
Decreased$4K (-0.3%)
Since last year
Increased$21K (+1.4%)
Since last sale
Decreased$66K (-4.1%)
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 +166% in the last 10 years
MonthEstimated value
2026
August 2026$1.53M
August 2026$1.53M
July 2026$1.54M
June 2026$1.6M
May 2026$1.55M
April 2026$1.32M
March 2026$1.28M
February 2026$1.27M
January 2026$1.51M
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
0.28
Single-Family Home
$1,500,000
10/14/25
4
3
2,496
435/434 West Wakefield Boulevard, Winsted, CT
0.37
Single-Family Home
$1,215,000
09/10/25
8
4.5
5,231
748 Lake Drive, Winsted, CT
1.06
Single-Family Home
$1,250,000
07/09/26
5
4
3,584
258 Perch Rock Trail, Winsted, CT
0.54
Single-Family Home
$925,000
06/04/26
4
2
1,373
129 East Lake Street, Winsted, CT
1.04
Single-Family Home
$1,475,000
06/09/26
3
3.5
2,699
878 West Wakefield Boulevard, Winsted, CT
1.14
Single-Family Home
$1,200,000
07/07/26
4
3
3,330
126 Forest Avenue, Winsted, CT
0.74
Single-Family Home
$375,000
10/28/25
3
1.5
1,833

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
406 A East Wakefield Boulevard, Winsted, CT 06098
0.02
$1,320,700
4
2.5
1,282
Off Market
414 East Wakefield Boulevard, Winsted, CT 06098
0.05
$850,000
-
-
-
For Sale
371 Norwood Road, Winsted, CT 06098
0.23
$193,400
1
1
592
Off Market
421 Unity Place, Winsted, CT 06098
0.23
$306,000
3
2
1,440
Off Market
538 Wheelers Point, Winchester, CT 06098
0.28
$1,577,600
4
3
2,496
Off Market
533 Wheeler Point, Winsted, CT 06098
0.31
$698,400
2
1.5
1,200
Off Market
347 W. Wakefield Boulevard, Winsted, CT 06098
0.32
$289,000
2
1
596
For Sale
343 West Wakefield Boulevard, Winsted, CT 06098
0.33
$250,400
2
1
674
Off Market
339 West Wakefield Boulevard, Winsted, CT 06098
0.34
$575,500
3
2
1,322
Off Market
325 Norcross Road, Winsted, CT 06098
0.40
$397,200
1
1
749
Off Market
322 Norcross Road, Winsted, CT 06098
0.42
$246,700
1
1
598
Off Market

Local Information

  • Map ViewExplore the area around 424 East Wakefield Boulevard.
  • Schools1 Preschool School2 Elementary Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1890
0.59 acre lot
3,693 sqft
$433/sqft
Garage

About this House

Stunning Lakehouse! Victorian charm! One of the earliest Highland Lake homes with extensive custom upgrades and quality renovation. A true lakefront sanctuary offering spacious living areas, extensive outdoor living areas and wide open lake views offering South and West exposure for incredible sunsets. Lakefront dock system with hydraulic boat lift, Recently renovated kitchen /dining with newer appliances and farm sink, open floorplan greatroom with fireplace. Separate oversized two car detached garage with second floor and HVAC units for heating/cooling. Newer roof, deep water hydraulic boat lift, newer oil tank, newer lower composite decking, custom copper cupola, invisible dog fencing, rebuilt chimneys, fire/security/CO2 alarm system, generator hookup, newer basement dehumidification system, de-ice system for lift/docks, propane system for stove, fireplace, bbq grill.
424 East Wakefield Boulevard, Winsted, CT 06098 is a 5 bedroom, 2 bathroom, 3,693 sqft single-family home built in 1890. It last sold for the $1,595,000 asking price on Jun 26, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,533,900, with a rent estimate of $2,965/month.
Last check for updates: about 2 hours ago
Listed by Karen Newton, (860) 309-0032
William Pitt Sotheby's Int'l, (860) 567-0806
Bought with: Megan Finn, (860) 485-5060, E.J. Murphy Realty, (860) 567-0813
Source: Smart MLS, MLS#24171266

Home Details for 424 East Wakefield Boulevard

Interior Features

Interior Details
Basement: Full,UnfinishedNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom, Great Room, Kitchen, Office, Rec Play Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 3693 Square Feet
Appliances & Utilities
Appliances: Gas Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Main LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,Electric,OilHas CoolingAir Conditioning: DuctlessHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 1Fireplace: InsertHas a Fireplace
Windows, Doors, Floors & Walls
Window: Thermopane WindowsDoor: French Doors
View
Has a ViewView: Water
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Screened, Porch, CoveredExterior: GardenFoundation: StoneGardenNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 4Parking: Detached,Driveway,Shared Driveway
Frontage
WaterfrontWaterfront: Waterfront, Lake, Dock or Mooring, Water CommunityOn Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 3693 Square Feet

Property Information

Year Built
Year Built: 1890
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Victorian
Building
Construction Materials: ClapboardNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 924848

Price & Status

Price
List Price: $1,595,000Price Per Sqft: $433/sqft
Status Change & Dates
Off Market Date: Tue Jun 02 2026Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: WinchesterCommunity: Winsted
School Information
Elementary School: Per Board of EdHigh School: Per Board of Ed

Building

Building Area
Building Area: 3693 Square Feet

Community

Community Features: Golf, Health Club, Medical Facilities, Public Rec Facilities, Shopping/Mall, Tennis Court(s)

HOA

No HOA

Lot Information

Lot Area: 0.59 acres

Energy

Energy Efficiency Features: Windows

Miscellaneous

BasementMls Number: 24171266Attic: Finished, Walk-upWater ViewWater View: WaterAttribution Contact: (860) 309-0032Above Grade Unfinished Area: 3693

Additional Information

GolfHealth ClubMedical FacilitiesPublic Rec FacilitiesShopping/MallTennis Court(s)

Price and Tax history

DateEventPrice
Jun 26, 2026
Source: Smart MLS #24171266
Sold
$1,600,000
Jun 2, 2026
Source: Smart MLS #24171266
Pending
$1,595,000
Apr 30, 2026
Source: Smart MLS #24171266
Listed For Sale
$1,595,000
Aug 1, 2025
Source: Smart MLS #24097125
ListingRemoved
$1,595,000
May 22, 2025
Source: Smart MLS #24097125
Listed For Sale
$1,595,000

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
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Frequently asked questions about 424 East Wakefield Boulevard

  • What is 424 East Wakefield Boulevard estimated to be worth?
    Trulia's estimated value for 424 East Wakefield Boulevard in Winsted, CT is $1,533,900.
  • What is the price history for 424 East Wakefield Boulevard?
    424 East Wakefield Boulevard in Winsted, CT last sold for $1,600,000 in June 2026.
  • Is Winsted a buyer's or seller's market?
    Winsted is currently a balanced market, based on recent for-sale activity.
  • What are the closest schools to 424 East Wakefield Boulevard?
    The closest schools to 424 East Wakefield Boulevard in Winsted, CT are Mary P. Hinsdale School (Pre-K/Elementary), Pearson Middle School (Elementary, rated 6/10).
  • Does 424 East Wakefield Boulevard have air conditioning?
    Yes, 424 East Wakefield Boulevard in Winsted, CT has air conditioning.
  • Does 424 East Wakefield Boulevard have laundry facilities?
    Yes, 424 East Wakefield Boulevard in Winsted, CT has in-unit laundry.

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