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

424 East Wakefield Boulevard
Winsted, CT 06098

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

$1,600,000

Last Sold: Jun 26, 2026
0% over list $1.59M
$433/sqft
Est. Refi. Payment $10,513/mo*
Refinance Your Home

$1,600,000

Last Sold: Jun 26, 2026
0% over list $1.59M
$433/sqft
Est. Refi. Payment $10,513/mo*
Refinance Your Home
5 Beds
2 Baths
3,693 sqft
(on 0.59 acres)

Local Information

  • Map ViewExplore the area around 424 East Wakefield Boulevard.
  • Schools1 Preschool School3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

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. It is currently off market. The Trulia Estimate is $1,600,400, with a rent estimate of $3,810/month.

Home Highlights

Parking
Garage
Outdoor
Porch
A/C
Heating & Cooling
HOA
None
Price/Sqft
$433/sqft
Listed
66 days ago

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)
Last check for updates: about 1 hour 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

Price History for 424 East Wakefield Boulevard

DatePriceEventSource
06/26/2026$1,600,000Sold
Smart MLS #24171266
06/02/2026$1,595,000PendingSmart MLS #24171266
04/30/2026$1,595,000Listed For SaleSmart MLS #24171266
08/01/2025$1,595,000ListingRemovedSmart MLS #24097125
05/22/2025$1,595,000Listed For SaleSmart MLS #24097125
08/27/2019$800,000Sold
Smart MLS #170176483
06/20/2019$875,000PendingAgent Provided
04/24/2019$875,000Listed For SaleAgent Provided
08/04/2012$1,300,000ListingRemovedAgent Provided
04/06/2012$1,300,000Listed For SaleAgent Provided
08/19/2004$575,000Sold
Smart MLS #L110660
12/20/2001$373,000Sold
N/A

Market trends in Winchester

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
15
4MoM
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Property Tax and Assessment

Year2025
Tax$22,026
Assessment$755,090
Home facts updated by county records

Comparable Sales for 424 East Wakefield Boulevard

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
258 Perch Rock Trail, Winsted, CT
0.54
Single-Family Home
$925,000
06/04/26
4
2
1,373
266 Perch Rock Trail, Winsted, CT
0.50
Single-Family Home
$800,000
08/04/25
3
2
1,488
129 East Lake Street, Winsted, CT
1.04
Single-Family Home
$1,475,000
06/09/26
3
3.5
2,699
200 Perch Rock Trail, Winsted, CT
0.75
Single-Family Home
$1,200,000
07/23/25
3
2.5
2,407
50 Lakeview Road, Winsted, CT
0.87
Single-Family Home
$425,000
08/13/25
4
2.5
2,086
126 Forest Avenue, Winsted, CT
0.74
Single-Family Home
$375,000
10/28/25
3
1.5
1,833

Nearby homes

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Assigned Schools

These are the assigned schools for 424 East Wakefield Boulevard.
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."
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Explore by feature - Pet Friendly

12 pet-friendly rentals in Winsted, CT

Homes for sale near 424 East Wakefield Boulevard

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Off Market Homes Near 424 East Wakefield Boulevard

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