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.
Sold for $1,600,000
$1,600,000
424 East Wakefield Boulevard, Winchester, CT 06098
5beds
3,693sqft
Single Family Residence
Built in 1890
0.59 Acres Lot
$1,600,400 Zestimate®
$433/sqft
$3,492 Estimated rent
Home value
$1,600,400
$1.47M - $1.74M
$3,492/mo
Zestimate® history
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$9,138/mo
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List your homeWhat's special
True lakefront sanctuaryNewer basement dehumidification systemRebuilt chimneysCustom copper cupolaInvisible dog fencingNewer lower composite deckingNewer roof
Zillow last checked:
Listing updated:
Listed by:
Karen Newton (860)309-0032,
William Pitt Sotheby's Int'l 860-567-0806
Bought with:
Megan Finn, RES.0825170
E.J. Murphy Realty
Source: Smart MLS,MLS#: 24171266
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Features: Palladian Window(s), Vaulted Ceiling(s), Hardwood Floor
- Level: Upper
- Area: 338 Square Feet
- Dimensions: 26 x 13
Bedroom
- Features: Hardwood Floor
- Level: Upper
- Area: 247 Square Feet
- Dimensions: 13 x 19
Bedroom
- Features: Hardwood Floor
- Level: Upper
- Area: 156 Square Feet
- Dimensions: 12 x 13
Bedroom
- Features: Hardwood Floor
- Level: Upper
- Area: 247 Square Feet
- Dimensions: 13 x 19
Bedroom
- Level: Upper
- Area: 100 Square Feet
- Dimensions: 10 x 10
Great room
- Features: Remodeled, Balcony/Deck, Built-in Features, Dining Area, Gas Log Fireplace, Hardwood Floor
- Level: Main
- Area: 616 Square Feet
- Dimensions: 28 x 22
Kitchen
- Features: Remodeled, Breakfast Bar, Granite Counters, Kitchen Island, Pantry
- Level: Main
- Area: 750 Square Feet
- Dimensions: 30 x 25
Office
- Features: Hardwood Floor
- Level: Main
- Area: 70 Square Feet
- Dimensions: 7 x 10
Rec play room
- Level: Other
- Area: 374 Square Feet
- Dimensions: 22 x 17
Heating
- Hot Water, Electric, Oil
Cooling
- Ductless
Appliances
- Included: Gas Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
- Laundry: Main Level
Features
- Wired for Data, Open Floorplan, Smart Thermostat
- Doors: French Doors
- Windows: Thermopane Windows
- Basement: Full,Unfinished
- Attic: Finished,Walk-up
- Number of fireplaces: 1
- Fireplace features: Insert
Interior area
- Total structure area: 3,693
- Total interior livable area: 3,693 sqft
- Finished area above ground: 3,693
Property
Parking
- Total spaces: 4
- Parking features: Detached, Driveway, Shared Driveway
- Garage spaces: 2
- Has uncovered spaces: Yes
Features
- Patio & porch: Screened, Porch, Covered
- Exterior features: Garden
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Waterfront, Lake, Dock or Mooring, Water Community
Lot
- Size: 0.59 Acres
Details
- Parcel number: 924848
- Zoning: HLD
- Other equipment: Generator Ready
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Victorian
- Property subtype: Single Family Residence
Materials
- Clapboard
- Foundation: Stone
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1890
Utilities & green energy
- Sewer: Public Sewer
- Water: Well
Green energy
- Energy efficient items: Windows
Community & neighborhood
Security
- Security features: Security System
Community
- Community features: Golf, Health Club, Medical Facilities, Public Rec Facilities, Shopping/Mall, Tennis Court(s)
Location
- Region: Winsted
- Subdivision: Winsted
Price history
| Date | Event | Price |
|---|---|---|
| 6/26/2026 | Sold | $1,600,000+0.3%$433/sqft |
Source:  Smart MLS #24171266 Report a problem | ||
| 6/2/2026 | Pending sale | $1,595,000$432/sqft |
Source: Smart MLS #24171266 Report a problem | ||
| 4/30/2026 | Listed for sale | $1,595,000$432/sqft |
Source: Smart MLS #24171266 Report a problem | ||
| 8/1/2025 | Listing removed | $1,595,000$432/sqft |
Source: Smart MLS #24097125 Report a problem | ||
| 5/22/2025 | Listed for sale | $1,595,000+99.4%$432/sqft |
Source: Smart MLS #24097125 Report a problem | ||
| 8/27/2019 | Sold | $800,000-8.6%$217/sqft |
Source: Smart MLS #170176483 Report a problem | ||
| 6/20/2019 | Pending sale | $875,000$237/sqft |
Source: William Pitt Sotheby's International Realty #170176483 Report a problem | ||
| 4/24/2019 | Listed for sale | $875,000-32.7%$237/sqft |
Source: William Pitt Sotheby's International Realty #170176483 Report a problem | ||
| 8/4/2012 | Listing removed | $1,300,000$352/sqft |
Source: Borla & Associates LLC Real Estate #L140243 Report a problem | ||
| 4/6/2012 | Listed for sale | $1,300,000+126.1%$352/sqft |
Source: Borla & Associates LLC Real Estate #L140243 Report a problem | ||
| 8/19/2004 | Sold | $575,000+54.2%$156/sqft |
Source: Smart MLS #L110660 Report a problem | ||
| 12/20/2001 | Sold | $373,000$101/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $22,026 +10.5% | $755,090 |
| 2024 | $19,927 | $755,090 |
| 2023 | $19,927 +22.3% | $755,090 +55.4% |
| 2022 | $16,298 | $485,940 |
| 2021 | $16,298 -2.7% | $485,940 -2.7% |
| 2020 | $16,747 | $499,310 |
| 2019 | $16,747 | $499,310 |
| 2018 | $16,747 +14.1% | $499,310 +14.1% |
| 2017 | $14,683 | $437,780 |
| 2016 | $14,683 +2.6% | $437,780 |
| 2015 | $14,315 +2.5% | $437,780 |
| 2014 | $13,970 +2.3% | $437,780 |
| 2013 | $13,659 +6.2% | $437,780 -13.4% |
| 2012 | $12,857 | $505,580 |
| 2011 | $12,857 +3.1% | $505,580 +3.1% |
| 2010 | $12,476 +3.1% | $490,600 |
| 2009 | $12,103 | $490,600 |
| 2008 | $12,103 +16.7% | $490,600 +62.1% |
| 2007 | $10,370 +2.8% | $302,610 |
| 2006 | $10,089 +2.9% | $302,610 +1.8% |
| 2005 | $9,807 +13.2% | $297,360 +3.4% |
| 2003 | $8,661 +77.3% | $287,560 +62.2% |
| 1995 | $4,886 | $177,280 |
Find assessor info on the county website
Neighborhood: 06098
Nearby schools
GreatSchools rating
- NABatcheller Early Education CenterGrades: PK-2Distance: 1 mi
- NAPearson AcademyGrades: Distance: 1.8 mi
- 6/10Pearson Middle SchoolGrades: 2-6Distance: 1.8 mi
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- Connecticut
- Litchfield County
- Winchester
- 06098
- 424 East Wakefield Boulevard
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