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424 East Wakefield Boulevard Winchester, CT $ 1,595,000
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$ 1,595,000 Get more info
424 East Wakefield Boulevard
$ 1,595,000
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424 East Wakefield Boulevard

Winchester, CT, 06098
$ 1,595,000
Bedrooms5 Baths2.0 Sq 3,693

Monthly Estimate*

$ 9,821

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Single Family Home for sale in Winchester, CT

for $1,595,000 with 5 bedrooms and 2 full baths. This 3,693 square foot home was built in 1890 on a lot size of 0.59.

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.

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Single Family Active

Price

$ 1,595,000

Bedrooms

5

Full Bath

2

Property Type

Single Family

Taxes

$ 22,026

Style

Lot Size

0.59

Year Built

1890

Town/City

Winchester

MLS | Web ID

24171266
Features
General
Zoning HLD
Neighborhood Winsted
County Litchfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 0.59
Directions GPS
High School Per Board of Ed
City Winchester
Elementary School Per Board of Ed
Sq Ft Total 3693
DOM 0
Year Built 1890
Style Victorian
Year Built Source Public Records
Energy Features Fireplace Insert Generator Ready Thermopane Windows
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Interior
Cooling System Split System
Total Rooms 8
Basement Description Full Unfinished
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Exterior
Water Source Private Well
Lot Description Water View
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* Excluded Features
List By
Karen Newton

Listing Agent

William Pitt Sotheby's Int'l

Broker

knewton@wpsir.com

Email

Affordability Calculator

$11,656
Per Month
84%
16%
0%
Monthly Principal & Interest
$9,821
Monthly Property Taxes
$1,836
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3092524 Elementary School
1232933 Middle School
Per Board of Ed High School High School
See complete school information
Pricing History
DatePricePrice ChangeDescription
4/30/2026$1,595,000 Listed Price

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424 East Wakefield Boulevard, Winchester, CT, 06098 is a Single Family Home for sale at $1,595,000 with 3,693 sqft and a lot size of 0.59. 424 East Wakefield Boulevard has 5 bedrooms, 2.0 baths, and was built in 1890. The property's zip code is 06098 which is in Winchester, CT

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