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424 East Wakefield Boulevard, Winchester, CT 06098

Single Family For Sale

$1,595,000
$432/sqft
424 East Wakefield Boulevard, Winchester, CT
Active
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5
Bedrooms
2
Bathrooms
3,693
Sq Ft
0.59
Acres
1890
Year Built

About This Home

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.

Listed by Karen Newton (860) 309-0032 with William Pitt Sotheby's Int'l (860) 567-0806

Listing Snapshot

Price $1,595,000 Days on Our Site 0 days
Property Tax $22,026/yr Style Victorian
Year Built 1890 Total Sq Ft 3,693
Lot Size 0.59 acres HOA Fees N/A
Bedrooms 5 Full Bathrooms 2
Total Rooms 8 Half Baths 0

Key Features

Interior
  • Cable - Pre-wired
  • Open Floor Plan
  • Security System
Appliances
  • Gas Range
  • Microwave
  • Refrigerator
  • Dishwasher
  • Washer
  • Dryer
Outdoor
  • Porch-Screened
  • Porch
  • Garden Area
  • Covered Deck
  • French Doors
  • Lake
  • Dock or Mooring
  • Water Community
Nearby
  • Golf Course
  • Health Club
  • Medical Facilities
  • Public Rec Facilities
  • Shopping/Mall
  • Tennis Courts

Structure & Parking

Construction Frame
Roof Asphalt Shingle
Garage Spaces 2
Garage Type Detached Garage, Driveway

Systems & Utilities

Heat Hot Water
Fuel Electric, Oil
Cooling Split System
Hot Water Domestic
Water Private Well
Sewer Public Sewer In Street

Schools

Elem Per Board of Ed
High Per Board of Ed

Mortgage Calculator

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Est. Monthly Payment —
Principal & Interest —
Est. Property Tax $1,836/mo
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Apr 30, 2026 Listed $1,595,000

Frequently Asked Questions

How much does 424 East Wakefield Boulevard in Winchester, CT cost?
This property is listed at $1,595,000, which works out to $432 per square foot.
How many bedrooms does 424 East Wakefield Boulevard have?
This home has 5 bedrooms and 2 bathrooms.
What is the square footage of 424 East Wakefield Boulevard?
The home is 3,693 square feet, situated on 0.59 acres.
When was 424 East Wakefield Boulevard in Winchester built?
This property was built in 1890.
Is 424 East Wakefield Boulevard, Winchester, CT still available?
The current MLS status of this property is "Active". Contact RYZE Realty Group for the latest availability.
What school district is 424 East Wakefield Boulevard, Winchester in?
This home is served by the Winchester public school system, with Per Board of Ed as the elementary school and Per Board of Ed as the high school.
How do I schedule a tour of 424 East Wakefield Boulevard, Winchester, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Karen Newton · (860) 309-0032

William Pitt Sotheby's Int'l · (860) 567-0806

MLS# 24171266 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Apr 30, 2026 2:20 PM UTC