Home Homes for Sale Winchester, CT 431 West Wakefield Boulevard

431 West Wakefield Boulevard, Winchester, CT 06098

Single Family For Sale

$1,850,000
$264/sqft
431 West Wakefield Boulevard, Winchester, CT Active
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9
Bedrooms
6
Bathrooms
7,000
Sq Ft
3
Acres
2002
Year Built

About This Home

Live the Highland Lake Dream - 431 W. Wakefield Blvd, Winchester, CT Summer is just around the corner - and in Winsted, resort living never ends. Recently named one of the most desirable towns to live in, with the breathtaking Highland Lake at its heart, Winchester offers the perfect blend of beauty and lifestyle. This waterfront estate at 431 W. Wakefield Blvd isn't just a home - it's your gateway to the ultimate lake life. Wake each morning to panoramic water views, and step outside to a world of four-season recreation. In summer, enjoy boating, jet skiing, swimming, and fishing right from your private dock, or simply relax by the shoreline. When winter arrives, the lake transforms into your own frozen wonderland for ice fishing, skating, and fireside gatherings. Inside, luxury awaits. The main home features gourmet finishes, a chef's kitchen, and custom craftsmanship throughout. A charming guest bungalow offers privacy for family, friends, or guests. Zoned for a bed and breakfast, and featuring an extra subdividable lot, the property offers immense potential - whether as a private retreat, an upscale B&B, or an investment in future development. Set on 425 feet of pristine water frontage, this estate captures the essence of Highland Lake living - natural beauty, year-round recreation, and endless opportunity.

Listed by Lisa Ogren (860) 416-2085 with Berkshire Hathaway NE Prop. (860) 677-7321

Listing Snapshot

Price $1,850,000 Days on Market 8 days
Property Tax $24,184/yr Style Cape Cod,Colonial
Year Built 2002 Total Sq Ft 7,000
Lot Size 3 acres HOA Fees N/A
Bedrooms 9 Full Bathrooms 5
Total Rooms 12 Half Baths 1

Key Features

Interior
  • Auto Garage Door Opener
  • Cable - Available
  • Central Vacuum
  • Security System
Appliances
  • Oven/Range
  • Microwave
  • Refrigerator
  • Dishwasher
  • Disposal
  • Dryer
Outdoor
  • Cabana
  • Deck
  • Covered Deck
  • French Doors
  • Lake
  • Beach
  • Dock or Mooring
  • Water Community
  • View
Nearby
  • Public Rec Facilities

Structure & Parking

Construction Frame
Roof Asphalt Shingle
Garage Spaces 2
Garage Type Barn, Under House Garage, Off Street Parking, Driveway
Below Grade 1,470 sq ft

Systems & Utilities

Heat Baseboard
Fuel Oil
Cooling Attic Fan, Window Unit
Hot Water Oil, Domestic
Water Private Well
Sewer Public Sewer Connected

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 $2,015/mo
Est. Home Insurance

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Mar 18, 2026 Listed $1,850,000

Frequently Asked Questions

How much does 431 West Wakefield Boulevard in Winchester, CT cost?
This property is listed at $1,850,000, which works out to $264 per square foot.
How many bedrooms does 431 West Wakefield Boulevard have?
This home has 9 bedrooms and 6 bathrooms.
What is the square footage of 431 West Wakefield Boulevard?
The home is 7,000 square feet, situated on 3 acres.
When was 431 West Wakefield Boulevard in Winchester built?
This property was built in 2002.
Is 431 West 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 431 West 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 431 West 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

Lisa Ogren · (860) 416-2085

Berkshire Hathaway NE Prop. · (860) 677-7321

MLS# 24159989 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Mar 26, 2026 8:48 PM UTC