431 West Wakefield Boulevard | Winchester N/A

$1,850,000 | 9 Beds | 6 Baths (5 Full, 1 Half) | 7,000 Sq. Ft.

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. SmartMLS 24159989

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MLS Listing ID: 
SmartMLS 24159989
Building Details
Details about the building on a property.
Architectural Style: 
Cape Cod
Year Built: 
2002
Living Area: 
7,000
Interior: 
Auto Garage Door Opener, Cable - Available, Central Vacuum, Security System
Fireplaces: 
4
Construction
Foundation Details: 
Concrete
Roof: 
Asphalt Shingle
Exterior: 
Vinyl Siding
Exterior Features: 
Cabana, Deck, Covered Deck, French Doors
Room Details
Details about the rooms in the building.
Total Rooms: 
12
Total Bedrooms: 
9
Total Bathrooms: 
6
Total Full-Bathrooms: 
5
Total Half-Bathrooms: 
1
Utilities
Information about utilities available on the property.
Heating System: 
Baseboard
Heating System Fuel: 
Oil
Cooling System: 
Attic Fan, Window Unit
Water Source: 
Private Well
Sewer: 
Public Sewer Connected
Lot/Land Details
Details about the lots and land features included on the property.
Acres: 
3
Waterfront: 
1
Water Body Category: 
Lake, Beach, Dock or Moor
Lot Features
Total Parking Spaces: 
9
Garage: 
Barn, Under House Garage, Off Street Parking, Driveway
Public Record
Parcel Number: 
924886
Annual Tax: 
$24,184.00
Property Zoning: 
HLD
Listing Dates
Dates involved in the transaction.
Listing Entry Date/Time: 
3/25/2026
Contract Details
Details about the listing contract.
Possession: 
Negotiable
Listing Participants
Participants (agents, offices, etc.) in the transaction.
Listing Agent Name: 
Lisa Ogren
Listing Office Name: 
Berkshire Hathaway NE Prop.