431 West Wakefield Boulevard, Winchester, CT 06098
Single Family For Sale
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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 Our Site | 84 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
- Auto Garage Door Opener
- Cable - Available
- Central Vacuum
- Security System
- Oven/Range
- Microwave
- Refrigerator
- Dishwasher
- Disposal
- Dryer
- Cabana
- Deck
- Covered Deck
- French Doors
- Lake
- Beach
- Dock or Mooring
- Water Community
- View
- Public Rec Facilities
Structure & Parking
Systems & Utilities
Schools
Mortgage Calculator
Estimate only. Contact a lender for accurate figures.
Listing History
| Date | Event | Price |
|---|---|---|
| Mar 18, 2026 | Listed | $1,850,000 |
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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 May 8, 2026 12:58 PM UTC
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431 West Wakefield Boulevard, Winchester CT, 06098
$1,850,000 • Active
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