Highland Pond Lakefront Property

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431 West Wakefield Boulevard
Winchester, CT 06098

Property

$1,850,000

Off-the-water

Single Family: Cape Cod,Colonial
rooms, 9 bed, 5 full baths, 1 half baths
Litchfield County
Color: White
Fireplaces: 4

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.

Property Information

Approx. Living Area: 7000 sq. ft.
Garage/Parking: 2, Barn,Under House Garage,Off Street Parking,Driveway
Approx. Acres: 3
Driveway: Private,Paved,Crushed Stone

Room Details:

Kitchen, Main level: (24 x 15) Bay/Bow Window,Eating Space
Dining Room, Main level: (16 x 13) Remodeled,Bay/Bow Window,Built-Ins,Patio/Terrace
Living Room, Main level: (33 x 46) Fireplace
Family Room, Lower level: Fireplace
Library, Main level: (16 x 13) 
Primary Bedroom, Main level: (21 x 16) Bedroom Suite,Ceiling Fan,Full Bath,Walk-In Closet
Bedroom, Upper level: (23 x 15) Ceiling Fan
Bedroom, Upper level: (23 x 13) Ceiling Fan
Bedroom, Upper level: (23 x 12) Ceiling Fan
Bedroom, Upper level: (23 x 12) Ceiling Fan
Bedroom, Upper level:
Bedroom, Upper level: (13 x 14) 
Bedroom, Upper level: (24 x 11) 
Bedroom, Upper level: (24 x 12) 
Other, Upper level: (23 x 11) 

Features

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Other Property Information

Year Built: 2002, Public Records

Tax Information

Assessed Value: $829,080
Taxes: $24,184
Parcel: 924886

Listed by Lisa Ogren of Berkshire Hathaway NE Prop.

CTMLS # 24159989

Connecticut State MLS data last updated on Sunday, April 5, 2026 at 10:50 AM

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