804 West Wakefield Boulevard

Winchester, CT 06098

Experience an everyday vacation at 804 W. Wakefield Blvd on beautiful Highland Lake! This exceptional turnkey, year-round waterfront retreat is ideal as a primary residence, weekend escape, vacation home, or income-producing rental. Perfectly positioned on the widest part of Highland Lake's coveted Third Bay, enjoy breathtaking sunrises, panoramic water views, and bald eagles soaring overhead from your expansive lakeside deck. With over $100,000 in owner upgrades, this move-in ready home offers effortless lakefront living with a newer roof, owned solar panels, updated systems, a permanent grandfathered dock, seawall, outdoor shower, firepit, and direct access to motorboating, kayaking, paddleboarding, swimming, and outstanding fishing. A rare additional 0.24-acre lot across the street provides a total of 5 parking spaces perfect for family and guests. Enjoy easy access to Route 8, a short drive to Bradley International Airport, and year-round recreation with nearby Ski Sundown, Butternut Ski Area, scenic hiking trails, wineries, breweries, restaurants, and charming New England towns. This is your opportunity to own one of Highland Lake's most desirable waterfront homes-simply unpack, relax, and make every day feel like a vacation. Located along the beautiful shores of Highland Lake in the foothills of the Berkshires, this exceptional location offers the best of Connecticut's four-season lifestyle. Highland Lake, one of the state's premier full-recreation lakes, stretches nearly three miles across more than 444 acres and is perfect for motorboating, kayaking, paddleboarding, swimming, and outstanding fishing, including trout. During the winter, the lake becomes a picturesque destination for ice skating, ice fishing, snowmobiling, and cross-country skiing. Just minutes away, downtown Winsted offers a variety of restaurants, cafes, shops, and everyday conveniences, while nearby Litchfield is known for its boutique shopping, acclaimed dining, and classic New England charm. Outdoor recreation abounds with Ski Sundown and Butternut Ski Area close by, along with popular destinations like Little Red Barn Brewers and Norbrook Farm Brewery. Conveniently situated near Routes 8 and 44, the property provides easy access to Hartford, Bradley International Airport, New Haven, and New York City. Whether you're looking for a full-time waterfront home, a vacation retreat, or an investment opportunity, this sought-after location combines natural beauty, year-round recreation, and everyday convenience.

Listing courtesy of Pamela Dostilio of Coldwell Banker Realty Office Phone: (203) 426-5679 Broker Contact: (860) 585-9381



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Last checked: 2026-10-02 07:01 AM UTC.