Highland Pond Lakefront Property

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804 West Wakefield Boulevard
Winchester, CT 06098

Property

$799,900

DIRECT lakefront

Single Family: Ranch,Cottage
rooms, 2 bed, 1 full baths, 0 half baths
Litchfield County
Color: Light Wood
Fireplaces: 0

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.

Property Information

Approx. Living Area: 1044 sq. ft.
Garage/Parking: 0, Off Street Parking,Driveway
Approx. Acres: 0.08
Driveway: Paved

Room Details:

Living Room, Main level: (11 x 12) Vaulted Ceiling,Beams,Hardwood Floor
Bedroom, Main level: (7 x 11) Vaulted Ceiling,Hardwood Floor
Primary Bedroom, Main level: (10 x 12) Skylight,Vaulted Ceiling,Hardwood Floor
Full Bath, Main level: Remodeled,Stall Shower
Office, Main level: (6 x 6) Hardwood Floor
Loft, Main level: (9 x 9) Hardwood Floor
Family Room, Lower level: (16 x 18) Beams,Dry Bar,Wood Stove,Patio/Terrace,Laminate Floor
Kitchen, Lower level: (10 x 17) Beams

Features

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Other Property Information

Year Built: 1924, Public Records

Tax Information

Assessed Value: $273,840
Taxes: $7,988
Parcel: 925619

Listed by Pamela Dostilio of Coldwell Banker Realty

CTMLS # 24195283

Connecticut State MLS data last updated on Thursday, August 20, 2026 at 9:33 AM

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