Pending

804 W Wakefield Boulevard

Winchester, CT 06098

$799,900 $3,372/Mo

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Overview

Bed

Bath

1,044

Sqft

0.08

Acre(Lot)

Description

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 prov ides 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.

Property Details

Property Type : Residential

Price : $799,900

AD Id : 89649499

MLS Id : 24195283

Beds : 2

Lot Size : 0.08 Acre

Living Area Size : 1,044 Sq. Ft

Tax Amount : $8,341

Year Built : 1924

County : Litchfield

Map

What's Nearby

Nearby Areas

Features

Bedroom Information

Total beds: 2

Bathroom Information

Total Baths: 1 Full Baths: 1

Room Information

Rooms Total: 6 Has Basement: Yes Basement: Crawl Space, Unfinished
Roofing Information

Asphalt
Interior Features

Open Floorplan Roof: Asphalt Appliances: Dryer, Range, Oven, Refrigerator, Washer, Electric Water Heater Laundry Features: Main Level
Heating & Cooling

Has Heating: Yes Heating: Active Solar Water front: 1

Building Information

Year Built: 1924 Building Area Total: 1044 Construction Materials: Wood Siding, Frame Patio And Porch Features: Deck, Patio Private Pool: No Water front Features: Beach Front, Lake, Beach Access View: Water
Exterior Features

Exterior Features: Dock

Lot Information

Lot Size Acres: 0.08 Lot Description: Level, Sloped, Waterfront

Listing Price Information

Listing Price: $799900

Tax Information

Parcel Number: 925619 Annual Tax: $8341

Parking Information

Parking Total: 5 Paved, Off Street, Driveway

School Information

Elementary School: Per Board of Ed

Junior High School: Per Board of Ed

Senior High School: Per Board of Ed
Location Information

Direction: GPS Friendly WaterSource: Well

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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.

ByOwner last updated this listing 10/06/2026 @ 07:00

MLS: 24195283 LISTED BY: Pamela Dostilio, Coldwell Banker Realty SOURCE: SmartMLS