804 West Wakefield Boulevard Winchester, CT $ 799,900
804 West Wakefield Boulevard
$ 799,900
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804 West Wakefield Boulevard

Winchester, CT, 06098
$ 799,900
Bedrooms2 Baths1.0 Sq 1,044

Monthly Estimate*

$ 5,051

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Single Family Home for sale in Winchester, CT

for $799,900 with 2 bedrooms and 1 full bath. This 1,044 square foot home was built in 1924 on a lot size of 0.08.

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.

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Single Family Active

Price

$ 799,900

Bedrooms

2

Full Bath

1

Property Type

Single Family

Taxes

$ 7,988

Style

Lot Size

0.08

Year Built

1924

Town/City

Winchester

MLS | Web ID

24195283

Features
General
Zoning HLD
Neighborhood N/A
County Litchfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 0.08
Directions GPS Friendly
High School Per Board of Ed
City Winchester
Elementary School Per Board of Ed
Sq Ft Total 1044
DOM 0
Year Built 1924
Style Ranch Cottage
Year Built Source Public Records
Energy Features Active Solar Extra Insulation
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Interior
Cooling System Split System
Total Rooms 6
Basement Description Crawl Space Unfinished
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Exterior
Water Source Private Well
Lot Description Level Lot Sloping Lot Professionally Landscaped Water View
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* Excluded Features
List By
Pamela Dostilio

Listing Agent

Coldwell Banker Realty

Broker

pamela.dostilio@cbmoves.com

Email

Affordability Calculator

$5,716
Per Month
88%
12%
0%
Monthly Principal & Interest
$5,051
Monthly Property Taxes
$666
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3092524 Elementary School
1232933 Middle School
Per Board of Ed High School High School
Pricing History
DatePricePrice ChangeDescription
8/17/2026$799,900 Listed Price

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804 West Wakefield Boulevard, Winchester, CT, 06098 is a Single Family Home for sale at $799,900 with 1,044 sqft and a lot size of 0.08. 804 West Wakefield Boulevard has 2 bedrooms, 1.0 baths, and was built in 1924. The property's zip code is 06098 which is in Winchester, CT