431 West Wakefield Boulevard Winchester, CT $ 1,850,000
431 West Wakefield Boulevard
$ 1,850,000
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431 West Wakefield Boulevard

Winchester, CT, 06098
$ 1,850,000
Bedrooms9 Baths5.1 Sq 7,000

Monthly Estimate*

$ 11,391

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Single Family Home for sale in Winchester, CT

for $1,850,000 with 9 bedrooms and 5 full baths, 1 half bath. This 7,000 square foot home was built in 2002 on a lot size of 3.

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.

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Single Family Active

Price

$ 1,850,000

Bedrooms

9

Full Bath

5

Half Bath

1

Property Type

Single Family

Taxes

$ 24,184

Style

Lot Size

3

Year Built

2002

Town/City

Winchester

MLS | Web ID

24159989

Features
General
Zoning HLD
Neighborhood N/A
County Litchfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 3
Directions GPS Friendly
High School Per Board of Ed
City Winchester
Elementary School Per Board of Ed
Sq Ft Total 7000
DOM 8
Year Built 2002
Style Cape Cod Colonial
Year Built Source Public Records
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Interior
Cooling System Attic Fan Window Unit
Total Rooms 12
Basement Description Full Heated Garage Access Interior Access Liveable Space Full With Walk-Out
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Exterior
Water Source Private Well
Lot Description Additional Land Avail. Lightly Wooded Level Lot Professionally Landscaped Rolling Water View
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* Excluded Features
List By
Lisa Ogren

Listing Agent

Berkshire Hathaway Ne Prop.

Broker

lisaogren@bhhsne.com

Email

Affordability Calculator

$13,406
Per Month
85%
15%
0%
Monthly Principal & Interest
$11,391
Monthly Property Taxes
$2,015
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% 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
3/25/2026$1,850,000 Listed Price

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431 West Wakefield Boulevard, Winchester, CT, 06098 is a Single Family Home for sale at $1,850,000 with 7,000 sqft and a lot size of 3. 431 West Wakefield Boulevard has 9 bedrooms, 5.1 baths, and was built in 2002. The property's zip code is 06098 which is in Winchester, CT