431 West Wakefield Boulevard
Winchester, CT, 06098 $ 2,199,000
Bedrooms9 Baths5.1 Sq 7,000 Monthly Estimate*
$ 13,719
for $2,199,000 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.
LOCAL NEWS JUST ANNOUNCED THAT WINSTED WAS 1 OF THE MOST DESIRABLE TOWNS TO LIVE WITH EMPHASIS ON BEAUTIFUL HIGHLAND LAKE. This waterfront estate at 431 W. Wakefield Blvd in Winchester, CT, is not just a home but the ultimate Highland Lake lifestyle. Imagine waking up each day to stunning lake views, with endless seasonal activities awaiting just beyond your doorstep. In the summer, dive into boating, jet skiing, swimming, and fishing right from your private dock, or simply unwind along the shoreline. As winter settles in, the lake becomes a playground for ice fishing, skating, and cozy fireside gatherings, making this a year-round sanctuary. With luxury finishes, a gourmet kitchen, and custom craftsmanship in the main home, plus a charming guest bungalow, this property is ideal for hosting family, friends, or even guests. Zoned for a bed and breakfast and featuring an extra subdividable lot, the estate also holds exciting potential for income generation or expansion. Whether you're envisioning a private retreat, an upscale B&B, or future development with a subdividable lot, this versatile property is the perfect setting for those seeking a dynamic, all-season lake life. 424 and 431 are all one property being sold. 424 West Wakefield is the guest cottage adding 612 sf waterfront with stone fireplace, kitchen, bath, patio & dock on 405 ft of direct choice waterfront property.
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FeaturesGeneralZoning HL
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 Gilbert
City Winchester
Elementary School Batcheller
Sq Ft Total 7000
DOM 405
Year Built 2002
Style Cape Cod Colonial
Year Built Source Public Records
Energy Features Thermopane Windows
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InteriorCooling System None
Total Rooms 12
Basement Description Full Heated Fully Finished Garage Access Cooled Interior Access Walk-out
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ExteriorWater Source Private Well
Lot Description Additional Land Avail. Lightly Wooded Level Lot Professionally Landscaped Rolling Water View
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* Excluded FeaturesList ByBerkshire Hathaway Ne Prop.Broker
lisaogren@bhhsne.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $13,719
- Monthly Property Taxes
- $2,015
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.375% 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.
Learn more about how to save NearbySingle family listings in Winchester, CT
Average List Price $525,267
Percent of Sale Price 76%
About Winchester, CT 11,188 Population
5% Since 2002
$ 59,013 Median Income
45.79 Median Age
21% Households with Children
Trends Information provided by ATTOM Data Solutions.
4604681 Elementary School
1415485 Middle School
Gilbert High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 10/14/2025 | $2,199,000 | | Listed Price |