431 West Wakefield Boulevard Winchester, CT $ 2,199,000
431 West Wakefield Boulevard
$ 2,199,000
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431 West Wakefield Boulevard

Winchester, CT, 06098
$ 2,199,000
Bedrooms9 Baths5.1 Sq 7,000

Monthly Estimate*

$ 13,719

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Single Family Home for sale in Winchester, CT

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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Single Family Active

Price

$ 2,199,000

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

24042374

Features
General
Zoning 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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Interior
Cooling System None
Total Rooms 12
Basement Description Full Heated Fully Finished Garage Access Cooled Interior Access 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

$15,734
Per Month
87%
13%
0%
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.
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Nearby
4604681 Elementary School
1415485 Middle School
Gilbert High School High School
Pricing History
DatePricePrice ChangeDescription
10/14/2025$2,199,000 Listed Price

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431 West Wakefield Boulevard, Winchester, CT, 06098 is a Single Family Home for sale at $2,199,000 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