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.
For sale
$2,600,000
431 West Wakefield Boulevard, Winchester, CT 06098
9beds
7,000sqft
Est.:
Single Family Residence
Built in 2002
3 Acres Lot
$-- Zestimate®
$371/sqft
$-- HOA
What's special
Waterfront estateCharming guest bungalowPrivate dockStunning lake viewsCustom craftsmanshipLuxury finishesGourmet kitchen
- 310 days
- on Zillow |
- 1,004 |
- 51 |
Zillow last checked: 7 hours ago
Listing updated: July 02, 2025 at 07:42pm
Listed by:
Lisa A. Ogren,
Berkshire Hathaway NE Prop.
Source: Smart MLS,MLS#: 24042374

Travel times
Tour with a buyer's agent
Tour with a buyer's agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 9
- Bathrooms: 6
- Full bathrooms: 5
- 1/2 bathrooms: 1
Rooms
- Room types: Bonus Room
Primary bedroom
- Features: Bedroom Suite, Ceiling Fan(s), Full Bath, Walk-In Closet(s)
- Level: Main
- Area: 336 Square Feet
- Dimensions: 21 x 16
Bedroom
- Level: Upper
- Area: 264 Square Feet
- Dimensions: 24 x 11
Bedroom
- Level: Upper
- Area: 288 Square Feet
- Dimensions: 24 x 12
Bedroom
- Level: Upper
Bedroom
- Features: Ceiling Fan(s)
- Level: Upper
- Area: 299 Square Feet
- Dimensions: 23 x 13
Bedroom
- Features: Ceiling Fan(s)
- Level: Upper
- Area: 276 Square Feet
- Dimensions: 23 x 12
Bedroom
- Level: Upper
- Area: 182 Square Feet
- Dimensions: 13 x 14
Bedroom
- Level: Upper
- Area: 276 Square Feet
- Dimensions: 23 x 12
Bedroom
- Features: Ceiling Fan(s)
- Level: Upper
- Area: 345 Square Feet
- Dimensions: 23 x 15
Dining room
- Features: Remodeled, Bay/Bow Window, Built-in Features, Patio/Terrace
- Level: Main
- Area: 208 Square Feet
- Dimensions: 16 x 13
Family room
- Features: Fireplace
- Level: Lower
Kitchen
- Features: Bay/Bow Window, Eating Space
- Level: Main
- Area: 360 Square Feet
- Dimensions: 24 x 15
Library
- Level: Main
- Area: 208 Square Feet
- Dimensions: 16 x 13
Living room
- Features: Fireplace
- Level: Main
- Area: 1518 Square Feet
- Dimensions: 33 x 46
Other
- Level: Upper
- Area: 253 Square Feet
- Dimensions: 23 x 11
Heating
- Baseboard, Oil
Cooling
- None
Appliances
- Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Disposal, Dryer, Water Heater
- Laundry: Lower Level
Features
- Central Vacuum
- Windows: Thermopane Windows
- Basement: Full,Heated,Finished,Garage Access,Cooled,Interior Entry,Walk-Out Access
- Attic: Heated,Finished,Floored
- Number of fireplaces: 4
Interior area
- Total structure area: 7,000
- Total interior livable area: 7,000 sqft
- Finished area above ground: 5,530
- Finished area below ground: 1,470
Property
Parking
- Total spaces: 9
- Parking features: Barn, Attached, Paved, Off Street, Driveway, Garage Door Opener, Private
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Features
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Waterfront, Lake, Dock or Mooring, Water Community, Beach
Lot
- Size: 3 Acres
- Features: Additional Land Avail., Few Trees, Level, Landscaped, Rolling Slope
Details
- Parcel number: 924886
- Zoning: HL
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape Cod,Colonial
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 2002
Utilities & green energy
- Sewer: Public Sewer
- Water: Well
- Utilities for property: Cable Available
Green energy
- Energy efficient items: Windows
Community & HOA
Community
- Features: Public Rec Facilities
- Security: Security System
HOA
- Has HOA: No
Location
- Region: Winsted
Financial & listing details
- Price per square foot: $371/sqft
- Tax assessed value: $829,080
- Annual tax amount: $24,184
- Date on market: 8/28/2024
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