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.

Interior

  • AppliancesOven/ Range, Microwave, Refrigerator, Dishwasher, Disposal, Dryer
  • BasementFull, Heated, Fully Finished, Garage Access, Cooled, Interior Access, Walk-out
  • A/CNone
  • HeatingBaseboard, Oil
  • FireplaceFireplaces: 4
  • GeneralAuto Garage Door Opener, Cable - Available, Central Vacuum, Security System
  • RoomsBonus Room
  • FlooringCarpet, Ceramic Tile, Wood
  • Disability Feature1st Flr Half Bath
  • Eco/Green FeatureRegionally- Sourced Materials
  • LaundryLower Level
  • Half Baths1

Exterior

  • GeneralFruit Trees, Porch, Deck, Gutters, Lighting, French Doors, Patio
  • StyleCape Cod, Colonial
  • ParkingParking spaces: 9
  • Other StructuresWrap Around, Screened
  • PoolHeated, Tile, In Ground Pool

Construction

  • RoofingAsphalt Shingle
  • WindowsThermopane
  • GeneralPost & Beam, Barn, Farm House, Poured Concrete

Location

  • CountyLitchfield
  • Originating MLSBerkshire County Board of REALTORSu00ae
  • School DistrictChatham

Lot

  • DrivewayPrivate, Paved, Crushed Stone
  • ZoningHL, 924886
  • ViewWater, Scenic, Pond, Pastoral, Distant, View
  • Current UseHobby Farm, Pasture, Water Shed
  • FencingWood

Utilities

  • WaterPrivate Well
  • SewerPublic Sewer Connected
  • Utilities100 Amp Service

Financial

  • SourceBerkshire County Board of REALTORSu00ae
  • Exclusionswater treatment system

Listing History

  • 03/26/2025$2,600,000 @ $371 per ft² 7.14%
  • 09/04/2024Active
  • 08/28/2024$2,800,000 @ $400 per ft²
  • 08/28/2024Coming Soon

Property Features

  • 100 Amp Service
  • 1st Flr Half Bath
  • 924886
  • Asphalt Shingle
  • Auto Garage Door Opener
  • Barn
  • Baseboard
  • Berkshire County Board of REALTORS®
  • Bonus Room
  • Cable Available
  • Cape Cod
  • Carpet
  • Central Vacuum
  • Ceramic Tile
  • Chatham
  • Colonial
  • Cooled
  • Crushed Stone
  • Deck
  • Distant
  • Farm House
  • Fireplaces: 4
  • French Doors
  • Fruit Trees
  • Full
  • Fully Finished
  • Garage Access
  • Gutters
  • Heated
  • HL
  • Hobby Farm
  • In- Ground Pool
  • Interior Access
  • Lighting
  • Litchfield
  • Lower Level
  • Oil
  • Parking spaces: 9
  • Pastoral
  • Pasture
  • Patio
  • Paved
  • Pond
  • Porch
  • Post & Beam
  • Poured Concrete
  • Private
  • Private Well
  • Public Sewer Connected
  • Regionally- Sourced Materials
  • Scenic
  • Screened
  • Security System
  • Thermopane
  • Tile
  • View
  • Walk- Out
  • Water
  • Water Shed
  • water treatment system
  • Wood
  • Wrap Around

Property Info

Property Details

Address: 431 West Wakefield Boulevard, Winchester, Connecticut 06098