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431 W Wakefield Boulevard

Winchester, CT 06098
  • $2,199,000
  • STATUS: Active
  • ON SITE: 505 Days
  • MLS #: 24042374
UPDATED: 16 min ago
$2,199,000
  • 9
    BEDS
  • 3
    ACRES
  • 5
    BATHS
  • 1
    1/2 BATHS
  • 5,530
    SQFT
  • $398
    $/SQFT
Type:
Single-Family Home
Built:
2002
County:
Area:

School Information

Elementary School:
Middle School:
High School:

Description

SHOW STOPPER!!!!!! IMAGINE LIVING THE RESORT LIFE YEAR ROUND!!!!! 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. Guest home is loaded with privacy sitting on 425ft of prime water frontage 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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The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc. Data last updated: 2026-01-16T14:10:07.19.
www.lowerhudsonvalleyproperties.com/homes/154253326
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431 W Wakefield Boulevard Winchester, CT 06098

  • Price: $2,199,000
  • Status: Active
  • On Site: 505 Days
  • Updated: 16 min ago
  • MLS #: 24042374
9
Beds
5
Baths
1
½ Baths
3
Acres
5,530
SQFT
$398
$/SQFT
2002
Built
County:
Litchfield
Area:
Winchester
Elementary School:
Batcheller
Middle School:
Pearson
High School:
Gilbert
Property Description
SHOW STOPPER!!!!!! IMAGINE LIVING THE RESORT LIFE YEAR ROUND!!!!! 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. Guest home is loaded with privacy sitting on 425ft of prime water frontage 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.
Exterior Features

Color White Direct Waterfront YN Yes Driveway Type PrivatePavedCrushed Stone Exterior Siding Vinyl Siding Garage And Parking BarnUnder House GaragePavedOff Street ParkingDriveway Lot Description Additional Land Avail.Lightly WoodedLevel LotProfessionally LandscapedRollingWater View Nearby Amenities Public Rec Facilities Parking Total Spaces 9 Roof Information Asphalt Shingle Style Cape CodColonial Swimming Pool YN No Waterfront Description LakeBeachDock or MooringWater CommunityView

Interior Features

Appliances Included Oven/RangeMicrowaveRefrigeratorDishwasherDisposalDryer Attic Description HeatedFinishedFlooredWalk-In Attic YN Yes Basement Description FullHeatedFully FinishedGarage AccessCooledInterior AccessWalk-out Cooling System None Fireplaces Total 4 Heat Type Baseboard In Law Access Lower LevelSeparate Entry In Law Apartment Possible Interior Features Auto Garage Door OpenerCable - AvailableCentral VacuumSecurity System Laundry Room Info Lower Level Laundry Room Location Lower Level Rooms Bedroom (Upper Level) Dining Room (Main Level RemodeledBay/Bow WindowBuilt-InsPatio/Terrace) Kitchen (Main Level Bay/Bow WindowEating Space) Living Room (Main Level Fireplace) Library (Main Level) Other (Upper Level) Bedroom (Upper Level Ceiling Fan) Bedroom (Upper Level) Family Room (Lower Level Fireplace) Primary Bedroom (Main Level Bedroom SuiteCeiling FanFull BathWalk-In Closet) Bedroom (Upper Level) Bedroom (Upper Level) Bedroom (Upper Level) Bedroom (Upper Level Rooms Additional Bonus Room Sq Ft Est Heated Above Grade 5530 Sq Ft Est Heated Below Grade 1470 Sq Ft Total 7000 Total Rooms 12

Property Features

Agent Owner YN No Bank Owned Property No Energy Features Thermopane Windows Foundation Type Concrete Fuel Tank Location Above Ground Heat Fuel Type Oil Home Owners Assocation No Home Warranty Offered YN No Hot Water Description OilDomestic New Construction Type No/Resale Potential Short Sale No Sewage System Public Sewer Connected Tax Year July 2025-June 2026 Under Agreement Yn No Water Source Private Well Zoning HL

Listing information © 2026 Smart MLS
Listing provided courtesy of Lisa Ogren of Berkshire Hathaway NE Prop.: (860) 677-7321.


The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc. Data last updated: 2026-01-16T14:10:07.19.
 
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