431 West Wakefield Boulevard
Winchester, Connecticut 06098
- Beds
- 9
- Baths
- 5 | 1
- SqFt
- 7,000
- Acres
- 3.00
- Year Built
- 2002
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Live the Highland Lake Dream - 431 W. Wakefield Blvd, Winchester, CT Summer is just around the corner - and in Winsted, resort living never ends. Recently named one of the most desirable towns to live in, with the breathtaking Highland Lake at its heart, Winchester offers the perfect blend of beauty and lifestyle. This waterfront estate at 431 W. Wakefield Blvd isn't just a home - it's your gateway to the ultimate lake life. Wake each morning to panoramic water views, and step outside to a world of four-season recreation. In summer, enjoy boating, jet skiing, swimming, and fishing right from your private dock, or simply relax by the shoreline. When winter arrives, the lake transforms into your own frozen wonderland for ice fishing, skating, and fireside gatherings. Inside, luxury awaits. The main home features gourmet finishes, a chef's kitchen, and custom craftsmanship throughout. A charming guest bungalow offers privacy for family, friends, or guests. Zoned for a bed and breakfast, and featuring an extra subdividable lot, the property offers immense potential - whether as a private retreat, an upscale B&B, or an investment in future development. Set on 425 feet of pristine water frontage, this estate captures the essence of Highland Lake living - natural beauty, year-round recreation, and endless opportunity.
Key Facts
- City/Town
- Winchester
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod,Colonial
- Year Built
- 2002
- Days on Market
- 126 days
- Beds
- 9
- Baths
- 5 full · 1 half
- Living Area
- 7,000 sq ft
- Lot Size
- 3.00 acres
- Garage / Parking
- 2 garage · 9 total
- Property Taxes
- $24,184 / Annually
Market Snapshot
The Winchester Market
Single Family · trailing 12 months
Active Listings
12
12 under contract
Median List Price
$524,900
12 active listings
Median Closed Price
$325,000
103 sales
Median Days on Market
40
12 active listings
Median $ / Sq Ft
$265
12 active listings
Sale-to-List Ratio
100.0%
103 sales
How this home compares
List Price
$1.85M
vs $524,900 median
3.5× the median
Price / Sq Ft
$264
vs $265 median
In line with median
Days on Market
126 days
vs 40 days median
86 days longer than median
Based on 12 active and 103 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of July 29, 2026.
Location
431 West Wakefield Boulevard, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$9,433
- Property Taxes$2,015
- Insurance$617
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Winchester
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Cape Cod,Colonial
- Year Built
- 2002
- New Construction
- No/Resale
- Living Area
- 7,000 sq ft
- Below Grade
- 1,470 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Baseboard
- Heat Fuel
- Oil
- Cooling
- Attic FanWindow Unit
- Fireplaces
- 4
- Laundry
- Lower Level
- Laundry Location
- Lower level
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasherDisposalDryer
- Basement
- FullHeatedGarage AccessInterior AccessLiveable SpaceFull With Walk-Out
- In-Law Apartment
- PossibleLower LevelSeparate Entry
- Interior Features
- Auto Garage Door OpenerCable - AvailableCentral VacuumSecurity System
- Additional Rooms
- Bonus Room
Exterior & Lot
- Lot Size
- 3.00 acres
- Zoning
- HLD
- Garage / Parking
- 2 garage spaces9 total parking spacesBarnUnder House GarageOff Street ParkingDrivewayPrivatePavedCrushed Stone
- Waterfront
- Direct waterfront
- Waterfront Details
- LakeBeachDock or MooringWater CommunityView
- Water Source
- Private Well
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- Vinyl Siding
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- CabanaDeckCovered DeckFrench Doors
- Lot Description
- Additional Land Avail.Lightly WoodedLevel LotProfessionally LandscapedRollingWater View
Listing & Financials
- Property Taxes
- $24,184 / Annually
- Days on Market
- 126
- MLS #
- 24159989
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/29/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/29/2026 at 10:10 AM UTC.