804 West Wakefield Boulevard
Winchester, Connecticut 06098
- Beds
- 2
- Baths
- 1
- SqFt
- 1,044
- Acres
- 0.08
- Year Built
- 1924
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Experience an everyday vacation at 804 W. Wakefield Blvd on beautiful Highland Lake! This exceptional turnkey, year-round waterfront retreat is ideal as a primary residence, weekend escape, vacation home, or income-producing rental. Perfectly positioned on the widest part of Highland Lake's coveted Third Bay, enjoy breathtaking sunrises, panoramic water views, and bald eagles soaring overhead from your expansive lakeside deck. With over $100,000 in owner upgrades, this move-in ready home offers effortless lakefront living with a newer roof, owned solar panels, updated systems, a permanent grandfathered dock, seawall, outdoor shower, firepit, and direct access to motorboating, kayaking, paddleboarding, swimming, and outstanding fishing. A rare additional 0.24-acre lot across the street provides a total of 5 parking spaces perfect for family and guests. Enjoy easy access to Route 8, a short drive to Bradley International Airport, and year-round recreation with nearby Ski Sundown, Butternut Ski Area, scenic hiking trails, wineries, breweries, restaurants, and charming New England towns. This is your opportunity to own one of Highland Lake's most desirable waterfront homes-simply unpack, relax, and make every day feel like a vacation.
Key Facts
- City/Town
- Winchester
- Neighborhood
- N/A
- Property / Style
- Single Family · Ranch,Cottage
- Year Built
- 1924
- Days on Market
- 0 days
- Beds
- 2
- Baths
- 1 full
- Living Area
- 1,044 sq ft
- Lot Size
- 0.08 acres
- Garage / Parking
- 5 total
- Property Taxes
- $7,988 / Annually
Market Snapshot
The Winchester Market
Single Family · trailing 12 months
Active Listings
11
12 under contract
Median List Price
$429,000
11 active listings
Median Closed Price
$320,500
102 sales
Median Days on Market
42
11 active listings
Median $ / Sq Ft
$212
11 active listings
Sale-to-List Ratio
100.0%
102 sales
How this home compares
List Price
$799,900
vs $429,000 median
86.5% above median
Price / Sq Ft
$766
vs $212 median
3.6× the median
Days on Market
0 days
vs 42 days median
42 days fresher than median
Based on 11 active and 102 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of August 17, 2026.
Location
804 West Wakefield Boulevard, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 13, 2026per month
- Principal & Interest$4,117
- Property Taxes$666
- Insurance$267
- 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
- Ranch,Cottage
- Year Built
- 1924
- New Construction
- No/Resale
- Living Area
- 1,044 sq ft
- Below Grade
- 406 sq ft
Schools
- Elementary
- Per Board of Ed
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- SolarWall UnitOther
- Heat Fuel
- Solar
- Cooling
- Split System
- Laundry
- Main Level
- Appliances
- Oven/RangeRefrigeratorWasherDryer
- Basement
- Crawl SpaceUnfinished
- In-Law Apartment
- No
- Interior Features
- Cable - AvailableOpen Floor Plan
Exterior & Lot
- Lot Size
- 0.08 acres
- Zoning
- HLD
- Garage / Parking
- 5 total parking spacesOff Street ParkingDrivewayPaved
- Waterfront
- Direct waterfront
- Waterfront Details
- LakeBeachDock or MooringBeach RightsView
- Water Source
- Private Well
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- Wood
- Color
- Light Wood
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Exterior Features
- DeckLightingStone WallPatio
- Lot Description
- Level LotSloping LotProfessionally LandscapedWater View
Listing & Financials
- Property Taxes
- $7,988 / Annually
- Days on Market
- 0
- MLS #
- 24195283
- 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 8/17/2026. 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 8/17/2026 at 7:31 PM UTC.