347 W. Wakefield Boulevard
Winchester, Connecticut 06098
- Beds
- 2
- Baths
- 1
- SqFt
- 596
- Acres
- 0.28
- Year Built
- 1920
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Welcome to this relaxing seasonal cottage, situated high above road level and offering breathtaking panoramic views of the 444-acre Highland Lake. Enter through the oversized screened porch, where you can unwind with family or friends while taking in the beautiful perennial plantings and natural surroundings. This charming cottage features two bedrooms, a loft, one full bath, an open-concept kitchen, dining area, and living room. For your comfort, oil heat and a mini-split unit provide heat and air conditioning. Additionally, there's a rear deck area perfect for outdoor dining & grilling. An extra outdoor shower is available to refresh after spending time on the lake.
Key Facts
- City/Town
- Winchester
- Neighborhood
- N/A
- Property / Style
- Single Family · Cottage
- Year Built
- 1920
- Days on Market
- 0 days
- Beds
- 2
- Baths
- 1 full
- Living Area
- 596 sq ft
- Lot Size
- 0.28 acres
- Garage / Parking
- 2 total
- Property Taxes
- $4,237 / Annually
Market Snapshot
The Winchester Market
Single Family · trailing 12 months
Active Listings
17
9 under contract
Median List Price
$429,000
17 active listings
Median Closed Price
$330,000
97 sales
Median Days on Market
28
17 active listings
Median $ / Sq Ft
$268
17 active listings
Sale-to-List Ratio
100.0%
97 sales
How this home compares
List Price
$289,000
vs $429,000 median
32.6% below median
Price / Sq Ft
$485
vs $268 median
81.0% above median
Days on Market
0 days
vs 28 days median
28 days fresher than median
Based on 17 active and 97 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of September 2, 2026.
Location
347 W. Wakefield Boulevard, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 27, 2026per month
- Principal & Interest$1,486
- Property Taxes$353
- Insurance$96
- 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
- Cottage
- Year Built
- 1920
- New Construction
- No/Resale
- Living Area
- 596 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Heat PumpHot Air
- Heat Fuel
- ElectricOil
- Cooling
- Ceiling FansSplit System
- Appliances
- Electric CooktopOven/RangeMicrowaveRefrigerator
- Basement
- PartialUnfinishedStorageDirt FloorPartial With Walk-Out
- Interior Features
- Open Floor Plan
Exterior & Lot
- Lot Size
- 0.28 acres
- Zoning
- HLD
- Garage / Parking
- 2 total parking spacesOn Street ParkingUnpaved
- Waterfront Details
- ViewSeasonal
- Water Source
- Other
- Sewer
- Public Sewer Connected
- Construction
- Wood
- Color
- white
- Roof
- Asphalt Shingle
- Foundation
- Piling
- Exterior Features
- PorchDeckGuttersGarden Area
- Lot Description
- RockySloping LotWater View
Listing & Financials
- Property Taxes
- $4,237 / Annually
- Days on Market
- 0
- MLS #
- 24202928
- MLS Status
- Coming Soon
Similar Properties
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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 9/2/2026. 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 9/2/2026 at 10:10 AM UTC.