325 East Wakefield Boulevard
Winchester, Connecticut 06098
- Beds
- 2
- Baths
- 2
- SqFt
- 1,192
- Acres
- 0.07
- Year Built
- 1930
- 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
Enjoy beautiful water views and access to Highland Lake from this inviting home offering comfortable living spaces and desirable features throughout. The main level features a galley kitchen with plentiful white cabinetry, laminate flooring, refrigerator, dishwasher, and electric range. A convenient powder room and stackable washer add functionality. The spacious living room/dining area features wide-plank wood flooring, a small dining area, and a walk-out porch leading to a Trex deck-perfect for enjoying the outdoors and water views. A small first-floor bedroom offers flexibility for guests, an office, or additional living space. Upstairs, the primary bedroom is generously sized to easily accommodate a king-size bed and features wood flooring and propane-fired baseboard heat. The second bedroom also offers wood flooring, a large closet, ceiling fan, two large windows, and propane-fired baseboard heat. The full bathroom includes a newer vanity, stall shower, and laminate tile flooring. Additional features include forced-air propane heating on the main level, window air-conditioning units, a carpeted stairway, and two off-street parking spaces. A boat slip on Highland Lake provides an exceptional opportunity to enjoy boating and waterfront recreation.Book a showing today. This property will not last!
Key Facts
- City/Town
- Winchester
- Neighborhood
- N/A
- Property / Style
- Single Family · Other
- Year Built
- 1930
- Days on Market
- 0 days
- Beds
- 2
- Baths
- 2 full
- Living Area
- 1,192 sq ft
- Lot Size
- 0.07 acres
- Garage / Parking
- 2 total
- Property Taxes
- $3,645 / Annually
Market Snapshot
The Winchester Market
Single Family · trailing 12 months
Active Listings
16
10 under contract
Median List Price
$414,450
16 active listings
Median Closed Price
$327,500
98 sales
Median Days on Market
33
16 active listings
Median $ / Sq Ft
$279
16 active listings
Sale-to-List Ratio
100.0%
98 sales
How this home compares
List Price
$319,900
vs $414,450 median
22.8% below median
Price / Sq Ft
$268
vs $279 median
In line with median
Days on Market
0 days
vs 33 days median
33 days fresher than median
Based on 16 active and 98 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of August 27, 2026.
Location
325 East Wakefield Boulevard, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 20, 2026per month
- Principal & Interest$1,643
- Property Taxes$304
- Insurance$107
- 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
- Other
- Year Built
- 1930
- New Construction
- No/Resale
- Living Area
- 1,192 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Propane
- Cooling
- Window Unit
- Laundry
- Main Level
- Laundry Location
- Main floor half bath
- Appliances
- Electric RangeRefrigeratorDishwasher
- Basement
- Crawl SpaceUnfinishedSump Pump
- In-Law Apartment
- No
- Interior Features
- Open Floor Plan
Exterior & Lot
- Lot Size
- 0.07 acres
- Zoning
- HLD
- Garage / Parking
- 2 total parking spacesOff Street ParkingDrivewayPrivatePaved
- Waterfront Details
- Walk to WaterViewAccess
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- Vinyl Siding
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Slab
- Exterior Features
- Porch
- Lot Description
- Level LotWater View
Listing & Financials
- Property Taxes
- $3,645 / Annually
- Days on Market
- 0
- MLS #
- 24201785
- MLS Status
- Active
- Financing
- FHA,VA,CHFA
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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 8/27/2026. 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 8/27/2026 at 11:10 PM UTC.