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325 East Wakefield Boulevard

Winchester, Connecticut 06098

ACTIVE - NEW$319,900
Beds
2
Baths
2
SqFt
1,192
Acres
0.07
Year Built
1930
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,054

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Anthony Gonsalves

(203) 704-0400

RE/MAX RISE

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.