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121 West Wakefield Boulevard

Winchester, Connecticut 06098

PENDING$679,000

Reduced from $769,000

Beds
4
Baths
3 | 1
SqFt
2,265
Acres
1.00
Year Built
1996
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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Waterfront2-Car Garage1 FireplacePrice Reduced

About This Home

PRICE REDUCTION !! Discover unparalleled Highland Lake living with this exceptional 1.00-acre retreat, boasting 50 feet of direct lake frontage and a newly renovated dock/deck. Enjoy breathtaking water views from your sunroom, dining room, and multiple bedrooms within this versatile 4/5 bedroom home. A unique first-floor suite with a separate exterior entrance offers ideal flexibility as a main-floor master or in-law accommodation. The upper-level primary suite boasts a private balcony perfect for savoring morning coffee while overlooking the shimmering lake. Entertain effortlessly in the large private backyard space, complete with an expansive 2 tier deck and built-in fire pit. Recent major upgrades ensure worry free enjoyment, including a high-efficiency HVAC (2024), new roof (2022), new siding, exterior doors, added insulation, two remodeled baths, full interior paint, and newer carpet throughout. Extensive landscaping has been completed, including new front railings, leveling and removal of several large trees. Previously a successful Airbnb, this property offers abundant parking, a two-car garage, and dual laundry facilities. Embrace all seasons on Highland Lake - from summer boating and fishing, lake is stocked with trout and bass for fishing enthusiasts, to winter ice skating/fishing. Your lakeside dream awaits!

Key Facts

City/Town
Winchester
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1996
Days on Market
117 days
Beds
4
Baths
3 full · 1 half
Living Area
2,265 sq ft
Lot Size
1.00 acres
Garage / Parking
2 garage
Property Taxes
$10,273 / Annually

Market Snapshot

The Winchester Market

Single Family · trailing 12 months

Median Days on Market

39

12 active listings

Median $ / Sq Ft

$265

12 active listings

Sale-to-List Ratio

100.0%

103 sales

How this home compares

List Price

$679,000

vs $524,900 median

29.4% above median

Price / Sq Ft

$300

vs $265 median

13.2% above median

Days on Market

117 days

vs 39 days median

78 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 28, 2026.

Location

121 West Wakefield Boulevard, Winchester, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,544

per month

  • Principal & Interest$3,462
  • Property Taxes$856
  • Insurance$226
  • 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
Colonial
Year Built
1996
New Construction
No/Resale
Living Area
2,265 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Heat PumpHot Air
Heat Fuel
ElectricOil
Cooling
Central Air
Fireplaces
1
Laundry
Upper Level
Laundry Location
Upper level and basement
Appliances
Cook TopMicrowaveRefrigeratorDishwasherWasherDryer
Basement
Full
In-Law Apartment
PossibleFirst Floor

Exterior & Lot

Lot Size
1.00 acres
Zoning
HLD
Garage / Parking
2 garage spacesDetached Garage
Waterfront
Direct waterfront
Waterfront Details
Lake
Water Source
Public Water Connected
Sewer
Public Sewer In Street
Flood Zone
No
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
Balcony
Lot Description
Rear LotLightly WoodedSloping Lot

Listing & Financials

Property Taxes
$10,273 / Annually
Days on Market
117
MLS #
24159801
MLS Status
Under Contract - Continue to Show

Similar Properties

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

Listed By

Elizabeth Stockwell

(860) 970-9615

Coldwell Banker Realty

(860) 674-0300

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 6:55 AM UTC.