121 West Wakefield Boulevard
Winchester, Connecticut 06098
Reduced from $769,000
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 2,265
- Acres
- 1.00
- Year Built
- 1996
- 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
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
Active Listings
12
12 under contract
Median List Price
$524,900
12 active listings
Median Closed Price
$325,000
103 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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.
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.