837 East Wakefield Boulevard
Winchester, Connecticut 06098
- Beds
- 3
- Baths
- 1 | 1
- SqFt
- 1,168
- Acres
- 0.76
- Year Built
- 1930
- Neighborhood
- Winsted
- 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 the best of Highland Lake living with this unique property offering a spacious home directly across the street from the lake along with your own separate waterfront parcel! The main house features 7 rooms, 3-4 bedrooms and 2 full baths, providing plenty of space for year-round living or a relaxing lake retreat. A deck overlooking the waterfront offers the perfect spot to enjoy the lake views, while a wonderful outdoor gathering area featuring a stone fireplace provides an ideal setting for entertaining family and friends. Just across the street, your private waterfront parcel takes lake living to another level with a 15' x 29' deck overlooking Highland Lake and a dock for your boat. Also located on the waterfront is a 240 sq. ft. structure with a half bath, offering excellent flexibility for storage, a lakeside retreat or additional sleeping accommodations. Spend your days boating, swimming, fishing or simply relaxing by the water, then retreat to the comfort of your home just steps away. A rare opportunity to enjoy your own private waterfront access and all that beautiful Highland Lake has to offer!
Key Facts
- City/Town
- Winchester
- Neighborhood
- Winsted
- Property / Style
- Single Family · Ranch
- Year Built
- 1930
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 1 full · 1 half
- Living Area
- 1,168 sq ft
- Lot Size
- 0.76 acres
- Property Taxes
- $2,573 / Annually
Market Snapshot
The Winchester Market
Single Family · trailing 12 months
Active Listings
12
12 under contract
Median List Price
$514,500
12 active listings
Median Closed Price
$327,500
98 sales
Median Days on Market
32
12 active listings
Median $ / Sq Ft
$248
12 active listings
Sale-to-List Ratio
100.0%
98 sales
How this home compares
List Price
$629,900
vs $514,500 median
22.4% above median
Price / Sq Ft
$539
vs $248 median
2.2× the median
Days on Market
0 days
vs 32 days median
32 days fresher than median
Based on 12 active and 98 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of August 26, 2026.
Location
837 East Wakefield Boulevard, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 20, 2026per month
- Principal & Interest$3,235
- Property Taxes$214
- Insurance$210
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Winchester
- Neighborhood
- Winsted
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Ranch
- Year Built
- 1930
- New Construction
- No/Resale
- Living Area
- 1,168 sq ft
- Below Grade
- 260 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Gilbert
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Window Unit
- Laundry
- Lower Level
- Appliances
- Oven/RangeRefrigeratorDishwasherWasherDryer
- Basement
- PartialPartially FinishedPartial With Walk-Out
- Interior Features
- Open Floor Plan
Exterior & Lot
- Lot Size
- 0.76 acres
- Zoning
- HLD
- Waterfront
- Direct waterfront
- Waterfront Details
- LakeDock or MooringView
- Water Source
- Private Well
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- DeckStone Wall
- Lot Description
- TreedSloping LotWater View
Listing & Financials
- Property Taxes
- $2,573 / Annually
- Days on Market
- 0
- MLS #
- 24199152
- MLS Status
- Active
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 8/26/2026. 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 8/26/2026 at 5:20 PM UTC.