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812 West Wakefield Boulevard

Winchester, Connecticut 06098

ACTIVE - NEW$749,900
Beds
2
Baths
1
SqFt
760
Acres
0.06
Year Built
1920
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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WaterfrontDock / Mooring1 Fireplace

About This Home

Year-round waterfront retreat with breathtaking sunrise views from one of the widest sections of the lake! This well-maintained 2-bedroom, 1 bath home offers comfortable living with a flexible loft area for additional sleeping space and a convenient half bath on the lake level. The updated kitchen and new windows provide modern comfort while showcasing expansive water views throughout the home. Outdoor amenities include a spacious waterfront patio, outdoor shower, and walk-in staircase for easy water access, making it ideal for swimming, boating, and relaxing lakeside. Adjacent to a state park, the property enjoys a picturesque setting with added privacy and natural surroundings. Move right in and enjoy as-is or update to suit your personal style. An additional parcel across the street is included, providing extra space and excellent long-term potential. Whether you're looking for a year-round residence, vacation getaway, or investment opportunity, this waterfront property offers an exceptional combination of location, views, and lifestyle.

Key Facts

City/Town
Winchester
Neighborhood
N/A
Property / Style
Single Family · Other
Year Built
1920
Days on Market
10 days
Beds
2
Baths
1 full
Living Area
760 sq ft
Lot Size
0.06 acres
Property Taxes
$7,412 / 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

$749,900

vs $524,900 median

42.9% above median

Price / Sq Ft

$987

vs $265 median

3.7× the median

Days on Market

10 days

vs 39 days median

29 days fresher 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

812 West Wakefield Boulevard, Winchester, Connecticut

Property + 11 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,692

per month

  • Principal & Interest$3,824
  • Property Taxes$618
  • Insurance$250
  • 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
1920
New Construction
No/Resale
Living Area
760 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot Air
Heat Fuel
Propane
Cooling
None
Fireplaces
1
Appliances
Electric RangeRefrigerator
Basement
Crawl SpaceHeatedStorageConcrete Floor

Exterior & Lot

Lot Size
0.06 acres
Zoning
HLD
Waterfront
Direct waterfront
Waterfront Details
LakeDock or MooringViewAccess
Water Source
Private Well
Sewer
Public Sewer Connected
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
Stone
Lot Description
Additional Land Avail.Sloping LotWater View

Listing & Financials

Property Taxes
$7,412 / Annually
Days on Market
10
MLS #
24192463
MLS Status
Active

Similar Properties

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

Listed By

Ryan Horvay

(860) 480-0357

Smith & DeGroat Real Estate

(516) 248-6905

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 6:15 AM UTC.