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359 Winchester Road

Winchester, Connecticut 06098

COMING SOON - NEW$850,000
Beds
3
Baths
3
SqFt
2,943
Acres
7.55
Year Built
2000
Matt Caiola

Matt Caiola

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About This Home

Breathtaking water views and master craftsmanship await in this pristine Colonial offering nearly 3,000 SF overlooking serene Highland Lake. This entertainer's dream home opens from an inviting two-story foyer into an airy, open layout where the living and dining rooms are joined by a floor-to-ceiling fieldstone fireplace. The spacious dining room easily accommodates large gatherings and flows seamlessly onto a delightful screened-in porch to enjoy the calm, serene setting with distant lake views. The gourmet kitchen is a master craftsman renovation featuring custom white birch cabinetry, rich soapstone countertops, stone subway tile backsplash, a farmhouse sink with a view, and a Sub-Zero refrigerator. Dedicated home office off front foyer, mudroom, laundry room, and half bath complete the main level. Upstairs features an en-suite primary bedroom, two additional nice-sized bedrooms, and a full guest bath. Accessed via a private second staircase off the kitchen, the expansive 27' x 21' "Skybox" family room (finished over the garage in 2017) boasts its own heating/cooling system, surround sound, and live music performance hook-ups. Property is flanked by a magnificent stone wall, emerald green meadows including a two-stall run-in shed with tack room. Hardwood floors main level, bamboo engineered floors upper level, oversized 2 car garage, walk-out basement. New well pump 2020, new whole house generator 2023. EZ commute to NYC & Boston from this ideal retreat. Rare opportunity.

Key Facts

City/Town
Winchester
Neighborhood
Winsted
Property / Style
Single Family · Colonial
Year Built
2000
Days on Market
0 days
Beds
3
Baths
3 full
Living Area
2,943 sq ft
Lot Size
7.55 acres
Garage / Parking
2 garage
Property Taxes
$8,400 / Annually

Market Snapshot

The Winchester Market

Single Family · trailing 12 months

Median Days on Market

28

23 active listings

Median $ / Sq Ft

$231

23 active listings

Sale-to-List Ratio

100.0%

95 sales

How this home compares

List Price

$850,000

vs $389,900 median

2.2× the median

Price / Sq Ft

$289

vs $231 median

25.1% above median

Days on Market

0 days

vs 28 days median

28 days fresher than median

Based on 23 active and 95 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of September 22, 2026.

Location

359 Winchester Road, Winchester, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,484

per month

  • Principal & Interest$4,501
  • Property Taxes$700
  • Insurance$283
  • 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
Colonial
Year Built
2000
New Construction
No/Resale
Living Area
2,943 sq ft

Schools

Elementary
Batcheller
High
Gilbert

Interior

Heating
BaseboardHot WaterZonedOther
Heat Fuel
Oil
Cooling
Central AirSplit System
Fireplaces
1
Laundry
Main Level
Appliances
Electric CooktopWall OvenMicrowaveRange HoodSubzeroDishwasherInstant Hot Water TapWasherDryer
Basement
FullUnfinishedStorageFull With Walk-Out
Interior Features
Auto Garage Door OpenerCable - Pre-wiredOpen Floor Plan
Additional Rooms
FoyerLaundry RoomMud Room

Exterior & Lot

Lot Size
7.55 acres
Zoning
RU-1
Garage / Parking
2 garage spacesAttached Garage
Waterfront Details
View
Water Source
Private Well
Sewer
Septic
Flood Zone
No
Construction
Vinyl Siding
Roof
Asphalt ShingleGable
Foundation
Concrete
Exterior Features
Porch-ScreenedUnderground UtilitiesShedBarnDeckGuttersLightingStone Wall
Lot Description
Fence - PartialFence - StoneSecludedSome WetlandsLightly WoodedWater View

Listing & Financials

Property Taxes
$8,400 / Annually
Days on Market
0
MLS #
24208872
MLS Status
Coming Soon

Similar Properties

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

Listed By

Catherine McCahill

(860) 480-6760

William Pitt Sotheby's Int'l

(860) 777-1800

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

The IDX display contains information sourced from SmartMLS, Inc. as of 9/22/2026. 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 9/22/2026 at 11:10 PM UTC.