359 Winchester Road
Winchester, Connecticut 06098
- Beds
- 3
- Baths
- 3
- SqFt
- 2,943
- Acres
- 7.55
- Year Built
- 2000
- Neighborhood
- Winsted
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
23
8 under contract
Median List Price
$389,900
23 active listings
Median Closed Price
$335,000
95 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 17, 2026per 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
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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.