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MLS 24208872 For Sale Updated September 26, 2026
359 Winchester Road

Winchester, Connecticut 06098

$850,000
On market 1 day
359 Winchester Road
1 / 39

About This Property

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.

Property Details

Interior

Heat
Baseboard,Hot Water,Zoned,Other — Oil
Cooling
Central Air,Split System
Fireplaces
1
Basement
Full,Unfinished,Storage,Full With Walk-Out
Interior Features
Auto Garage Door Opener Cable - Pre-wired Open Floor Plan

Exterior & Lot

Roof
Asphalt Shingle,Gable
Construction
Construction
Waterfront
View
Exterior Features
Porch-Screened Underground Utilities Shed Barn Deck Gutters Lighting Stone Wall
Lot Description
Fence - Partial Fence - Stone Secluded Some Wetlands Lightly Wooded Water View
Garage & Parking
Attached Garage

Utilities & Systems

Water Source
Private Well
Sewer
Septic
Energy Features
Generator Programmable Thermostat Thermopane Windows

Community & Schools

Elementary
Batcheller
Middle
Pearson
High
Gilbert
Neighborhood
Winsted
Nearby Amenities
Lake Library Medical Facilities Park Playground/Tot Lot Public Rec Facilities Stables/Riding Tennis Courts

Appliances

Included
Electric Cooktop Wall Oven Microwave Range Hood Subzero Dishwasher Instant Hot Water Tap Washer Dryer

359 Winchester Road

Winchester , Connecticut 06098

$850,000

On market 1 day

Beds
3
Baths
3
SqFt
2,943
Type
Single Family
County Litchfield
Garage 2
Rooms -
Lot Size 7.55 Acres
Property Tax $8,400
Assessed Value $355,600
Year Built 2000
Style Colonial
Zoning RU-1

Payment Estimate

30-year fixed. Includes taxes; estimates only.

Estimated Monthly Payment
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Property Map

Map location is based on the property address.

Listing information is deemed reliable but not guaranteed and is sourced from the local MLS feed. Brokerage shown: PSOTH00.

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