359 Winchester Road, Winchester, Connecticut

$850,000

Previous Next

3

Beds

3

Baths

2,943

Square feet

7.55

Acres

About 359 Winchester Road

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.

Features of 359 Winchester Road

MLS® # 24208872
Price $850,000
Bedrooms 3
Bathrooms 3.00
Full Baths 3
Square Footage 2,943
Acres 7.55
Type Single Family For Sale
Style Colonial
Status Under Contract - Continue to Show

Community Information

Address 359 Winchester Road
Area Winsted
City Winchester
County Litchfield
State Connecticut
Zip Code 06098

Amenities

Features Generator, Programmable Thermostat, Thermopane Windows
Parking Attached Garage
# of Garages 2
Is Waterfront No
Waterfront View
Has Pool No

Interior

Interior Features Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan
Appliances Electric Cooktop, Wall Oven, Microwave, Range Hood, Subzero, Dishwasher, Instant Hot Water Tap, Washer, Dryer
Heating Baseboard, Hot Water, Zoned, Other, Oil
Cooling Central Air, Split System
Fireplace Yes
# of Fireplaces 1
Has Basement Yes
Basement Full, Unfinished, Storage, Full With Walk-Out

Exterior

Exterior Vinyl Siding
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
Roof Asphalt Shingle, Gable
Foundation Concrete

School Information

Elementary Batcheller
Middle Pearson
High Gilbert

Additional Information

Date Listed September 22nd, 2026
Days on Market 8
Zoning RU-1
RE / Bank Owned No

Listing Details

OfficeWilliam Pitt Sotheby's Int'l

Listing Map

Request a Showing

Provide a valid email address.
When would you like to view this property?

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement.
Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale.
Property information displayed is deemed reliable but is not guaranteed.
Copyright 2026 SmartMLS, Inc.

Listing information last updated on October 3rd, 2026 at 2:29pm EDT.