Active Under Contract
Single family home for sale at 359 Winchester Rd, Winsted, CT 06098 | MLS# 24208872 | Listing updated on 2026-09-30
Photo 1 of Single family home for sale at 359 Winchester Rd, Winsted, CT 06098 | MLS# 24208872 | Listing updated on 2026-09-30
Photo 2 of Single family home for sale at 359 Winchester Rd, Winsted, CT 06098 | MLS# 24208872 | Listing updated on 2026-09-30
Photo 3 of Single family home for sale at 359 Winchester Rd, Winsted, CT 06098 | MLS# 24208872 | Listing updated on 2026-09-30
Photo 4 of Single family home for sale at 359 Winchester Rd, Winsted, CT 06098 | MLS# 24208872 | Listing updated on 2026-09-30
35+
Beds Icon

Street View

$850,000

Monthly Est:$4,231

  • Beds Icon3 Beds
  • Beds Icon
    3 Baths
  • Beds Icon2,943sqft

359 Winchester Rd, Winsted, CT 06098

$4,231/moEst:

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  • Single Family Residence

  • Built in 2000

  • $-- HOA

  • 7.55 acres lot

  • $289/sq.ft

Description

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.

  • Houzeo last checked: 12 hours ago
  • Listing updated: September 30, 2026 at 6:47 pm
  • Listing Provided by: Catherine McCahill | William Pitt Sotheby's Int'l
  • Source: SMART MLS-CT | MLS#: 24208872 SMART MLS-CT

Property Details

  • Status

    Active Under Contract

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Litchfield County

  • City

    Winsted

  • Neighborhood

    --

  • Year Built

    2000

  • HOA Fees

    -

  • Finished Area

    2,943 sqft

  • Lot Size

    7.55 acres lot

  • Basement Area

    - sqft

  • MLS Name

    SMART MLS

  • MLS Number

    24208872

  • MLS Status

    Under Contract - Continue to Show

  • Days on Market

    15

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Location

HOA Management

0

HOA Fees

$-/

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 3

    Bathrooms: 3

Interior

  • Heating

    Oil, Baseboard, Zoned, Hot Water, Other

  • Appliances

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

  • Interior Features

    Auto Garage Door Opener, Cable Pre Wired, Open Floor Plan

  • Exterior Features

    Porch Screened, Underground Utilities, Shed, Barn, Deck, Gutters, Lighting, Stone Wall

  • Sewer

    Septic

  • Cooling

    Central Air, Split System

Construction

  • Year Built

    Year Built: 2000

  • Home type

    Single Family Residence

  • Roof

    Asphalt Shingle, Gable

  • Foundation Details

    Concrete

  • Architectural Style

    Colonial

Utilities & Energy

  • Water Source

    Private Well

  • Laundry Features

    Main Level

  • Parking Features

    Attached Garage

  • Basement

    Full, Unfinished, Storage, Full With Walk Out

Other Features

  • Lot Features

    Fence Partial, Fence Stone, Secluded, Some Wetlands, Lightly Wooded, Water View

  • Subdivision Name

    Winsted

Price History

DateEventPrice

09/30/2026

Source: mls_logoSMART MLS-CT #24208872

Contingent (Active Under Contract)

$850,000

$289/sqft

09/24/2026

Source: mls_logoSMART MLS-CT #24208872

Listed for Sale

$850,000

$289/sqft

09/22/2026

Source: mls_logoSMART MLS-CT #24208872

Coming Soon

$850,000

$289/sqft

Nearby Homes

Based on information provided to and compiled by the SMART MLS, Inc. through Oct 07, 2026, 11:30AM. IDX information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. ©2026 SMART MLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group