Richard Thomas

359 Winchester Road

Winchester, CT
$ 850,000 Beds 3 Baths 3 Sq 2,943 Virtual Tour
Monthly Estimate* How much can I afford?

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.

Single Family

  • Price
  • $ 850,000
  • City
  • Winchester
  • Bedrooms
  • 3
  • Full Bathrooms
  • 3
  • County
  • Litchfield
  • Half Bathrooms
  • 0
  • Area
  • Lot Size
  • 7.55 Acres
  • Zip
  • 06098
  • Sqr Footage
  • 2,943
  • Year Built
  • 2000
  • Taxes
  • $ 8400
  • Style
  • MLS#
  • 24208872
Listed By: Catherine McCahill 860-480-6760 with William Pitt Sotheby's Int'l. - (860) 777-1800
Data Source: Smart MLS

Features

General

Zoning RU-1
Neighborhood Winsted
County Litchfield
Tax Year July 2026-June 2027
Property Type Single Family For Sale
Status Active
Acres 7.55
Directions Turn onto Lake street at Red Barn Brewery 2nd right onto Route 263 1 mile on left from turn. Home sits across the street from landmark "35 mile per hour sign" at Crystal Lake. (Second Driveway on left after Morgan Drive)
High School Gilbert
City Winchester
Elementary School Batcheller
Sq Ft Total 2943
Year Built 2000
Style Colonial
Year Built Source Public Records
Energy Features Generator,Programmable Thermostat,Thermopane Windows

Interior Features

Cooling System Central Air,Split System
Total Rooms 8
Basement Description Full,Unfinished,Storage,Full With Walk-Out

Exterior Features

Water Source Private Well
Lot Description Fence - Partial,Fence - Stone,Secluded,Some Wetlands,Lightly Wooded,Water View

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Torrington, CT office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Batcheller Elementary School
Middle School Unknown Middle School
High School Gilbert High School

Price History

9/22/2026 Listed $850,000

Property vs Zip Code Average in 06098

Price
AVG $570K
$850K
Taxes
AVG $7,409
$8,400
Year Built
AVG 1943
2000

In The Neighborhood

Areas That We Cover

359 Winchester Road Winchester, CT is a Single Family Home for sale at $850000 with 2943 sqft and a lot size of 7.55 Acres Acre(s). 359 Winchester Road Winchester has 3 bedrooms, 3 baths and was built in 2000. The property's zip code is 06098 which is in Winchester, CT

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site 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.

Richard Thomas

Richard Thomas

929-930-7343

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