359 Winchester Road Winchester, CT $ 850,000
359 Winchester Road
$ 850,000
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359 Winchester Road

Winchester, CT, 06098
$ 850,000
Bedrooms3 Baths3.0 Sq 2,943

Monthly Estimate*

$ 5,367

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Single Family Home for sale in Winchester, CT

for $850,000 with 3 bedrooms and 3 full baths. This 2,943 square foot home was built in 2000 on a lot size of 7.55.

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.

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Single Family Contingent

Price

$ 850,000

Bedrooms

3

Full Bath

3

Property Type

Single Family

Taxes

$ 8,400

Style

Lot Size

7.55

Year Built

2000

Town/City

Winchester

MLS | Web ID

24208872

Features
General
Zoning RU-1
Neighborhood Winsted
County Litchfield
Tax Year July 2026-June 2027
Property Type Single Family For Sale
Status Under Contract - Continue to Show
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
DOM 6
Year Built 2000
Style Colonial
Year Built Source Public Records
Energy Features Generator Programmable Thermostat Thermopane Windows
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Interior
Cooling System Central Air Split System
Total Rooms 8
Basement Description Full Unfinished Storage Full With Walk-Out
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Exterior
Water Source Private Well
Lot Description Fence - Partial Fence - Stone Secluded Some Wetlands Lightly Wooded Water View
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* Excluded Features
List By
Catherine McCahill

Listing Agent

William Pitt Sotheby's Int'l

Broker

cmccahill@wpsir.com

Email

Affordability Calculator

$6,067
Per Month
88%
12%
0%
Monthly Principal & Interest
$5,367
Monthly Property Taxes
$700
Monthly Home Insurance
--
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.
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Nearby
4604681 Elementary School
1415485 Middle School
Gilbert High School High School
Pricing History
DatePricePrice ChangeDescription
9/22/2026$850,000 Listed Price

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359 Winchester Road, Winchester, CT, 06098 is a Single Family Home for sale at $850,000 with 2,943 sqft and a lot size of 7.55. 359 Winchester Road has 3 bedrooms, 3.0 baths, and was built in 2000. The property's zip code is 06098 which is in Winchester, CT