359 Winchester Road

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Floor Plan 1st floor
Floor Plan 2nd floor
Active
$850,000
3 beds2,943 sqft
359 Winchester Rd, Winchester, CT 06098
Est: $5,092/moGet pre-approved
Single FamilyProperty Type
7.55 acresLot Size
2000Year Built
$289/sq ftPrice per sq ft
2 carsParking Spaces

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....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.
Days on Market Listed Today
  • Listed by: Catherine A McCahill 860.480.6760 cmccahill@wpsir.com • William Pitt Sotheby's Int'l
Last updated: 09/24/2026 04:05 AM • Source: SMARTMLS, MLS#: 24208872

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Listing Courtesy of William Pitt Sotheby's Int'l, Catherine A McCahill
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$5,092 per month

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Property Taxes

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Property Information for 359 Winchester Road

Property Details
  • Taxes: $8,400 / year
  • MLS Type: Residential
  • County: Litchfield County
  • Basement Description: Full, Unfinished, Storage, Full With Walk-Out
  • Direct Waterfront: No
  • Expected Active Date: 09-24-2026
  • Garages Number: 2
  • Neighborhood: Winsted
  • Style: Colonial
  • Garage Parking Info: Attached Garage
  • Swimming Pool: No
  • Expected On Market Date: 09-24-2026
Building Information
  • Year Built: 2000
  • Lot Size: 7.55 AC / 328,878 SF
Summary
Property and Location
  • Acres Source: Public Records
  • 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)
  • Elementary School: Batcheller
  • Flood Zone: No
  • High School: Gilbert
  • Latitude: 41.917526
  • Longitude: -73.09912
  • Middle Jr High School: Pearson
  • Neighborhood Amenities: Lake, Library, Medical Facilities, Park, Playground/Tot Lot, Public Rec Facilities, Stables/Riding, Tennis Courts
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2026-June 2027
  • Property Tax: $8,400
Interior and Exterior Features
Exterior Features
  • Exterior Features: Porch-Screened, Underground Utilities, Shed, Barn, Deck, Gutters, Lighting, Stone Wall
  • Waterfront Description: View
Interior Features
  • Appliances Included: Electric Cooktop, Wall Oven, Microwave, Range Hood, Subzero, Dishwasher, Instant Hot Water Tap, Washer, Dryer
  • Attic Description: Storage Space, Floored, Pull-Down Stairs
  • Cooling System: Central Air, Split System
  • Heat Type: Baseboard, Hot Water, Zoned, Other
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Interior Features: Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan
  • Laundry Room Info: Main Level
  • Rooms Additional: Foyer, Laundry Room, Mud Room
  • Rooms Total: 8
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace,Hardwood Floor,L-Shaped
  • Room Length: 15.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 13.0
Room 2
  • Room Entry Order: 2
  • Room Features: Hardwood Floor
  • Room Length: 15.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 13.0
Room 3
  • Room Entry Order: 3
  • Room Features: French Doors,Hardwood Floor
  • Room Length: 14.0
  • Room Level: Main
  • Room Type: Study
  • Room Width: 13.0
Room 4
  • Room Entry Order: 4
  • Room Features: Corian Counters,Full Bath,Hardwood Floor,Tile Floor,Walk-In Closet
  • Room Length: 17.0
  • Room Level: Upper
  • Room Type: Primary BR Suite
  • Room Width: 15.0
Room 5
  • Listing Key: 5C09DDDC872415EAE0631A01100A76AE
  • Room Entry Order: 5
  • Room Features: Hardwood Floor
  • Room Length: 13.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 13.0
Room 6
  • Room Entry Order: 6
  • Room Features: Hardwood Floor
  • Room Length: 13.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 10.0
Room 7
  • Room Entry Order: 7
  • Room Features: Cathedral Ceiling,Ceiling Fan
  • Room Length: 27.0
  • Room Level: Upper
  • Room Type: Family Room
  • Room Width: 21.0
Property
Property and Assessments
  • Construction Description: Frame
  • Exterior Siding: Vinyl Siding
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Property Info: Horse Property
  • Roof: Asphalt Shingle, Gable
  • Year Built: 2000
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Sq Ft Est Heated Below Grade: 0
  • Living Area SQFT Per Public Records: 2943
Lot Information
  • Lot Description: Fence - Partial, Fence - Stone, Secluded, Some Wetlands, Lightly Wooded, Water View
  • Parcel Number: 2329588
  • Sq Ft Est Heated Above Grade: 2943.0
  • Sq Ft Total: 2943.0
  • Zoning: RU-1
Utilities
  • Energy Features: Generator, Programmable Thermostat, Thermopane Windows
  • Heat Fuel Type: Oil
  • Hot Water Description: 50 Gallon Tank
  • Radon Mitigation Air: Yes
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 359 Winchester Road

DateEvent & SourcePriceAppreciation
Aug 13, 2021

Closed (Public Record)

Public Record #1469682669

$653,500

+3.2% / yr

Jan 6, 2004

Closed (Public Record)

Public Record #131247948

$378,500—
DateEvent & SourcePrice
08/13/2021

Closed (Public Record)

Public Record #1469682669

$653,500

+3.2% / yr

01/06/2004

Closed (Public Record)

Public Record #131247948

$378,500

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 359 Winchester Road

Taxable ValueLand$83,300Additions$272,300Total$355,600
Tax Record2025$10,373 ($864 / month)
Home Facts
Beds3Baths3.5Total Finished SqFt2,943 SqFtAbove Grade Finished SqFt2,943 SqFtUnfinished Basement SqFt440 SqFtStories2Lot Size328,878 SqFtStyleSingle Family ResidenceYear Built2000Year Renovated2000ZoningRU-1CountyNORTHWEST HILLSAPNWSTR M:027 B:153 L:006F

Schools near 359 Winchester Road

This home is within Winchester School District.
Rating
School
Type
Grades
Distance
Pearson Middle School
Public - 2 to 6
Able School
Public - 1 to 4
Mary P. Hinsdale School
Public - PK to 2
St Anthony School
Private - PK to 8
Rating
School
Distance
Pearson Middle School
Public2 to 6

Able School
Public1 to 4

Mary P. Hinsdale School
PublicPK to 2

St Anthony School
PrivatePK to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 359 Winchester Road, Winchester, CT 06098

359 Winchester Road is a single family home for sale in Winchester, CT 06098. This listing's school district is Winchester School District. Nearby schools include Pearson Middle School, Able School and Mary P. Hinsdale School. 359 Winchester Road is a 3-bed, 3-bath, 2,943 sqft single family home built in 2000.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Pitt Sotheby's Int'l, Catherine A McCahill

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.