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$850,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 3 Full Baths
  • 2,943 Sq. Ft.
  • 2 Car Garage
  • Updated 2 days ago
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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.

Full Property Details for 359 Winchester Rd

General

  • Price: $850,000
  • Taxes: (July 2026-June 2027)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24208872
  • Updated: 9/24/2026
  • Added to Site: 2 day(s) ago

Interior

  • Number of Rooms: 8
  • Rooms/Areas: Foyer, Laundry Room, Mud Room
  • Interior Features: Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Electric Cooktop, Wall Oven, Microwave, Range Hood, Subzero, Dishwasher, Instant Hot Water Tap, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 3
  • Primary Suite: Corian Counters, Full Bath, Hardwood Floor, Tile Floo, 17 x 15, Upper
  • Bedroom 1: Bedroom - Hardwood Floor, 13 x 10, Upper
  • Bedroom 2: Bedroom - Hardwood Floor, 13 x 13, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, Hardwood Floor, L-Shaped, 15 x 13, Main
  • Family Room: Family Room - Cathedral Ceiling, Ceiling Fan, 27 x 21, Upper
  • Dining Room: Dining Room - Hardwood Floor, 15 x 13, Main
  • Study: French Doors, Hardwood Floor, 14 x 13, Main
  • Laundry: Main Level

Exterior

  • Exterior Features: Porch-Screened, Underground Utilities, Shed, Barn, Deck, Gutters, Lighting, Stone Wall

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: Litchfield
  • Neighborhood: Winsted
  • Driving 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)

School Information

  • Elementary School: Batcheller
  • Middle School: Pearson
  • High School: Gilbert

Community

  • Community Name: Winsted

Heating & Cooling

  • Cooling Type: Central Air, Split System
  • Heating Type: Baseboard, Hot Water, Zoned, Other, Oil
  • Heating Fuel: Oil
  • Water Heater: 50 Gallon Tank

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Description/Design: Horse Property
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Full, Unfinished, Storage, Full With Walk-Out
  • Roof: Asphalt Shingle, Gable
  • Attic: Yes
  • Square Feet: 2,943
  • Above Ground: 2,943 Sq. Ft.
  • Year Built: 2000

Lot Features

  • Lot Size (Acres): 7.55
  • Zoning: RU-1
  • Lot Description: Fence - Partial, Fence - Stone, Secluded, Some Wetlands, Lightly Wooded, Water View

Horse Property

  • Horse Property: Yes

Water Features

  • Water Front Desc.: View

Green Features

  • Energy Features: Generator, Programmable Thermostat, Thermopane Windows

Financial Considerations

  • Assessment Amount: $355,600
  • Tax Year: July 2026-June 2027

Disclosures and Reports

  • Property ID: 2329588

Listed by William Pitt Sotheby's Int'l, Catherine McCahill

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Listing agent

— 359 Winchester Rd —

  • Catherine McCahill

    William Pitt Sotheby's Int'l

Agent Contact: (860) 480-6760 Office Contact: (860) 777-1800

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 359 Winchester Rd

School District:Winchester School District
NameGradesDistance
Batcheller Early Education Center
201 Pratt Street, Winsted, CT 06098
PK-21.3 mi
Pearson Middle School
2 Wetmore Avenue, Winsted, CT 06098
3-61.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 359 Winchester Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/24/2026
Listed
$850,000
30.07%
MLS
8/13/2021
Sold
$653,500
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 359 Winchester Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$10,373
7%
$355,600
—
2023
$9,687
3%
$355,600
—
2023
$9,384
10%
$355,600
40%
2022
$8,520
1%
$254,030
1%
2021
$8,400
—
$250,460
—
2020
$8,400
—
$250,460
—
2019
$8,400
—
$250,460
—
2018
$8,400
8%
$250,460
8%
2017
$7,787
—
$232,160
—
2016
$7,787
3%
$232,160
—
2015
$7,592
2%
$232,160
—
2014
$7,408
2%
$232,160
—
2011
$7,243
—
$232,160
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 359 Winchester Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by William Pitt Sotheby's Int'l, Catherine McCahill

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359 Winchester Road, Winchester, CT 06098 (MLS# 24208872) is a Single Family property with 3 bedrooms and 3 full bathrooms. 359 Winchester Road is currently listed for $850,000 and was received on September 24, 2026. Want to learn more about 359 Winchester Road? Do you have questions about finding other Single Family real estate for sale in Winsted? You can browse all Winsted real estate or contact a Coldwell Banker agent to request more information.

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