205 Perch Rock Trail
Winchester, Connecticut 06098
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,407
- Acres
- 0.17
- Year Built
- 1970
- Neighborhood
- Winsted
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Valued by Redfin at $497,000 and Realtor at $516,000 - this house is a gem! Welcome to 205 Perch Rock Trail, a spacious 4-bedroom, 2.5-bath home in the highly desirable Highland Lake area of Winsted. Offering an incredible combination of space, location, and value, this property is a rare opportunity for a buyer looking to create something special. The home needs renovations and is being sold As Is, but the potential is substantial.The home offers approximately 2,369 square feet of living space, including a finished lower level with a kitchenette and full bath - ideal for an in-law setup, guest suite, home office, recreation space, or extended-family living. Enjoy lake views, nearby water access, a private backyard, two fireplaces, a balcony, generous storage, and an under-house garage. Public water and public sewer. With 4 bedrooms, multiple living areas, and flexible lower-level space, the possibilities here are exceptional. Whether you are looking for a year-round residence, weekend lake retreat, renovation opportunity, or investment property, 205 Perch Rock Trail offers tremendous upside. Bring your vision and make this Highland Lake gem your own!
Key Facts
- City/Town
- Winchester
- Neighborhood
- Winsted
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1970
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 2,407 sq ft
- Lot Size
- 0.17 acres
- Garage / Parking
- 1 garage
- Property Taxes
- $8,100 / Annually
Market Snapshot
The Winchester Market
Single Family · trailing 12 months
Active Listings
23
13 under contract
Median List Price
$425,000
23 active listings
Median Closed Price
$341,000
91 sales
Median Days on Market
33
23 active listings
Median $ / Sq Ft
$256
23 active listings
Sale-to-List Ratio
100.0%
91 sales
How this home compares
List Price
$300,000
vs $425,000 median
29.4% below median
Price / Sq Ft
$125
vs $256 median
51.2% below median
Days on Market
0 days
vs 33 days median
33 days fresher than median
Based on 23 active and 91 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of September 29, 2026.
Location
205 Perch Rock Trail, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 24, 2026per month
- Principal & Interest$1,602
- Property Taxes$675
- Insurance$100
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Winchester
- Neighborhood
- Winsted
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Cape Cod
- Year Built
- 1970
- New Construction
- No/Resale
- Living Area
- 2,407 sq ft
Schools
- Elementary
- Per Board of Ed
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Baseboard
- Heat Fuel
- Electric
- Cooling
- Window Unit
- Fireplaces
- 2
- Appliances
- None
- Basement
- Full
Exterior & Lot
- Lot Size
- 0.17 acres
- Zoning
- HL
- Garage / Parking
- 1 garage spaceAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $8,100 / Annually
- Days on Market
- 0
- MLS #
- 24210637
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/29/2026. This information 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 or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 9/29/2026 at 5:55 PM UTC.