50 Overlook Road
Winchester, Connecticut 06098
- Beds
- 3
- Baths
- 1
- SqFt
- 1,488
- Acres
- 0.97
- Year Built
- 1949
- Neighborhood
- Winsted
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Lovingly maintained by the same family since it was built in 1949, this 3-bedroom Colonial offers approximately 1,500 sq. ft. of living space on a 1-acre lot on the outskirts of town, yet within walking distance to the beach at Highland Lake. The main level features a spacious living room, large kitchen, dining room, full bath and inviting 3-season porch. Upstairs are three comfortable bedrooms with ample closet space. Hardwood floors run throughout the home, adding to its classic charm. Energy-conscious features include three heating sources: an oil-fired boiler, pellet stove in the living room and a magnificent soapstone wood stove in the lower level. The home also offers plenty of insulation, thermopane windows and a roof installed in 2021. Outside, you'll find excellent garage and storage space, including a large barn/garage with room for vehicles and a workshop, plus an additional detached garage. Set on nearly an acre with convenient access to Highland Lake and town amenities, this well-cared-for home is ready for its next chapter. This one is worth seeing!
Key Facts
- City/Town
- Winchester
- Neighborhood
- Winsted
- Property / Style
- Single Family · Colonial
- Year Built
- 1949
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 1 full
- Living Area
- 1,488 sq ft
- Lot Size
- 0.97 acres
- Garage / Parking
- 3 garage · 8 total
- Property Taxes
- $4,284 / Annually
Market Snapshot
The Winchester Market
Single Family · trailing 12 months
Active Listings
22
11 under contract
Median List Price
$417,500
22 active listings
Median Closed Price
$340,500
92 sales
Median Days on Market
32
22 active listings
Median $ / Sq Ft
$272
22 active listings
Sale-to-List Ratio
100.0%
92 sales
How this home compares
List Price
$339,900
vs $417,500 median
18.6% below median
Price / Sq Ft
$228
vs $272 median
16.2% below median
Days on Market
0 days
vs 32 days median
32 days fresher than median
Based on 22 active and 92 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of September 26, 2026.
Location
50 Overlook Road, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 24, 2026per month
- Principal & Interest$1,815
- Property Taxes$357
- Insurance$113
- 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
- Colonial
- Year Built
- 1949
- New Construction
- No/Resale
- Living Area
- 1,488 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Gilbert
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- None
- Laundry
- Lower Level
- Appliances
- Oven/RangeRefrigeratorWasherDryer
- Basement
- FullConcrete FloorFull With Hatchway
- Interior Features
- Cable - Available
Exterior & Lot
- Lot Size
- 0.97 acres
- Zoning
- TSF
- Garage / Parking
- 3 garage spaces8 total parking spacesBarnDetached GarageOff Street Parking
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- BlockConcrete
- Exterior Features
- Porch
- Lot Description
- Corner LotLightly WoodedLevel Lot
Listing & Financials
- Property Taxes
- $4,284 / Annually
- Days on Market
- 0
- MLS #
- 24210012
- MLS Status
- Active
- Financing
- FHA,VA,CHFA,USDA
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Amy Sartirana
Northwest CT Realty
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/26/2026. 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 9/26/2026 at 6:00 PM UTC.