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MLS 24210012 For Sale Updated September 28, 2026
50 Overlook Road

Winchester, Connecticut 06098

$339,900
On market 2 days
50 Overlook Road
1 / 36

About This Property

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!

Property Details

Interior

Heat
Hot Water — Oil
Cooling
None
Basement
Full,Concrete Floor,Full With Hatchway
Interior Features
Cable - Available

Exterior & Lot

Roof
Asphalt Shingle
Construction
Construction
Exterior Features
Porch
Lot Description
Corner Lot Lightly Wooded Level Lot
Garage & Parking
Barn Detached Garage Off Street Parking

Utilities & Systems

Water Source
Public Water Connected
Sewer
Public Sewer Connected
Energy Features
Generator Ready Thermopane Windows

Community & Schools

Elementary
Per Board of Ed
High
Gilbert
Neighborhood
Winsted
Nearby Amenities
Golf Course Lake Library Medical Facilities Park Public Transportation

Appliances

Included
Oven/Range Refrigerator Washer Dryer

50 Overlook Road

Winchester , Connecticut 06098

$339,900

On market 2 days

Beds
3
Baths
1
SqFt
1,488
Type
Single Family
County Litchfield
Garage 3
Rooms -
Lot Size 0.97 Acres
Property Tax $4,284
Assessed Value $142,800
Year Built 1949
Style Colonial
Zoning TSF
Parking Spaces 8

Payment Estimate

30-year fixed. Includes taxes; estimates only.

Estimated Monthly Payment
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Property Map

Map location is based on the property address.

Listing information is deemed reliable but not guaranteed and is sourced from the local MLS feed. Brokerage shown: NWCT40.

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