Breeya Evans

50 Overlook Road

Winchester, CT
$ 339,900 Beds 3 Baths 1 Sq 1,488
Monthly Estimate* How much can I afford?

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!

Single Family

  • Price
  • $ 339,900
  • City
  • Winchester
  • Bedrooms
  • 3
  • Full Bathrooms
  • 1
  • County
  • Litchfield
  • Half Bathrooms
  • 0
  • Area
  • Lot Size
  • 0.97 Acres
  • Zip
  • 06098
  • Sqr Footage
  • 1,488
  • Year Built
  • 1949
  • Taxes
  • $ 4284
  • Style
  • MLS#
  • 24210012
Listed By: David Sartirana 860-806-0225 with Northwest CT Realty. - (860) 379-7245
Data Source: Smart MLS

Features

General

Zoning TSF
Neighborhood Winsted
County Litchfield
Tax Year July 2026-June 2027
Property Type Single Family For Sale
Status Active
Acres 0.97
Directions 50 Overlook Rd
High School Gilbert
City Winchester
Elementary School Per Board of Ed
Sq Ft Total 1488
DOM 1
Year Built 1949
Style Colonial
Year Built Source Public Records
Energy Features Generator Ready,Thermopane Windows

Interior Features

Cooling System None
Total Rooms 7
Basement Description Full,Concrete Floor,Full With Hatchway

Exterior Features

Water Source Public Water Connected
Lot Description Corner Lot,Lightly Wooded,Level Lot

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Torrington, CT office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Per Board of Ed Elementary School
Middle School Unknown Middle School
High School Gilbert High School

Price History

9/26/2026 Listed $339,900

Property vs Zip Code Average in 06098

Price
AVG $560K
$340K
Taxes
AVG $7,322
$4,284
Year Built
AVG 1943
1949

In The Neighborhood

Areas That We Cover

50 Overlook Road Winchester, CT is a Single Family Home for sale at $339900 with 1488 sqft and a lot size of 0.97 Acres Acre(s). 50 Overlook Road Winchester has 3 bedrooms, 1 baths and was built in 1949. The property's zip code is 06098 which is in Winchester, CT

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site 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.

Breeya Evans

Breeya Evans

914-893-7116

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