50 Overlook Road Winchester, CT $ 339,900
50 Overlook Road
$ 339,900
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50 Overlook Road

Winchester, CT, 06098
$ 339,900
Bedrooms3 Baths1.0 Sq 1,488

Monthly Estimate*

$ 2,146

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Single Family Home for sale in Winchester, CT

for $339,900 with 3 bedrooms and 1 full bath. This 1,488 square foot home was built in 1949 on a lot size of 0.97.

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!

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Single Family Active

Price

$ 339,900

Bedrooms

3

Full Bath

1

Property Type

Single Family

Taxes

$ 4,284

Style

Lot Size

0.97

Year Built

1949

Town/City

Winchester

MLS | Web ID

24210012

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 10
Year Built 1949
Style Colonial
Year Built Source Public Records
Energy Features Generator Ready Thermopane Windows
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Interior
Cooling System None
Total Rooms 7
Basement Description Full Concrete Floor Full With Hatchway
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Exterior
Water Source Public Water Connected
Lot Description Corner Lot Lightly Wooded Level Lot
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* Excluded Features
List By
David Sartirana

Listing Agent

Northwest Ct Realty

Broker

dsart3@hotmail.com

Email

Affordability Calculator

$2,503
Per Month
86%
14%
0%
Monthly Principal & Interest
$2,146
Monthly Property Taxes
$357
Monthly Home Insurance
--
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.
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Nearby
2060047 Elementary School
1415485 Middle School
Gilbert High School High School
Pricing History
DatePricePrice ChangeDescription
9/26/2026$339,900 Listed Price

Map


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50 Overlook Road, Winchester, CT, 06098 is a Single Family Home for sale at $339,900 with 1,488 sqft and a lot size of 0.97. 50 Overlook Road has 3 bedrooms, 1.0 baths, and was built in 1949. The property's zip code is 06098 which is in Winchester, CT