Winsted Homes under $250,000

Winsted Homes under $250,000

Welcome to Winsted, a charming neighborhood nestled within the picturesque town of Winchester, Connecticut. This hidden gem in Litchfield County offers a delightful blend of small-town charm and modern convenience, making it an ideal place to call home. With its rich history and vibrant community, Winsted is perfect for families, first-time homebuyers, and anyone looking to enjoy a peaceful lifestyle while still being close to urban amenities.

One of the standout features of Winsted is its affordability. With homes available for under $250,000, this neighborhood opens the door to homeownership for many who may have thought it out of reach. From quaint single-family homes to charming bungalows, Winsted offers a variety of properties that cater to different tastes and needs. Imagine settling into a cozy residence with a backyard garden or a charming front porch, perfect for sipping your morning coffee while enjoying the serene surroundings.

The community is rich in recreational opportunities, with nearby parks, hiking trails, and the scenic Highland Lake, providing ample options for outdoor enthusiasts. Additionally, Winsted boasts a strong sense of community, with local events and gatherings that foster connections among neighbors.

With its affordable housing options, welcoming atmosphere, and beautiful natural surroundings, Winsted is not just a place to live; it’s a place to thrive. Discover your dream home in this delightful neighborhood and experience all that Winsted has to offer!

Newest Winsted Homes under $250,000

111 Riverton Road Unit 22, Winchester
$204,900
2 Beds ⋅ 2 Baths ⋅ 24214904 MLS ⋅ Riverwalk BLDG.
An END-unit condo in the Riverwalk Complex which runs along the Still River. This end unit adds privacy and is loaded with lots of natural light. Includes an oversized two car garage with generous parking and storage. A new pellet stove for efficient, cozy heating - with extra pellets included. The hot water heater - only 4 years old. Carpets professionally cleaned - fresh and ready for the next owner. Chimney cleaned in May 2026 - recently serviced and ready to use. Pets allowed. Schedule your showing today!

111 Riverton Road Unit 22, Winchester
35 Prospect St, Winchester
$239,900
3 Beds ⋅ 1 Baths ⋅ 24210294 MLS
3 bedroom home offering comfortable living with the convenience of gas heat as well as a wood stove and main level laundry. The layout provides plenty of space for everyday living, relaxing, and entertaining. Enjoy Highland Lake with Resha Beach just a half mile away, perfect for summer days by the water. A short drive takes you to the nearby boat launch, making it easy to enjoy boating, fishing, and all that the area's lakes have to offer.

35 Prospect St, Winchester
Winchester
$239,000
7 Beds ⋅ 3 Baths ⋅ 24169258 MLS
Brand new to the market. Must see large 2 story Colonial featuring 13 rooms, 7 Bedrooms, 3 Bathrooms, Walk up attic and full basement. Includes a 2 story barn. Convenient location in the heart of town lends itself to easy access to many nearby amenities. As an investment this residence also has great potential to convert to a multi family home or could be renovated for commercial office space. The possibilities are endless. The barn has the capability for multiple uses as well such as a workshop, studio, office, storage or to just park vehicles.

Winchester
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The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

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