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    Winchester, CT Real Estate

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    Homes For Sale In Winchester, CT

    Browse current homes for sale in Winchester, CT. Can't find a home that fits your needs? Try our Advanced MLS search. You can easily filter properties by location, price, amenities, and more to find exactly what you're looking for.

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    Explore Homes for sale in Winchester with our interactive MLS Map

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    Gearing up to buy or sell a home soon in Winchester? Call Mike Gregor at (860) 866-7470. Your Winchester realty team is here to help navigate the Winchester real estate market.

    Homes for Sale in Winchester, CT

    52 Overlook  Road, Winchester image
    52 Overlook Road, Winchester $279,900

    Come enjoy this spacious home with large eat in kitchen and living room. 2-3 bedrooms. Front porch facing Highland Lake perfect for relaxing. Home was just hooked up to c...

    • 2 Beds
    • 2 Baths
    • 170557057 MLS
    139 Boyd  Street, Winchester image
    139 Boyd Street, Winchester $249,900

    Very nice duplex style home features 2 units . Left side unit has 5 rooms 2 bedrooms and gas heat . Right side unit has 4 rooms 2 bedrooms and gas heat . The basement is ...

    • 4 Beds
    • 2 Baths
    • 170554262 MLS
    . Norwood  Road, Winchester image
    . Norwood Road, Winchester $14,500 ▲

    Ideal location for storing your boat, rv or any other toys that take up garage space. 25x100 lot

    • 170553198 MLS
    _ Norwood  Road, Winchester image
    _ Norwood Road, Winchester $8,990

    Ideal location for storing your boat, rv or any other toys that take up garage space. 25x100 lot

    • 170552729 MLS
    522 West Wakefield  Boulevard, Winchester image
    522 West Wakefield Boulevard, Winchester $899,900

    LOCATION! LOCATION! LOCATION! Direct Waterfront Lake Property on a VERY RARE 1 ACRE level & private CORNER LOT with tons of parking on the highly sought after pristine, g...

    • 2 Beds
    • 1 Baths
    • 170551900 MLS
    66 Spencer Hill  Road, Winchester image
    66 Spencer Hill Road, Winchester $59,000

    Tired of LOOKING for a home ????? Here is a Rare Opportunity to Build a New Home rather than settling for choices in Existing Home inventory . Surveyed .6 Acre Building ...

    • 170551219 MLS
    18-4A Taylor Brook  Road, Winchester image
    18-4A Taylor Brook Road, Winchester $650,000

    Beautiful custom built gem situated on a private site with a stream! Bright, sunny open floor plan with 3 bedrooms, 2.5 baths, great bonus room. Gleaming hardwood floors ...

    • 3 Beds
    • 3 Baths
    • 170551066 MLS
    44 Spencer  Street, Winchester image
    44 Spencer Street, Winchester $339,999 ▼

    This 3 bedroom 1.5 bathroom Victorian home with over 2000 sq ft of living is ready for its new owners. Many recent updates, and this home still has gorgeous original feat...

    • 3 Beds
    • 2 Baths
    • 170549265 MLS
    146 Spencer Hill  Road, Winchester image
    146 Spencer Hill Road, Winchester $544,900 ▼

    Built to Last! Nicely updated Colonial with in law potential and mountainviews. This property features 5 beds, 4 baths, over 3200 square feet of living space, an eat-in k...

    • 5 Beds
    • 4 Baths
    • 170547725 MLS
    216 South  Road, Winchester image
    216 South Road, Winchester $749,000 ▼

    Situated on 2.5 mostly level and cleared acres, you will find this custom built dream home, where no detail has been missed. Drive up the paved driveway lined with cobble...

    • 4 Beds
    • 3 Baths
    • 170545911 MLS
    981 Main  Street, Winchester image
    981 Main Street, Winchester $699,000

    7+ Acres. Split on two sides of River. (roughly 3 acres & 4 acres). Long frontage on RTE 44. Includes historic barn (ex-firehouse?) at 161 Meadow Sytreet. Includes ci...

    • 170547550 MLS
    232 Perch Rock  Trail, Winchester image
    232 Perch Rock Trail, Winchester $659,900 ▼

    LOCATION! LOCATION! LOCATION! This 4 bed, 2 bath, 4 season home is located on a quiet side street directly on Highland Lake. Public records list it as a 2 family home, t...

    • 4 Beds
    • 2 Baths
    • 170542297 MLS
    57 Main  Street, Winchester image
    57 Main Street, Winchester $350,000

    Well established cleaners on very busy Main St location . Lots of visibility.   Right next to McDonalds, CVS, and College.  Downtown Winsted right across from town green....

    • 170534633 MLS
    208 Coe  Street, Winchester image
    208 Coe Street, Winchester $725,000 ▼

    Welcome to "THE OVERLOOK" Aptly named as it overlooks a gently sloping vast yard complete with fruit trees, tiki hut, garden shed, and the Indian Meadow Stream. An amazi...

    • 5 Beds
    • 6 Baths
    • 170533300 MLS
    01 Rowley  Street, Winchester image
    01 Rowley Street, Winchester $50,000

    Looking for excess land @ 4,000 an acre? This is your opportunity to purchase land for your outdoor enjoyment. Large trees, steep slope. See sign on Rowley St - Zones TG ...

    • 170533254 MLS
    294 Main  Street, Winchester image
    294 Main Street, Winchester $375,000

    Right in the center of downtown is this immaculate commercial property. Anchored by a busy little pharmacy, this property offers some very versatile spaces. Lots of off s...

    • 170531528 MLS
    232 Perch Rock  Trail, Winchester image
    232 Perch Rock Trail, Winchester $659,900 ▼

    LOCATION! LOCATION! LOCATION! This 4 bed, 2 bath, 4 season home is located on a quiet side street directly on Highland Lake. Public records list it as a 2 family home, t...

    • 4 Beds
    • 2 Baths
    • 170526283 MLS
    90 Reaching Hill  Road, Winchester image
    90 Reaching Hill Road, Winchester $40,000

    Get a piece of land in an amazing location. This property is overlooking one of the prettiest and most popular lakes in CT. Private spot with tons of potential. This pro...

    • 170524468 MLS
    19 Walnut  Street, Winchester image
    19 Walnut Street, Winchester $230,000 ▼

    This single-owner home is ready to be brought into the 21st century revitalization in the historic architectural community of Winchester where: local shops, Northwestern ...

    • 4 Beds
    • 3 Baths
    • 170522595 MLS
    108 Riverton  Road, Winchester image
    108 Riverton Road, Winchester $34,900 ▲

    Great lot to build your home or investment property. Close to route 8 and to downtown area of Winsted. Blueprint available for a septic plan that has building approval. ...

    • 170488953 MLS

    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 2023 SmartMLS, Inc.

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