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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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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

94 Colony  Drive, Winchester image
94 Colony Drive, Winchester $239,900

Well maintained Cape with private fenced in back yard and attached garage eat in kitchen with fireplaced den two full baths public utilities and a short distance to sho...

  • 2 Beds
  • 2 Baths
  • 170481492 MLS
24 High  Street, Winchester image
24 High Street, Winchester $129,000

Incredible opportunity to transform this beautiful 3 bedroom, 1.5 bath colonial into your perfect home! The main level offers a large kitchen, a formal dining room, a liv...

  • 3 Beds
  • 2 Baths
  • 170491156 MLS
78 Gay  Street, Winchester image
78 Gay Street, Winchester $149,900

This lovely, well maintained 3 bed, 1 full bath cape boasts over 1100 sqft of living space and is located in the Winsted neighborhood of Winchester. This home is perfect ...

  • 3 Beds
  • 1 Baths
  • 170490059 MLS
496 Main  Street, Winchester image
496 Main Street, Winchester $99,900

Own a piece of Winsted history! Original Railroad Car Diner transferred from New Rochelle, NY. In business since 1931. High traffic area. Tremendous opportunity for a tak...

  • 170490833 MLS
21-31 Charles  Street, Winchester image
21-31 Charles Street, Winchester $199,900

two family home in a great location, updated and well maintained. Just a short drive to Highland lake. Secluded and private large flat lot. All public and separate utili...

  • 4 Beds
  • 2 Baths
  • 170487732 MLS
108 Riverton  Road, Winchester image
108 Riverton Road, Winchester $39,900

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
874 West Wakefield  Boulevard, Winchester image
874 West Wakefield Boulevard, Winchester $875,000

Looking for your year round retreat? This builder/designer's immaculate home is set in a private cove waterside. A lifetime of memories will be made here. Newly built, t...

  • 3 Beds
  • 2 Baths
  • 170486677 MLS
807 East Wakefield  Boulevard, Winchester image
807 East Wakefield Boulevard, Winchester $269,000 ▼

Standing proud on a picturesque 0.23-acre lot and showcasing shimmering views of Highland Lake is this gorgeous single-family home. This three-bedroom, 2.5-bathroom layou...

  • 3 Beds
  • 3 Baths
  • 170483799 MLS
227 Walnut  Street, Winchester image
227 Walnut Street, Winchester $225,000

Great Income Potential! Second floor recently updated. Two 3 Bedroom units, 2 car garage. Close to town.

  • 6 Beds
  • 2 Baths
  • 170486928 MLS
347 West Wakefield  Boulevard, Winchester image
347 West Wakefield Boulevard, Winchester $159,900

This "turn-key" quaintly decorated cottage that sits high above West Wakefield Blvd. directly across from the lake. Initial entry into the "oversized" screened porch offe...

  • 2 Beds
  • 1 Baths
  • 170479874 MLS
142 Main  Street, Winchester image
142 Main Street, Winchester $379,900

Great investment property, in beautiful Downtown Winchester Connecticut.

  • 170484455 MLS
230 Coe  Street, Winchester image
230 Coe Street, Winchester $199,900

Cute colonial style farm house. Quaint kitchen, dining room with built ins, and living room with natural wood burning fire place. First floor full bathroom and laundry. ...

  • 2 Beds
  • 1 Baths
  • 170484695 MLS
715 West Wakefield  Boulevard, Winchester image
715 West Wakefield Boulevard, Winchester $599,900

Welcome to 715 West Wakefield Blvd. located on Highland Lake! This property feels like a private getaway. It is tucked back from the road, overlooking the Third Bay, and ...

  • 4 Beds
  • 2 Baths
  • 170480057 MLS
113 Chapel  Road, Winchester image
113 Chapel Road, Winchester $459,900

Great opportunity to own this well cared for Cape in Winchester! Peace and quiet surround this hidden gem. Open floor plan with fireplace and eat in kitchen. Beautiful wo...

  • 4 Beds
  • 2 Baths
  • 170479300 MLS
66 Munro  Place, Winchester image
66 Munro Place, Winchester $550,000

"THE GOVERNOR'S MANSION" circa 1896 Home of Governor Lorrin A. Cooke 1896-1899 is located in Winsted Connecticut in a historic neighborhood on .4 acres, just a half-mil...

  • 5 Beds
  • 3 Baths
  • 170472423 MLS
118 & 130 Main  Street, Winchester image
118 & 130 Main Street, Winchester $479,000

Single story 3660 square foot building with full basement and 22 car parking lot. This amazing building and location are prime to continue as retail or transform into off...

  • 170474427 MLS
294 Main  Street, Winchester image
294 Main Street, Winchester $425,000

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 st...

  • 170472951 MLS
57 Main  Street, Winchester image
57 Main Street, Winchester $350,000

The home of Winsted's only dry cleaner is now for sale. With no competition in the area it might be the right time to give this a shot. If you don't want to be in that bu...

  • 170472295 MLS
3 Carey  Avenue, Winchester image
3 Carey Avenue, Winchester $199,900

Rare Opportunity to own prime location on Highland lake in the highly desired Berkshire mountains of Litchfield County. Located within a 5 minute walk to Resha Beach (unl...

  • 3 Beds
  • 2 Baths
  • 170471932 MLS
206 Smith Hill  Road, Winchester image
206 Smith Hill Road, Winchester $53,900

3.8 Acres with its own private pond for sale. Located close to town yet has plenty of privacy, with over almost 500 feet of road frontage

  • 170471833 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 2022 SmartMLS, Inc.

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Mike Gregor | Realtor®
Cohen Agency SiM, LLC
535 Main Street, P.O. Box 1003, New Hartford, CT 06057
Tel: (860) 866-7470 | e-mail: mike@sellitmike.com

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