Winchester, CT Real Estate
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Homes For Sale In Winchester, CT
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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
An exceptional opportunity to create your dream home on the shores of highly sought-after Highland Lake. This waterfront property at 414 E Wakefield Boulevard offers the ...
- 24196886 MLS
Bring your horses home! There's something special about country living-stepping outside with your coffee, seeing your horses grazing, hearing the chickens scratching arou...
- 3 Beds
- 2 Baths
- 24204002 MLS
Welcome to this relaxing seasonal cottage, situated high above road level and offering breathtaking panoramic views of the 444-acre Highland Lake. Enter through the overs...
- 2 Beds
- 1 Baths
- 24202928 MLS
Welcome to 136 Losaw Rd! Built in 1984, this nicely maintained and updated home offers 1,977 sq. ft. of living space with 4 bedrooms, 2 full baths, and a comfortable open...
- 4 Beds
- 2 Baths
- 24202969 MLS
Enjoy beautiful water views and access to Highland Lake from this inviting home offering comfortable living spaces and desirable features throughout. The main level featu...
- 2 Beds
- 2 Baths
- 24201785 MLS
Investment Opportunity! Well-maintained two-family house offering the ideal combination of functionality and income potential. Each unit features 5 rooms, including 2 bed...
- 4 Beds
- 3 Baths
- 24199882 MLS
Enjoy the best of Highland Lake living with this unique property offering a spacious home directly across the street from the lake along with your own separate waterfront...
- 3 Beds
- 2 Baths
- 24199152 MLS
Welcome home to this beautifully maintained 2bedroom Cape offering the perfect blend of comfort, character, and modern updates. Set in a soughtafter neighborhood, this pr...
- 2 Beds
- 2 Baths
- 24201146 MLS
New Construction - Easy to Maintain - Open Floor Plan - Central Air - Vinyl Plank flooring throughout. White Shaker Kitchen with Island and granite countertops. All stain...
- 2 Beds
- 1 Baths
- 24200816 MLS
Welcome to this beautifully crafted 3,486 sq. ft. Colonial, offering exceptional quality, thoughtful design, and plenty of space both inside and out. Set privately on 2.0...
- 4 Beds
- 3 Baths
- 24200204 MLS
Well-maintained two-family home offering spacious apartments, separate utilities, and a convenient location within walking distance to downtown amenities. The first-floor...
- 4 Beds
- 2 Baths
- 24199721 MLS
Experience an everyday vacation at 804 W. Wakefield Blvd on beautiful Highland Lake! This exceptional turnkey, year-round waterfront retreat is ideal as a primary residen...
- 2 Beds
- 1 Baths
- 24195283 MLS
Nestled along the coveted east shore of Highland Lake, 600 East Wakefield Boulevard presents a rare opportunity to own a piece of one of Connecticut's most sought-after w...
- 2 Beds
- 1 Baths
- 24198153 MLS
Well-maintained 4-bedroom Colonial tucked away on a quiet dead-end street. This inviting home features a newly renovated eat-in kitchen with updated cabinetry, countertop...
- 4 Beds
- 2 Baths
- 24196702 MLS
Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access ...
- 4 Beds
- 2 Baths
- 24191163 MLS
Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access ...
- 4 Beds
- 2 Baths
- 24191186 MLS
Flexible Commercial Building Medical * Office * Wellness * Redevelopment Opportunity 1 Lake Street presents a rare opportunity to acquire a highly adaptable commercial ...
- 3 Baths
- 24191570 MLS
Where Opportunity Meets Lifestyle! Unlock the potential of this exceptional mixed-use property located in the heart of downtown Winsted. Positioned on a bustling Main Str...
- 3 Beds
- 2 Baths
- 24190347 MLS
Please submit your client's highest and best offer by Sunday 07/19 at 3:00 PM. Beautifully remodeled and move-in ready, 195 Reaching Hill Rd in Winsted, CT features moder...
- 3 Beds
- 2 Baths
- 24190790 MLS
Build Your Dream Retreat in Litchfield County! Escape the noise and pace of the city and discover 6.18 private wooded acres nestled in the scenic hills of Winchester, Con...
- 24188290 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 2026 SmartMLS, Inc.