Winchester Real Estate

Winchester Real Estate

Welcome to Winchester, Connecticut – a hidden gem nestled in the heart of Litchfield County. This picturesque town, steeped in history and natural beauty, offers a perfect blend of small-town charm and modern convenience. With its serene lakes, lush forests, and rolling hills, Winchester is a haven for outdoor enthusiasts and families alike.

At the center of the community lies the stunning Lake Winchester, a popular destination for swimming, fishing, and boating during the warm summer months. The surrounding parks and nature trails provide ample opportunities for hiking, biking, and enjoying the breathtaking scenery that each season brings. Whether you're taking a leisurely stroll through the quaint downtown area or exploring the expansive parks, the natural beauty of Winchester is sure to captivate you.

Winchester boasts a rich historical background, with landmarks that tell the story of its past. The town is home to several charming historical buildings, including the elegant Winchester Center and the iconic Town Hall, which reflect the architectural beauty of yesteryear. The local community is warm and welcoming, with a vibrant calendar of events that bring residents together throughout the year, from farmers' markets to seasonal festivals.

For families, Winchester offers a strong sense of community and excellent educational opportunities, with well-regarded schools that prioritize student success. With its convenient location just a short drive from larger cities, residents enjoy the peace of suburban living while still having easy access to urban amenities.

Discover the unique allure of Winchester, CT – where history, nature, and community come together to create an idyllic place to call home.

Newest Listings in Winchester

19 Walnut St, Winchester
$285,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24217238 MLS
Offering over 2,800 square feet of living space and 11 rooms, this spacious home in Winsted CT, presents a fantastic opportunity for homeowners, investors, or anyone looking to add value. Recent updates include a newly installed kitchen and a new roof in 2025, complete with solar to help offset electricity costs. Conveniently located close to downtown, you'll enjoy easy access to local shops, restaurants, and everyday amenities. With generous space, major updates already completed, and a little additional work, this property has the potential to become a wonderful home or a rewarding investment.

19 Walnut St, Winchester
264 Florence St, Winchester
$265,000
3 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24213670 MLS
Charming 3 bedroom 2 bath Cape, Oil heat with Natural gas connected if you'd prefer to switch over at some point. Nicely landscaped yard, repl windows, propane insert fireplace, wood floors, wired for a portable generator, new garage door (2025), furnace (2003), hot water heater (2026), 100 amp service, Central air. Well established, wonderful neighborhood, priced to sell. Rare opportunity to downsize or realize the dream of your 1st home!

264 Florence St, Winchester
240 Florence St, Winchester
$264,900
2 Beds ⋅ 1 Baths ⋅ COMING SOON Status ⋅ 24213928 MLS
Make yourself at home while exploring the possibilities this property has to offer. Fresh paint in both bedrooms, the bathroom, and hallway, along with refinished hardwood floors in both bedrooms, gives the interior a refreshed feel. Enjoy the enclosed porch, three garage spaces for vehicles or hobbies, and a spacious unfinished attic with potential for additional living space additional living space. Features include replacement windows, 200-amp electrical service, an on-demand hot water heater, and a furnace installed in 2016. Home is generator ready. The sale includes two 0.55-acre parcels totaling approximately 1.10 acres, offering additional outdoor space to enjoy. Enjoy privacy, an expansive yard, and room to garden in a convenient Winsted location. Existing garden beds offer a head start for growing vegetables or flowers, with plenty of outdoor space for entertaining or simply relaxing.

240 Florence St, Winchester
111 Riverton Road Unit 22, Winchester
$195,000
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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
Winchester
$950,000
ACTIVE Status ⋅ 24214621 MLS
Tucked away in one of New England's most untouched pockets, Grantville Meadows presents a rare 60+ acre canvas designed for complete privacy, creative restoration, or an inspired architectural vision. Sited just over two hours from New York City and Boston, it offers an escape while keeping you minutes from the historic mill towns of Winsted and Torrington - home to cultural spots, independent shops, diverse dining, and industrial heritage. Nearby Norfolk offers live music at Yale's Music Shed and Infinity Hall, and craft brews with views at Norbrook Farm Brewery. The Berkshires and Hudson Valley are within easy reach - just 7 miles to the Massachusetts border. Bordered by conserved Nature Conservancy land and the Mad River, the setting delivers total seclusion. The land unfolds across rolling meadows, antique stone walls, tapped sugar maples, woodland trails, and a natural swimming hole. At the edge of the grounds stands an antique farmhouse. Brimming with irreplaceable character, it features wide-plank floors, four fireplaces, and bay windows framing sweeping pastoral views. Whether you restore the antique home or build a bold retreat along the ridge-line, the groundwork is done. Perc tests and perimeter surveys are complete, alongside a 30 kW solar array with battery storage generating a substantial surplus. Hold over 60 acres as a sanctuary, tap syrup, or run the organic farm. Grantville Meadows is a rare chance to build something lasting in Litchfield County.

Winchester
139 Grantville Rd, Winchester
$950,000
5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24213967 MLS
Tucked away in one of New England's most untouched pockets, Grantville Meadows presents a rare 60+ acre canvas designed for complete privacy, creative restoration, or an inspired architectural vision. Sited just over two hours from New York City and Boston, it offers an escape while keeping you minutes from the historic mill towns of Winsted and Torrington - home to cultural spots, independent shops, diverse dining, and industrial heritage. Nearby Norfolk offers live music at Yale's Music Shed and Infinity Hall, and craft brews with views at Norbrook Farm Brewery. The Berkshires and Hudson Valley are within easy reach - just 7 miles to the Massachusetts border. Bordered by conserved Nature Conservancy land and the Mad River, the setting delivers total seclusion. The land unfolds across rolling meadows, antique stone walls, tapped sugar maples, woodland trails, and a natural swimming hole. At the edge of the grounds stands an antique farmhouse. Brimming with irreplaceable character, it features wide-plank floors, four fireplaces, and bay windows framing sweeping pastoral views. Whether you restore the antique home or build a bold retreat along the ridge-line, the groundwork is done. Perc tests and perimeter surveys are complete, alongside a 30 kW solar array with battery storage generating a substantial surplus. Hold over 60 acres as a sanctuary, tap syrup, or run the organic farm. Grantville Meadows is a rare chance to build something lasting in Litchfield County.

139 Grantville Rd, Winchester
218 Oak St, Winchester
$235,000
3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24213052 MLS
Bring your design ideas to this classic shingle-sided home. With a fully functional interior, the main floor features an open kitchen-dining area with living room, fireplace and hardwood flooring. The side entrance has a dedicated area perfect for a mudroom to keep the main living space organized. The second level hosts two bedrooms with hardwood floors and a full bath with shower. The top level was previously used as the third bedroom and contains an extra large closet perfect for storage. There are dual entrances on the main level as well as a lower level walk out basement to the quaint and private back yard. A storage shed exists for your outdoor equipment or gardening supplies along with a covered cabana style sitting area. If you are looking for a blank canvas waiting for a fresh coat of paint and some finishing touches, this home is for you.

218 Oak St, Winchester
205 Perch Rock Trl, Winchester
$350,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24210637 MLS
Valued by Redfin at $497,000 and Realtor at $516,000 - this house is a gem! 205 Perch Rock Trail, a spacious 4-bedroom, 2.5-bath home in the highly desirable Highland Lake area of Winsted. New siding and roof October 2026. Offering an incredible combination of space, location, and value, this property is a rare opportunity for a buyer looking to create something special. The home needs renovations and is being sold As Is, but the potential is substantial.The home offers approximately 2,369 square feet of living space, including a finished lower level with a kitchenette and full bath - ideal for an in-law setup, guest suite, home office, recreation space, or extended-family living. Enjoy lake views, nearby water access, a private backyard, two fireplaces, a balcony, generous storage, and an under-house garage. Public water and public sewer. With 4 bedrooms, multiple living areas, and flexible lower-level space, the possibilities here are exceptional. Whether you are looking for a year-round residence, weekend lake retreat, renovation opportunity, or investment property, 205 Perch Rock Trail offers tremendous upside. Bring your vision and make this Highland Lake gem your own!

205 Perch Rock Trl, Winchester
99 High St, Winchester
$575,000
14 Beds ⋅ 12 Baths ⋅ ACTIVE Status ⋅ 24209933 MLS
99 High St, Winsted, CT 06098 is a multi family residential property. The Building was built in 1958 and includes 4 units as well as a garage for multi purpose storage warehouse use. It has a large swing up garage door for excellent storage. There is also a small office with an interior bathroom. 1 unit is a 2 bedroom 1.5 bath. 3 units are a 1 bedroom, 1 bath. Each unit is rented with a stable long term paying tenant. The garage is also rented to a long term tenant. The driveway parking area was recently redone with new concrete for parking access. The exterior was recently painted and has been well maintained, a new furnace has been added as well, 3 of the 4 units have been updated.

99 High St, Winchester
95 Williams Ave, Winchester
$374,900
6 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24207726 MLS
Opportunity and flexibility come together at 95 Williams Street in Winsted. Offering approximately 2,887 square feet of living space, this spacious multi-family property is currently configured as two generously sized units with plenty of room both inside and out. Set on a uniquely large .49-acre corner lot, the property offers an impressive amount of outdoor space and privacy-something rarely found with a multi-family home. The left-side unit features four bedrooms and two full baths, while the right-side unit offers three bedrooms and one full bath-providing a total of seven bedrooms and three full baths. Each unit also benefits from additional attic and basement storage, a feature that is always appreciated in a multi-family home. According to the property card, the home is classified as a three-family property. The two units on the left side were previously combined, creating the larger four-bedroom residence that exists today. A future owner may have the opportunity to separate the space again and restore the property to a three-unit configuration, subject to any required municipal approvals. Whether you're looking for an investment property, an owner-occupied multi-family with rental income, or a property with the potential for a future three-unit configuration, 95 Williams Street offers an unusual combination of space, versatility, privacy and possibilities that are increasingly hard to find. Property being sold AS IS, WHERE IS.

95 Williams Ave, Winchester
150 E Lake St, Winchester
$449,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24208283 MLS
Enjoy lake living with this inviting 3 bedroom, two and a half bath home located directly across the street from Highland Lake. Offering water views and a convenient location, this property is a wonderful opportunity for a year round residence or weekend getaway. The home features a two car garage and plenty of parking and storage. Enjoy the convenience of having two beaches and a boat launch within walking distance, making it easy to spend your days swimming, boating, fishing, or simply relaxing by the water. Come take a look!

150 E Lake St, Winchester
50 Palmer Ave, Winchester
$429,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24206936 MLS
Originally built in 1940, this charming Cape has been completely transformed-taken down to the studs and thoughtfully renovated from top to bottom, blending classic character with the comfort and style of a modern home. The inviting open floor plan features a gorgeous kitchen with a large center island, granite countertops and stainless-steel appliances, flowing seamlessly into the spacious living area. The main-level primary suite is a true retreat with its own fireplace and private full bath. A convenient laundry room completes the first floor. Upstairs, you'll find two generously sized bedrooms and a beautifully updated full bath. The renovated lower level provides additional usable space and includes a garage bay under the house. Adding even more versatility is a detached two-car garage equipped with heating and air conditioning-ideal for a workshop, hobby space, car enthusiast or additional storage set in a peaceful location with a park directly across the street, this beautifully reimagined home offers the charm of a 1940 Cape with the extensive updates and functionality today's buyers are looking for. Truly move-in ready and a must-see!

50 Palmer Ave, 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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