Winchester Real Estate

Winchester Real Estate

Welcome to Winchester, a charming town nestled in Litchfield County, Connecticut. Winchester offers a perfect blend of small-town charm and natural beauty, making it an ideal place to call home.

Located in the scenic northwest corner of Connecticut, Winchester boasts picturesque views of rolling hills, lush forests, and sparkling lakes. Outdoor enthusiasts will appreciate the abundance of recreational opportunities, from hiking and biking along scenic trails to fishing and boating on the pristine waters of Highland Lake.

Winchester is also rich in history and culture, with historic buildings, museums, and art galleries dotting the town. Explore the Winchester Historical Society Museum to learn about the town's fascinating past, or browse local art galleries to discover the work of talented local artists.

In Winchester, you'll find a tight-knit community that values a high quality of life. The town is known for its excellent schools, safe neighborhoods, and vibrant local economy. Whether you're looking to raise a family or enjoy a peaceful retirement, Winchester offers a welcoming and friendly atmosphere for residents of all ages.

With its stunning natural scenery, rich history, and strong sense of community, Winchester is a place where you can truly feel at home. Come discover all that this charming town has to offer and find your perfect piece of paradise in Litchfield County, Connecticut.

Newest Listings in Winchester

510 Reaching Hill Rd, Winchester
$199,000
24217752 MLS
Discover the possibilities with this versatile, wooded parcel offering endless potential. Whether you're dreaming of building a private residence, establishing a small farm, or creating an equestrian retreat, this property provides the space and flexibility to bring your vision to life. The land is primarily wooded, offering privacy and a peaceful natural setting, and does have clearings throughout the property. A wonderful opportunity for those seeking a rural lifestyle with a variety of potential uses. This parcel can be purchased with parcel 1: 435 Platt Hilld Road, MLS #24217754, and parcel 2: 510 Reaching Hill Road, MLS #24217752.

510 Reaching Hill Rd, Winchester
476 Reaching Hill Rd, Winchester
$150,000
24217750 MLS
Bring your vision to life on this versatile parcel offering endless possibilities for residential, farming, or equestrian use. The property features mostly open land, making it ideal for farming, horses, or building your dream home. Existing improvements include a barn, horse stables, and a riding arena, providing an excellent setup for equestrian enthusiasts or those looking to establish a hobby farm. Enjoy the flexibility and open space this unique property has to offer while creating the lifestyle you've been dreaming of. This parcel can be purchased with parcel 1: 435 Platt Hilld Road, MLS #24217754, and parcel 3: 476 Reaching Hill Road, MLS #24217750.

476 Reaching Hill Rd, Winchester
435 Platt Hill Rd, Winchester
$110,000
24217754 MLS
Discover the possibilities with this versatile, corner, wooded parcel offering endless potential. Whether you're dreaming of building a private residence, establishing a small farm, or creating an equestrian retreat, this property provides the space and flexibility to bring your vision to life. The land is primarily wooded, offering privacy and a peaceful natural setting, and includes an existing Quonset hut for storage or future use. A wonderful opportunity for those seeking a rural lifestyle with a variety of potential uses. This parcel can be purchased with parcel 2: 510 Reaching Hill Road, MLS # 24217752, and parcel 3: 476 Reaching Hill Road, MLS #24217750.

435 Platt Hill Rd, Winchester
no property photo
$35,000
24218700 MLS
OPPORTUNITY AWAITS! This .37-acre vacant lot is situated in a quiet neighborhood within easy walking distance of Tatro's Pond. The property was once improved with a single-family home and detached garage, offering a unique opportunity for someone looking to bring new life to the site. Access to the property is provided by a 12-foot right-of-way from the street. Buyers are encouraged to perform their own due diligence regarding permitted uses, building requirements, and access.

16 Brook St, Winchester
19 Hill St, Winchester
$23,900
24218695 MLS
Located on a lightly traveled side street, this .22-acre lot offers a peaceful getaway with easy access to downtown. The property features a flat area at the street before gently sloping upward, creating a unique setting for potential future use. City water and sewer are available in the street, but buyers should conduct their own due diligence regarding buildability. Whether you're looking for a retreat or an investment opportunity, this lot holds great potential. Explore the possibilities today!

19 Hill St, Winchester
19 Walnut St, Winchester
$285,000
4 Beds ⋅ 3 Baths ⋅ 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 ⋅ 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 ⋅ 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 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. 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. The rear 0.55-acre parcel may offer potential as a separate building lot, subject to buyer verification and all necessary municipal approvals. 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 ⋅ 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
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 ⋅ 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 the Litchfield Hills.

139 Grantville Rd, Winchester
111 Riverton Road Unit 65, Winchester
$220,000
2 Beds ⋅ 2 Baths ⋅ 24213555 MLS ⋅ Riverwalk BLDG.
This 2 Bedroom Condo offers the perfect blend of comfort and convivence. Inside, you will find low-maintenance with wood and tile flooring, elegant decorative ceilings, and a stylish updated kitchen featuring quartz counters. An additional upgrade is the Two Energy efficient mini splits for Heat/AC. Siders go to back deck which is complete with installed Awning ideal for outdoor retreat or relaxing while enjoying views featuring trees planted by previous owner. The two car garage has heat if you want to tinker on your car. Close to: Rt 8, Highland Lake and Restaurants

111 Riverton Road Unit 65, 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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