Winchester Homes for Sale

Welcome to Winchester, a charming town located in Litchfield County, Connecticut. Known for its picturesque landscapes, Winchester offers a perfect blend of small-town charm and natural beauty.

With a variety of homes for sale in Winchester, you can find your dream property in this idyllic location. Whether you're looking for a cozy cottage, a historic farmhouse, or a modern family home, Winchester has something to offer for everyone.

Imagine waking up to the tranquil sounds of nature, taking a leisurely stroll through the quaint streets, and enjoying the stunning views of the surrounding hills. Winchester provides a peaceful and serene setting for those looking to escape the hustle and bustle of city life.

From outdoor enthusiasts to history buffs, Winchester has something for everyone. Explore the nearby hiking trails, visit the local museums, or simply relax and unwind in this beautiful town.

If you're ready to make Winchester your home, browse through the available homes for sale and find your perfect match. Whether you're looking for a cozy retreat or a spacious family home, Winchester has the perfect property waiting for you. Don't miss the opportunity to experience the beauty and charm of Winchester – your dream home awaits!

Newest Winchester Homes for Sale

$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

$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

$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

$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

$225,000

3 Beds ⋅ 1 Baths ⋅ 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

$350,000

4 Beds ⋅ 3 Baths ⋅ 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

$239,900

3 Beds ⋅ 1 Baths ⋅ 24210294 MLS

3 bedroom home offering comfortable living with the convenience of gas heat as well as a wood stove and main level laundry. The layout provides plenty of space for everyday living, relaxing, and entertaining. Enjoy Highland Lake with Resha Beach just a half mile away, perfect for summer days by the water. A short drive takes you to the nearby boat launch, making it easy to enjoy boating, fishing, and all that the area's lakes have to offer.

35 Prospect St, Winchester

$449,000

3 Beds ⋅ 3 Baths ⋅ 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

$429,000

3 Beds ⋅ 2 Baths ⋅ 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

$399,000

3 Beds ⋅ 2 Baths ⋅ 24198146 MLS

Situated on a side street just outside the town, this contemporary 3-bedroom residence exudes an open and spacious ambiance, enhanced by vaulted ceilings that impart a sense of grandeur to the living room. The home features numerous updates, including a stunning kitchen, two living areas, a separate dining space, and two decks accessible from both the dining and living rooms. The first-floor laundry room is convenient and adjacent to the half bath. The upper level comprises three bedrooms and a full bath. Additionally, a finished lower level and an attached garage complete this home's layout. This Winchester property offers a private yard and a convenient location, placing you in the heart of Litchfield County.

120 Moore Ave, Winchester

$260,000

3 Beds ⋅ 2 Baths ⋅ 24204964 MLS

This charming historic home, built in 1860, blends timeless character with thoughtful updates. Featuring 3-4 bedrooms, this property offers flexible living space to meet your needs. The beautifully remodeled upstairs bathroom is a standout feature, offering modern comfort within this classic home. Enjoy your LARGE eat-in kitchen with laundry hook ups and plenty of natural lighting and ample amounts of storage. The home sits on a flat, level yard with a huge storage shed, perfect for outdoor gatherings, storage, gardening, and play. Multiple decks off the home create inviting spaces to relax and take in the surroundings. Located just moments from a local boat launch, this property is ideal for those who love recreational water access. You're also close to the town green, shops, and everyday conveniences, making this home the perfect blend of historic charm and modern lifestyle. Schedule to view today!!

118 Meadow St, Winchester

$595,900

8 Beds ⋅ 5 Baths ⋅ 24200869 MLS

One of the finest grand classic Colonial homes where timeless charm and beautiful details can still be found throughout. Features include elegant crown molding, rich wood paneling, wide baseboard molding, gleaming hardwood floors, and a sweeping grand staircase-all adding to the warmth and character of this truly special home. This home features formal dining room, sitting room with fireplace, remolded kitchen offering two sinks, granite counter large palladium windows allowing in natural light a main floor study with fireplace /built in bookshelves. On second floor are 6 bedrooms and 3 full baths, primary bedroom has unique alcove with sink /dressing area. Vintage Blue stone patio is for quiet times to enjoy watching the wildlife, or you can play a game of billiards on the standard size table in the game room. Only three families have lived in this elegant 101 year young home. A home filled with elegance, history and warmth All this elegance can be yours. Wonderful home for extended family or possible Bed & Breakfast. There is many possibilities with this property. Minutes from Rt 8, easy drive to Bradley Airport, enjoy recreation at Highland lake.

143 Holabird Ave, Winchester

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Winchester Homes for Sale

Newest Winchester Homes for Sale

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