Winchester Homes for Sale

Welcome to Winchester, Connecticut, a hidden gem nestled in the picturesque Litchfield County. Known for its rich history and stunning natural landscapes, Winchester offers a harmonious blend of small-town charm and modern conveniences. With its serene lakes, lush parks, and vibrant community spirit, it’s no wonder that homebuyers are flocking to this delightful town.

Winchester is home to the beautiful Highland Lake, a favorite among locals for boating, fishing, and enjoying peaceful picnics by the water. The town boasts an array of outdoor activities, including hiking trails, parks, and recreational facilities, making it an ideal location for families and nature enthusiasts alike. The historic downtown area features quaint shops, cozy cafes, and friendly eateries, creating a warm and inviting atmosphere for residents and visitors.

When it comes to real estate, Winchester offers an impressive selection of homes for sale that cater to various lifestyles and budgets. From charming single-family homes with character to modern condos that emphasize convenience, there’s something for everyone in this vibrant community. Many properties boast stunning views of the surrounding landscapes, providing a tranquil retreat from the hustle and bustle of city life.

Whether you’re looking for a starter home, a place to raise a family, or a peaceful retirement haven, Winchester, CT, has it all. With its strong sense of community, excellent schools, and easy access to nearby cities, it’s the perfect place to call home. Explore the homes for sale in Winchester today and discover the enchanting lifestyle that awaits you!

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 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

$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 Litchfield County.

139 Grantville Rd, Winchester

$235,000

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

$339,900

3 Beds ⋅ 1 Baths ⋅ 24210012 MLS

Lovingly maintained by the same family since it was built in 1949, this 3-bedroom Colonial offers approximately 1,500 sq. ft. of living space on a 1-acre lot on the outskirts of town, yet within walking distance to the beach at Highland Lake. The main level features a spacious living room, large kitchen, dining room, full bath and inviting 3-season porch. Upstairs are three comfortable bedrooms with ample closet space. Hardwood floors run throughout the home, adding to its classic charm. Energy-conscious features include three heating sources: an oil-fired boiler, pellet stove in the living room and a magnificent soapstone wood stove in the lower level. The home also offers plenty of insulation, thermopane windows and a roof installed in 2021. Outside, you'll find excellent garage and storage space, including a large barn/garage with room for vehicles and a workshop, plus an additional detached garage. Set on nearly an acre with convenient access to Highland Lake and town amenities, this well-cared-for home is ready for its next chapter. This one is worth seeing!

50 Overlook Rd, Winchester

$850,000

3 Beds ⋅ 3 Baths ⋅ 24208872 MLS

Breathtaking water views and master craftsmanship await in this pristine Colonial offering nearly 3,000 SF overlooking serene Highland Lake. This entertainer's dream home opens from an inviting two-story foyer into an airy, open layout where the living and dining rooms are joined by a floor-to-ceiling fieldstone fireplace. The spacious dining room easily accommodates large gatherings and flows seamlessly onto a delightful screened-in porch to enjoy the calm, serene setting with distant lake views. The gourmet kitchen is a master craftsman renovation featuring custom white birch cabinetry, rich soapstone countertops, stone subway tile backsplash, a farmhouse sink with a view, and a Sub-Zero refrigerator. Dedicated home office off front foyer, mudroom, laundry room, and half bath complete the main level. Upstairs features an en-suite primary bedroom, two additional nice-sized bedrooms, and a full guest bath. Accessed via a private second staircase off the kitchen, the expansive 27' x 21' "Skybox" family room (finished over the garage in 2017) boasts its own heating/cooling system, surround sound, and live music performance hook-ups. Property is flanked by a magnificent stone wall, emerald green meadows including a two-stall run-in shed with tack room. Hardwood floors main level, bamboo engineered floors upper level, oversized 2 car garage, walk-out basement. New well pump 2020, new whole house generator 2023. EZ commute to NYC & Boston from this ideal retreat. Rare opportunity.

359 Winchester Rd, 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

$405,000

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

Start Your Search

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.

Winchester Homes for Sale

Newest Winchester Homes for Sale

How much is your home worth?

How much is your home worth?