Winchester CT Real Estate & Homes for Sale

Winsted Ranch awaits your personal touch and design! Resting on a lush level .35acres, this home offers 3 bedrooms, 2 full bathrooms and 1,274sqft of single level living space. Freshly painted inside and out adds the finishing touches to a great home! The open floor concept allows you to entertain with ease as the kitchen w/plenty of storage and bay window opens to a formal dining room offering swinging French doors granting access to the bright and cheerful sunroom. Primary bedroom with plush new carpets and vaulted ceilings! Another bedroom features a loft and built-in bookshelves. Beautiful hardwood floors, walkout lower level with 1 car garage, peaceful backyard with large deck, firepit & large shed is ideal for hosting your next gathering! Lower level with laundry area, work bench, utilities, plenty of storage space & generator transfer switch! Looking to downsize or just starting out, this home is it! Come and explore all that your new town has to offer!

Welcome to this immaculate 2 bedroom, end unit condo at Riverwalk, completely remodeled to pristine move-in condition. Enjoy the spaciousness and privacy of this upgraded home featuring a stylish kitchen, modern bathrooms, and fresh paint throughout. This unit boasts a 2-car garage, a rare find in the area, along with larger-than-average parking spaces for convenience. The open floor plan and ample natural light create an inviting atmosphere ideal for relaxing or entertaining guests. Located in a desirable community with scenic views and easy access to local amenities, this condo offers both comfort and convenience. Don't miss out on the opportunity to make this beautiful condo your new home!

Contemporary ranch home has great room with vaulted natural wood ceiling featuring kitchen with granite counters, Sub Zero six burner gas cook top, Meile double oven and a large center island. Dining area has large windows and french doors leading out to an extra-large deck with amazing views. The spacious living room has a brick fireplace/pellet stove insert. Primary bedroom suite has new wall to wall carpet a walk-in closet and a lavish stone tiled bathroom with double sink and large shower stall. Den off living room has wood ceilings and lovely views of the inground pool and the pond in the back of the property. The other side of the home features two nice sized bedrooms another full bath and an upstairs office or playroom all with new wall-to-wall carpeting. Basement has french doors leading out just waiting to be finished off if you need some extra space. Home has whole house generator. Property abuts a beautiful meadow owned by the state and Platt State park.

Welcome to Highland Lake ! Look no further this is a Perfect Year Round or Vacation Home where you can have all the enjoyment offered of lake living yet have privacy. This Beautiful home features 3/4 Bedroom with 3 Full Bathrooms. The Main Floor with open plan features Brazilian Cherry flooring in Living & Dining Rm. Second Floor features Large primary suite & bathroom with stunning views of the lake. The listing includes a grassy water front property with dock for your boat or jet ski. Perfect for swimming, picnic, paddle board or enjoying making memories. Dont miss the opportunity!!!!!!

Welcome to 276 West Lake Street, Winchester, CT! This charming and fully updated 2-bedroom, 2-bathroom home is perfect for modern living in a serene setting. Nestled on a generous lot, the property features a detached 2-car garage, providing ample storage and parking space. Step inside to find a beautifully updated interior, complete with contemporary finishes and thoughtful details throughout. The spacious living areas and well-appointed kitchen make entertaining a breeze. Both bedrooms offer comfort and tranquility, while the updated bathrooms add a touch of luxury to your daily routine. Located directly across from the pristine Highland Lake and the convenient Highland Lake Boat Launch, this home is a dream come true for water enthusiasts. Enjoy stunning lake views, boating, fishing, and all the recreational activities the lake has to offer right at your doorstep. Don't miss this rare opportunity to own a delightful home in a fantastic location. Experience the perfect blend of modern living and natural beauty at 276 West Lake Street!

Welcome to 493 N. Main St in Winchester! This enchanting Cape Cod style home is a hidden gem nestled on a sprawling 1.30-acre lot. Perfectly situated close to shopping and downtown, this home offers both tranquility and convenience. As you step inside, you'll be greeted by a beautifully updated interior featuring new flooring throughout. The spacious living area, complete with a cozy sitting nook, provides a warm and inviting atmosphere for both relaxation and entertaining. The kitchen is a chef's dream, boasting stainless steel appliances that perfectly complement the modern yet timeless design. Adjacent to the kitchen, the charming dining room features built-ins that add a touch of character and ample storage. Upstairs, you'll find spacious bedrooms with new carpet, ensuring comfort and style. The updated bathroom showcases contemporary finishes, creating a spa-like retreat. Beyond the main house, a large outbuilding awaits, perfect for storage or a versatile work area, catering to all your needs. This property offers a unique blend of classic charm and modern amenities, creating an ideal haven. Don't miss the opportunity to make this delightful Cape Cod home yours and discover the endless possibilities it holds!

This charming two-bedroom, one and one half -bathroom house is situate in Highland Lake community. The property boasts a generous 1,278 square feet of living space, with an open floor plan that creates a spacious and airy feel. Custom moldings, New doors, high quality hardware/ lighting fixtures have been installed, beautiful attention to style detail. The kitchen has been recently updated with stainless steel appliances, refinished cabinetry, butcher block counter tops a breakfast bar island and new flooring providing a updated touch to the home. There is a slider to the large deck off of the kitchen. The bedrooms and laundry room are all located on the main level, making it easy to navigate the home. The foyer is large enough to be used as a home office, with a view of the lake. Living room has an electric fireplace that also gives off heat for your winter comfort. There is a bonus room in the basement that is walk out level to the back yard. The unfinished part of the basement has been improved with French drains and a sump pump. The furnace was replaced in 2020. Highland Lake has a public boat launch, making it perfect for water activities such as boating, waterskiing, jet skiing, or a quiet kayak or canoe paddle. The city water and sewer connection is a huge bonus, providing convenience and reliability. This home is being sold furnished so move right in and start enjoying the lake this summer. Don't miss out on the opportunity to own this beautiful property!

Step into a picturesque farm-style home, where every detail exudes charm and comfort. As you enter, original hardwood floors gleam warmly underfoot, reflecting the natural light that streams through the windows. The kitchen boasts exquisite ceramic tile, enhancing its rustic elegance and seamlessly blending with an open design that connects effortlessly to the dining area and inviting living room. Imagine evenings spent gathered around a cozy fireplace, its crackling warmth creating an atmosphere of relaxation and intimacy. This three-bedroom retreat offers each room as a haven of tranquility, while a thoughtfully designed bathroom ensures both practicality and style. Outside, the allure continues with expansive land offering unparalleled serenity. A two-car garage and a convenient storage shed provide ample space for vehicles and tools, complemented by recent upgrades including 5-year young driveway, windows, roof, furnace, water heater, oil tank, and well pump. This home is not just a place to live but a sanctuary where comfort harmonizes beautifully with the timeless appeal of a countryside lifestyle.

This country escape home is located in Litchfield County, just outside of quaint Winchester Center. If a quiet setting is what you're seeking, then this is the home for you. Situated on over 10 acres, you travel over a bridge and up a long driveway to find yourself immersed in complete privacy. Enjoy long warm summer nights and refreshing fall days in all that nature has to offer. This is a one-owner home and the first time it is being offered for sale. The main floor plan is open and airy with a cathedral ceiling, anchored by a floor-to-ceiling fireplace. If more room is what you need, have no worries because this home was built with an oversized septic system. The home also features a full-size walk-out basement where even more space can be added. This part of Litchfield County is convenient to so much to do. Boating, hiking, fishing, golfing, skiing, tubing, and many more outdoor activities are all just a short drive away. There are plenty of arts activities also minutes away in Torrington, where you'll find the Warner Theater, Nutmeg Ballet, 5 Points Gallery, and all the restaurants and shops you could need. This home would make a great 2nd home escape from the hustle and bustle of city life or a full time residence.

3500 sqft 2 family home featuring 1800's architecture including massive period correct windows, wrap around porch, beautiful stone foundation, and detached 2 car garage. 5 bed, 2 1/2 bath main house with 2 bed, 1 bath attic apartment currently under renovation. Brand new heating system! Property includes two parcels totaling nearly 4 acres of land.

Three properties totaling 4.41 acres for one price! 1. 3500 sq ft 2 family home featuring 1800's architecture including massive period correct windows, wrap around porch, beautiful stone foundation, and detached 2 car garage. 5 bed, 2 1/2 bath main house with 2 bed, 1 bath attic apartment, currently under renovation. Brand new whole house natural gas heating system! 1.13 acres 2. Updated 960 sq ft ranch. 3 bed, 1 bath, walk out basement, great backyard with tons of potential. .37 acres. 3. 2.9 acres of undeveloped land. Potential for multiple access points. Condo's? Apartments? Parking garage? Bring your ideas and imagination. All properties sold together. Tax & Square footage is total for all three properties.

Welcome to Strong Island, a waterfront retreat on Highland Lake. The clean waters of Highland Lake in the town of Winchester in Litchfield County surround this 1.6 acres island. History abounds for this property as the original house dates back to 1890. There were significant alterations made in 1920 that added several rooms, a boat house, a barn and porch. Babe Ruth made several trips to Strong Island for his weekends and vacations away from NYC. Strong Island is one of the largest islands on Highland Lake and has the best views. The position of this island give it the longest view of the lake on a North view and also on an Easterly view. The position of the main house on the island, the various docks, piers and out buildings make this property unable to be duplicated today. Strong Island is a trophy property that needs some polishing, but incredible in so many ways.

Great opportunity for Investors. This is a total renovation project being offered to serious qualified buyers only. 1608 sqft incl. 3 bedroom and 2.5 baths, dining and living room open concept, patio in backyard and water feature in front yard. Interior mix of tiled and HW floors. Located within walking distance downtown Winsted, Northwestern Community College, Whiting Mills building home to various artists, craftsman, retail shops. Property has amazing opportunities to rejuvenate this New England colonial back to its unique original charm once again. Perfect setting for an Airbnb rental, weekender or simply a year-round home. Just minutes away to beautiful lakes, rivers, skiing, various unique eateries, cultural events and endless outdoor activities. Just minutes away to beautiful Highland Lake, fishing, kayaking, bicycling and walking trails and endless adventures to explore. Cash or 203K Renovation Loan financing.

Your private oasis nestled in historic Winchester Center, offering serenity, lakes, trails and more. Contemporary Cape w/an abundance of spacious, light-filled rooms. This home w/ 3+ bedrooms/3 full baths boasts a mix of old-world charm and newer installations throughout. Rooms are adorned w/crown molding, beams, skylights and oversized windows, bringing the beauty of the outside in. Gazing out the windows, you'll see mature plantings, flowers, wildlife and your very own private pond. The main level of this home features a spacious kitchen w/ walk-in pantry, mudroom, dining rm, formal living rm, library, den, office, sunroom and primary bedroom, which can be utilized as a great room. Enjoy the Gunite pool and terrace directly outside the sunroom, with several seating areas overlooking beautiful views - a perfect place for entertainment or to retreat for relaxation, reading and conversation with family and friends. Options for primary bedroom on main or upper level. Upper level boasts a primary suite with spa-like full bath w/soaking tub, an additional 2 bedrooms w/en suite full bath, laundry room and a central loft overlooking the formal fireplaced living rm. Home equipped w/4 garage bays - ideal for those w/oversized toys and desire for a workshop. This truly is a must-see home! Close proximity to Winchester & Highland Lakes, 4 state parks (incl. Burr Pond), private Park Pond Club, skiing, and Norfolk's Yale Summer School of Music. Just 2.5 hours from NYC and Boston.

HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Buyer, whether You're an ANTIQUARIAN, HORSE & ANIMAL LOVER, or just seeking for a PEACEFUL & TRANQUIL LOCATION, this LITCHFIELD COUNTY HOME could possibly fit your Criteria. Stately 1789 11 Room 3,088 Sq. Ft. Colonial expresses Love, Warmth & Care. From the Solid Beams, Chestnut Wide-Board Floors, to the 12 over 12 Windows and Fireplaces, Displays the Charm & Character in this Residence! For a more Modern Twist, there is a Fully Remodeled Eat-in Kitchen with Quartz Counters, as well as Remodeled Bathrooms. 4 TO 5 Bedrooms, 3 Full Baths, Formal Dining Room & Comfortable Living Room. Spacious Sunken 20' x 21' Family Room with Cathedral Ceiling. Unique Loft offers a Birdseye View to the Family Room. Level 7 Acre Lot Enhanced by Stone Walls and Nice Plantings. Outbuildings include a 30' x 35' 4 Stall Horse Barn with Tack Room & Hayloft. 2 paddocks and a 25' X 30' Storage Building. Mechanicals include Oil Hot-Air Furnace, 200 AMP Electrical Service, Well Water & Septic System. A Quaint and Rural Atmosphere, but within Close Proximity to Major Shopping, access to State Parks, Lakes, Golf Courses, Ski Areas, and Local Arts and Cultural Venues. The Photo Library Partially tells the Story, but prospective Buyers need to Visit / Tour this Lovely Property in order to Appreciate its Attributes!!