Winchester Homes for Sale

Welcome to Winchester, Connecticut—a hidden gem nestled in the picturesque Litchfield County. Known for its stunning landscapes and rich history, Winchester offers a unique blend of small-town charm and modern living. Surrounded by the natural beauty of the Litchfield Hills, residents enjoy a wealth of outdoor activities, from hiking and fishing to boating on the serene waters of Lake Winchester.

This vibrant community boasts a strong sense of belonging, where neighbors become friends and local events bring everyone together. The town features a variety of amenities, including quaint shops, delightful eateries, and community parks, making it an ideal place for families, retirees, and everyone in between.

For those looking to make Winchester their home, you’ll find a diverse selection of homes for sale that cater to various tastes and budgets. Whether you’re seeking a cozy cottage with vintage charm, a spacious family home with modern amenities, or a serene retreat surrounded by nature, Winchester has something to offer everyone. With its competitive real estate market, now is the perfect time to explore the possibilities of homeownership in this delightful town.

As you embark on your journey to find the perfect property, you’ll discover that Winchester not only provides a beautiful backdrop for your life but also a welcoming community that makes every day feel special. Come and experience the enchanting allure of Winchester, where your dream home awaits!

Newest Winchester Homes for Sale

$959,900

2 Beds ⋅ 2 Baths ⋅ 24194765 MLS

Exceptional Highland Lake waterfront Colonial rebuilt in 1996 to modern standards and codes, offering quality construction and timeless appeal. Perfectly positioned with 58 feet of direct northwest-facing waterfront, this home is designed to capture breathtaking lake views from nearly every angle. The spacious living/great room features a dramatic fieldstone fireplace and walls of glass with multiple sliders leading to a large wraparound waterfront deck, creating a seamless connection between indoor and outdoor living. The beautiful oak kitchen is highlighted by quartz countertops, newer stainless steel appliances, and an open layout that flows effortlessly into the main living areas, making it ideal for entertaining. Upstairs, the primary bedroom boasts soaring 12-foot cathedral ceilings and an abundance of windows overlooking the lake, providing a spectacular place to wake up each morning. Outside, the waterfront has been thoughtfully improved with an updated seawall that includes an aluminum dock, making it easy to enjoy boating, swimming, fishing. Highland Lake is a pristine 444-acre lake renowned for its clean water. Conveniently located just 45 minutes from Hartford and Bradley International Airport, and within easy reach of the Berkshires, Infinity Music Hall, the Warner Theatre, New York City, and Boston, this property offers the perfect blend of year-round living and a weekend retreat. A rare opportunity to create a lifetime of memories.

204 E Wakefield Blvd, Winchester

$749,900

2 Beds ⋅ 1 Baths ⋅ 24192463 MLS

Year-round waterfront retreat with breathtaking sunrise views from one of the widest sections of the lake! This well-maintained 2-bedroom, 1 bath home offers comfortable living with a flexible loft area for additional sleeping space and a convenient half bath on the lake level. The updated kitchen and new windows provide modern comfort while showcasing expansive water views throughout the home. Outdoor amenities include a spacious waterfront patio, outdoor shower, and walk-in staircase for easy water access, making it ideal for swimming, boating, and relaxing lakeside. Adjacent to a state park, the property enjoys a picturesque setting with added privacy and natural surroundings. Move right in and enjoy as-is or update to suit your personal style. An additional parcel across the street is included, providing extra space and excellent long-term potential. Whether you're looking for a year-round residence, vacation getaway, or investment opportunity, this waterfront property offers an exceptional combination of location, views, and lifestyle.

812 W Wakefield Blvd, Winchester

$849,900

4 Beds ⋅ 2 Baths ⋅ 24191186 MLS

Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay, this beautifully renovated two-family home can be enjoyed as a single-family retreat or an income-generating investment. Featuring modern upgrades throughout, the home boasts C/A, high-efficiency propane furnaces, newer appliances, windows, and siding-all designed for comfort and style. Inside, you'll find gorgeous details at every turn. The first-floor unit showcases a custom rustic kitchen with granite countertops, a Sub-Zero refrigerator, beverage fridge, gas range, and dishwasher. A luxurious marble-accented bathroom with a walk-in shower, two spacious bedrooms, and a large family room with French doors leading to a wraparound covered porch complete this level-perfect for soaking in those incredible views! The second-floor unit offers flexibility, featuring a kitchenette, dining room/office space, two additional bedrooms, and a family room with sliding doors opening to another covered porch-all with the same stunning lake vistas! Addt'l highlights include an oversized two-car detached garage with a carport, a hot tub (sold as-is), a level yard area, and a side deck. Situated just steps from the water, this home provides easy access to all lake activities. Rustic charm meets upscale living!

119 W Wakefield Blvd, Winchester

$353,500

3 Beds ⋅ 2 Baths ⋅ 24190790 MLS

Please submit your client's highest and best offer by Sunday 07/19 at 3:00 PM. Beautifully remodeled and move-in ready, 195 Reaching Hill Rd in Winsted, CT features modern updates, comfort, and functionality throughout. This 3-bedroom, 2-bath conventional-style home sits on nearly one acre of land and showcases a bright open-concept layout with beautiful hardwood floors, a spacious living area, and a dedicated dining space with large sliding glass doors overlooking the backyard. The main floor includes a bedroom and full bathroom, providing flexibility for a variety of uses such as a guest room, home office, or convenient one-level living arrangement. The finished lower level with a walk-out entrance and full basement adds valuable additional space with endless possibilities for a recreation room, home gym, playroom, workshop, or additional storage. Enjoy the comfort of central air conditioning, along with a relaxing porch, outdoor shed, and a private backyard with plenty of space to relax, garden, or entertain. Located near Highland Lake, this property provides convenient access to outdoor recreation throughout the seasons. With thoughtful renovations, spacious rooms, and a great indoor-outdoor connection, this home is ready for its next owner. Schedule your private showing today and see everything this beautifully updated Winsted property has to provide.

195 Reaching Hill Rd, Winchester

$369,900

4 Beds ⋅ 2 Baths ⋅ 24189288 MLS

Step back in time and experience the timeless elegance of this spacious 2,722 sq. ft. Victorian offering 10 rooms, 5 bedrooms, and 1.5 baths. Rich in original character and architectural detail, this classic home showcases beautiful hardwood floors, impressive natural woodwork, pocket doors, built-ins, decorative moldings, and stunning stained-glass accents that capture the craftsmanship of a bygone era. A welcoming foyer leads to the formal living room, formal dining room with pantry, spacious eat-in kitchen, comfortable family room, half bath, and convenient first-floor laundry. The living room features a fireplace that has been sealed but offers the potential to be restored, while the kitchen includes a flue for a wood stove for those who appreciate the warmth and ambiance of wood heat. The second floor offers five bedrooms and a full bath, with several layout possibilities to create a spacious primary suite. Above, the walk-up attic-offering several finished rooms along with additional expansion space (not included in the home's square footage)-provides endless possibilities for a home office, studio, recreation room, or additional living space. Additional amenities include natural gas heat, thermopane windows, and a roof that is approximately 15 years old. Victorian homes of this size and character are becoming increasingly difficult to find. A rare opportunity to own a true piece of architectural history.

70 Walnut St, Winchester

$1,600,000

4 Beds ⋅ 3 Baths ⋅ 24187886 MLS

Experience the best of lakefront living with breathtaking views, spectacular sunsets, and exceptional outdoor spaces. This amazing waterfront home features a brand-new 100' x 14' Brazilian hardwood deck, a 35' x 6' stationary Trex and steel dock, and a private cabana-perfect for relaxing, boating, swimming, and entertaining. Soak in panoramic water views from multiple vantage points, including the expansive patio, upper wraparound deck, front sunroom, and many windows throughout the home. The interior also offers numerous updates, including renovated kitchens and bathrooms, beautiful hardwood flooring, and an open-concept main living area with a cozy fireplace. The inviting layout provides the perfect setting for everyday living and entertaining. A finished lower-level studio apartment adds valuable versatility, offering ideal guest accommodations, a private retreat, home office space, or potential rental income opportunity. Don't miss this exceptional waterfront property offering the perfect blend of comfort, updates, and year-round lake enjoyment!

752 Lake Dr, Winchester

$679,900

3 Beds ⋅ 3 Baths ⋅ 24186150 MLS

Custom built log Home!This home sits on a 3 acre, private landscaped lot with mountains laurel and a park nearby. This sprawling home with a covered front porch(28x 8)is perfect for relaxing and features over 1100 sq of decking which wraps around the house for entertaining. The Home features a stunning living room with interior balcony, chandeliers, field stone wood fireplace, cathedral ceiling, and sliders to a deck.The kitchen has a breakfast bar, stainless steel appliances and a pizza oven. It's opened to a dining room with a scenic view. The 1st floor primary bedroom suite has a cathedral ceiling, wood floors,2 walk in closets, one is cedar lined, the bath features a whirlpool tub and full shower, marble sink, tile floor and vaulted ceiling.Open the sliders from the bedroom to enjoy views from a 4 season sunroom.There is a 2nd bedroom on the main level and a 2nd full bath. Upstairs there is bedroom ,a 1/2 bath ,plus a Den (used as a bedroom).The lower level features a family room and a fieldstone wood fireplace .The full basement has a laundry room,utility room, storage, and a workshop.The oversized 2 car garage has a wood stove, and a 1000 gallon oil tank. All windows are energy efficient with krypton argon gas. The solar panels are lease at $68 a month.The large shed has electric and concrete floor .It's a short drive to great fishing, hiking ,swimming,skiing, town,shopping, restaurants, theaters, entertainment, festivals and vineyards. Enjoy Litchfield County.

426 Platt Hill Rd, Winchester

$305,000

3 Beds ⋅ 2 Baths ⋅ 24186089 MLS

Well-maintained Cape in a desirable rural setting, yet just minutes from shopping, dining, schools, and other everyday conveniences. This 7-room home offers 3 bedrooms and 1.5 baths with a flexible floor plan designed for comfortable living. The main level features a formal living room, dining room, kitchen, family room, primary bedroom, and a full bath w/laundry, providing the convenience of one-level living. Upstairs you'll find two additional bedrooms and a half bath. Lovingly cared for over the years, the home features central air conditioning, a standby generator, and a security system with fire and smoke monitoring for added comfort and peace of mind. Enjoy your morning coffee or evening relaxation on the covered deck overlooking the yard. Additional amenities include a one-car garage under the home and a location that offers the perfect balance of privacy and accessibility. A wonderful opportunity to own a move-in ready home in a convenient country setting.

103 Cordano Rd, Winchester

$495,000

4 Beds ⋅ 3 Baths ⋅ 24185819 MLS

Unique opportunity to own this spacious 4-bedroom Colonial set on 27 acres in Winchester, CT. Previously home to animals, this property offers endless possibilities for hobby farming, equestrian pursuits, recreation, or simply enjoying the privacy and beauty of the countryside. Ideally located directly across the street from Green Woods Country Club, you'll enjoy convenient access to golf, and beautiful scenic views right at your doorstep. Inside, you'll find an expansive kitchen featuring abundant cabinetry, gas cooktop, double ovens, generous counter space, and plenty of room for family and friends to gather. The main level offers a formal dining room, a large family room, and a welcoming living room with a fireplace and direct access to the back deck, perfect for outdoor dining and entertaining on warm summer evenings. The walk-out lower level provides excellent potential for additional finished living space and already includes a bar area, making it ideal for a future recreation room, home gym, or media space. With its combination of acreage, functionality, and room to grow, this property presents a rare opportunity to create the lifestyle you've been dreaming of. Conveniently located with easy access to dining, shopping, recreational amenities, and major commuter routes, this property offers the perfect balance of peaceful country living and everyday convenience.

293 Torringford St, Winchester

$579,900

4 Beds ⋅ 3 Baths ⋅ 24185645 MLS

Welcome to 237 Wallens Hill Road, where comfort, quality, and exceptional entertaining spaces come together in a beautiful rural setting. This 9-room Colonial with a farmhouse front porch is set on .80 acres and offers 4 bedrooms and 2.5 baths. The main level features a formal dining room, large family room, mudroom, and an impressive eat-in kitchen with quartz countertops, stainless steel appliances, built-in microwave, stainless hood system, and a large center island with seating for four. A standout feature is the dedicated entertaining room complete with a custom walnut bar, kegerator, and a 5-foot stainless steel hood system over a built-in grill and flat-top griddle. Upstairs, the primary suite offers his-and-her closets and a beautiful full bath, while two additional bedrooms share a full bath. The fourth bedroom could also be used as an office, is located in the lower level. Additional features include hardwood floors throughout most rooms, multi-zone heat, central air conditioning with separate zones for the main and upper levels, a hybrid hot water heater, and a generator transfer switch. Step outside to enjoy a 14-foot pavilion on a stamped concrete and paver patio with a built-in fire pit, and spacious open backyard. Conveniently located near the Farmington River and Peoples State Forest, with easy access to hiking, fishing, kayaking, and other outdoor recreation while remaining close to shopping, dining, and everyday conveniences.

237 Wallens Hill Rd, Winchester

$365,000

3 Beds ⋅ 2 Baths ⋅ 24184417 MLS

Welcome to East Lake Street at Highland Lake, where privacy, comfort, and lake living come together. Set back from the road on a private lot in the desirable First Bay area, this well-maintained lake-style home offers a quiet setting with seasonal lake views and refreshing breezes throughout. Offering 1,820 square feet, the home is listed as a 3-bedroom with a first-floor finished 4th room for added flexibility. The updated kitchen features quartz counter tops, stainless steel appliances, and ample cabinetry, with warm pine ceilings adding character throughout. Additional features include two full baths, first-floor laundry, newer windows, public water and sewer, natural gas, on-demand hot water, and a wood stove. Outside, enjoy a peaceful backyard garden and convenient rear access from Ontario Street. Located within one mile of local schools and a half mile of town, the home offers easy access to everyday amenities while maintaining a peaceful lake setting.

132 E Lake St, Winchester

$349,000

3 Beds ⋅ 2 Baths ⋅ 24177410 MLS

Peaceful country living with unlimited potential! Nestled on a quiet Winsted street, this three bedroom, two bathroom ranch sits on nearly 2 acres of private, setback land. It offers excellant structural bones and a functonal layout, making it an ideal candidate for a rewarding renovation project. The large living and dining space features high cathedral ceilings and exposed wood beams with the focal point of the living room being a floor to ceiling fireplace equipped with a wood stove insert. Convenient one-level living at it's best! A two car attached garage leads to a breezeway room, ideal for a home office or studio. The home requires updates throughout and is being sold strictly "as is." The price of this property reflects its current condition, offering a solid foundation to buyers looking to customize a home.

107 Roberts Ave, Winchester

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