Winsted Homes for Sale

Welcome to Winsted, a charming neighborhood nestled within the picturesque town of Winchester, Connecticut. Known for its rich history and vibrant community spirit, Winsted offers a delightful blend of small-town charm and modern conveniences. Surrounded by the stunning landscapes of Litchfield County, residents enjoy an abundance of outdoor activities, from hiking and fishing in nearby parks to leisurely walks along the serene Farmington River.

Winsted boasts a diverse range of homes for sale, making it an ideal destination for families, first-time buyers, and those seeking a peaceful retreat. Whether you’re looking for a cozy bungalow, a spacious colonial, or a classic Victorian, you’ll find properties that reflect the unique character of this welcoming community. Many homes feature beautiful architectural details, lush gardens, and easy access to local amenities.

The neighborhood is well-equipped with essential services, including schools, shopping, and dining options, ensuring that everything you need is just a stone’s throw away. The local schools are highly regarded, fostering a nurturing environment for children to grow and learn. Community events and farmers' markets provide opportunities to connect with neighbors and celebrate the vibrant culture of Winsted.

With its idyllic setting and a strong sense of community, Winsted is more than just a place to live; it’s a place to thrive. Explore the homes for sale in this enchanting neighborhood today, and discover the perfect backdrop for your next chapter in life. Your dream home awaits in Winsted!

Newest Winsted Homes for Sale

$425,000

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

$350,000

4 Beds ⋅ 2 Baths ⋅ 24207462 MLS

3.7-acre property offering a 4-bedroom, 2-bath Cape with plenty of room and flexibility. Formerly operated as a small farm, the property provides space for gardening, animals, recreation, or other uses. The first floor features an open floor plan with impressive 10-foot ceilings and a layout that can adapt to a variety of needs. Four bedrooms provide room for family, guests, or a home office. A unique opportunity for buyers looking for acreage, space, and the ability to make a property their own.

100 Norfolk Rd, Winchester

$629,000

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

$199,000

3 Beds ⋅ 1 Baths ⋅ 24206541 MLS

Welcome to 416 Horne Ave, a charming 3-bedroom, 1-bath home offering approximately 1,056 square feet of comfortable living space in Winsted. Built in 1979 and situated on approximately 0.29 acres, this property offers a practical layout with room to make it your own. The home provides a welcoming setting for everyday living, with three bedrooms offering flexibility for family, guests, a home office, or hobbies. Enjoy the convenience of a residential location close to local amenities, schools, shopping, dining, and outdoor recreation. An excellent opportunity for homeowners or investors seeking value in the Winsted community.

416 Horne Ave, Winchester

$339,900

2 Beds ⋅ 2 Baths ⋅ 24206905 MLS

Private Country Living on 16 Acres! Enjoy the peace and privacy of this charming ranch nestled on expansive acreage, offering the feel of a true country compound. Features include 2 bedrooms, a family room with fireplace, kitchen, three-season enclosed porch, heated possible office, and large deck. Plenty of cleared land surrounds the homesite while mature trees provide exceptional privacy. Possible subdivision potential adds even more opportunity. Buyer to verify with the town. A rare opportunity for those seeking space, privacy, and endless possibilities!

320 Colebrook Rd, Winchester

$749,900

3 Beds ⋅ 2 Baths ⋅ 24206406 MLS

Welcome to 180 Shore Dr - your own beautifully renovated waterfront retreat on highly desirable Lake! This exceptional year-round home offers the perfect combination of modern comfort, stunning water views, and the lake lifestyle you've been dreaming about. Featuring 3 bedrooms and 2 full bathrooms, the home has been extensively remodeled with quality finishes and thoughtful attention to detail throughout. Step inside to a bright, inviting interior filled with natural light from newer Andersen windows and doors. The beautifully renovated kitchen features modern appliances, sleek countertops, abundant cabinetry, and an open, welcoming feel that's perfect for entertaining after a day on the lake. Both full bathrooms have been tastefully remodeled, while LifeProof luxury plank flooring provides durability and easy maintenance. Enjoy year-round comfort with updated heating and central air conditioning. Outside is where this property truly shines! A newer deck and patio overlook Highland Lake, creating the perfect setting for morning coffee, summer dinners, sunsets, and unforgettable gatherings with family and friends. Step outside and enjoy direct access to one of Connecticut's most beautiful recreational lakes. Whether you're searching for a primary residence, weekend escape, or spectacular AirBnB, 180 Shore Dr delivers the lifestyle, location, and views that make waterfront ownership so special. Don't just buy a home - start living the Highland Lake lifestyle!

180 Shore Dr, Winchester

$439,900

4 Beds ⋅ 2 Baths ⋅ 24202969 MLS

Welcome to 136 Losaw Rd! Built in 1984, this nicely maintained and updated home offers 1,977 sq. ft. of living space with 4 bedrooms, 2 full baths, and a comfortable open floor plan, all set on 1.76 acres. The main living level features an open dining area and kitchen with breakfast bar overlooking the sunken living room, highlighted by a beautiful arched fieldstone fireplace with propane log set. Two modest-sized bedrooms and a full bath complete this level. Upstairs, you'll find two generously sized bedrooms, a second full bath, and a large storage closet. The lower level features a fieldstone hearth and approximately 400 sq. ft. of additional space ready to be finished to suit your needs. Outside, the property offers a two-stall horse barn with additional room for hay and storage, adding great versatility for equestrian use, hobbies, or additional storage. Nicely maintained and thoughtfully updated over the years, this property offers plenty of space both inside and out. Don't let this one slip away!

136 Losaw Rd, Winchester

$629,900

3 Beds ⋅ 2 Baths ⋅ 24199152 MLS

Enjoy the best of Highland Lake living with this unique property offering a spacious home directly across the street from the lake along with your own separate waterfront parcel! The main house features 7 rooms, 3-4 bedrooms and 2 full baths, providing plenty of space for year-round living or a relaxing lake retreat. A deck overlooking the waterfront offers the perfect spot to enjoy the lake views, while a wonderful outdoor gathering area featuring a stone fireplace provides an ideal setting for entertaining family and friends. Just across the street, your private waterfront parcel takes lake living to another level with a 15' x 29' deck overlooking Highland Lake and a dock for your boat. Also located on the waterfront is a 240 sq. ft. structure with a half bath, offering excellent flexibility for storage, a lakeside retreat or additional sleeping accommodations. Spend your days boating, swimming, fishing or simply relaxing by the water, then retreat to the comfort of your home just steps away. A rare opportunity to enjoy your own private waterfront access and all that beautiful Highland Lake has to offer!

837 E Wakefield Blvd, Winchester

$319,900

2 Beds ⋅ 1 Baths ⋅ 24200816 MLS

New Construction - Easy to Maintain - Open Floor Plan - Central Air - Vinyl Plank flooring throughout. White Shaker Kitchen with Island and granite countertops. All stainless steel kitchen appliances. Separate laundry room on main level. Glass paneled door to covered deck off the living room area. Two spacious bedrooms with large closets. Entry foyer with large walkin closet Large heated garage with area for a work space. Garage door opener, Paved driveway. Room dimensions are approximate.

14 Bank St, Winchester

$649,900

2 Beds ⋅ 1 Baths ⋅ 24198153 MLS

Nestled along the coveted east shore of Highland Lake, 600 East Wakefield Boulevard presents a rare opportunity to own a piece of one of Connecticut's most sought-after waterfront communities. Filled with charm and character, this lakeside property offers the perfect canvas to create a custom retreat that reflects your vision and lifestyle. Spend your days swimming, boating, kayaking, and enjoying all that Highland Lake has to offer, with easy lake access and a nearby semi-private boat launch. As evening arrives, breathtaking panoramic sunsets paint the water, creating an unforgettable backdrop for lakeside living. What truly sets this property apart is that, unlike many waterfront homes and open parcels around the lake, it benefits from both a DEEP PRIVATE WELL and PUBLIC SEWER service, offering convenience, reliability, and added value that are increasingly difficult to find. Whether you're seeking a seasonal getaway, YEAR-ROUND waterfront residence, or renovation opportunity, this exceptional property is ready for its next chapter. With waterfront opportunities on Highland Lake becoming increasingly scarce, this is your chance to secure a truly unique lakefront setting. Subject to Probate Court approval. Property sold as-is.

600 E Wakefield Blvd, Winchester

$389,900

4 Beds ⋅ 2 Baths ⋅ 24196702 MLS

Welcome home to this well-maintained 4-bedroom Colonial tucked away on a quiet dead-end street. The newly renovated eat-in kitchen features updated cabinetry, countertops, and finishes, creating a great space for everyday living and gathering. The spacious living room and dining area offer plenty of room to make the home your own, while four bedrooms provide flexibility for family, guests, or a home office. Outside, enjoy the large yard, charming enclosed front porch, and back deck with a Sunsetter awning for comfortable outdoor living. A generator adds peace of mind. Conveniently located close to town, shopping, and everyday amenities, this move-in-ready home offers a great combination of updates, space, and the opportunity to add your own personal touch and make it truly yours.

122 Standard Ave, 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

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