Winsted Real Estate

Welcome to Winsted, a charming neighborhood nestled within the picturesque town of Winchester, Connecticut. This vibrant community is part of Litchfield County, renowned for its scenic beauty and rich history. Winsted offers a delightful blend of small-town charm and modern conveniences, making it an ideal place for families, young professionals, and retirees alike.

As you stroll through Winsted, you'll be captivated by its historic architecture and friendly atmosphere. The downtown area is brimming with quaint shops, local eateries, and community events that foster a strong sense of belonging. The annual Winsted Winter Festival, for instance, brings residents together for fun-filled activities, showcasing the community spirit that defines this neighborhood.

Nature enthusiasts will appreciate Winsted’s proximity to stunning outdoor spaces. The nearby Highland Lake offers opportunities for fishing, kayaking, and picnicking, while the surrounding hills provide ample hiking trails with breathtaking views of the Connecticut landscape. For those who enjoy a more tranquil setting, the peaceful parks scattered throughout the area are perfect for leisurely walks or family outings.

Winsted is also conveniently located, providing easy access to major highways, making commutes to nearby cities a breeze. With excellent schools and a close-knit community, Winsted is a place where families can thrive and forge lasting connections.

Whether you're looking for a cozy home or a vibrant community, Winsted, CT, promises a fulfilling lifestyle amidst the natural beauty and historical richness of Litchfield County. Come explore all that this enchanting neighborhood has to offer!

Newest Listings in Winsted

$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

$299,900

5 Beds ⋅ 2 Baths ⋅ 24206151 MLS

Well-maintained two-family home offering excellent owner-occupant or investment potential. First-floor unit features 3 bedrooms, kitchen, and living room and is currently rented. Second-floor unit is vacant and offers 2 bedrooms, living room, and kitchen. Separate utilities and laundry for each unit. Full basement provides additional storage. Entire home has undergone lead remediation. Great opportunity to live in one unit while generating rental income.

18 Pratt St, 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

$325,000

4 Beds ⋅ 3 Baths ⋅ 24199882 MLS

Investment Opportunity! Well-maintained two-family house offering the ideal combination of functionality and income potential. Each unit features 5 rooms, including 2 bedrooms and 1 full bath. Enjoy the benefits of a convenient downtown location, close to schools, shopping, dining, and everyday conveniences. Both units are currently rented, making this property a strong choice for investors seeking steady cash flow.

48 Center St, 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

$324,900

4 Beds ⋅ 2 Baths ⋅ 24199721 MLS

Well-maintained two-family home offering spacious apartments, separate utilities, and a convenient location within walking distance to downtown amenities. The first-floor apartment features approximately 1,620 sq. ft. with a kitchen, living room, dining room, full bath, and 2-3 bedrooms. The second-floor apartment offers approximately 1,424 sq. ft. with a similar layout including a kitchen, living room, dining room, full bath, and 2-3 bedrooms. Each unit is serviced by its own efficient natural gas boiler and hot water and features a covered porch for additional outdoor living space. Situated on a generous .56-acre lot, the property also includes a two-story barn offering excellent storage and additional possibilities. A nicely maintained property with spacious units and a desirable location close to shopping, restaurants, and other downtown conveniences. An excellent opportunity for an owner-occupant or investor.

50 High 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

$399,900

4 Beds ⋅ 2 Baths ⋅ 24196702 MLS

Well-maintained 4-bedroom Colonial tucked away on a quiet dead-end street. This inviting home features a newly renovated eat-in kitchen with updated cabinetry, countertops, and finishes, perfect for everyday living and gathering. The comfortable layout includes a spacious living room and dining area, while four bedrooms offer flexibility for family, guests, or a home office. Enjoy the large yard, a back deck with a Sunsetter awning for shaded outdoor living, and a charming enclosed front porch. A generator adds peace of mind. Conveniently located close to town, shopping, and everyday amenities, this move-in-ready home offers both comfort and convenience.

122 Standard Ave, Winchester

$849,900

4 Beds ⋅ 2 Baths ⋅ 24191163 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

$849,900

4 Beds ⋅ 2 Baths ⋅ 24191186 MLS

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

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