Winsted Real Estate

Welcome to Winsted, a charming neighborhood nestled in the heart of Winchester, Connecticut, within the picturesque Litchfield County. This delightful community is known for its rich history, friendly atmosphere, and stunning natural surroundings, making it an ideal place for families, retirees, and anyone looking to enjoy a peaceful yet vibrant lifestyle.

Winsted boasts a unique blend of small-town charm and modern amenities. Stroll through its tree-lined streets, where you’ll find beautifully preserved historic buildings that tell the story of the town’s past. The centerpiece of the neighborhood is the serene Winsted Lake, perfect for outdoor enthusiasts who enjoy fishing, kayaking, or simply soaking in the natural beauty of the area. The nearby parks provide ample opportunities for hiking, picnicking, and family gatherings, ensuring that residents can enjoy the great outdoors year-round.

In addition to its scenic beauty, Winsted is home to a tight-knit community that hosts various events throughout the year, including farmers' markets, seasonal festivals, and art shows. The local schools are highly rated, making it an attractive option for families looking to provide their children with a quality education.

Conveniently located just a short drive from larger cities, Winsted offers a peaceful retreat while still providing easy access to shopping, dining, and entertainment. With its perfect blend of history, community spirit, and natural beauty, Winsted is a hidden gem waiting to be discovered. Come and experience the warmth and charm of this wonderful neighborhood—your new home awaits!

Newest Listings in Winsted

$285,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$195,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24214904 MLS ⋅ Riverwalk BLDG.

An END-unit condo in the Riverwalk Complex which runs along the Still River. This end unit adds privacy and is loaded with lots of natural light. Includes an oversized two car garage with generous parking and storage. A new pellet stove for efficient, cozy heating - with extra pellets included. The hot water heater - only 4 years old. Carpets professionally cleaned - fresh and ready for the next owner. Chimney cleaned in May 2026 - recently serviced and ready to use. Pets allowed. Schedule your showing today!

111 Riverton Road Unit 22, Winchester

$350,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$575,000

14 Beds ⋅ 12 Baths ⋅ ACTIVE Status ⋅ 24209933 MLS

99 High St, Winsted, CT 06098 is a multi family residential property. The Building was built in 1958 and includes 4 units as well as a garage for multi purpose storage warehouse use. It has a large swing up garage door for excellent storage. There is also a small office with an interior bathroom. 1 unit is a 2 bedroom 1.5 bath. 3 units are a 1 bedroom, 1 bath. Each unit is rented with a stable long term paying tenant. The garage is also rented to a long term tenant. The driveway parking area was recently redone with new concrete for parking access. The exterior was recently painted and has been well maintained, a new furnace has been added as well, 3 of the 4 units have been updated.

99 High St, Winchester

$449,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$405,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

$595,900

8 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 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

$325,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

$379,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

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Winsted Real Estate

Newest Listings in Winsted

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