Winsted, CT Homes for Sale

Exceptional Waterfront Living on Highland Lake - Your Dream Home Awaits! Seize this rare opportunity to own a stunning YEAR-ROUND WATERFRONT property on the highly sought-after EAST SIDE of Highland Lake! This turnkey gem is move-in ready and packed with modern features, offering the ultimate retreat for those seeking the serenity and excitement of lake life. Step into an open-concept kitchen and

Annie Simard LPT Realty

Live like you're on vacation every day! This beautifully updated lakefront home sits directly on the water in Highland Lake's first Bay, offering a level backyard & a private dock just steps from your door. With 50+ feet of direct waterfront and a fenced, low-maintenance yard, this charming year-round home is the perfect blend of comfort, style, & lakefront living. The interior boasts an open

Nancy Reardon Berkshire Hathaway NE Prop.

Nestled in a peaceful rural setting of Winchester Center, this charming home offers a perfect blend of rustic character and modern convenience. The property is located on over 3.3 acres of land and is adjacent to a scenic pond. Inside you will find a three bedroom two bath home with an additional in law apartment with one full bath and one bedroom and its own private entrance. The home also

Christina Niziolek William Raveis Real Estate

HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Customer, 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,

Marshall Cohen Cohen Agency

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

Mela Veltri Case KW Legacy Partners

Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family

David Sartirana Northwest CT Realty

3 Bedroom Split Level Ranch on 1.4 acres awaiting your creativity. Hardwood floors, newer siding and roof (6 Yrs) and large open Living room. To be sold "as is". Bring your ideas to this affordable property. Barkhamsted is home to great recreation including Barkhamsted Reservoir, Peoples state forest and the designated wild and scenic Farmington River.

Scott Holmes William Pitt Sotheby's Int'l

Not afraid of some peeling paint or rotting wood? This is the house for you! 30 Mountain Ave with 5 beds, 1.5 baths is your opportunity to bring a vision to life. Located in a welcoming neighborhood, it offers a generous layout ready for customization and renovation. Whether you're a seasoned investor or a first-time buyer with a knack for design, this home has the bones to become something

Derek Greene Derek Greene

Charming Country Cape with Cottagecore appeal on just over an acre of land and situated on a culd-de-sac. Located off the beaten path in the quiet hills of Winchester, this storybook Cape-style home offers the perfect blend of rustic charm and modern comfort. Convenient to Route 8 and just minutes to town amenities. Enjoy the natural beauty surrounding the property while relaxing on the deck and

Lisa Bredice William Raveis Real Estate

Welcome to 284 Gilbert Avenue-a charming 4-bedroom Cape that combines efficient updates with inviting living spaces. Approximately 1,849 sq ft of sun-splashed interiors begin with a spacious eat-in kitchen featuring generous cabinetry, a dining area, and sliders that open to an elevated deck-perfect for grilling while enjoying the privacy of the beautifully manicured backyard. The main level also

David Sartirana Northwest CT Realty

Your oasis awaits!!! Schedule your appointment today and come view this adorable Bungalow. There is so much potential to be made here. Bring your ideas and creativity as the seller is motivated, bring all offers!!!

Patrick Precourt Dorrance Realty

This solid 5-bedroom colonial in Winsted has been in the same hands for over 40 years and been well taken care of the whole time. With almost 2,500 square feet there's plenty of space for whatever you need, whether it's family, guests, or just room to spread out. Inside, you'll find large living and dining areas, good-sized bedrooms, and lots of natural light. If you're looking for space,

Austin Brochu Sullivan Real Estate Inc

Stunning Lakehouse! Victorian charm! One of the earliest Highland Lake homes with extensive custom upgrades and quality renovation. A true lakefront sanctuary offering spacious living areas, extensive outdoor living areas and wide open lake views offering South and West exposure for incredible sunsets. Lakefront dock system with hydraulic boat lift, Recently renovated kitchen /dining with newer

KAREN NEWTON William Pitt Sotheby's Int'l

Discover the Perfect Canvas for Your Dream Home in Winchester, Connecticut! This exceptional .41-acre parcel (owner reports closer to .5 ac) combines eight contiguous lots to create a prime opportunity for building your ideal residence. Nestled in the serene surroundings of the Highland Lake neighborhood, the property is lightly wooded with mature, straight-standing hardwoods and features a

Suzie Larson Turning Point Realty, LLC

Highland Lake, 3 Bedroom, 2 Bath, well maintained home. Lake views, newer appliances, hardwood floors, move-in ready, lake rights. 6,500 watt whole house generator. 8x12 shed with power, 35 Amp out side outlet for camper, working chimney for wood stove on lower level, ASSUMABLE MORTGAGE!

Josh Dionne Commercial Services Realty

A RARE OPPORTUNITY on HIGHLAND LAKE! This approved buildable lot is ready and waiting for you to build your dream! Lake life is a great life, make it yours!

Annie Simard LPT Realty

Back on the market, buyer's financing fell through. Welcome to this beautifully updated 3-bedroom, 1.5-bath colonial in the heart of Winsted! This home seamlessly blends classic charm with modern conveniences, featuring a spacious layout, abundant natural light, and stylish updates throughout. The inviting living room offers a cozy atmosphere perfect for gatherings. The updated kitchen boasts

Michael J Flaherty Jr Sullivan Real Estate Inc

Plot Of Land Valued at $32,060 Property ID #: 033 105C 044+45 Zoning: HL

Dillon Cass eRealty Advisors, Inc.

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

Mela Veltri Case KW Legacy Partners

99 Hubbard St. - Private Lot Near Downtown & Highland Lake. Tucked away at the end of a quiet dead-end street, this .37-acre lot offers both privacy and convenience. While enjoying a peaceful setting, you're still just minutes from downtown with easy access to shopping, dining, and entertainment. Plus, Highland Lake is just a short distance away, providing endless opportunities for boating,

David Sartirana Northwest CT Realty

124 Rockwell St. - Versatile .44-Acre Lot Near Downtown This .44-acre lot offers a prime location close to downtown with city water and sewer available in the street. The previous home sat at street level, while the majority of the lot slopes below, creating a unique landscape with plenty of potential. With a little imagination and the right site contractor, this property presents endless

David Sartirana Northwest CT Realty

Welcome to this beautifully renovated home, nicely tucked away in historic Winsted. This lovely property features over 2,200 square feet of gross interior living space. The large kitchen, dining, and living room areas provide a seamless flow, perfect for entertaining. The home boasts four spacious bedrooms and one and a half baths. The beautifully renovated attic adds even more charm and

Lourdes Galvan-Dominguez Coldwell Banker Realty

Addresses include 175 Main Street and 183 Main Street in Winsted, CT. Amazing opportunity to acquire a 9 Unit Asset (7 Apartments + 2 Retail) in Winsted with anchor tenant Noli's Restaurant (Rent $2,266 w 3% increase/year) w over 20 years in business! Pride of Ownership is evident with Capital Improvements made by the current owners, including: new water heaters, heating zones, electrical

Ryan Rea Berkshire Hathaway NE Prop.

Lakefront Historic Architecture meets Modern Styling on private waterfront penninsula with 360' direct lake frontage! Split timber tudor architecture offers unique features - leaded glass, stone flooring, window seats, paneling and mouldings, brick and stone appointments. A stunning kitchen for folks who cook, charming diningroom with bar and window seat overlooking the waterfront, and spacious

KAREN NEWTON William Pitt Sotheby's Int'l

Welcome to this spectacular Highland Lake estate, offering a unique blend of luxury & tranquility. Situated on 1.3 acres of level land, the property includes a large barn/garage capable of housing multiple cars, boats, & equipment. The main home boasts generously sized rooms w/ high ceilings, offering an open, airy feel throughout. The kitchen has been updated w/ hardwood cabinets, featuring

Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

This waterfront estate at 431 W. Wakefield Blvd in Winchester, CT, is not just a home but the ultimate Highland Lake lifestyle. Imagine waking up each day to stunning lake views, with endless seasonal activities awaiting just beyond your doorstep. In the summer, dive into boating, jet skiing, swimming, and fishing right from your private dock, or simply unwind along the shoreline. As winter

Lisa Ogren Berkshire Hathaway NE Prop.

WINCHESTER CREST 51 acres of forested gently rolling land sited upland in Winchester Center. There is a former homesite and multiple choices for additional homesites affording complete privacy. There is abundant wildlife, trails, intermittent streams, dense and sparse forest. Perfect for year round home site, weekend retreat or recreational land.

Tom McGowan Elyse Harney Real Estate

Prime Building Lot Near Downtown & Highland Lake-Discover the perfect setting for your dream home on this 2 acre lot at 503 N Main Street. The Property has over 500' of road frontage, permitted uses include; accessory residential uses, family day care home, farm, seasonal cottages, single family dwelling. The property offers a peaceful atmosphere while maintaining easy access to downtown

Charles Albertario William Raveis Real Estate

THREE PROPERTIES ONE PRICE!!! Includes single family, multi family & additional lot totaling 4.36 acres. 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, freshly updated. Brand new whole house natural gas

RYAN HORVAY Smith & DeGroat Real Estate

Nestled just steps from downtown, this .15-acre lot offers a fantastic opportunity in a highly convenient location. The property is fairly level and provides easy access to shopping, restaurants, The Gilson Theater, and Little Red Barn Brewery. With city water and sewer available, this lot is ready for your vision. Whether you're looking to build or invest, this prime spot puts you right in the

David Sartirana Northwest CT Realty

Located on a lightly traveled side street, this .22-acre lot offers a peaceful getaway with easy access to downtown. The property features a flat area at the street before gently sloping upward, creating a unique setting for potential future use. City water and sewer are available in the street, but buyers should conduct their own due diligence regarding buildability. Whether you're looking for a

David Sartirana Northwest CT Realty

A charming ranch-style home, located in a desirable area, offers the convenience of single-level living. It features 4 bedrooms and 3 bathrooms, making it perfect for families or anyone in need of extra space. Upon entering the main floor, you'll find a spacious living room filled with natural light, which creates a warm and inviting atmosphere. The kitchen provides ample counter space and opens

Marcy D'Angelo Coldwell Banker Realty

This versatile 2-family home would make a perfect owner occupant first floor unit with 3 bedrooms, with a 2 bedroom second floor apartment. Private entrances with separate utilities. Let your rental income help pay your mortgage. Each unit comes with formal living and dining rooms. Refinished original wide pine flooring. Large main Kitchen with lots of cabinet space which walks out to a

Christine Hunter Hunter Real Estate, LLC

COMING SOON - Live the Highland Lake Lifestyle! Located just a short walk to Holland Beach and a 3-minute drive to the public boat launch, this classic Colonial sits proudly on a level corner lot in an established neighborhood. Enjoy all the amenities of Connecticut's second largest lake-from swimming and boating to peaceful lakeside strolls-right from your doorstep. This is more than a home;

Paula Nelson William Raveis Real Estate