Winchester CT Real Estate & Homes for Sale

WOW - Welcome to 220 Gilbert Ave! Stop by for a visit and view the amazing transformation of this FABULOUS 2 family dwelling. Home has been completely remodeled inside and out. Relax and enjoy the level, private back yard or the sprawling, open front porch. The open floor plan boasts, spacious rooms, space for everyone and storage galore! The list of amenities is endless in this beautiful home! Nothing left to do but unpack and enjoy!

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 family room with granite fireplace with views in all directions. Sunroom with radiant heated stone flooring, extensive stone patios, pergola, gardens, terraces, sandy beach/swimming area. This is it!

Rarely Available End Unit at Riverwalk Condos! This pristine 2-bedroom, 1.5-bath condo offers a move-in ready experience with stunning river views and modern upgrades. The open-concept living space is filled with natural light and features crown molding and recessed lighting, adding an elegant touch to the living room. The stylish kitchen includes a new microwave, glass-top stove, and fresh paint throughout. Stay comfortable year-round with new A/C units and ceiling fans in the bedrooms. The setup for a pellet stove adds cozy potential to the space. A rare find in the area, this unit comes with a 2-car garage under the unit, along with spacious parking for convenience. Nestled in a well-cared-for complex, enjoy the perfect balance of privacy and community, with easy access to local amenities. Don't miss your chance to own this beautifully maintained home!

Welcome to your dream home in Winchester, Connecticut, just minutes from the serene Highland Lake. Park your boat o. Your property and use the public boat launch! This charming residence boasts a large, flat wooded lot, offering plenty of space for outdoor activities and privacy. The meticulously landscaped yard features vinyl siding, a spacious two-car garage, and ample parking. Step inside to discover a bright and inviting large living room with a cozy fireplace, perfect for gatherings. The main level also includes a convenient bathroom and a stunning enclosed porch that floods the space with natural light. The expansive kitchen seamlessly flows into the dining room, creating an ideal space for entertaining. A dedicated office room and a second living room with beautiful hardwood floors through and newer windows complete the main floor layout, along with an additional bathroom. Upstairs, you'll find four generously sized bedrooms, providing plenty of space for family or guests, alongside a full bathroom. With its combination of comfort, style, and functionality, this home is truly a must-see! Don't miss the chance to make it yours

Rare opportunity to secure 8 units under one roof! Fantastic location within walking distance of downtown Winsted and Northwestern Community College. Well-maintained and managed, this property presents a new owner the opportunity for cash flow out of the gate, with value to be added. 5 of the 8 units are connected with a state subsidy program allowing for guaranteed monthly income. Additional value add opportunity with a spacious basement for storage and coin-op laundry in basement (currently not in use, but functional). Numerous upgrades have been done to the property including unit updates, plumbing/sewer lines replacement, roof, windows, gutters, foundation repointing, and numerous mechanicals replaced. Plenty of off street parking available for tenants. This property is historically run at 100% occupancy and will continue to be a low maintenance, cash producing asset for years to come!

This single family home has 3 generous bedrooms and 1.5 bathrooms. It features a spacious kitchen with hardwood cabinets and black appliances. There are hardwood floors throughout the entire house, a dedicated laundry room, and a heated finished basement. This home is situated on a cul-de-sac and is close to highways and shopping. It also features a serene backyard that is ready for enjoyment.

Make this newly renovated house in the sought after Highland Lake community your full time residence or your home away from home! This home has gone through an extensive remodel including brand new roof, insulated siding, energy efficient windows, and LVP flooring. The home features a new large eat-in kitchen with brand new smart stainless steel appliances, living room, and remodeled full bathroom, with a bluetooth enabled exhaust fan, downstairs. Upstairs features 3 bedrooms plus an additional room that can be used as an office or playroom with newly added baseboard heat and partial views of Highland Lake. Make memories with friends and family in the nicely sized, flat yard. Imagine yourself enjoying life in this stunning home close to beach access and boat launch- make it yours today, this won't last long!

. The Main house features a Huge Stone fire-placed family room , plus a fire-placed Living room,for cozier gatherings. The home also includes a walk-out basement,. There is finished space ideal for an in-law suite on the second floor, located above the oversized attached 2-car garage. Outdoor living is enhanced by a rear deck that overlooks a tranquil pond, dam, and wooded area, making it a peaceful retreat. For gardening enthusiasts, an attached 9 x 26 Greenhouse is available. In addition to the main house, the property includes a 2-stall Barn, a Bunkhouse, and a detached 2-car garage with workshop, offering ample space for storage or hobbies. This property provides privacy, space, and endless opportunities for customization, making it an ideal choice for those looking for both comfort and potential. In need of Work , but well worth the effort. Being Sold "AS IS "

Attention investors! This 2-bedroom, 1-bathroom single ranch style home is a prime opportunity for a complete rehab. The property was involved in a fire and requires a full rehab with a 1-car garage and is being sold as-is. Subject to probate approval.

Lovely Country home located on the outskirts of town features 8 rooms 4 bedrooms and 2 full baths . The living room has a cathedral ceiling with a pellet stove and is open to the fully applianced remodeled Cherry kitchen with granite counters and tiled floor. The breakfast nook features a sliders that walks out to a spacious screened sunroom. The formal dining room has wood floors and a bay window .The 1st floor family room has a cathedral ceiling and beautiful built in cabinets and book shelves . There is access to the master suite from this wing of the house. There are 3 bedrooms ,a laundry room and a full bath on the main level . The master suite has a private staircase to the 2nd floor .The master bedroom is a sunny room with a cathedral ceiling , built in shelving and has a walk in closet and full bath . This home has great space . There is a pull down attic access for storage and a large 2 car garage with attic storage . As you walk around the level yard you notice a garden area and shed , nice fire pit and a deck . There is a full house generator that runs on propane. The roof has architectural shingles . The house has vinly siding . There is a small pond in the woods but is not in view or used .

Welcome to 19 Cottage Street, a stunning turnkey Colonial in the heart of Winsted that beautifully blends modern functionality with classic charm. As you enter, a spacious foyer with new tile flooring leads into a bright living room featuring gleaming hardwood floors, create a warm, inviting atmosphere. A dedicated office space presents an ideal setting for productivity, while the heart of the home-the expansive kitchen-boasts custom cabinetry, quartz countertops, and sleek appliances. The large island, which seats four, is perfect for casual dining or gatherings. Just off the kitchen, a sun-drenched sunroom is ideal for enjoying morning coffee with natural light pouring in. The first floor also features a chic half bath and washer/dryer hookups for added convenience. Upstairs, the master bedroom impresses with a spacious walk-in closet, while two additional bedrooms and two full baths make it perfect for family living or hosting guests. The third level also includes three versatile rooms and an additional half bath-perfect for a home office, playroom, or guest suite. Outside, a new driveway and garage doors add curb appeal, while freshly laid masonry lines the front and back yards, offering stylish outdoor spaces. With its blend of modern updates and timeless design, this home is truly move-in ready. Schedule a viewing today and make 19 Cottage Street your new home!

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 updated appliances, a spacious eat-in area, & an oversized island perfect for meal prep & entertaining. The rest of the main floor is ideal for hosting guests, w/ expansive windows providing stunning views of Highland Lake from every angle. Step outside to a covered front porch, where you can take in breathtaking sunrise views over the water. The second floor is home to the huge Primary bedroom, complete w/ a recently remodeled full bath & two walk-in closets. Four additional spacious bedrooms share Jack & Jill bathrooms, & a second-floor summer porch offers a serene spot to enjoy the natural beauty of the lake. The third floor adds even more space, w/ three additional bedrooms & a full bath that could be updated to reflect your needs. Directly on the lake is a 1/4 acre lot w/ 150+/- ft of water frontage, you'll find a charming lakeside cottage that features a cozy fireplace, kitchenette, full bath, & wrap-around deck. Whether you're relaxing on the dock or enjoying the cottage's amenities, this entire property is perfect for experiencing the best of lakefront living.

If you are looking for a mini estate look no further. This completely remodeled home has everything you need. New eat in kitchen with a bay window overlooking the rear yard. Quartz c/tops and new appliances. Formal dining room, den with fireplace and wood stove insert. Sliders to rear deck and pool. Large living room with hardwood floors. Primary bedroom with full bath and two walk in closets. Two additional bedrooms and another full bath on the second floor. Step outside onto the well landscaped picturesque grounds. You are on a private almost 5 acre parcel that provides privacy but yet close to everything. Take a look!

Welcome to 14 Curtice - Offering 3 beds 1 bath, and over 1200 sqft, with a bit of vision this house could be turned back into a home. Property has new siding, new windows, and a newer roof, all it needs is a cosmetic facelift. Schedule your appointment today!

Welcome to a piece of history with this enchanting Cape farmhouse, a true gem nestled in the picturesque town of Winchester. Built in 1830, this home radiates classic charm with its original details and timeless character. The property features two inviting fireplaces, perfect for cozy evenings, and an oversized country kitchen that offers ample space for culinary creativity and family gatherings. The living room exudes warmth and charm, making it an ideal space for relaxation, while the cozy dining room provides a welcoming setting for meals with loved ones. With three bedrooms, this home offers comfortable living spaces that maintain its historical allure. The magnificent and private 13-acre lot presents a rare opportunity for renovation, expansion, or even subdivision. Whether you envision restoring the farmhouse to its former glory, expanding to create your dream estate, or exploring the potential for development, the possibilities are endless. Don't miss out on this unique chance to own a piece of Winchester's history and make it your own. This charming farmhouse is not just a home; it's a canvas for your dreams. Act quickly-opportunities like this are truly one of a kind.

DIRECT WATERFRONT PROPERTY!!!! The estate at 431 W. Wakefield Blvd in Winchester, CT, is truly a gem with its stunning views of Highland Lake and unique amenities. The combination of a main home with high-end finishes, Gourmet kitchen, Custom craftsmanship throughout, a guest bungalow, and the potential for subdivision or development boast a wealth of possibilities. Whether it's creating a luxurious private retreat, expanding the property, or even starting a Bed and Breakfast, this property is versatile and filled with potential. This year-round home truly embraces the best of all seasons. Whether it's the thrill of boating and jet skiing in the summer, relaxing on the beach, or enjoying winter activities like ice fishing, the opportunities for recreation are endless. This versatility makes the property even more appealing to potential buyers looking for a dynamic lifestyle, where they can enjoy the great outdoors year-round.

Welcome to 315 East Wakefield Blvd, a charming 3-bedroom, 1-bath ranch offering stunning views and easy access to Highland Lake. This home is in impeccable condition, featuring an updated kitchen and bath, along with newer hard surface flooring. The inviting living room boasts a propane fireplace, wood stove, and a picture window perfectly framing the serene lake views. The updated eat-in kitchen opens to a covered deck and a fenced-in rear yard, providing additional outdoor space with more picturesque views of the lake. This well-cared-for home is not only a cozy retreat but also a gateway to the year-round recreational activities that Highland Lake offers. Spanning 444 acres, the lake is renowned for its watersports, trophy trout and bass fishing, and a marina where you can rent a slip or even a boat. Whether you're seeking a peaceful lakeside residence or an active lifestyle, 315 East Wakefield Blvd is the perfect place to call home.

Welcome home! This inviting residence features an open, airy feel with abundant natural light from big windows and multiple skylights. The main level boasts solid hardwood floors and tiles, while the spacious eat-in kitchen, though older, is well-maintained and perfect for family meals. Enjoy three full bathrooms, a central vacuum system, and tons of storage space throughout. The primary bedroom is a cozy retreat with its own fireplace, and the large living room also includes a fireplace for added charm. Outside, you'll find a deck, mature plantings, flower beds, and a handy shed. With a big 2-car garage and a fantastic laundry room, this home has everything you need! This property is being sold As-Is. All inspections for informational purposes only.

Stunning Lake Vistas! Have you been dreaming of a lake view and a property that is Special, Unique and TURN KEY? Fifty feet of waterfront property is included with boat dock and lift for lake enthusiasts! Nestled across from the serene First Bay, this beautifully renovated two-family home can be used as a single family and offers breathtaking water views and modern comforts. Perfect as a family retreat or an income-generating property, the home is fully renovated with upscale finishes throughout and boasts central air, newer appliances, windows, siding, and high-efficiency propane-fueled furnaces. Gorgeous details throughout make this a truly exceptional property. On the first floor, you'll find a rustic custom kitchen w granite, upgraded appliances (sub zero refrigerator and bevg fridge, gas range, dishwasher), a full bathroom w marble and walk-in shower, two spacious bedrooms, and a large family room w French doors leading to a covered wrap around porch to enjoy that view! The second floor unit features a kitchenette with fridge, dishwasher, and range, dining room/office, two bedrooms, and a family room with sliders to a covered porch offering the same amazing landscape! Additional highlights include an oversized two-car detached garage and carport, hot tub(sold as is), level yard area, and side deck. This home is situated just across the street from the water, providing easy access to all lake activities. Rustic yet Upscale! A RARE FIND!

Stunning Lake Vistas! Have you been dreaming of a lake view and a property that is Special, Unique and TURN KEY? Fifty feet of waterfront property is included with boat dock and lift for lake enthusiasts! Nestled across from the serene First Bay, this beautifully renovated two-family home can be used as a single family and offers breathtaking water views and modern comforts. Perfect as a family retreat or an income-generating property, the home is fully renovated with upscale finishes throughout and boasts central air, newer appliances, windows, siding, and high-efficiency propane-fueled furnaces. Gorgeous details throughout make this a truly exceptional property. On the first floor, you'll find a rustic custom kitchen w granite, upgraded appliances (sub zero refrigerator and bevg fridge, gas range, dishwasher), a full bathroom w marble and walk-in shower, two spacious bedrooms, and a large family room w French doors leading to a covered wrap around porch to enjoy that view! The second floor unit features a kitchenette with fridge, dishwasher, and range, dining room/office, two bedrooms, and a family room with sliders to a covered porch offering the same amazing landscape! Additional highlights include an oversized two-car detached garage and carport, hot tub (sold as is), level yard area, and side deck. This home is situated just across the street from the water, providing easy access to all lake activities. Rustic yet Upscale! A RARE FIND!

Build your DREAM home! Largest lot available on the lake with great views and parking! Will build to suite. Don't miss this wonderful opportunity! WELL IS LOT CORNER at Forest Ave FRONTAGES ARE MARKED IN RED. +-a2 map and topo in documents.

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 upgrades, fire rated tenant main doors & new fire alarms/strobes in both buildings. The unit mix is: 1, 4 bedroom ($1,100); 4, 2 bedrooms ($1,000; $1,050; $900; the other can be rented for up to $1500 per month) and 2, 1 bedroom units ($950 each). The 175 Main St had a roof replacement in 2021, a privacy fence enclosure installed & all 4 residential units have gone through renovations. 183 Main St has had a roof replacement in 2023, aft wall structural repair, new studs, insulation, beams & siding. 183 2A has been refurbished. One retail space is leased to Noli's Restaurant which has a patio. Noli's pays their heat and electric. The current owner leased the second retail space to Northwest Soup & Deli ($1500 then $1650 on 1/1/2025) and this establishment has all new equipment. They pay their own electric and a fixed gas, water/sewer reimbursement to the Owner. The residential tenants pay their electric. Owners are very meticulous and detail oriented. This is a seamless opportunity to own a well-run asset. Properties being sold together.

A Perfect Year Round or Vacation Home where you can have all the enjoyment offered of lake living with a water front lot yet a home with privacy. This Beautiful home features 3/4 Bedroom with 3 Full Bathrooms. The Main Floor with open plan features Brazilian Cherry flooring in Living & Dining Rm. Second Floor features Large primary suite & bathroom with stunning views of the lake. The listing includes a grassy water front property with dock for your boat or jet ski. Perfect for swimming, picnic, paddle board or enjoying making memories. Don't miss the opportunity!!!!!!

3500 sqft 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 currently under renovation. Brand new heating system! Property includes two parcels totaling nearly 4 acres of land.

Three properties totaling 4.41 acres for one price! 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, currently under renovation. Brand new whole house natural gas heating system! 1.13 acres 2. Updated 960 sq ft ranch. 3 bed, 1 bath, walk out basement, great backyard with tons of potential. .37 acres. 3. 2.9 acres of undeveloped land. Potential for multiple access points. Condo's? Apartments? Parking garage? Bring your ideas and imagination. All properties sold together. Tax & Square footage is total for all three properties.