Winsted CT Real Estate & Homes for Sale

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 functionality to the space. Additional highlights include modern stainless steel appliances, with all appliances included, and hardwood flooring throughout the home. The beautifully landscaped yard creates a perfect outdoor space for relaxation and gatherings. Conveniently located near local amenities, this home provides easy access to shopping, dining, and more. Experience this beautiful home firsthand Don't miss the opportunity to make this move-in ready gem your new home.

Introducing 29 Walnut: a grand Victorian home with a front porch view complimented by perennial rose gardens, a terrace fit for garden parties, and a large back yard. Upon entry, look upward to high ceilings, a spacious entryway and a grand, swirling staircase. Note precise finish work and period correct trim as you move into the open living, kitchen, and dining area with a chic half bath. Make your way upstairs to a vast landing made light and bright by charismatic arched windows. Experience purposefully designed bedrooms, laundry, and a full bath on this level, with space and plumbing prepared to add another luxurious restroom. Our third floor features additional finished living space with half bath, and unfinished attic space for storage. This antique stunner continues: to the basement! This level features a quiet, finished space showcasing the meticulously restored, massive foundation stones. Perfect for potential in-law or quiet space to relax together, this area is made complete with a walkout to the backyard. The lower level also houses a top of the line heating system and storage opportunities. More space abounds in the barn, with a stunning studio area on the top floor and workshop/parking below. Built in the late 1800s, 29 Walnut has been brought into the 21st century while preserving and accentuating important historical elements. While there are still finishing touches to be added, this home is ready for you to experience its classic Victorian elegance.

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 sleek countertops, stainless steel appliances, and ample cabinet space. Upstairs, you'll find three generously sized bedrooms and a refreshed full bath. Additional highlights include a convenient half bath on the main level as well as a cozy den. The backyard provides plenty of space for outdoor entertaining or gardening. Located in a desirable neighborhood close to local shops, restaurants, and parks, this move-in-ready gem won't last long! Schedule your showing today! Available financing: FHA, FHA 203k ($100 down), Conventional, Cash. Insured w Escrow Repair (IE).

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 dwellings, and home farming. Additionally, with a special permit, the property may accommodate a variety of uses, including affordable housing, bed and breakfasts, boarding houses, congregate residences, convalescent/nursing homes, country inns, home occupations, mixed-use buildings, multi-family dwellings, outdoor private recreation and entertainment facilities, restaurants, schools, two-family dwellings, and places of worship. The first floor features spacious rooms that could accommodate a kitchen, pantry, dining room, formal living room, family room, and office. The second floor provides ample space for four to five bedrooms, while the third floor boasts a generously sized apartment, adding flexibility to the layout. A standout feature is the impressive 2,300 sq. ft. three-story barn/garage, offering abundant storage, workshop space, and potential for various uses. Whether you're seeking a unique investment opportunity or a property brimming with character, this exceptional offering is ready for its next chapter.

Charming ranch within walking distance of Highland Lake! Features include a newly renovated bathroom, 2-car garage, and an extra large room. Enjoy a private backyard with a shed and endless potential. A well-maintained home with room to make it your own!

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 floor plan with water views from the eat-in kitchen, the fireplaced living room with hardwood floors, & the stunning great room with a wall of windows and French doors. The kitchen features a center island and skylights, creating a bright and inviting space to gather. The main level includes two bedrooms, one full bath, a half bath & laundry. The beautifully designed walk-out lower level adds 829 sq ft of finished living space, including a third bedroom, a half bath, recreation room, built-ins, & ample storage. There's even potential for further expansion in the unfinished portion. Step outside to enjoy a large L-shaped deck and a patio space right by the water's edge-ideal for relaxing, entertaining, or sitting by the fire pit. The home has been thoughtfully updated throughout, including the roof, siding, windows, decks, patios, and more. With public water and sewer, this prime location is close to the marina, Resha Beach, Red Barn Brewery, the town center, & offers an easy commute to Rte 44

Step inside this charming Cape Cod style home as you walk in the front door your in a large living room with wood floors, big picture window and lots of sunshine and seasonal views. The kitchen is bright and sunny and has room for a large table. The master bedroom is also on the main level and features double closets and wood floors. The full bath is also on this level . There is a cozy sunroom that leads you out back . As you walk upstairs you find a den with laminate floors and another Bedroom with wood floors and extra storage closets . The basement area has additional partially finished space for hobbies or play area , laundry and storage. Once you step outside you see a Beautiful 1/2 acre corner lot with lovely plantings and a spacious backyard with a shed and a detached 2 garage is at the end of a long paved driveway which can accommodate visitors and extra vehicles . Enjoy al fresco dining, relaxing and unwinding on the oversized deck. Great location in town ,perfect starter home, downsizing home or weekend country home! Winsted as great restaurants, Community College, Highland Lake , Parks, Beardsley Library, Mural Project, many shops and community events to enjoy .

Highland Lake, 3 Bedroom, 2 Bath, well maintained home. Lake views, newer appliances, hardwood floors, move-in ready, lake rights. Photos to come. 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

Sweeping Views, Exceptional Craftsmanship, and Lake Life at Its Finest.Set on a rare half-acre double lot across from Highland Lake, this custom-built 5-6 bedroom home offers panoramic views over First Bay and deeded dock access just steps from your front door-perfectly positioned beside Holland Beach for the ultimate lake lifestyle. Thoughtfully designed and meticulously maintained, the home spans over 3,200 square feet, delivering both impressive scale and everyday livability. The main level is ideal for one-floor living and entertaining, with an open-concept layout that includes a spacious kitchen with large center island, a sunlit dining area, and a living room that flows seamlessly onto a lakeside deck-where the vistas are truly breathtaking. A full bath and laundry room add convenience, while the main-level primary suite provides a private haven with water views you'll never tire of waking up to. Upstairs, you'll find four additional bedrooms and a full bath-perfect for hosting guests or accommodating a large family. The lower level offers flexible space, including a potential sixth bedroom, a kitchenette, and a half bath that's easily convertible to a full bath, plus ample storage for all your lake gear. Outdoor living is just as impressive, with multiple decks, a patio, and an outdoor shower to enhance your lake experience. Interior highlights include hardwood floors throughout and premium mechanicals:radiant heat powered by a high-efficiency Buderus natural

Beautiful custom built gem situated on a private site with a stream! Bright, sunny open floor plan with 3 bedrooms, 2.5 baths, great bonus room. Gleaming hardwood floors thru-out, granite tops, stone/marble baths, walk up attic. Large deck off kitchen. Don't miss this incredible opportunity!

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!

Welcome to easy, one-level living in this rarely available first-floor end unit at Gilbert Commons! This well-maintained 1 bedroom, 1 full bathroom condo offers approximately 570 square feet of comfortable living space with plenty of natural light and privacy. Inside, you'll find a spacious living room, a well-appointed kitchen with generous cabinet storage, and your own dedicated laundry room. The oversized bedroom includes three closets and an office area, plus direct access to your private outdoor patio-perfect for morning coffee or evening relaxation. Ideally located just minutes from Route 8, this condo is close to shopping, dining, medical offices, and more. Whether you're downsizing, just starting out, or seeking an affordable alternative to renting, this unit is a must-see!

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 appliances and farm sink, open floorplan greatroom with fireplace. Separate oversized two car detached garage with second floor and HVAC units for heating/cooling.

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!

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 settles in, the lake becomes a playground for ice fishing, skating, and cozy fireside gatherings, making this a year-round sanctuary. With luxury finishes, a gourmet kitchen, and custom craftsmanship in the main home, plus a charming guest bungalow, this property is ideal for hosting family, friends, or even guests. Zoned for a bed and breakfast and featuring an extra subdividable lot, the estate also holds exciting potential for income generation or expansion. Whether you're envisioning a private retreat, an upscale B&B, or future development with a subdividable lot, this versatile property is the perfect setting for those seeking a dynamic, all-season lake life.

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.

Back on Market due to inexperienced buyer's and capabilities to complete as discribed. Investors and Contractors Take Notice!!! This home is located in a well sought after and convenient area of Barkhamsted with many amenities within a short distance. The seller has Totally gutted this home down to the stud walls and waiting for your completion. Seller has cleared most of the .92 acres for a lovely private back yard / building site exspansion. Bring your imagination and see this today!

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.

Welcome to your own private paradise! Nestled on an incredible 55 acres, this one-of-a-kind property offers peace, privacy, and the perfect blend of comfort and outdoor adventure. Featuring a ranch-style layout with 3 bedrooms and 2 full baths, this home is ideal for easy one-level living. Step inside to find hardwood floors throughout and three cozy fireplaces that bring warmth and character to every room. Recent upgrades include brand-new distribution boxes in the septic system, offering added peace of mind for years to come.The expansive grounds feature a detached 2-car garage and a massive 3-car detached garage with a loft, perfect for a workshop, studio, or storing equipment and outdoor toys. Enjoy the natural beauty of fruit trees, grape vines, and a peaceful gazebo, along with private trails for ATV riding and exploration. Surrounded by nature, this property offers the ultimate in seclusion, yet you're just minutes from downtown amenities, dining, and shopping. Whether you're dreaming of a serene homestead, a recreational retreat, or simply room to roam, this extraordinary estate is a rare and remarkable opportunity you won't want to miss.

Charming Post & Beam Retreat with Expansive Garages and Workshop on 2.9 Acres Discover the perfect blend of rustic elegance and modern comfort in this beautifully maintained post and beam home, nestled on a serene 2.9-acre lot. Boasting approximately 2,700 sq ft of living space (as per owner), this residence features 3 spacious bedrooms, 2 full bathrooms, and a finished lower level, offering ample room for relaxation and entertainment. Car enthusiasts and hobbyists will appreciate the two separate 2-car garages, accommodating up to 4 vehicles, complemented by a substantial workshop and additional storage space above. The freshly painted exterior enhances the home's timeless appeal, while inside, soaring ceilings with exposed beams and ceiling fans create an airy ambiance. The gourmet kitchen is adorned with granite countertops, perfect for culinary adventures. Stay comfortable year-round with central air conditioning and cozy wood stoves. Outdoor living is elevated with a screened-in porch, expansive deck, inviting patio, and a charming cabana featuring a built-in bar-ideal for gatherings and relaxation. This unique property offers a harmonious blend of craftsmanship, functionality, and natural beauty-a true sanctuary to call home.

Enchanting Antique Dutch Colonial Estate with Carriage House and Barn. Nestled in a serene and private 51.2-acre haven, this stately home is a harmonious blend of historic charm and modern sophistication. As you traverse the meandering stone walls and explore the mix of sun-kissed meadows and whispering forests, you'll discover a world where time stands still, yet every modern convenience is at your fingertips. The property's outdoor allure is undeniable. Multiple walking or riding trails invite adventure, and the gardens, barn, carriage house and stone outbuilding offer endless possibilities for outdoor enjoyment. Step inside and be greeted by the warm embrace of rich hardwood floors, two fireplaces, French doors, and meticulously crafted woodwork that tell tales of yesteryear. The updated kitchen, equipped with a premium Wolf gas stove and a convenient butler's pantry, offers a perfect stage for culinary exploration. The living room, anchored by a cozy fireplace, formal dining room, and library, are infused with great natural light that dances across the spaces. The primary bedroom suite, a sanctuary of comfort, boasts its own fireplace, ensuring a restful retreat at day's end. Accommodate guests in style with four additional bedrooms, including a secluded guest room with a private stairway. Located in the heart of nature's playground in Litchfield county. Close to skiing, hiking, restaurants, and parks in Norfolk and Barkhamsted, and near the Farmington River.

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, to the 12 over 12 Windows and Fireplaces, Displays the Charm & Character in this Residence! For a more Modern Twist, there is a Fully Remodeled Eat-in Kitchen with Quartz Counters, as well as Remodeled Bathrooms. 4 TO 5 Bedrooms, 3 Full Baths, Formal Dining Room & Comfortable Living Room. Spacious Sunken 20' x 21' Family Room with Cathedral Ceiling. Unique Loft offers a Birdseye View to the Family Room. Level 7 Acre Lot Enhanced by Stone Walls and Nice Plantings. Outbuildings include a 30' x 35' 4 Stall Horse Barn with Tack Room & Hayloft. 2 paddocks and a 25' X 30' Storage Building. Mechanicals include Oil Hot-Air Furnace, 200 AMP Electrical Service, Well Water & Septic System. A Quaint and Rural Atmosphere, but within Close Proximity to Major Shopping, access to State Parks, Lakes, Golf Courses, Ski Areas, and Local Arts and Cultural Venues. The Photo Library Partially tells the Story, but prospective Buyers need to Visit / Tour this Lovely Property in order to Appreciate its Attributes!!

4-bedroom Lookout model in excellent condition. End unit, easy access and with expanded deck. The enclosed double-sized mudroom has a tile floor and a skylight. It also has two storage closets. The main level has a family/living/dining room, kitchen & powder room. A wood burning fireplace anchors the living rm. The kitchen has white appliances and a breakfast counter. The second level has 2 guest bedrooms, a full bathroom and the laundry. The primary has a vaulted ceiling, a dressing area and a full bath. The third floor has the fourth bedroom and another bath. Plus it has an area perfect for a desk. This area is well suited for guests or teenagers as it provides great privacy. Lakeridge is comprised of 235 acres surrounded on 3 sides by the Paugnut Forest and 100 acre Burr Pond. It is a four season community with indoor and outdoor tennis and swimming pools. There are 19 tennis courts (3 are indoors), pickle ball, basketball, volleyball, softball diamond, fitness centre, garden plots. It also has its own ski slope with a double chairlift and snowmaking/grooming capability. Located in the foothills of the Berkshires, there is easy access to all that Litchfield and Berkshire counties have to offer.

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 offers a Generac whole house generator for your convenience. There is also a spacious wine cellar in the basement. Outside you will find rock walls throughout the property, an inviting patio, and a large shed for your storage needs.

Backing up to the Winchester Land Trust, this property has beautiful view of woods from your back deck. The Lookout has 4 bedrooms and 3.5 bathrooms. It has a very easy short path access and just two steps to the unit. You enter the wood panelled foyer which is perfect for shoes, winter gear, etc. This unit has both a living room and a family room. The family room is off the foyer and proceeds into the kitchen, dining and living room. The foyer, family room and kitchen have hard wood flooring. The dining room (currently used as an office) has two sets of sliders which give access to the deck and the view of Winchester Land Trust. The living room has a wood burning fireplace. Upstairs, the primary is en suite and has a vaulted ceiling. Again, the view from the windows is of trees, trees, trees. Two other bedrooms and another full bath complete the second level. The third level has a bedroom with vaulted ceiling, an area for an easy chair or another office and a full bath. The three units, 233,234,235, all love the privacy in this area.