Winsted CT Real Estate & Homes for Sale

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.

Estate Owned 3 to 4 Bedroom Colonial in Immaculate Move In Condition! Tucked away on a quiet street but within walking distance of Schools, Medical Facilities and Shopping. Special features include a huge cedar closet, Hardwood floors throughout the entire house, bay windows, 24' x 14' Family Room with Propane Gas Stove and an Oversized Full Bath The Master Bedroom features its own office. Relaxing Enclosed Porch. Park-Like Landscaped Grounds. Parking for 6 vehicles plus a free standing one car garage. Washer/Dryer included.

Perched atop Pratt Street in Winsted, this traditional farmhouse offers a peaceful retreat on a generous 1.75-acre lot. Tucked away from the hustle and bustle, the property provides a quiet sanctuary surrounded by nature, perfect for those yearning to live out their farming dreams. The home itself features a classic farmhouse charm with inviting living spaces. You'll find warm hardwood floors throughout many of the rooms, including a cozy living area with ample natural light streaming in through large windows and French doors. A wood-burning stove provides a rustic focal point and a source of warmth. The property boasts expansive green lawns, mature trees, and well-maintained garden areas with very purposeful planting and design so something is blooming throughout the spring and summer, offering a picturesque setting. For aspiring farmers or those who simply enjoy fresh eggs, a chicken coop is already in place, ready for your feathered friends. The considerable acreage provides plenty of space for gardening, recreation, or even small-scale farming endeavors.This Winsted farmhouse presents an ideal opportunity for those seeking a tranquil country lifestyle with the convenience of a ready-to-go setup for hobby farming.

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!

Charming Colonial on Nearly an Acre! Discover the perfect blend of comfort and space in this 3-bedroom, 1.5-bathroom Colonial home. Situated on almost an acre of flat, usable land, the property features a brand new grand circular driveway and a detached two-car garage. The inviting exterior, with its covered front porch, welcomes you into a home ready for its next chapter. Complete with a picturesque pond and a chicken coop, this property is a rare find with endless outdoor possibilities! A great location in the small town of Winsted but still very convenient to all of the shopping in Torrington.

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.

Welcome to lake living at its finest! Built in 2014 and first time on the market. Impeccably maintained, this stunning three bedroom, 3 bath home on Highland Lake, Winchester offers the perfect blend of comfort, style, and breathtaking VIEWS! From the moment you enter you will be captivated by the open-concept design, high-end finishes and panoramic lake views from both inside and out. Enjoy effortless indoor-outdoor living with a walkout lower level leading to a covered patio, hot tub and your own private dock-already in place and ready for summer fun. The two-car attached garage, basement storage and workshop, location off main road and numerous upgrades add convenience and value. Whether you're watching the sunrise or sunset, relaxing by the water, or entertaining friends and family, this home offers year-round vacation vibes and in immaculate condition. A rare opportunity on one of Connecticut's most desirable lakes-don't miss it!

SEASONAL HOME ONLY!!!! Season starts April 15 and ends October 15. This **seasonal** cottage is located in the beautiful West Hill Lake Community in Litchfield County. With access to the private beach and parking, you can enjoy swimming, boating, kayaking, and fishing. Be part of all the community activities on the Beach and at the Circle. This home sleeps up to 8, which includes a first-floor bedroom, pullout sofa and a 2nd floor bedroom area that sleeps 4 ! Possibilities are endless with this wonderful home! Nicely landscaped backyard with patio, fire pit, and shed for storage.

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!!

Welcome to this beautifully updated country retreat home, nestled in a peaceful setting, just minutes from everyday amenities. Enjoy serene summer evenings on the inviting covered front porch, where the sounds of nature & a nearby river within walking distance create the perfect ambiance. Ideal for entertaining, the outdoor space features a spacious deck, bluestone patio & hot tub. Inside, the main level offers a tastefully remodeled ktch w/granite countertops, SS appliances, & a beverage fridge. The open concept living room boasts soaring cathedral ceilings & a striking FP. The upper level inc 2 comfortable en suite bdrms, while the raised lower level provides an additional bedrm and flex office/bdrm perfect for a home office, guest suite, or playroom-conveniently located off the 3.5-car garage. The primary suite is a true retreat, featuring vaulted ceilings & a luxurious bathroom w/ radiant heated floors. An expansive newly finished space above the garage offers the ultimate workout area or perfect home business area with stairs conveniently down to the garage. Located just minutes from historic Riverton Center, enjoy world-class fly fishing & kayaking on the Farmington River, as well as nearby hiking, biking, & dining at the iconic Riverton Inn or General Store. Only 30 minutes to Hartford & Bradley International Airport. Whether you're seeking a full-time residence or a weekend getaway, this move-in-ready gem offers the perfect blend of luxury, charm, and convenience.

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. Owner/Agent

Perched up higher than the rest with sweeping views up a private driveway in beautiful Winchester Center you'll find this custom built 4,953 sq ft Colonial nestled in on 3.97 serene & bucolic acres. For the car enthusiasts, you'll see a 3 bay garage that can fit up to at least 7 cars if lifts are installed including a bonus 2 car tandem garage within the 3 bays. Plenty of room for oversized vehicles, equipment and workspace! Inside this home you'll find an open floor plan with newer oak hardwood flooring & recessed lighting on the Main Level with grand foyer, Palladian window, large living room with majestic column entranceway, FDR with chair rail, architecturally unique sunroom for those lazy mornings or weekends, eat-in-kitchen with island & plenty of cabinetry for storage, family room w/French doors leading out to the private grounds, sitting room with floor to ceiling fireplace, half bath & large pantry. You have your choice of 2 interior stairways up to 3 Bedroom Suites each with their own full baths, the Primary with hw flooring, full bath with stall shower & whirlpool tub in a spa like setting, laundry room and a bonus room which could be a 4th bedroom, just add a door to the alcove for a closet, access to the huge walk-up attic is through this bonus room.

99 Norfolk Rd, Winsted CT - Opportunity Knocks! This cute 3-bedroom Cape sits proudly on 1.3 acres and is ready for its next chapter! With vinyl siding, replacement windows, and a lovely setting perched high up from the road, the bones are here-now it just needs your vision. For those seeking an investment opportunity or ready to roll up their sleeves and bring this gem back to life, this could be the one. Whether you're a savvy investor or a creative homeowner-to-be, there's room to build equity and make it your own. Don't miss out on the potential packed into this charming country Cape. A little effort could go a long way here! Located in scenic Winsted-a town known for its small-town charm, vibrant arts scene, and proximity to lakes, trails, and the Litchfield Hills-you'll be perfectly positioned to enjoy both outdoor adventure and community charm.

LIVE WHERE NATURE MEETS LUXURY-Welcome to Lakeridge! This stylishly updated 2-bed, 2-bath townhouse blends modern finishes with serene woodland views in one of Connecticut's most sought-after amenity-rich communities. The remodeled kitchen stuns with white shaker cabinets, marble-look quartz countertops, a custom backsplash, and stainless appliances. A sunny open-concept dining area flows into a spacious living room, perfect for entertaining. Upstairs, the vaulted primary suite includes a walk-in closet, private office nook, and en-suite bath. Hardwood floors, laundry on the main level, and bonus skylit loft space offer added comfort and versatility. Enjoy your own private deck, then explore all that Lakeridge has to offer-24/7 gated security, indoor/outdoor pools, tennis, clubhouse, trails, lake, and more. Tucked in the Litchfield Hills just minutes to downtown Torrington, shops, dining, skiing, and culture. Whether year-round or weekend retreat, this is your turnkey escape. Tenant in place. Please make the EMD check payable to "Gennaro Bizzarro, Trustee", and note the property address on the memo line. PLEASE HAND DELIVER THE EMD CHECK WITHIN 24 HOURS. OF SIGNED CONTRACT TO: Regency Real Estate, LLC 424 Main St, Watertown CT 06795.

Welcome to 90 Woodside Circle - one of the largest and most desirable homes currently available in the sought-after LakeRidge community. This beautifully maintained 4-bedroom, 3.5-bathroom townhome offers over 2,000 sq ft of comfortable living space, thoughtfully designed for year-round enjoyment. Step inside to find a bright, inviting main level with all-new luxury vinyl flooring and an open layout perfect for entertaining. An expanded rear deck offers serene, wooded views, while the enclosed front porch includes a generous storage area, ideal for outdoor gear and seasonal items. Several bedrooms and bathrooms feature fresh, elegant paint for a modern and polished look. Stay cozy all winter with a brand-new, high-efficiency propane heating stove, a stylish and cost-effective addition to your comfort. LakeRidge is more than a home-it's a lifestyle. Residents enjoy secure gated access, indoor and outdoor pools, tennis courts, a private ski slope, equestrian stables, hiking trails, and countless other amenities that make every day feel like a vacation. Don't miss your chance to own a rare, spacious unit in this incredible community. Come experience paradise at 90 Woodside Circle!

Hearthstone model in small cul-de-sac. Living room has field stone wood burning fireplace. The remodelled kitchen has hardwood flooring & stainless appliances. The primary bedroom has a vaulted ceiling and full bath. The finished attic is accessed from the primary and has multiple uses, i.e., office, yoga, play room, etc. Two other bedrooms share another full bathroom on this level. Deck has been expanded and is ready for grilling season. The shed has been enclosed as a mudroom and is perfect for storage, etc. On the west side of the property, this unit is closer to the indoor pool, tennis courts, exercise room and the stables, garden plots and dog run.

MAJOR PRICE REDUCTION!!!!!!!!! Welcome to 274 Cliffside Drive(Lakeridge). COMPLETELY remodeled unit. New Kitchen with stove , microwave, and dishwasher. Granite countertops. Open Floor plan. Skylights, Fireplace, and Vaulted Ceilings. New Flooring, Light Fixtures and paint throughout home. Two new FULL BATHS-walk in shower off Primary Bedroom. Large outdoor deck. The amenities include walking and hiking trails, indoor/outdoor pool, canoeing, skiing, basketball, and pickleball courts. Nothing to do but move in.

HUGE Price reduction on this Hideaway unit at Lakeridge! Tucked in a scenic, gated community located in the heart of Litchfield County in the Northwest corner of CT and nestled on 235 beautiful acres of protected forest preserve - just two hours from both NYC and Boston. The Hideaway, is a 2 bdrm, 2 bath unit which is a perfect combination of both contemporary architecture and country ambience. The unit has been remodeled with newer kitchen cabinets, and SS appliances and newer interior windows. The living room is the center of the home with a cathedral ceiling, and a handsome stone fireplace for sitting by the fire after a day of enjoying the ski slopes, hiking in the woods or simply to just relax. An opening at the stair-landing provides a view of the first-floor and leads to the private primary bedroom, complete with walk-in closet and full remodeled bath. The dining area has sliders to a private sun deck/balcony where you can relax and unwind with your morning cup of coffee or an evening beverage to take in the natural surroundings. Lakeridge has so much to offer the nature enthusiast with its East and West Lodges, 2 pools; one indoor and one outdoors, fitness center, hiking trails, tennis courts and much more. Live like your on vacation everyday.

Experience the best of Lakeridge living in this Tanglewood-style 3-bedroom, 2-bathroom condo, nestled within 235 acres of protected forest. Whether you're seeking a permanent home or a weekend escape, this residence offers both tranquility and convenience. Recent updates, including new windows and a rear slider installed in 2022, enhance the home's natural light and energy efficiency. The rear slider off the dining area provides seamless indoor-outdoor flow, perfect for enjoying the wooded surroundings on your secluded deck. For added warmth and ambiance during the colder months, the propane fireplace creates a cozy retreat, making winter evenings even more inviting. Located between the East and West Lodge, this home offers easy access to two pools (indoor and outdoor), a fitness center, library, hiking trails, tennis courts, horseback riding, and even a private ski slope, ensuring year-round recreation. With its prime location and resort-style amenities, this condo is the perfect blend of adventure and relaxation. Schedule your tour today and make this retreat your own! See Lakeridgect.com for more details on this complex.

One of the most popular models at Lakeridge, this stately corner Tanglewood model sits on a knoll overlooking vast open space. Gently exterior stairs lead from the parking area of only six homes. This remarkable home is ready for you to move in - many new windows, newly painted (both interior and deck), all new flooring including beautiful wood floor covering the living room and dining room. There is a propane fireplace with tank big enough for a propane stove in kitchen. Sliders open to the the private expanded deck. A spacious entry offers ample storage closets. The flexible design of the end-unit Tanglewood offers the possibility of finishing the wall to the loft to make it a more private BR, or use as guest/office space.