5,102

Winchester, CT Homes

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  • 77 Hubbard St, Winsted, CT 06098
    77 Hubbard St, Winsted, CT 06098
    77 Hubbard St, Winsted, CT 06098
    /8

    $299,900 Pending

    • 6 Beds
    • 2 Baths
    • 2,699 Sq Ft

    77 Hubbard St, Winsted, CT 06098

    Discover this versatile two-family residence offering a blend of modern updates and timeless charm. Each unit boasts three bedrooms and a full bath, providing ample space and comfort for tenants or multi-generational living. The first-floor unit has been beautifully renovated, featuring a brand-new kitchen with stylish finishes, updated bath, gleaming hardwood floors, and plush new carpet in the

    Agent Photo

    Amy Rio

    Executive Real Estate Inc.

    (860) 452-3957

    77 Hubbard St, Winsted, CT 06098
  • 101 Whiting St, Winsted, CT 06098
    101 Whiting St, Winsted, CT 06098
    101 Whiting St, Winsted, CT 06098
    /34

    $1,500 - $1,800 per month

    Mill at Still River

    1-2 Beds

    101 Whiting St, Winsted, CT 06098

    By far the best place to live in Winsted, Connecticut. Turn of the century construction, every unit overlooks the beautiful Still River, our 700-1000 square-foot one and two bedroom interiors are bright and charming and feature exposed wood beams, 10-foot ceilings, oversized industrial windows, and exposed brick walls. We deliver nature at your door. Our community amenities include same-floor

    101 Whiting St, Winsted, CT 06098
  • 174 Boyd St, Winsted, CT 06098

    $280,000 Sold Jun 16, 2025

    • 1,424 Sq Ft
    • $197/SF
    • 110 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1900

    174 Boyd St, Winsted, CT 06098

    A charming house located 2 blocks from highland lake. This 3 bedroom, 1 large full bath is move-in ready. The dining room has a beautiful built in, the 3 large windows allowing for natural light to brighten the room. Off of the dining room is a nice family room. The kitchen is large and spacious and off the kitchen in the back is a lovely sunroom with a fireplace (natural gas) that has sliders

    Margaret Alexson Elyse Harney Real Estate

    174 Boyd St, Winsted, CT 06098
  • 111 South Rd, Winsted, CT 06098
    111 South Rd, Winsted, CT 06098
    111 South Rd, Winsted, CT 06098
    /39

    $779,900

    • 3 Beds
    • 3.5 Baths
    • 4,953 Sq Ft

    111 South Rd, Winsted, CT 06098

    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

    Dawn Rousseau Showcase Realty, Inc.

    111 South Rd, Winsted, CT 06098
  • 936 Main St Unit 7, Winchester, CT 06098
    936 Main St Unit 7, Winchester, CT 06098
    936 Main St Unit 7, Winchester, CT 06098
    /9

    $1,400 per month

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • Property for Rent

    936 Main St Unit 7, Winchester, CT 06098

    Recently purchased and re-built manufactured home community in Winsted in final stages of being completed. The entrance to the property is being changed and will be much nicer than now. This is the final phase. Beautiful free standing ranch style homes, 2 bedroom with 2 baths available as well as an attached entrance enclosed porch. This is the only house available, all others are rented to good

    Michael Block Building Blocks LLC

    936 Main St Unit 7, Winchester, CT 06098
  • 704 W Wakefield Blvd, Winsted, CT 06098

    $495,000 Sold Jun 09, 2025

    • 754 Sq Ft
    • $656/SF
    • 4 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1911

    704 W Wakefield Blvd, Winsted, CT 06098

    Quintessential New England Lake Cottage! Three season sweet lakefront retreat with charm and character on Highland Lake - one of CT's largest lakes. Waterfront dock, deck offering long views over the lake and plenty of seating for family bbq's. Recently remodeled kitchen, charming livingroom with stone fireplace, hardwood floors, beams, newer windows / sliding doors, half bath and shower lower

    KAREN NEWTON William Pitt Sotheby's Int'l

    704 W Wakefield Blvd, Winsted, CT 06098
  • 115 Old Robertsville Rd, Winsted, CT 06098
    115 Old Robertsville Rd, Winsted, CT 06098
    115 Old Robertsville Rd, Winsted, CT 06098
    /13

    $649,900

    • 5 Beds
    • 1.5 Baths
    • 2,304 Sq Ft

    115 Old Robertsville Rd, Winsted, CT 06098

    Development Opportunity! 41.23 Acres with Historic Home & Barn - Subdivision Possible Rare chance to own a prime 41.23-acre parcel in New England with an 1800 Antique Colonial Farmhouse and classic English/New England hybrid barn. The land may be subdividable and is located near the highly desirable Riverwalk Condominiums, making it ideal for new condo development (subject to approvals). The

    Jared Tedesco Litchfield County Real Estate

    115 Old Robertsville Rd, Winsted, CT 06098
  • 13 Wallens St, Winsted, CT 06098
    13 Wallens St, Winsted, CT 06098
    13 Wallens St, Winsted, CT 06098
    /20

    $1,000 - $1,450 per month

    Gilbert Clock Apartments

    Studio-2 Beds

    13 Wallens St, Winsted, CT 06098

    At Gilbert Clock Apartments , our designer-inspired amenities set us apart from the competition. We pride ourselves on providing top-quality apartments outfitted with the everyday amenities you expect as well as luxury amenities to delight your senses and enhance your modern life. Indulge your culinary instincts in your state-of-the-art kitchen, furnished with Beautiful and energy-efficient

    13 Wallens St, Winsted, CT 06098
  • 421 Unity Place, Winsted, CT 06098

    $286,000 Sold Jun 09, 2025

    • 1,440 Sq Ft
    • $199/SF
    • 25 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1927

    421 Unity Place, Winsted, CT 06098

    UPDATED | SERENE | CHARMING | 2 LOTS | This Highland Lake retreat is ideal for the 1st time homeowner, getaway retreat or investment opportunity. Nestled in New England's natural beauty, you are sure to enjoy your lush surroundings & stunning views, truly a nature lovers delight. 3+ generous bedrooms, 2 full bathrooms, dining room, fireplaced living room, updated kitchen with stainless

    Michelle Lorenzetti Premier Re Group LLC

    421 Unity Place, Winsted, CT 06098
  • 112 Shore Dr, Winsted, CT 06098
    112 Shore Dr, Winsted, CT 06098
    112 Shore Dr, Winsted, CT 06098
    /40

    $889,000

    • 3 Beds
    • 3 Baths
    • 2,113 Sq Ft

    112 Shore Dr, Winsted, CT 06098

    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.

    112 Shore Dr, Winsted, CT 06098
  • 111 Rockwell St, Winsted, CT 06098
    111 Rockwell St, Winsted, CT 06098
    111 Rockwell St, Winsted, CT 06098
    /15

    $1,275 per month

    • 2 Beds
    • 1 Bath
    • 1,512 Sq Ft
    • House for Rent

    111 Rockwell St, Winsted, CT 06098

    Charming 2-bedroom, 1-bath unit located in a quiet Winsted neighborhood on a spacious corner lot. This home features a well-appointed kitchen with ample cabinet space, a cozy island, and appliances. The unit includes beautiful hardwood floors throughout the living spaces and large windows that fill the rooms with natural light. Outside, enjoy a private entrance and a shared green space.

    Colin Murray Dorrance Realty

    111 Rockwell St, Winsted, CT 06098
  • 323 E Wakefield Blvd, Winsted, CT 06098

    $397,000 Sold Jun 04, 2025

    • 1,426 Sq Ft
    • $278/SF
    • 4 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1989

    323 E Wakefield Blvd, Winsted, CT 06098

    Charming 3-Bedroom Cape in Sought-After Lake Community. Welcome to this beautifully updated 3-bedroom, 2.5-bath Cape nestled in a vibrant lake community offering year-round fun! Enjoy boating, waterskiing, tubing, and all the perks of lake life just steps from your door, with serene water views to enjoy every day. The main level features a bright, inviting living room with hardwood floors and a

    Heather Crabtree Coldwell Banker Realty

    323 E Wakefield Blvd, Winsted, CT 06098
  • 469 Platt Hill Rd, Winsted, CT 06098
    469 Platt Hill Rd, Winsted, CT 06098
    469 Platt Hill Rd, Winsted, CT 06098
    /39

    $995,000

    • 4 Beds
    • 2 Baths
    • 3,088 Sq Ft

    469 Platt Hill Rd, Winsted, CT 06098

    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

    469 Platt Hill Rd, Winsted, CT 06098
  • 12 Beach St Unit 7, Winsted, CT 06098
    12 Beach St Unit 7, Winsted, CT 06098
    /2

    $1,050 per month

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    12 Beach St Unit 7, Winsted, CT 06098

    Property Id: 1615805Total 8 - 1 BED ROOM UNITS in the building CLOSE to Route 8 & WINSTED Mainstreet, on-site parking, coin operated laundry, REAR BALCONY.

    12 Beach St Unit 7, Winsted, CT 06098
  • 155 Mathew Rd, Winsted, CT 06098

    $314,000 Sold May 30, 2025

    • 1,536 Sq Ft
    • $204/SF
    • 56 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1979

    155 Mathew Rd, Winsted, CT 06098

    Situated on a private road with views of Highland Lake, this beautifully updated home offers a perfect blend of modern comfort and quiet surroundings. Boasting a brand-new roof, siding, windows, as well as new front and back porches this home is ready to go for anyone looking for a great home. Step inside to discover an inviting, light-filled interior with contemporary finishes throughout. The

    Austin Brochu Sullivan Real Estate Inc

    155 Mathew Rd, Winsted, CT 06098
  • 119 W Wakefield Blvd, Winsted, CT 06098
    119 W Wakefield Blvd, Winsted, CT 06098
    119 W Wakefield Blvd, Winsted, CT 06098
    /35

    $849,900

    • 4 Beds
    • 2 Baths
    • 1,781 Sq Ft

    119 W Wakefield Blvd, Winsted, CT 06098

    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

    119 W Wakefield Blvd, Winsted, CT 06098
  • 175 N Main St Unit 2B, Winsted, CT 06098
    175 N Main St Unit 2B, Winsted, CT 06098
    175 N Main St Unit 2B, Winsted, CT 06098
    /11

    $1,100 per month

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft
    • Apartment for Rent

    175 N Main St Unit 2B, Winsted, CT 06098

    Located in the heart of downtown. The actual address is 175 Main not N Main as displayed on some websites. This 2 bedroom unit has been freshly painted and is ready to move in. Rent includes heat and hot water. NO pets and NO smoking in unit. Nice view of the Mad River and ballparks from back balcony.

    David Sartirana Northwest CT Realty

    175 N Main St Unit 2B, Winsted, CT 06098
  • 150 Meadow St, Winsted, CT 06098

    $250,000 Sold May 30, 2025

    • 2,094 Sq Ft
    • $119/SF
    • 80 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1860

    150 Meadow St, Winsted, CT 06098

    Steeped in history and charm, this 1860-built home offers a blend of classic character and modern updates. With 8 rooms, 4 bedrooms, and 2 baths, this spacious home provides versatile living options. The main level features a kitchen with recent updates, a dining room, a cozy living room, a primary bedroom with an en-suite bath, and a home office. Upstairs, you'll find three bedrooms, a study

    David Sartirana Northwest CT Realty

    150 Meadow St, Winsted, CT 06098
  • 55 Walnut St, Winsted, CT 06098
    55 Walnut St, Winsted, CT 06098
    55 Walnut St, Winsted, CT 06098
    /37

    $525,000

    • 5 Beds
    • 4 Baths
    • 5,016 Sq Ft

    55 Walnut St, Winsted, CT 06098

    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

    55 Walnut St, Winsted, CT 06098
  • 279 N Main St Unit 6, Winchester, CT 06098
    279 N Main St Unit 6, Winchester, CT 06098
    279 N Main St Unit 6, Winchester, CT 06098
    /9

    $799 per month

    • 1 Bed
    • 1 Bath
    • 575 Sq Ft
    • Condo for Rent

    279 N Main St Unit 6, Winchester, CT 06098

    Modern 1-bedroom apartment built in 2005 - Kitchen with lots of cabinet space. Spacious bathroom. Hardwood floors. Plenty of closet space. Open layout/floorplan. Freshly painted. NO PETS!!!Credit check required. Reach out to Matthew at contacts listed Email/Text message preferred

    279 N Main St Unit 6, Winchester, CT 06098
  • 9 Loomis St, Winsted, CT 06098

    $144,000 Sold May 29, 2025

    • 1,768 Sq Ft
    • $81/SF
    • 18 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1910

    9 Loomis St, Winsted, CT 06098

    ZONING IS TG Regulations are tailored to promote desired development patterns that promote an appropriate transition from rural to town uses. Certain uses are permitted, while others require a Special Permit. Nestled just minutes from Highland Lake and downtown Winchester, 9 Loomis Street presents an excellent opportunity for those seeking a fixer-upper with great potential. This colonial-style

    Kristen Duchene Litchfield County Real Estate

    9 Loomis St, Winsted, CT 06098
  • 144 Marshall St, Winsted, CT 06098
    144 Marshall St, Winsted, CT 06098
    144 Marshall St, Winsted, CT 06098
    /39

    $559,999 Pending

    • 3 Beds
    • 2 Baths
    • 1,744 Sq Ft

    144 Marshall St, Winsted, CT 06098

    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

    Monica Palmerie RE/MAX RISE

    144 Marshall St, Winsted, CT 06098
  • 19 Center St Unit 1, Winsted, CT 06098
    19 Center St Unit 1, Winsted, CT 06098
    19 Center St Unit 1, Winsted, CT 06098
    /5

    $1,575 per month

    • 3 Beds
    • 1 Bath
    • 900 Sq Ft
    • House for Rent

    19 Center St Unit 1, Winsted, CT 06098

    Three bedroom apartment on the first floor. Large kitchen, light filled living room and a recently remodeled bath. Washer/dryer can be added for an additional $75 per month. Pets considered. Off-street parking. First month and two months security, if applicable. Credit and background check required.

    Amanda Balaski Northwest CT Realty

    19 Center St Unit 1, Winsted, CT 06098
  • 173 Torringford St, Winsted, CT 06098

    $355,000 Sold May 29, 2025

    • 2,239 Sq Ft
    • $159/SF
    • 46 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1955

    173 Torringford St, Winsted, CT 06098

    Welcome to this beautiful Cape Cod home, offering 2239 square feet of living space. Nestled on a serene 1.79 acre lot, this inviting property provides a perfect blend of comfort and style. Step inside to a generous entry that flows seamlessly into the open living and dining areas, creating an ideal space for both everyday living and entertaining. The huge family room is a true highlight,

    Sandy Fehrs Lamacchia Realty

    173 Torringford St, Winsted, CT 06098
  • 200 Perch Rock Trail, Winsted, CT 06098
    200 Perch Rock Trail, Winsted, CT 06098
    200 Perch Rock Trail, Winsted, CT 06098
    /25

    $989,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,407 Sq Ft

    200 Perch Rock Trail, Winsted, CT 06098

    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

    200 Perch Rock Trail, Winsted, CT 06098
  • 188 E Lake St, Winsted, CT 06098
    188 E Lake St, Winsted, CT 06098
    188 E Lake St, Winsted, CT 06098
    /11

    $2,200 per month

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Townhouse for Rent

    188 E Lake St, Winsted, CT 06098

    Welcome to our beautiful lakeside apartment! 2 bedroom/1 Bath. Situated on the picturesque shores of Highland Lake, this fully renovated and furnished apartment offers stunning views and serenity. The apartment features a spacious living area, a fully equipped kitchen, huge primary bedroom with lake views, dedicated office space and in unit laundry. Whether you are looking for a peaceful

    Annie Simard LPT Realty

    188 E Lake St, Winsted, CT 06098
  • 56 Lakeview Rd, Winsted, CT 06098

    $279,000 Sold May 19, 2025

    • 1,101 Sq Ft
    • $253/SF
    • 6 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1956

    56 Lakeview Rd, Winsted, CT 06098

    Don't miss this 3 bedroom Ranch with a 2 car attached garage and an amazing view of Highland Lake - very close proximity to state boat launch and public beach. Some TLC will be well worth the effort here! Roof (2019), heating system (November 2017), and central air!

    Tony Goia The Washington Agency

    56 Lakeview Rd, Winsted, CT 06098
  • 97 Taylor Rd, Barkhamsted, CT 06063
    97 Taylor Rd, Barkhamsted, CT 06063
    97 Taylor Rd, Barkhamsted, CT 06063
    /34

    $599,900 Open Sun 12PM - 3PM

    • 4 Beds
    • 3 Baths
    • 3,100 Sq Ft

    97 Taylor Rd, Barkhamsted, CT 06063

    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

    Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

    97 Taylor Rd, Barkhamsted, CT 06063
  • 47 Moore Ave, Winsted, CT 06098

    $320,000 Sold May 16, 2025

    • 1,509 Sq Ft
    • $212/SF
    • 29 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1964

    47 Moore Ave, Winsted, CT 06098

    Nestled in the charming town of Winchester, Connecticut, this beautifully remodeled ranch home offers the perfect blend of modern elegance and cozy comfort. Boasting four spacious bedrooms and seven total rooms, this residence features hardwood floors throughout and a thoughtfully updated galley kitchen that will inspire your inner chef. Gorgeous granite counters and new appliances, with a quaint

    Suzie Larson Turning Point Realty, LLC

    47 Moore Ave, Winsted, CT 06098
  • 102 Hollow Hill Rd, Winsted, CT 06098
    102 Hollow Hill Rd, Winsted, CT 06098
    102 Hollow Hill Rd, Winsted, CT 06098
    /40

    $589,900 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 2,692 Sq Ft

    102 Hollow Hill Rd, Winsted, CT 06098

    Highest & Best Due by 6/17/2025 at 5PM. First time to the market this turnkey 2,692 sq ft Grand Ranch is nestled in on 2.78 bucolic acres surrounded by nature & mature trees. Lovingly maintained, this home provides the perfect set up for stress free living & entertaining boasting a large eat in kitchen with center island, dining area, SS appliances, dual wall ovens and propane cooktop, French

    Dawn Rousseau Showcase Realty, Inc.

    102 Hollow Hill Rd, Winsted, CT 06098

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