Winchester, CT Homes

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  /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

  

  Amy Rio

  Executive Real Estate Inc.

  (860) 452-3957

  77 Hubbard St, Winsted, CT 06098
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  Explore Winchester

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  /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
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  $380,000 Sold Sep 17, 2025

  • 1,196 Sq Ft
  • $318/SF
  • 38 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1974

  226 E Wakefield Blvd, Winsted, CT 06098

  Welcome to your dream retreat on beautiful Highland Lake-a fully renovated gem offering the perfect blend of charm, comfort & modern updates. This lovingly maintained 3-bedroom, 1.5-bath home has been thoughtfully refreshed from top to bottom, making it truly move-in ready. Step inside to discover fresh paint throughout, newly installed floors, and beautifully updated bathrooms. The spacious

  Pascale Nejaime William Pitt Sotheby's Int'l

  226 E Wakefield Blvd, Winsted, CT 06098
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  Est $482,720 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,933 Sq Ft

  125 Old Rd N, Winchester, CT 06098

  125 Old Rd N, Winchester, CT 06098
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  /30

  $394,900 Under Contract

  • 2 Beds
  • 1 Bath
  • 512 Sq Ft

  548 E Wakefield Blvd, Winsted, CT 06098

  Start your lakeside legacy at this rare waterfront cottage on Highland Lake. With stunning westerly views and a private dock, this is the perfect New England retreat for daily sunsets over the water. This intimate 512-square-foot home offers two bedrooms, a sunroom, Modern Eat-in Kitchen and a versatile loft space. with a newer roof, plumbing, electrical, and blown-in insulation, providing a

  

  Amy Rio

  Executive Real Estate Inc.

  (860) 777-1120

  548 E Wakefield Blvd, Winsted, CT 06098
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  /20

  $2,500 per month

  • 3 Beds
  • 1.5 Baths
  • 1,654 Sq Ft
  • House for Rent

  220 Walnut St, Winsted, CT 06098

  Location, location, location! Just a short drive to the shores of the ever-popular Highland Lake, you must put 220 Walnut St. at the top of your list. Lovingly updated (while keeping all of its antique charms) and customized by a local artist. This offering, ready for immediate occupancy, is a true must-see in person. The heating system has been replaced, new appliances, newer roof, fresh paint,

  Justin Mokerzecki Glanville Real Estate

  220 Walnut St, Winsted, CT 06098
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  $275,000 Sold Sep 13, 2025

  • 1,744 Sq Ft
  • $158/SF
  • 46 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1981

  179 Gilbert Ave, Winsted, CT 06098

  Welcome to 179 Gilbert Avenue! This charming Ranch-style home offers a total of over 1,700 square feet of comfortable living space, with 1,144 sq ft on the main level featuring a cozy living room, an eat-in kitchen, full bathroom, and three bedrooms. The finished lower level adds approximately 600 sq ft and provides great flexibility with a spacious family room, a second full bath, and an

  David Sartirana Northwest CT Realty

  179 Gilbert Ave, Winsted, CT 06098
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  Est $379,921 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft

  126 Newfield Rd, Winchester, CT 06098

  126 Newfield Rd, Winchester, CT 06098
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  /31

  $350,000 Open Sun 12PM - 3PM

  • 6 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  157 Elm St, Winsted, CT 06098

  Victorian Charm Meets Modern Potential - 6-Bedroom Home Across from Pearson School Step into timeless elegance with this spacious 6-bedroom, 2.1-bath Victorian-style home located directly across from Pearson School in Winsted. Featuring hardwood floors throughout and a beautifully updated kitchen, this property blends classic character with modern convenience. From its distinctive architectural

  

  Doreen Gagnon

  Coldwell Banker Realty

  (860) 590-4676

  157 Elm St, Winsted, CT 06098
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  /23

  $1,150 - $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
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  $279,900 Sold Sep 12, 2025

  • 1,183 Sq Ft
  • $237/SF
  • 65 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1969

  39 Colony Dr, Winsted, CT 06098

  Well-maintained 3-bedroom, 1-bath Cape located in a quiet neighborhood in Winchester. Features include dining area with hardwood floors, natural gas heat, and a top notch alarm system. Roof is less than 10 years old. Functional layout with flexible living space and a manageable yard for outdoor enjoyment. Sale is contingent upon successful purchase of seller's new property.

  Alison Behlman Tier 1 Real Estate

  39 Colony Dr, Winsted, CT 06098
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  Est $395,090 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,203 Sq Ft

  191 Danbury Quarter Rd, Winchester Center, CT 06098

  191 Danbury Quarter Rd, Winchester Center, CT 06098
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  /38

  $1,270,000

  • 3 Beds
  • 3 Baths
  • 2,420 Sq Ft

  722 Lake Dr, Winsted, CT 06098

  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

  Joanne Donne The Washington Agency

  722 Lake Dr, Winsted, CT 06098
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  /7

  $1,250 per month

  • 2 Beds
  • 1 Bath
  • 2,388 Sq Ft
  • Apartment for Rent

  217 N Main St Unit 2, Winsted, CT 06098

  Very nice, recently renovated first floor apartment for rent in a four unit building set back up private driveway. New flooring in living rooms and bedroom(s). Additional room can be used as a second bedroom or home office space. New paint throughout and new appliances as well as new countertops and cabinets in the kitchen. Full bathroom off of kitchen. Apartment has a covered front porch which

  Michaela Rousseau Showcase Realty, Inc.

  217 N Main St Unit 2, Winsted, CT 06098
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  $302,500 Sold Sep 12, 2025

  • 2,861 Sq Ft
  • $106/SF
  • 70 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1850

  267 Rockwell St, Winsted, CT 06098

  Great opportunity to own a spacious, fully rented 3-family property on a level .86 acre lot, just a short walk to Highland Lake. This home includes a 2-3 bedroom multi level apartment as well as two 1 bedroom apartments, ideal for tenants or extended family. The property features a large parking area and 3 garage spaces, perfect for storage or added rental value. Enjoy the open yard, and a

  Austin Brochu Sullivan Real Estate Inc

  267 Rockwell St, Winsted, CT 06098
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  Est $305,297 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,267 Sq Ft

  151 Newfield Rd, Winchester, CT 06098

  151 Newfield Rd, Winchester, CT 06098
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  /21

  $500,000

  • 3 Beds
  • 2 Baths
  • 2,186 Sq Ft

  11 Old Creamery Rd, Colebrook, CT 06021

  Gutted to the studs and completely rebuilt, this home is fully insulated, energy-efficient, and enhanced with solar panels for low utility costs. The open floor plan and cozy fireplace create the perfect space for gatherings, while multiple decks, an above-ground pool, and serene natural surroundings provide a tranquil retreat-ideal for year-round living or a weekend getaway. Fully Renovated |

  Dani Dorman Real Broker CT, LLC

  11 Old Creamery Rd, Colebrook, CT 06021
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  /7

  $2,200 per month

  • 2 Beds
  • 1 Bath
  • 1,128 Sq Ft
  • House for Rent

  473 Winchester Rd, Winsted, CT 06098

  Sweet home in a Country Setting, this two bedroom ranch style home offers Hard Wood Floors, large eat-in kitchen and a convenient heated mud room that might be used as a office. Bonus is the open large yard for you to enjoy.

  Linda Ganem Borla & Associates Real Estate

  473 Winchester Rd, Winsted, CT 06098
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  $383,000 Sold Sep 10, 2025

  • 2,531 Sq Ft
  • $151/SF
  • 39 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1910

  41 Lovely St, Winsted, CT 06098

  Highest and Best by Wednesday at 1 pm. Lovely 2 family home on a side street ,not far from Highland lake, parks, town hall, restaurants and shopping . The home is in move in condition and features updated ,fully applianced kitchens & updated baths, wood floors and Vinyl windows.The 1st floor features 6 rooms , 3 bedrooms and 1 bath with access to the basement. The second floor features 5 rooms ,

  Mary Mary LeBlanc Realty

  41 Lovely St, Winsted, CT 06098
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  Est $341,841 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,606 Sq Ft

  283 Colebrook Rd, Winsted, CT 06098

  283 Colebrook Rd, Winsted, CT 06098
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  /27

  $399,900 Open Sat 11AM - 1PM

  • 2 Beds
  • 1.5 Baths
  • 1,440 Sq Ft

  212 Spencer Hill Rd, Winsted, CT 06098

  Welcome to your peaceful retreat in the heart of Winchester - a quiet, scenic town surrounded by natural beauty. Tucked away on a private lot, this thoughtfully maintained home offers a perfect blend of rustic charm and modern comfort, with every detail designed to enhance your connection to the outdoors. Step inside to discover gleaming original hardwood floors that stretch across the sun-filled

  Tammy Powling Coldwell Banker Realty

  212 Spencer Hill Rd, Winsted, CT 06098
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  /16

  $1,750 per month

  • 2 Beds
  • 1 Bath
  • 528 Sq Ft
  • House for Rent

  12 Charles St, Winsted, CT 06098

  Adorable two-bedroom cottage near Highland Lake available first week of October. Tile in kitchen, new lighting and gleaming hardwood living room floors. Washer/ Dryer in basement w/ plenty of storage. Spacious Enclosed mudroom/porch. Off street parking for 2 cars. Close to shops and restaurants. Requirements: Background/credit check, no eviction, one year lease and one month security.

  Jessica Chavez Turning Point Realty, LLC

  12 Charles St, Winsted, CT 06098
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  $1,215,000 Sold Sep 10, 2025

  • 5,231 Sq Ft
  • $232/SF
  • 347 Days On Market

  • 8 Beds
  • 4.5 Baths
  • Built 1930

  435 W Wakefield Blvd, Winsted, CT 06098

  Welcome to this spectacular Highland Lake estate, offering a unique blend of luxury & tranquility. Situated on 1.51 acres of combined 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.

  435 W Wakefield Blvd, Winsted, CT 06098
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  Est $48,204 Not Listed For Sale

  90 Reaching Hill Rd, Winsted, CT 06098

  90 Reaching Hill Rd, Winsted, CT 06098
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  /34

  $625,000

  • 5 Beds
  • 3 Baths
  • 3,404 Sq Ft

  441 Platt Hill Rd, Winsted, CT 06098

  Welcome to 441 Platt Hill Road - a home that offers warmth, charm, and plenty of space to make memories. This inviting residence features an open and airy layout filled with natural light thanks to large windows and multiple skylights. Solid hardwood floors and tile run throughout the main level, creating a timeless foundation for your personal touch. The spacious eat-in kitchen, while vintage in

  David Sartirana Northwest CT Realty

  441 Platt Hill Rd, Winsted, CT 06098
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  /12

  $1,375 per month

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

  111 Rockwell St Unit 2, Winsted, CT 06098

  Bright and peaceful 2-bedroom, 1-bath second-floor apartment featuring a charming kitchen and a private deck. Conveniently located near downtown with off-street parking for one vehicle.

  Colin Murray Dorrance Realty

  111 Rockwell St Unit 2, Winsted, CT 06098
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  $240,000 Sold Sep 09, 2025

  • 1,008 Sq Ft
  • $238/SF
  • 6 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1956

  42 Maloney Ct, Winsted, CT 06098

  Cute affordable turn key Ranch. Situated on a corner lot in a quiet convenient neighborhood. 3 bedroom's 1 bath. Basement has potential to be nicely finished space. Broker/owner.

  James Walsh James Walsh

  42 Maloney Ct, Winsted, CT 06098
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  Est $762,856 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,860 Sq Ft

  404 Colebrook Rd, Colebrook, CT 06021

  404 Colebrook Rd, Colebrook, CT 06021
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  /27

  $429,000 Open Sat 1PM - 2PM

  • 4 Beds
  • 1.5 Baths
  • 2,239 Sq Ft

  51 Pratt St, Winsted, CT 06098

  This stunning Renovated home is perfectly situated in the beautiful town of Winsted could be yours! Just a leisurely walk from the beautiful Highland Lake. Offering more than 2,200 square feet of thoughtfully designed living space, this home blends timeless charm with modern updates. The bright and spacious kitchen opens effortlessly into a welcoming dining area and a cozy yet expansive living

  Arlene Gonzalez The Gonzalez Property Group

  51 Pratt St, Winsted, CT 06098
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  /9

  $1,275 per month

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

  111 Rockwell St Unit 1st Floor, 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 updated 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 Unit 1st Floor, Winsted, CT 06098
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  $260,000 Sold Sep 05, 2025

  • 1,352 Sq Ft
  • $192/SF
  • 1 Day On Market

  • 2 Beds
  • 2 Baths
  • Built 2005

  174 Wallens St Unit D3, Winsted, CT 06098

  SELDOM AVAILABLE 2 BR MOVE IN CONDITION RANCH AT THE CLOCMAKERS HILL ADULT COMMUNITY FOR 55 AND OVER.SPECIAL END UNIT WITH LOTS OF SUNNY WINDOWS-COVERED FRONT PORCH AND ATTACHED GARAGE-CAIR GAS-HIGH CEILINGS-HICKORY KITCHEN CABINETS WITH CORIAN COUNTERS-REMODELED BATHS -GAS FIREPLACED LIVING ROOM OPEN TO FORMAL DINING ROOM WITH LOTS OF SUNNY WINDOWS-MASTER BEDROOM WITH WALKIN CLOSET AND FULL

  Mary New Berkshire Hathaway NE Prop.

  174 Wallens St Unit D3, Winsted, CT 06098
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  Est $110,229 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft

  11 Gibbs St Unit 6, Winsted, CT 06098

  11 Gibbs St Unit 6, Winsted, CT 06098
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  /26

  $365,000

  • 4 Beds
  • 2 Baths
  • 1,910 Sq Ft

  147 Smith Hill Rd, Winsted, CT 06098

  Tucked away on a wooded lot, this meticulously maintained Cape features 4 spacious bedrooms and a full bathroom on each floor. Enjoy watching the birds & other wildlife on the huge rear deck or enjoy the peaceful setting on the enclosed porch. They don't make them like this anymore! The grounds have been lovingly maintained. You will want to move right in.

  SHARON GILSON Northwest CT Realty

  147 Smith Hill Rd, Winsted, CT 06098
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  /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
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  $320,000 Sold Sep 03, 2025

  • 1,616 Sq Ft
  • $198/SF
  • 24 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1973

  107 Old Rd N, Winchester, CT 06098

  Completely Updated Raised Ranch on a Peaceful, Secluded Lot in Winsted! Escape the noise and discover this beautifully updated Raised Ranch, set on a private 0.78-acre lot in the quiet town of Winsted. Surrounded by nature and tucked away in a serene setting, this home offers the perfect balance of indoor comfort and outdoor living. Inside, you'll love the bright, open layout and thoughtful

  Jill Rubino Century 21 AllPoints Realty

  107 Old Rd N, Winchester, CT 06098
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  Est $109,725 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft

  11 Gibbs St Unit 4, Winsted, CT 06098

  11 Gibbs St Unit 4, Winsted, CT 06098
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  /35

  $450,000

  • 3 Beds
  • 3 Baths
  • 2,747 Sq Ft

  117 South Rd, Winsted, CT 06098

  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

  117 South Rd, Winsted, CT 06098
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  $178,500 Sold Aug 29, 2025

  • 2,310 Sq Ft
  • $77/SF
  • 74 Days On Market

  • 5 Beds
  • 1.5 Baths
  • Built 1873

  30 Mountain Ave, Winsted, CT 06098

  Buyer couldn't get funding. Bring all offers! 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,

  Derek Greene Derek Greene

  30 Mountain Ave, Winsted, CT 06098
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  Est $395,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft

  111 Mundry Rd, Torrington, CT 06790

  111 Mundry Rd, Torrington, CT 06790
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  /37

  $515,000

  • 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

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