Winchester, CT Homes

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  /31

  $339,999

  • 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
• Explore Winchester

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  /7

  $1,475 total monthly price

  • 3 Beds
  • 1 Bath
  • 2,817 Sq Ft
  • House for Rent

  103 Elm St Unit 105, Winsted, CT 06098

  First Floor, three bedroom apartment. In-town location, eat-in kitchen, laundry room and off street parking. Pets considered. Background and credit check required. First month and two months security.

  

  Amanda Balaski

  Northwest CT Realty

  (860) 431-1157

  103 Elm St Unit 105, Winsted, CT 06098
• 

  $345,000 Sold Oct 31, 2025

  • 2,100 Sq Ft
  • $164/SF
  • 27 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1962

  115 Wallens St, Winsted, CT 06098

  Coming Soon! Spacious Cape-style home offering over 2,000 sq. ft. with 4 bedrooms and 2 full baths. This solid home sits on a beautiful lot and is ready for your personal finishing touches. Features include a 2-car garage, 2 fireplaces, and a large, beamed family room just off the kitchen. Recent updates include a new furnace and hot water heater, plus a newer roof for peace of mind. With

  Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

  115 Wallens St, Winsted, CT 06098
• 

  Est $473,763 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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  /7

  $259,000

  • 3 Beds
  • 1 Bath
  • 1,488 Sq Ft

  312 Colebrook River Rd, Colebrook, CT 06021

  Charming Colonial on a 2-acre lot. Inside, you'll find an updated kitchen featuring granite countertops and newer appliances. The large, sunny family room on the first floor is filled with natural light, creating a warm and inviting atmosphere. A combined living and dining room with a cozy wood stove adds charm and functionality to the main level. Recent upgrades to the home include a new roof in

  

  Amanda Balaski

  Northwest CT Realty

  (860) 891-2072

  312 Colebrook River Rd, Colebrook, CT 06021
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  /18

  $1,600 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,890 Sq Ft
  • Townhouse for Rent

  29 Benton St, Winsted, CT 06098

  Adorable Duplex, newly remodeled Kitchen and bath. Harwood floors throughout with a new gas furnace. Deck off kitchen. A must see!

  

  Victoria Stillings

  Coldwell Banker Realty

  (860) 364-6692

  29 Benton St, Winsted, CT 06098
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  $288,557 Sold Oct 29, 2025

  • 1,538 Sq Ft
  • $188/SF
  • 38 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1900

  15 John St, Winsted, CT 06098

  Feels Like New - Without the New Construction Price! Looking for a move-in ready home that won't break the bank? This freshly renovated 3-bedroom, 2-bath home has been updated from top to bottom - with a brand-new roof, siding, doors (inside and out), electrical, plumbing, carpet, kitchen, and two full bathrooms. Everything's done and ready for you to move in. It sits on a nice, level yard on a

  Amanda Balaski Northwest CT Realty

  15 John St, Winsted, CT 06098
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  Est $380,157 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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  /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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  $1,500 - $2,000 per month plus fees

  Mill at Still River

  1 - 3 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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  $388,750 Sold Oct 29, 2025

  • 1,584 Sq Ft
  • $245/SF
  • 65 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1973

  111 Old Rd N, Winchester, CT 06098

  Two parcels for the price of one! Discover this beautifully maintained split-level ranch at 111 Old North Road in Winchester, offered together with the adjoining already-subdivided 2.5-acre buildable lot at 113 Old North Road. Enjoy the home as-is or explore the endless possibilities-build an in-law house, sell the lot, or develop it as an investment. Inside, the home features a unique layout

  Christopher Clarke Coldwell Banker Realty

  111 Old Rd N, Winchester, CT 06098
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  Est $389,168 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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  /37

  $4,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft
  • House for Rent

  880 W Wakefield Blvd, Winsted, CT 06098

  Discover lakeside living at its finest with this fully renovated 3 bedroom, sleeps 10, 2 full-baths, family estate set on a half acre of professionally landscaped grounds overlooking picturesque Highland Lake. Located just 0.6 miles from Main Street Winsted and Red Barn Brewing, this property combines serene lakefront living with convenient access to local amenities. Enjoy use of a private dock

  Matt Crossen Coldwell Banker Realty

  880 W Wakefield Blvd, Winsted, CT 06098
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  $440,000 Sold Oct 29, 2025

  • 1,940 Sq Ft
  • $227/SF
  • 73 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1800

  159 Sandy Brook Rd, Colebrook, CT 06021

  Introducing Sandy Brook Cottage. Perched gently near the banks of the meandering Sandy Brook, this c.1800 home exudes quiet charm and understated elegance. Set on over 3 picturesque acres in the hidden gem of Colebrook. It is a true country escape. One that offers privacy, character, and an effortless connection to nature. Winding stone walls trace the contours of the rolling landscape, creating

  Lenore Mallett William Pitt Sotheby's Int'l

  159 Sandy Brook Rd, Colebrook, CT 06021
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  Est $322,345 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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  $499,000

  • 3 Beds
  • 2 Baths
  • 2,167 Sq Ft

  197 Spencer Hill Rd, Winsted, CT 06098

  Discover the charm of this spacious contemporary Cape, set on a peaceful one-acre lot in a desirable rural neighborhood. Offering over 3,000 square feet of living space, this well-maintained home provides a flexible layout ideal for today's lifestyle. The main level features a formal living room, dining room, updated kitchen, den, sunroom with fireplace and hot tub, full bath, and convenient

  David Sartirana Northwest CT Realty

  197 Spencer Hill Rd, Winsted, CT 06098
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  /23

  $1,150 - $1,450 per month plus fees

  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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  $375,000 Sold Oct 28, 2025

  • 1,833 Sq Ft
  • $205/SF
  • 24 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1986

  126 Forest Ave, Winsted, CT 06098

  Charming Cape 2 minutes to Highland Lake. Welcome to this one owner, 3 bedroom, two bath Cape Cod home offering over 1,800 sq. ft. of living space on nearly one acre of land. Owned by the original family. This property has been lovingly maintained and thoughtfully update. Step inside to find a fully appliance kitchen, fresh carpeting, and updated windows and gutters. The flexible seven- room

  Joanne Donne The Washington Agency

  126 Forest Ave, Winsted, CT 06098
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  Est $353,370 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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  /40

  $560,000

  • 3 Beds
  • 2 Baths
  • 1,745 Sq Ft

  106A Pinney St, Colebrook, CT 06021

  Nature Lover's Retreat on 26 Acres!!! Tucked away on 26.12 private acres, this contemporary Cape offers peace, privacy, and a deep connection to nature. A long, winding driveway leads to this stunning home featuring soaring ceilings and dramatic two-story windows that fill the living room with natural light. The open layout includes a warm wood stove, first-floor laundry, and two comfortable

  Kelly Sullivan Sullivan Real Estate Inc

  106A Pinney St, Colebrook, CT 06021
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  /27

  $1,950 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,470 Sq Ft
  • House for Rent

  69 Upson Ave Unit 71, Winsted, CT 06098

  Opportunity is Knocking! Beautifully Renovated Apartment for Rent. Step into this fully renovated second-floor apartment offering a flexible layout that can suit your lifestyle! Enjoy 3 bedrooms plus a formal dining room and living room - or convert it into a 4-bedroom home with a spacious living area. Features include: *Brand-new kitchen with granite countertops and stainless steel appliances

  Gabby Addison Keller Williams Realty

  69 Upson Ave Unit 71, Winsted, CT 06098
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  $425,000 Sold Oct 28, 2025

  • 512 Sq Ft
  • $830/SF
  • 60 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1936

  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.

  548 E Wakefield Blvd, Winsted, CT 06098
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  Est $55,108 Not Listed For Sale

  287 Colebrook Rd, Winsted, CT 06098

  287 Colebrook Rd, Winsted, CT 06098
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  /37

  $500,000

  • 4 Beds
  • 2.5 Baths
  • 3,416 Sq Ft

  440 Platt Hill Rd, Winsted, CT 06098

  Distinctive Country Estate with Two Homes on 9.6 Rolling Acres Set amid 9.6 picturesque country acres, this unique property offers two homes and endless potential. The stone and stucco main residence features eight spacious rooms, including four bedrooms and four fireplaces, blending classic character with old-world charm. Rolling open land and mature trees surround the home, providing an ideal

  David D'Amore Northwest CT Realty

  440 Platt Hill Rd, Winsted, CT 06098
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  /8

  $2,500 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft
  • House for Rent

  26 Elm St, Winchester, CT 06098

  Be the first to live in this completely renovated 3-bedroom, 1-bath apartment located just half a block from Main Street - walkable to all your favorite shops and restaurants! This bright and spacious home features a wide open floor plan with brand-new floors, all new appliances, modern cabinets, and granite countertops. Every detail has been thoughtfully upgraded, including new blinds and a

  Annie Simard LPT Realty

  26 Elm St, Winchester, CT 06098
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  $198,000 Sold Oct 28, 2025

  • 1,204 Sq Ft
  • $164/SF
  • 48 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1987

  111 Riverton Rd Unit 37, Winsted, CT 06098

  Picture yourselves in this bright, roomy end unit condominium with room to spare! Totally renovated bathtub and fixtures in the full bath. Lovely, updated kitchen that not only has a pantry but sliding glass doors that lead out to the brand-new deck. 3-year-old pellet stove that will keep your entire unit toasty all winter long. The living room features beautiful sliding glass doors that also

  Sandra Marchetti The Washington Agency

  111 Riverton Rd Unit 37, Winsted, CT 06098
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  Est $46,941 Not Listed For Sale

  90 Reaching Hill Rd, Winsted, CT 06098

  90 Reaching Hill Rd, Winsted, CT 06098
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  /22

  $499,000

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

  11 Old Creamery Rd, Colebrook, CT 06021

  FULLY RENOVATED! In addition 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. Located perfectly on a beautiful

  Dani Dorman Real Broker CT, LLC

  11 Old Creamery Rd, Colebrook, CT 06021
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  /29

  $4,000 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 2,265 Sq Ft
  • House for Rent

  121 W Wakefield Blvd, Winsted, CT 06098

  Discover lakeside living at its finest with this renovated 5-bedroom, 4-bath family estate set privately on a full acre overlooking picturesque Highland Lake. Located just 0.7 miles from Main Street Winsted and Red Barn Brewing, this property combines serene lakefront living with convenient access to local amenities. Enjoy use of a private dock and waterfront deck located directly across the

  Elizabeth Stockwell Coldwell Banker Realty

  121 W Wakefield Blvd, Winsted, CT 06098
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  $240,000 Sold Oct 22, 2025

  • 1,056 Sq Ft
  • $227/SF
  • 46 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1988

  210 Walnut St, Winsted, CT 06098

  Discover the potential in this raised ranch located in beautiful Winsted, CT! Featuring 3 bedrooms and 1.5 bathrooms, this home offers a functional layout and a great opportunity to bring your vision to life. An attached two-car garage adds everyday convenience and plenty of storage. Set on a nice lot, the property is close to town amenities, schools, and outdoor recreation that make Winsted

  Nicole Araujo Trend 2000 Real Estate

  210 Walnut St, Winsted, CT 06098
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  Est $773,342 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

  $394,900

  • 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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  /20

  $2,500 total monthly price

  • 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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  $320,000 Sold Oct 21, 2025

  • 1,674 Sq Ft
  • $191/SF
  • 11 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1950

  160 Walnut St, Winsted, CT 06098

  Have you been looking to find a classic colonial home set in Litchfield county? This quintessential home is it! The first floor has a fireplace which is encircled by hardwood floors which are throughout the oversized living room and formal dining room both leading into the cozy kitchen. A wonderful sun room opens up to a lovely stone patio. Completing the main floor next to the kitchen is a half

  Jeremy Beamer William Raveis Real Estate

  160 Walnut St, Winsted, CT 06098
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  Est $359,433 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,635 Sq Ft

  268 Smith Hill Rd, Colebrook, CT 06021

  268 Smith Hill Rd, Colebrook, CT 06021
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  /34

  $599,900

  • 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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  /7

  $1,250 total monthly price

  • 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
• 

  $2,200,000 Sold Oct 21, 2025

  • 4,327 Sq Ft
  • $508/SF
  • 28 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1795

  381 Smith Hill Rd, Colebrook, CT 06021

  Welcome to Stones Throw Farm. A rare and magical estate tucked on over 23 rolling, pastoral acres in the heart of Colebrook, a true New England country retreat where timeless beauty and refined simplicity come together in perfect harmony. Set along a quiet country road, this idyllic sanctuary offers an extraordinary lifestyle steeped in elegance, comfort, and the gentle rhythms of nature. At the

  Elvia Gignoux William Pitt Sotheby's Int'l

  381 Smith Hill Rd, Colebrook, CT 06021
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  Est $114,879 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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