Winchester, CT Homes

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  $260,000 Open Sun 11AM - 1PM

  • 5 Beds
  • 2 Baths
  • 1,962 Sq Ft

  120 Torrington Rd, Winsted, CT 06098

  This spacious 5-bedroom, 2-bath Colonial offers incredible flexibility and room to grow. The first floor features a large eat-in kitchen, a sun-filled dining room with a charming brick hearth fireplace, a massive family room, two bedrooms, and a full bath with laundry. Upstairs you'll find three generously sized bedrooms and a freshly painted second full bath. Set on a nice lot with a newer

  Dave Bolduc Bolduc Realty Group

  120 Torrington Rd, Winsted, CT 06098
• 

  $395,000 Sold Apr 08, 2025

  • 1,818 Sq Ft
  • $217/SF
  • 106 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1875

  47 Orchard St, Winsted, CT 06098

  Renovated to 4 Bedroom and 3 Full-bath home with 2028 SQFT, this stunning Colonial on Private Road a short walk to Highland Lake. This newly remodeled 1875 home seamlessly blends historic charm with modern amenities. Inside discover a spacious floor plan offering an abundance of natural light perfect for both entertaining and everyday living. The custom kitchen is a chef's dream featuring sleek

  Bryan Palladino Showcase Realty, Inc.

  47 Orchard St, Winsted, CT 06098
• 

  Est $250,953 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,104 Sq Ft

  139 Boyd St, Winsted, CT 06098

  139 Boyd St, Winsted, CT 06098
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  /22

  $269,900

  • 3 Beds
  • 1 Bath
  • 2,754 Sq Ft

  25 Center St, Winsted, CT 06098

  Introducing 25 Center St. - A Prime Mixed-Use Investment Property in Winsted! Looking for a great opportunity to expand your real estate portfolio? Look no further than 25 Center St., a fantastic mixed-use property located in the heart of Winsted's business district. This property offers instant rental income, making it a smart investment for any savvy investor. First Floor: A spacious 1,625

  Jessica Lopez Our Home Realty Advisors

  25 Center St, Winsted, CT 06098
• 

  $305,000 Sold Apr 07, 2025

  • 1,826 Sq Ft
  • $167/SF
  • 62 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1900

  178 Boyd St, Winsted, CT 06098

  Rare Side-by-Side Duplex with Highland Lake Views Don't miss this unique side-by-side duplex offering stunning views of Highland Lake! This versatile property features an open-concept layout on the first floor in both units, creating a spacious and inviting atmosphere. One unit boasts a vaulted ceiling in the updated kitchen, while the other offers a finished attic that adds two additional

  David Sartirana Northwest CT Realty

  178 Boyd St, Winsted, CT 06098
• 

  Est $259,507 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft

  174 Wallens St Unit D3, Winsted, CT 06098

  174 Wallens St Unit D3, Winsted, CT 06098
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  $225,000

  • Land
  • 0.23 Acre
  • $978,261 per Acre

  129 Shore Dr, Winsted, CT 06098

  A RARE OPPORTUNITY on HIGHLAND LAKE! This approved buildable lot is ready and waiting for you to build your dream! Lake life is a great life, make it yours!

  Annie Simard LPT Realty

  129 Shore Dr, Winsted, CT 06098
• 

  $206,000 Sold Apr 01, 2025

  • 1,204 Sq Ft
  • $171/SF
  • 22 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1987

  111 Riverton Rd Unit 9, Winsted, CT 06098

  This 3-story condominium boasts two large bedrooms, and 1.5 bathrooms, as well as a 2-car garage with a private indoor entrance. The primary bedroom provides lofty ceilings, a walk-in closet, and its own entry way into the full bath. On the main level, the pellet stove is powerful enough to heat the entire living space whilst having its own thermostat to ensure a comfortable temperature

  Kathleen Miller CT Home Pro, LLC

  111 Riverton Rd Unit 9, Winsted, CT 06098
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  Est $238,522 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft

  174 Wallens St Unit D2, Winsted, CT 06098

  174 Wallens St Unit D2, Winsted, CT 06098
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  $739,900

  • Land
  • 93 Acres
  • $7,924 per Acre

  0 Old Robertsville Rd, Winchester, CT 06098

  Nestled along a peaceful country road near the Colebrook and Barkhamsted town lines, this breathtaking 93.38-acre parcel embodies the timeless charm of rural New England. Once part of a cherished family farm, the land offers a harmonious blend of rolling meadows, majestic forests, and the gentle, winding presence of the Still River, which meanders through a substantial portion of the property.

  David Sartirana Northwest CT Realty

  0 Old Robertsville Rd, Winchester, CT 06098
• 

  $270,000 Sold Mar 31, 2025

  • 1,192 Sq Ft
  • $227/SF
  • 39 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1930

  325 E Wakefield Blvd, Winsted, CT 06098

  Enjoy water views from this charming Colonial located just across the street from Highland Lake. This cozy retreat blends historic charm with modern updates, offering a perfect escape for year-round living or a weekend getaway. Inside, refinished wide-plank hardwood floors add warmth and character, while the freshly painted interior enhances the bright and inviting atmosphere. The living room

  Brigitte Richter William Pitt Sotheby's Int'l

  325 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $240,771 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft

  174 Wallens St Unit D1, Winsted, CT 06098

  174 Wallens St Unit D1, Winsted, CT 06098
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  $17,999

  • Land
  • 0.12 Acre
  • $149,992 per Acre

  320 White Oak Trail, Winchester, CT 06098

  Plot Of Land Valued at $32,060 Property ID #: 033 105C 044+45 Zoning: HL

  Dillon Cass eRealty Advisors, Inc.

  320 White Oak Trail, Winchester, CT 06098
• 

  $395,000 Sold Mar 28, 2025

  • 1,792 Sq Ft
  • $220/SF
  • 25 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1990

  102 Sunny Ridge Dr, Winsted, CT 06098

  Charming One-Owner Split Level in a Private Rural Setting. Discover the perfect blend of privacy, space, and convenience in this beautifully maintained 1,800 sq. ft. split-level home, nestled on a serene 1-acre lot at the end of a cul-de-sac abutting the Barkhamsted town line. This home offers seven well-appointed rooms, including a spacious living room with a propane stove set in the fireplace,

  David Sartirana Northwest CT Realty

  102 Sunny Ridge Dr, Winsted, CT 06098
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  Est $284,322 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,946 Sq Ft

  174 Wallens St Unit C3, Winsted, CT 06098

  174 Wallens St Unit C3, Winsted, CT 06098
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  $849,900 Open Sat 1PM - 3PM

  • 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
• 

  $85,000 Sold Mar 27, 2025

  • Land
  • 3.06 Acres
  • $27,742 per Acre

  • 5 Days On Market

  0 Platt Hill Rd Unit 24079213, Winsted, CT 06098

  Build on this 3+ acre lot that adjoins Winchester Land Trust. Old soil tests, would need to be re-tested.

  Nadia Corvo Northwest CT Realty

  0 Platt Hill Rd Unit 24079213, Winsted, CT 06098
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  Est $542,790 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,804 Sq Ft

  452 Platt Hill Rd, Winsted, CT 06098

  452 Platt Hill Rd, Winsted, CT 06098
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  /2

  $49,000

  • Land
  • 0.37 Acre
  • $132,432 per Acre

  99 Hubbard St, Winsted, CT 06098

  99 Hubbard St. - Private Lot Near Downtown & Highland Lake. Tucked away at the end of a quiet dead-end street, this .37-acre lot offers both privacy and convenience. While enjoying a peaceful setting, you're still just minutes from downtown with easy access to shopping, dining, and entertainment. Plus, Highland Lake is just a short distance away, providing endless opportunities for boating,

  David Sartirana Northwest CT Realty

  99 Hubbard St, Winsted, CT 06098
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  $135,000 Sold Mar 27, 2025

  • 643 Sq Ft
  • $210/SF
  • 72 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1986

  13 Riveredge Dr Unit 13, Winsted, CT 06098

  This is your chance to experience turnkey condo-style living with modern upgrades and unbeatable comfort. The remodeled kitchen boasts newer appliances, sleek granite countertops, and stylish flooring, perfect for everyday living and entertaining. Enjoy peace of mind with a five-year-old water heater with a 10-year warranty. Imagine waking up to the serene, calming sounds of the river through

  James Bradshaw Berkshire Hathaway NE Prop.

  13 Riveredge Dr Unit 13, Winsted, CT 06098
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  Est $1,021,616 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,963 Sq Ft

  411 W Wakefield Blvd, Winsted, CT 06098

  411 W Wakefield Blvd, Winsted, CT 06098
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  /2

  $29,000

  • Land
  • 0.44 Acre
  • $65,909 per Acre

  124 Rockwell St, Winsted, CT 06098

  124 Rockwell St. - Versatile .44-Acre Lot Near Downtown This .44-acre lot offers a prime location close to downtown with city water and sewer available in the street. The previous home sat at street level, while the majority of the lot slopes below, creating a unique landscape with plenty of potential. With a little imagination and the right site contractor, this property presents endless

  David Sartirana Northwest CT Realty

  124 Rockwell St, Winsted, CT 06098
• 

  $268,000 Sold Mar 18, 2025

  • 1,428 Sq Ft
  • $188/SF
  • 128 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1880

  86 Maple St, Winsted, CT 06098

  Completely renovated. Brand new appliances. Roof and furnace approx. 10 years old. Nice open yard. New gravel driveway. Walk up attic with plenty of storage. New floors and windows. Large eat-in kitchen with marble counters and stainless steel appliances. Main floor laundry. Two full baths; one upstairs and one on main level. One main level bedroom. 86 Maple St is waiting for you to make it your

  Chris LaCava Coldwell Banker Realty

  86 Maple St, Winsted, CT 06098
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  Est $445,322 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,512 Sq Ft

  129 Blue St, Winsted, CT 06098

  129 Blue St, Winsted, CT 06098
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  $950,000

  • 14 Beds
  • 7 Baths
  • 4,860 Sq Ft

  175 N Main St, Winsted, CT 06098

  Addresses include 175 Main Street and 183 Main Street in Winsted, CT. Amazing opportunity to acquire a 9 Unit Asset (7 Apartments + 2 Retail) in Winsted with anchor tenant Noli's Restaurant (Rent $2,266 w 3% increase/year) w over 20 years in business! Pride of Ownership is evident with Capital Improvements made by the current owners, including: new water heaters, heating zones, electrical

  Ryan Rea Berkshire Hathaway NE Prop.

  175 N Main St, Winsted, CT 06098
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  $105,000 Sold Mar 14, 2025

  • 720 Sq Ft
  • $146/SF
  • 33 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1950

  350 Walnut St, Winsted, CT 06098

  Attention investors! This 2-bedroom, 1-bathroom single ranch style home is a prime opportunity for a complete rehab. The property was involved in a fire and requires a full rehab with a 1-car garage and is being sold as-is. Subject to probate approval.

  Vincent Miller Hudson Home Services LLC

  350 Walnut St, Winsted, CT 06098
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  Est $275,301 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,040 Sq Ft

  17 Colony Dr, Winsted, CT 06098

  17 Colony Dr, Winsted, CT 06098
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  /40

  $1,699,500

  • 4 Beds
  • 3 Baths
  • 2,496 Sq Ft

  538 Wheelers Point, Winsted, CT 06098

  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

  KAREN NEWTON William Pitt Sotheby's Int'l

  538 Wheelers Point, Winsted, CT 06098
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  $199,900 Sold Mar 12, 2025

  • 1,204 Sq Ft
  • $166/SF
  • 87 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1987

  111 Riverton Rd Unit 17, Winsted, CT 06098

  Two bedroom, 1 & 1/2 bath end unit Townhouse with wood floors throughout, living room with fireplace and sliders to deck, primary bedroom with walk in closet, deck has just been painted, Spacious 2 car garage. Unit has lower-level laundry room with entry into garage. Great space and ready for New Owner.

  Joanne Donne The Washington Agency

  111 Riverton Rd Unit 17, Winsted, CT 06098
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  Est $623,118 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,318 Sq Ft

  715 W Wakefield Blvd, Winsted, CT 06098

  715 W Wakefield Blvd, Winsted, CT 06098
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  /40

  $1,500,000

  • 8 Beds
  • 4.5 Baths
  • 5,231 Sq Ft

  435 W Wakefield Blvd, Winsted, CT 06098

  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

  Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

  435 W Wakefield Blvd, Winsted, CT 06098
• 

  $260,000 Sold Mar 10, 2025

  • 1,888 Sq Ft
  • $138/SF
  • 27 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1973

  14 Hamill Dr, Winsted, CT 06098

  Welcome to this single family home nestled at the end of a peaceful cul-de-sac. Featuring 3 spacious bedrooms and a full bathroom on the main lever, and a cozy lower-level family room complete with a half bath and ample storage. This home has both comfort and functionality.

  Eva Casoria eXp Realty

  14 Hamill Dr, Winsted, CT 06098
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  Est $250,102 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  159 Pratt St, Winsted, CT 06098

  159 Pratt St, Winsted, CT 06098
• 

  /2

  $349,900

  • 3 Beds
  • 1 Bath
  • 1,491 Sq Ft

  116 Ashley Rd, Norfolk, CT 06058

  Welcome to a piece of history with this enchanting Cape farmhouse, a true gem nestled in the picturesque town of Winchester. Built in 1830, this home radiates classic charm with its original details and timeless character. The property features two inviting fireplaces, perfect for cozy evenings, and an oversized country kitchen that offers ample space for culinary creativity and family

  Michael Morris Vylla Home (CT) LLC

  116 Ashley Rd, Norfolk, CT 06058
• 

  $325,000 Sold Mar 07, 2025

  • 1,324 Sq Ft
  • $245/SF
  • 1 Day On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1962

  11 Cherry St, Winsted, CT 06098

  Welcome to 11 Cherry Street! This move-in ready ranch-style home features 3 bedrooms, 1.5 bathrooms, and is just around the corner from Highland Lake. Step into the kitchen directly from the heated 2-car garage. The kitchen features plenty of white cabinets, shiplap, and a brick backsplash, creating a stylish industrial modern vibe. It also overlooks the spacious dining room perfect for

  Haylee Munchgesang Coldwell Banker Realty

  11 Cherry St, Winsted, CT 06098
• 

  Est $180,680 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  17 Front St, Winsted, CT 06098

  17 Front St, Winsted, CT 06098
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  /40

  $2,600,000

  • 9 Beds
  • 5.5 Baths
  • 7,000 Sq Ft

  431 W Wakefield Blvd, Winsted, CT 06098

  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

  Lisa Ogren Berkshire Hathaway NE Prop.

  431 W Wakefield Blvd, Winsted, CT 06098
• 

  $400,000 Sold Mar 03, 2025

  • 4,253 Sq Ft
  • $94/SF
  • 132 Days On Market

  • 7 Beds
  • 3.5 Baths
  • Built 1958

  296 Colebrook Rd, Winsted, CT 06098

  . The Main house features a Huge Stone fire-placed family room , plus a fire-placed Living room,for cozier gatherings. The home also includes a walk-out basement,. There is finished space ideal for an in-law suite on the second floor, located above the oversized attached 2-car garage. Outdoor living is enhanced by a rear deck that overlooks a tranquil pond, dam, and wooded area, making it a

  David D'Amore Northwest CT Realty

  296 Colebrook Rd, Winsted, CT 06098
• 

  Est $233,646 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,010 Sq Ft

  22 Stanton Ave, Winsted, CT 06098

  22 Stanton Ave, Winsted, CT 06098
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  /3

  $320,000

  • Land
  • 0.61 Acre
  • $524,590 per Acre

  711 W Wakefield Blvd, Winchester Center, CT 06098

  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.

  Peter Kores The Washington Agency

  711 W Wakefield Blvd, Winchester Center, CT 06098

Showing Results 41 - 80, Page 2 of 18