Winsted Homes

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  /17

  $349,000 Open Sun 10AM - 12PM

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft

  150 Mathew Rd, Winsted, CT 06098

  Highland Lake, 3 Bedroom, 2 Bath, well maintained home. Lake views, newer appliances, hardwood floors, move-in ready, lake rights. Photos to come. 6,500 watt whole house generator. 8x12 shed with power, 35 Amp out side outlet for camper, working chimney for wood stove on lower level

  Josh Dionne Commercial Services Realty

  150 Mathew Rd, Winsted, CT 06098
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  /34

  $1,500 - $1,750 per month

  Mill at Still River

  1 Bed

  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
• 

  $70,000 Sold May 01, 2025

  • 2,016 Sq Ft
  • $35/SF
  • 18 Days On Market

  • 5 Beds
  • Built 1800

  50-52 Cottage St, Winchester, CT 06098

  Investor Special! This four-level, two-family property at 50-52 Cottage St. was previously prepared for demolition but may still hold potential for the right investor. A complete rehab or possible teardown, this property is being sold as-is and will require vision, expertise, and cash-no financing will qualify. Whether you're looking for a full-scale renovation project or a lot for future

  David Sartirana Northwest CT Realty

  50-52 Cottage St, Winchester, CT 06098
• 

  Est $189,316 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,759 Sq Ft

  11 Orchard St, Winsted, CT 06098

  11 Orchard St, Winsted, CT 06098
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  /33

  $480,000

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

  51 Pratt St, Winsted, CT 06098

  Welcome to this beautifully renovated home, nicely tucked away in historic Winsted. This lovely property features over 2,200 square feet of gross interior living space. The large kitchen, dining, and living room areas provide a seamless flow, perfect for entertaining. The home boasts four spacious bedrooms and one and a half baths. The beautifully renovated attic adds even more charm and

  Lourdes Galvan-Dominguez Coldwell Banker Realty

  51 Pratt St, Winsted, CT 06098
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  /6

  $1,195 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • House for Rent

  174 Main St Unit C, Winsted, CT 06098

  One bedroom apartment on the first floor. Large kitchen with pantry and a recently remodeled bath. Pets considered. First month and two months security, if applicable. Credit and background check required.

  Amanda Balaski Northwest CT Realty

  174 Main St Unit C, Winsted, CT 06098
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  $160,000 Sold Apr 29, 2025

  • 992 Sq Ft
  • $161/SF
  • 0 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1986

  14 Riveredge Dr Unit 14, Winsted, CT 06098

  Come see this wonderful sought after condo in a great neighborhood that has been freshly painted and all new appliances in the kitchen as well as a newer water heater that is just a few years old. Close proximity to town and route 8 and just down the street from the Northwestern Connecticut Community College. This unit has a garage that is directly across from the condo and has an additional

  Maria Smith Turning Point Realty, LLC

  14 Riveredge Dr Unit 14, Winsted, CT 06098
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  Est $298,653 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,476 Sq Ft

  118 E Mountain Ave, Winchester, CT 06098

  118 E Mountain Ave, Winchester, CT 06098
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  /37

  $550,000

  • 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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  /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
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  $220,000 Sold Apr 24, 2025

  • 3,115 Sq Ft
  • $71/SF
  • 14 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1900

  830 Main St, Winsted, CT 06098

  Large side by side duplex with 1 and half baths on each side and a finished attic on each side. Lots of potential here but freeze damage as well. As is sale or repairs possible.

  Michelle Grant Coldwell Banker Premier Real Estate

  830 Main St, Winsted, CT 06098
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  Est $101,942 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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  /31

  $375,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,426 Sq Ft

  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
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  /5

  $1,295 per month

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

  88 Spencer St Unit 2, Winsted, CT 06098

  Two bedroom, 1st flr apartment close to town. Private fronch porch. A washer-dryer can be provided for an extra $50 per month. Pets considered, and a background and credit check are required.

  Amanda Balaski Northwest CT Realty

  88 Spencer St Unit 2, Winsted, CT 06098
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  $275,000 Sold Apr 23, 2025

  • 2,191 Sq Ft
  • $126/SF
  • 41 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1880

  151 Elm St, Winsted, CT 06098

  Step into the warmth and character of this beautiful 5-bedroom single-family home, ideally located in the heart of Winsted. With a wrap-around front porch and a screened rear porch, this home offers the perfect blend of classic charm and modern convenience. Inside, you'll find hardwood floors throughout most of the house, a full bay window in the living room that fills the space with natural

  Jeffrey Liskin Northwest CT Realty

  151 Elm St, Winsted, CT 06098
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  Est $108,442 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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  /40

  $979,000

  • 5 Beds
  • 3.5 Baths
  • 3,216 Sq Ft

  355 W Lake St, Winsted, CT 06098

  Sweeping Views, Exceptional Craftsmanship, and Lake Life at Its Finest.Set on a rare half-acre double lot across from Highland Lake, this custom-built 5-6 bedroom home offers panoramic views over First Bay and deeded dock access just steps from your front door-perfectly positioned beside Holland Beach for the ultimate lake lifestyle. Thoughtfully designed and meticulously maintained, the home

  David Sartirana Northwest CT Realty

  355 W Lake St, 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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  $289,900 Sold Apr 21, 2025

  • 988 Sq Ft
  • $293/SF
  • 61 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1980

  315 E Wakefield Blvd, Winsted, CT 06098

  Charming ranch style home with year round water views! This beautifully updated 3-bedroom, 1-bath ranch home in the sought-after Highland Lake community in Winsted is a true gem. The home has been meticulously cared for, blending modern updates with classic charm. Inside, you'll find a cozy, well-maintained living space that feels inviting and comfortable. The property boasts a spacious, full

  Heather Crabtree Coldwell Banker Realty

  315 E Wakefield Blvd, Winsted, CT 06098
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  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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  /23

  $158,000

  • 1 Bed
  • 1.5 Baths
  • 1,172 Sq Ft

  9 John St, Winsted, CT 06098

  Perfect property for a tiny home enthusiasts looking for easy maintenance-free living. Small lot, so no mowing. Economical gas heat. Although the property is one bedroom, the bedroom is upstairs and the downstairs is very large and open. There is a bathroom on the main level and a bathroom upstairs. Wood floors. Still some work to be done so come and make it yours.

  Michelle Grant Coldwell Banker Premier Real Estate

  9 John St, Winsted, CT 06098
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  $290,000 Sold Apr 21, 2025

  • 2,338 Sq Ft
  • $124/SF
  • 6 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1886

  18 Upland Rd, Winsted, CT 06098

  A Great Investment opportunity in this classic charming multi two unit home. The location is convenient to many amenities including Dining, Community College, Highland Lake recreation and much more. Each unit has Washer & Dryer hookups. Up grades include New High Gas Efficiency Furnaces and Hot Water Heaters in 2020. New Thermal Windows & Blown In Insulation 2021 & 2022. Two Car Garage, Large

  Linda Ganem Borla & Associates Real Estate

  18 Upland Rd, Winsted, CT 06098
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  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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  /19

  $199,900

  • 3 Beds
  • 2 Baths
  • 1,768 Sq Ft

  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
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  $275,000 Sold Apr 17, 2025

  • 1,287 Sq Ft
  • $214/SF
  • 22 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1948

  58 Cherry St, Winsted, CT 06098

  Charming Cape Cod retreat just a short stroll from the beautiful beaches of Highland Lake! This well-maintained 3-bedroom, 2-bath home has been a cherished getaway for years, offering the perfect blend of comfort and convenience. The main level features a sun-filled living room, a dining room ideal for gatherings, and a kitchen with a center island for easy meal prep. A cozy bedroom and a full

  David Sartirana Northwest CT Realty

  58 Cherry St, 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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  /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
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  $275,000 Sold Apr 16, 2025

  • 1,277 Sq Ft
  • $215/SF
  • 114 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1940

  493 N Main St, Winsted, CT 06098

  Highest and best by 3/10 at 6 PM. Back on the market! Enjoy living in your own home nestled in the scenic Litchfield Hills in this newly renovated three-bedroom house with many updates: Refrigerator, range, microwave, dishwasher, and first floor washer/dryer less than a year old. Hot water heater 2023. Updated electrical 2024. Furnace serviced and updated with new burner 2024. 3 new exterior

  Jessica Sperry Maverick Realty

  493 N Main St, Winsted, CT 06098
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  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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  /3

  $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
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  $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
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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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  /4

  $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
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  $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 $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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  /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
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  $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
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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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  /36

  $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
• 

  $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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