Winsted, CT Homes

• 

  $290,000

  Sold Aug 28, 2025

  279 Pratt St, Winsted, CT 06098

  • 4 Beds
  • 1 Bath
  • 1,978 Sq Ft
  • Built 1880

  Last Sold Summary

  • 24% Below List Price
  • $147/SF
  • 49 Days On Market

  Current Estimated Value $305,571

  Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  279 Pratt St, Winsted, CT 06098
• 

  Est $314,272

  Not Listed For Sale

  160 Hinsdale Ave, Winsted, CT 06098

  • 4 Beds
  • 1.5 Baths
  • 2,379 Sq Ft
  • Built 1930

  160 Hinsdale Ave, Winsted, CT 06098

  Last Sold Summary

  • 46 Days On Market
• 

  

  

  /19

  $349,000

  Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,888 Sq Ft

  107 Roberts Ave, Winsted, CT 06098

  Peaceful country living with unlimited potential! Nestled on a quiet Winsted street, this three bedroom, two bathroom ranch sits on nearly 2 acres of private, setback land. It offers excellant structural bones and a functonal layout, making it an ideal candidate for a rewarding renovation project. The large living and dining space features high cathedral ceilings and exposed wood beams with the

  Mary Anne Casey D. Beckley Realty

  107 Roberts Ave, Winsted, CT 06098
• 

  $639,000

  Sold Jul 31, 2025

  102 Hollow Hill Rd, Winsted, CT 06098

  • 3 Beds
  • 2.5 Baths
  • 2,692 Sq Ft
  • Built 2004

  Last Sold Summary

  • 8% Above List Price
  • $237/SF
  • 49 Days On Market

  Current Estimated Value $645,800

  Last Listing Agent Dawn Rousseau Showcase Realty, Inc.

  102 Hollow Hill Rd, Winsted, CT 06098
• 

  Est $273,887

  Not Listed For Sale

  234 Oak St, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft
  • Built 1890

  234 Oak St, Winsted, CT 06098

  Last Sold Summary

  • 29 Days On Market
• 

  

  /34

  $399,000

  Pending

  • 5 Beds
  • 4 Baths
  • 2,779 Sq Ft

  217 Walnut St, Winsted, CT 06098

  In-Town Victorian 2-Family - Exceptional Condition & Versatility Rare opportunity to own a beautifully maintained, vinyl-sided Victorian-style side-by-side two-family home in a prime in-town location! This unique property offers incredible flexibility for investors, owner-occupants, or multi-generational living. Each unit features its own private entrance and spacious layout-one side offering a

  David D'Amore Northwest CT Realty

  217 Walnut St, Winsted, CT 06098
• 

  $255,000

  Sold May 08, 2026

  94 Holabird Ave, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,422 Sq Ft
  • Built 1942

  Last Sold Summary

  • 2% Above List Price
  • $179/SF
  • 47 Days On Market

  Current Estimated Value $248,612

  Last Listing Agent Rob Rosa Berkshire Hathaway NE Prop.

  94 Holabird Ave, Winsted, CT 06098
• 

  Est $283,052

  Not Listed For Sale

  24 Union St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 2,582 Sq Ft
  • Built 1895

  24 Union St, Winsted, CT 06098

  Last Sold Summary

  • 47 Days On Market
• 

  

  /27

  $375,000

  Pending

  • 3 Beds
  • 3,660 Sq Ft

  57 Main St, Winsted, CT 06098

  Wonderful multiuse property on Main St. in Winsted. Currently used as a cleaners on the first floor and residential unit on the second floor. Multiple possibilities for this building which is in a prime location. Potential to take over the current business and rent or live in second floor, covert to multifamily or start a new business venture. This property is also listed as commercial with MLS

  Stacy LaQuerre Regall Realty, LLC

  57 Main St, Winsted, CT 06098
• 

  $319,900

  Sold Aug 29, 2025

  389 Colebrook River Rd, Winsted, CT 06098

  • 2 Beds
  • 1.5 Baths
  • 1,034 Sq Ft
  • Built 1950

  Last Sold Summary

  • $309/SF
  • 57 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty

  389 Colebrook River Rd, Winsted, CT 06098
• 

  Est $398,090

  Not Listed For Sale

  323 E Wakefield Blvd, Winsted, CT 06098

  • 3 Beds
  • 2.5 Baths
  • 1,426 Sq Ft
  • Built 1989

  323 E Wakefield Blvd, Winsted, CT 06098

  Last Sold Summary

  • 4 Days On Market
• 

  

  /31

  $269,999

  $20K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,652 Sq Ft

  118 Meadow St, Winsted, CT 06098

  This charming historic home, built in 1860, blends timeless character with thoughtful updates. Featuring 3-4 bedrooms, this property offers flexible living space to meet your needs. The beautifully remodeled upstairs bathroom is a standout feature, offering modern comfort within this classic home. Enjoy your LARGE eat-in kitchen with laundry hook ups and plenty of natural lighting and ample

  Ashley Henry The Washington Agency

  118 Meadow St, Winsted, CT 06098
• 

  $383,000

  Sold Sep 10, 2025

  41 Lovely St, Winsted, CT 06098

  • 5 Beds
  • 2 Baths
  • 2,531 Sq Ft
  • Built 1910

  Last Sold Summary

  • 9% Above List Price
  • $151/SF
  • 39 Days On Market

  Current Estimated Value $381,098

  Last Listing Agent Mary Mary LeBlanc Realty

  41 Lovely St, Winsted, CT 06098
• 

  Not Listed For Sale

  174 Wallens St Unit C7, Winsted, CT 06098

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft
  • Built 2005

  174 Wallens St Unit C7, Winsted, CT 06098

  Last Sold Summary

  • 36 Days On Market
• 

  

  /29

  $279,900

  $20K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 702 Sq Ft

  147 E Wakefield Blvd, Winsted, CT 06098

  Come enjoy Highland Lake living just in time for Summer. Relax in this one level living, cozy cottage home with views of the lake from your deck and just a short distance to Resha beach. Enter through a large mudroom to your open living room with large window to let in natural light, updated kitchen, 2 bedrooms, 1 full bath, main level laundry, front and rear deck, large yard & shed. New flooring

  Mary Mary LeBlanc Realty

  147 E Wakefield Blvd, Winsted, CT 06098
• 

  $370,000

  Sold Nov 14, 2025

  166 Torringford St, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 2,024 Sq Ft
  • Built 1898

  Last Sold Summary

  • 3% Below List Price
  • $183/SF
  • 77 Days On Market

  Current Estimated Value $371,453

  Last Listing Agent Lana Van Valkenburgh Vision Real Estate

  166 Torringford St, Winsted, CT 06098
• 

  Est $254,943

  Not Listed For Sale

  42 Upland Rd, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 1,236 Sq Ft
  • Built 1891

  42 Upland Rd, Winsted, CT 06098

  Last Sold Summary

  • 71 Days On Market
• 

  

  /37

  $765,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 4,387 Sq Ft

  184 Smith Hill Rd, Winsted, CT 06098

  Beautiful Private Brick/Clapboard Tudor set back on 8.46 private acres (which includes an extra 2+ acre abutting lot). New Hand Split Cedar Shingled Roof and new rebuilt brick chimney set off this custom elegant home. All warm cherry wood floors and special custom moldings throughout the home add charm. Classy center island Kit with new subzero, granite counters & bow window-Fireplaced Dining

  Mary New Berkshire Hathaway NE Prop.

  184 Smith Hill Rd, Winsted, CT 06098
• 

  $389,900

  Sold Nov 06, 2025

  27 Thibault Ave, Winsted, CT 06098

  • 8 Beds
  • 5 Baths
  • 7,372 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Below List Price
  • $53/SF
  • 57 Days On Market

  Last Listing Agent Cathy Macias Northwest CT Realty

  27 Thibault Ave, Winsted, CT 06098
• 

  Est $294,848

  Not Listed For Sale

  125 E Mountain Ave, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,622 Sq Ft
  • Built 1953

  125 E Mountain Ave, Winsted, CT 06098

  Last Sold Summary

  • 39 Days On Market
• 

  

  /37

  $1,850,000

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

  431 W Wakefield Blvd, Winsted, CT 06098

  Live the Highland Lake Dream - 431 W. Wakefield Blvd, Winchester, CT Summer is just around the corner - and in Winsted, resort living never ends. Recently named one of the most desirable towns to live in, with the breathtaking Highland Lake at its heart, Winchester offers the perfect blend of beauty and lifestyle. This waterfront estate at 431 W. Wakefield Blvd isn't just a home - it's your

  Lisa Ogren Berkshire Hathaway NE Prop.

  431 W Wakefield Blvd, Winsted, CT 06098
• 

  $388,000

  Sold Aug 27, 2025

  409 N Main St, Winsted, CT 06098

  • 5 Beds
  • 2 Baths
  • 2,403 Sq Ft
  • Built 1868

  Last Sold Summary

  • $161/SF
  • 70 Days On Market

  Current Estimated Value $357,534

  Last Listing Agent Christine Hunter Hunter Real Estate, LLC

  409 N Main St, Winsted, CT 06098
• 

  Est $270,468

  Not Listed For Sale

  103 E Mountain Ave, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,304 Sq Ft
  • Built 1955

  103 E Mountain Ave, Winsted, CT 06098

  Last Sold Summary

  • 29 Days On Market
• 

  

  /36

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,820 Sq Ft

  132 E Lake St, Winsted, CT 06098

  Welcome to East Lake Street at Highland Lake, where privacy, comfort, and year-round recreation come together. Set back from the road on a private lot in the desirable First Bay area, this well-maintained 2-story home offers peaceful surroundings, refreshing breezes, and glimpses of Highland Lake through the trees from the front porch and sun-room. Offering 1,820 square feet of living space, this

  Bryan Palladino Showcase Realty, Inc.

  132 E Lake St, Winsted, CT 06098
• 

  $288,557

  Sold Oct 29, 2025

  15 John St, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,538 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Below List Price
  • $188/SF
  • 38 Days On Market

  Current Estimated Value $280,094

  Last Listing Agent Amanda Balaski Northwest CT Realty

  15 John St, Winsted, CT 06098
• 

  Est $610,665

  Not Listed For Sale

  129 Forest Ave, Winsted, CT 06098

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • Built 2007

  129 Forest Ave, Winsted, CT 06098

  Last Sold Summary

  • 195 Days On Market
• 

  

  /40

  $495,000

  • 4 Beds
  • 2.5 Baths
  • 3,834 Sq Ft

  293 Torringford St, Winsted, CT 06098

  Unique opportunity to own this spacious 4-bedroom Colonial set on 27 acres in Winchester, CT. Previously home to animals, this property offers endless possibilities for hobby farming, equestrian pursuits, recreation, or simply enjoying the privacy and beauty of the countryside. Ideally located directly across the street from Green Woods Country Club, you'll enjoy convenient access to golf, and

  Shawna Mucherino Coldwell Banker Realty

  293 Torringford St, Winsted, CT 06098
• 

  $235,000

  Sold Nov 24, 2025

  30 Rock St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 2,299 Sq Ft
  • Built 1874

  Last Sold Summary

  • 4% Above List Price
  • $102/SF
  • 8 Days On Market

  Current Estimated Value $230,695

  Last Listing Agent Patrick Precourt Meridian Realty Group LLC

  30 Rock St, Winsted, CT 06098
• 

  Est $354,159

  Not Listed For Sale

  143 Mountain Rd, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 1,249 Sq Ft
  • Built 1920

  143 Mountain Rd, Winsted, CT 06098

  Last Sold Summary

  • 92 Days On Market
• 

  

  /19

  $549,000

  $30K PRICE DROP

  • 11 Beds
  • 5.5 Baths
  • 5,233 Sq Ft

  150 Oak St, Winsted, CT 06098

  *PRICE REDUCTION* 150 Oak St. is a fully rented, rare, charming 1920's 5-family apartment home located in a beautiful residential neighborhood in Winsted/Winchester, CT. Old World charm with original woodwork, high ceilings, mostly hardwood floors, and hallways connecting the spacious rooms in 4 of the units -which feature 2 bedrooms and a dining room. The 5th floor is a 3-4 bedroom, 1 1/2 bath

  Pamela Silvestri Turning Point Realty, LLC

  150 Oak St, Winsted, CT 06098
• 

  $368,500

  Sold Jun 16, 2026

  102 Wallens St, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,898 Sq Ft
  • Built 1905

  Last Sold Summary

  • 5% Above List Price
  • $194/SF
  • 48 Days On Market

  Current Estimated Value $351,142

  Last Listing Agent Amanda Balaski Northwest CT Realty

  102 Wallens St, Winsted, CT 06098
• 

  Est $234,449

  Not Listed For Sale

  11 Orchard St, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,759 Sq Ft
  • Built 1900

  11 Orchard St, Winsted, CT 06098

  Last Sold Summary

  • 19 Days On Market
• 

  

  /19

  $469,900

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

  9 Loomis St, Winsted, CT 06098

  Spacious 3 to 4 Bedroom Colonial Style Home on a 0.35 Acre Lot, plus located on a No Through Street. OPEN FLOOR PLAN. Beautifully Remodeled from "TOP TO BOTTOM" for Energy Efficient Living. Redesigned Country Style Kitchen offers Ample Cabinetry and includes New Oven/Range, Microwave, Refrigerator & Dishwasher.. 27' x 12' Living/Dining Combo with Bay/Bow Window that takes in Natural Light on

  Marshall Cohen Cohen Agency

  9 Loomis St, Winsted, CT 06098
• 

  $862,500

  Sold Jul 23, 2025

  112 Shore Dr, Winsted, CT 06098

  • 3 Beds
  • 3 Baths
  • 2,113 Sq Ft
  • Built 1955

  Last Sold Summary

  • 11% Below List Price
  • $408/SF
  • 61 Days On Market

  Current Estimated Value $861,005

  Last Listing Agent Nancy Reardon Berkshire Hathaway NE Prop.

  112 Shore Dr, Winsted, CT 06098
• 

  Est $285,475

  Not Listed For Sale

  303 E Wakefield Blvd, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1986

  303 E Wakefield Blvd, Winsted, CT 06098

  Last Sold Summary

  • 21 Days On Market
• 

  

  /38

  $345,000

  Under Contract

  • 5 Beds
  • 3 Baths
  • 2,602 Sq Ft

  63 Meadow St, Winsted, CT 06098

  Discover 63 Meadow, a turnkey 3-unit asset where thoughtful updates, strong rental performance, and a prime location come together to prove a high confidence investment opportunity. The property offers three well-proportioned units, a two-car attached garage, off-street parking spaces, and shared outdoor area that tenants appreciate. The current owner continued to elevate the building's value and

  Lauren Hill Mark Tavares Realty, LLC

  63 Meadow St, Winsted, CT 06098
• 

  $151,000

  Sold Jun 10, 2026

  35 Riveredge Dr Unit 35, Winsted, CT 06098

  • 2 Beds
  • 1.5 Baths
  • 992 Sq Ft
  • Built 1986

  Last Sold Summary

  • 8% Below List Price
  • $152/SF
  • 127 Days On Market

  Current Estimated Value $161,284

  Last Listing Agent Joanne Donne The Washington Agency

  35 Riveredge Dr Unit 35, Winsted, CT 06098
• 

  Est $269,607

  Not Listed For Sale

  151 Hinsdale Ave, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,634 Sq Ft
  • Built 1948

  151 Hinsdale Ave, Winsted, CT 06098

  Last Sold Summary

  • 154 Days On Market
• 

  

  /38

  $749,000

  $20K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,265 Sq Ft

  121 W Wakefield Blvd, Winsted, CT 06098

  Discover unparalleled Highland Lake living with this exceptional 1.00-acre retreat, boasting 50 feet of direct lake frontage and a newly renovated dock/deck. Enjoy breathtaking water views from your sunroom, dining room, and multiple bedrooms within this versatile 4/5 bedroom home. A unique first-floor suite with a separate exterior entrance offers ideal flexibility as a main-floor master or

  Elizabeth Stockwell Coldwell Banker Realty

  121 W Wakefield Blvd, Winsted, CT 06098
• 

  $320,000

  Sold Sep 30, 2025

  128 Danbury Quarter Rd, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1965

  Last Sold Summary

  • 8% Above List Price
  • $333/SF
  • 34 Days On Market

  Current Estimated Value $317,097

  Last Listing Agent Kim Trumbull William Raveis Real Estate

  128 Danbury Quarter Rd, Winsted, CT 06098

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