4,844

Winsted, CT Homes

Section Image
    • 111 Riverton Rd Unit 30, Winsted, CT 06098

      Est $194,996

      Not Listed For Sale

      111 Riverton Rd Unit 30, Winsted, CT 06098

      • 2 Beds
      • 1.5 Baths
      • 1,204 Sq Ft
      • Built 1987
      111 Riverton Rd Unit 30, Winsted, CT 06098

      Last Sold Summary

      • 11% Above List Price
      • $145/SF
      • 0 Days On Market
      • Last Sold Price $175,000
      • Jan 31, 2024

      Last Listing Agent Patricia Scarpa Marino Realty LLC

  • 35 Riveredge Dr Unit 35, Winsted, CT 06098
    35 Riveredge Dr Unit 35, Winsted, CT 06098
    35 Riveredge Dr Unit 35, Winsted, CT 06098
    /30

    $159,500

    $5K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 992 Sq Ft

    35 Riveredge Dr Unit 35, Winsted, CT 06098

    Charming Riverview Townhouse with Patio Enjoy easy living in this well-located two-bedroom townhouse set on a slab and overlooking the river. The main level features a living room, dining room, and functional kitchen, perfect for everyday comfort and entertaining. Sliding glass doors lead to a private patio where you can relax and enjoy the peaceful water views. Upstairs offers two comfortable

    Joanne Donne The Washington Agency

    35 Riveredge Dr Unit 35, Winsted, CT 06098
  • 39 Colony Dr, Winsted, CT 06098

    $279,900

    Sold Sep 12, 2025

    39 Colony Dr, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,183 Sq Ft
    • Built 1969

    Last Sold Summary

    • $237/SF
    • 65 Days On Market

    Current Estimated Value $286,943

    Last Listing Agent Alison Behlman Tier 1 Real Estate

    39 Colony Dr, Winsted, CT 06098
    • 182 Florence St, Winsted, CT 06098

      Est $293,623

      Not Listed For Sale

      182 Florence St, Winsted, CT 06098

      • 3 Beds
      • 1.5 Baths
      • 1,982 Sq Ft
      • Built 1979
      182 Florence St, Winsted, CT 06098

      Last Sold Summary

      • $148/SF
      • 40 Days On Market
      • Last Sold Price $293,000
      • Oct 31, 2024

      Last Listing Agent Heidi Picard-Ramsay Berkshire Hathaway Home Services

  • 1 Hamill Dr, Winsted, CT 06098
    1 Hamill Dr, Winsted, CT 06098
    1 Hamill Dr, Winsted, CT 06098
    /29

    $349,900

    $10K PRICE DROP Under Contract
    • 3 Beds
    • 1.5 Baths
    • 1,600 Sq Ft

    1 Hamill Dr, Winsted, CT 06098

    Step into luxury in this nicely updated 3-bedroom raised ranch, perfectly positioned on a quiet cul-de-sac. The interior shines with hardwood floors and a designer kitchen boasting new custom cabinetry, quartz countertops and stainless-steel appliances. Lower level is completely finished featuring a large family room with natural gas stove. Enjoy maintenance-free living with a newer roof (less

    Paul Duh Realty ONE Group Connect

    1 Hamill Dr, Winsted, CT 06098
  • 56 Lakeview Rd, Winsted, CT 06098

    $279,000

    Sold May 19, 2025

    56 Lakeview Rd, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,101 Sq Ft
    • Built 1956

    Last Sold Summary

    • 16% Above List Price
    • $253/SF
    • 6 Days On Market

    Current Estimated Value $247,177

    Last Listing Agent Tony Goia The Washington Agency

    56 Lakeview Rd, Winsted, CT 06098
    • 36 Charles St, Winsted, CT 06098

      Est $245,448

      Not Listed For Sale

      36 Charles St, Winsted, CT 06098

      • 3 Beds
      • 1 Bath
      • 1,180 Sq Ft
      • Built 1957
      36 Charles St, Winsted, CT 06098

      Last Sold Summary

      • 2% Above List Price
      • $203/SF
      • 5 Days On Market
      • Last Sold Price $240,000
      • Oct 06, 2023

      Last Listing Agent Judy Guarco Berkshire Hathaway Home Services

  • 69 Prospect St, Winsted, CT 06098
    69 Prospect St, Winsted, CT 06098
    69 Prospect St, Winsted, CT 06098
    /32

    $274,900

    • 7 Beds
    • 3 Baths
    • 2,204 Sq Ft

    69 Prospect St, Winsted, CT 06098

    Opportunity awaits with this versatile 3-family property located at 69 Prospect Street in Winchester, perfect for both investors and owner-occupants alike. Whether you're looking to expand your investment portfolio or offset your mortgage with rental income, this multi-family offers flexibility, functionality, and strong potential in a convenient location. The property features 3 separate units

    Adam Cannon Coldwell Banker Realty

    69 Prospect St, Winsted, CT 06098
  • 62 Fruit St Unit 64, Winsted, CT 06098

    $326,000

    Sold Oct 31, 2025

    62 Fruit St Unit 64, Winsted, CT 06098

    • 6 Beds
    • 2 Baths
    • 3,078 Sq Ft
    • Built 1902

    Last Sold Summary

    • $106/SF
    • 13 Days On Market

    Current Estimated Value $313,013

    Last Listing Agent Antonio De La Cruz Eagle Eye Realty PLLC

    62 Fruit St Unit 64, Winsted, CT 06098
    • 133 E Wakefield Blvd, Winsted, CT 06098

      Est $358,412

      Not Listed For Sale

      133 E Wakefield Blvd, Winsted, CT 06098

      • 3 Beds
      • 2 Baths
      • 1,594 Sq Ft
      • Built 1962
      133 E Wakefield Blvd, Winsted, CT 06098

      Last Sold Summary

      • 16% Above List Price
      • $194/SF
      • 26 Days On Market
      • Last Sold Price $310,000
      • Nov 30, 2023

      Last Listing Agent David Sartirana Northwest CT Realty

  • 748 Lake Dr, Winsted, CT 06098
    748 Lake Dr, Winsted, CT 06098
    748 Lake Dr, Winsted, CT 06098
    /40

    $1,249,900

    Under Contract
    • 5 Beds
    • 4 Baths
    • 3,584 Sq Ft

    748 Lake Dr, Winsted, CT 06098

    Rare opportunities like this do not come around often on Highland Lake! Located on the east side of 3rd bay, this unique waterfront property offers beautiful views and magnificent sunsets. This unique waterfront layout offers endless opportunities; from a family compound, multi generational living, guest space or a private lake retreat! Enjoy outdoor living on the massive deck, custom dock, and

    Ryan Horvay Smith & DeGroat Real Estate

    748 Lake Dr, Winsted, CT 06098
  • 226 E Wakefield Blvd, Winsted, CT 06098

    $380,000

    Sold Sep 17, 2025

    226 E Wakefield Blvd, Winsted, CT 06098

    • 3 Beds
    • 1.5 Baths
    • 1,196 Sq Ft
    • Built 1974

    Last Sold Summary

    • 3% Above List Price
    • $318/SF
    • 38 Days On Market

    Current Estimated Value $378,607

    Last Listing Agent Pascale Nejaime William Pitt Sotheby's Int'l

    226 E Wakefield Blvd, Winsted, CT 06098
    • 14 Hamill Dr, Winsted, CT 06098

      Est $261,067

      Not Listed For Sale

      14 Hamill Dr, Winsted, CT 06098

      • 3 Beds
      • 1.5 Baths
      • 1,888 Sq Ft
      • Built 1973
      14 Hamill Dr, Winsted, CT 06098

      Last Sold Summary

      • $138/SF
      • 27 Days On Market
      • Last Sold Price $260,000
      • Mar 10, 2025

      Last Listing Agent Eva Casoria eXp Realty

  • 115 Old Robertsville Rd, Winsted, CT 06098
    115 Old Robertsville Rd, Winsted, CT 06098
    115 Old Robertsville Rd, Winsted, CT 06098
    /13

    $649,900

    Pending
    • Land
    • 41.23 Acres
    • $15,763 per Acre

    115 Old Robertsville Rd, Winsted, CT 06098

    Development Opportunity! 41.23 Acres with Historic Home & Barn - Subdivision Possible Rare chance to own a prime 41.23-acre parcel in New England with an 1800 Antique Colonial Farmhouse and classic English/New England hybrid barn. The land may be subdividable and is located near the highly desirable Riverwalk Condominiums, making it ideal for new condo development (subject to approvals). The home

    Jared Tedesco Litchfield County Real Estate

    115 Old Robertsville Rd, Winsted, CT 06098
  • 343 W Wakefield Blvd, Winsted, CT 06098

    $236,434

    Sold Aug 25, 2025

    343 W Wakefield Blvd, Winsted, CT 06098

    • 2 Beds
    • 1 Bath
    • 674 Sq Ft
    • Built 1923

    Last Sold Summary

    • 15% Below List Price
    • $351/SF
    • 40 Days On Market

    Current Estimated Value $259,078

    Last Listing Agent Patrick Precourt Meridian Realty Group LLC

    343 W Wakefield Blvd, Winsted, CT 06098
    • 830 Main St, Winsted, CT 06098

      Est $221,236

      Not Listed For Sale

      830 Main St, Winsted, CT 06098

      • 5 Beds
      • 4 Baths
      • 3,115 Sq Ft
      • Built 1900
      830 Main St, Winsted, CT 06098

      Last Sold Summary

      • 1% Above List Price
      • $71/SF
      • 14 Days On Market
      • Last Sold Price $220,000
      • Apr 24, 2025

      Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  • 107 Birdsall St, Winsted, CT 06098
    107 Birdsall St, Winsted, CT 06098
    107 Birdsall St, Winsted, CT 06098
    /5

    $240,000

    $10K PRICE DROP Under Contract
    • 4 Beds
    • 2 Baths
    • 1,874 Sq Ft

    107 Birdsall St, Winsted, CT 06098

    Spacious colonial with 4 bedrooms, 2 full baths, generous size living room, dining room, sitting room, sunroom. Looking for space, this home definitely has it. Harwood floors thorough, granite countertops, marble backsplash, Island in kitchen. Short walk to highland Lake With a little TLC this home will be a GEM! Home being sold AS-IS.

    Jesica Beaulieu Dave Jones Realty, LLC

    107 Birdsall St, Winsted, CT 06098
  • 131 Willow St, Winsted, CT 06098

    $293,000

    Sold Oct 30, 2025

    131 Willow St, Winsted, CT 06098

    • 6 Beds
    • 2 Baths
    • 2,160 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Below List Price
    • $136/SF
    • 83 Days On Market

    Last Listing Agent Amanda Balaski Northwest CT Realty

    131 Willow St, Winsted, CT 06098
    • 257 Walnut St, Winsted, CT 06098

      Est $279,218

      Not Listed For Sale

      257 Walnut St, Winsted, CT 06098

      • 3 Beds
      • 1.5 Baths
      • 1,490 Sq Ft
      • Built 1900
      257 Walnut St, Winsted, CT 06098

      Last Sold Summary

      • 12% Above List Price
      • $167/SF
      • 21 Days On Market
      • Last Sold Price $249,000
      • Dec 14, 2023

      Last Listing Agent Meagan Albert Tier 1 Real Estate

  • 123 Old North Rd, Winsted, CT 06098
    123 Old North Rd, Winsted, CT 06098
    123 Old North Rd, Winsted, CT 06098
    /28

    $425,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,781 Sq Ft

    123 Old North Rd, Winsted, CT 06098

    This one-of-a-kind custom Ranch is tucked well back from the road for exceptional privacy and was thoughtfully designed for its present owner. The stunning kitchen is truly the heart of the home, featuring a dramatic floor-to-ceiling stone fireplace, an expansive island with breakfast bar, an endless array of cabinets, and a built-in range with gas cooktop. The dining area flows seamlessly from

    Rick Berkenstock CENTURY 21 AllPoints Realty

    123 Old North Rd, Winsted, CT 06098
  • 17 Adams St, Winsted, CT 06098

    $315,000

    Sold Sep 29, 2025

    17 Adams St, Winsted, CT 06098

    • 3 Beds
    • 1.5 Baths
    • 1,747 Sq Ft
    • Built 1900

    Last Sold Summary

    • 5% Above List Price
    • $180/SF
    • 85 Days On Market

    Current Estimated Value $312,418

    Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

    17 Adams St, Winsted, CT 06098
    • 204 Gilbert Ave, Winsted, CT 06098

      Est $307,661

      Not Listed For Sale

      204 Gilbert Ave, Winsted, CT 06098

      • 5 Beds
      • 2,820 Sq Ft
      • Built 1875
      204 Gilbert Ave, Winsted, CT 06098

      Last Sold Summary

      • 12% Above List Price
      • $98/SF
      • 10 Days On Market
      • Last Sold Price $275,000
      • Jun 12, 2023

      Last Listing Agent Austin Brochu Sullivan Real Estate Inc

  • 34 Hannifin Rd, Winsted, CT 06098
    34 Hannifin Rd, Winsted, CT 06098
    34 Hannifin Rd, Winsted, CT 06098
    /16

    $85,000

    • 3 Beds
    • 1 Bath
    • 1,435 Sq Ft

    34 Hannifin Rd, Winsted, CT 06098

    Set on 1.8 private acres amid the scenic rolling hills of Winsted, this circa-1850 home offers a rare opportunity to restore and reimagine a property rich with character. A compelling value with exceptional upside, this property invites buyers, investors, or renovators to unlock its full potential. Inside, you'll find timeless details including wide plank flooring and a fireplaced living room,

    Michael Barnes Coldwell Banker Realty

    34 Hannifin Rd, Winsted, CT 06098
  • 22 Curtice St, Winsted, CT 06098

    $243,000

    Sold Nov 17, 2025

    22 Curtice St, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,334 Sq Ft
    • Built 1900

    Last Sold Summary

    • $182/SF
    • 33 Days On Market

    Current Estimated Value $248,437

    Last Listing Agent Terence Dominick Exceptional Real Estate LLC

    22 Curtice St, Winsted, CT 06098
    • 111 Riverton Rd Unit 53, Winsted, CT 06098

      Est $196,426

      Not Listed For Sale

      111 Riverton Rd Unit 53, Winsted, CT 06098

      • 2 Beds
      • 1.5 Baths
      • 1,204 Sq Ft
      • Built 1987
      111 Riverton Rd Unit 53, Winsted, CT 06098

      Last Sold Summary

      • 1% Below List Price
      • $165/SF
      • 12 Days On Market
      • Last Sold Price $199,000
      • Dec 31, 2024

      Last Listing Agent Samantha Behm William Pitt

  • 424 E Wakefield Blvd, Winsted, CT 06098
    424 E Wakefield Blvd, Winsted, CT 06098
    424 E Wakefield Blvd, Winsted, CT 06098
    /40

    $1,595,000

    Open Sun 12PM - 2PM
    • 5 Beds
    • 2 Baths
    • 3,693 Sq Ft

    424 E Wakefield Blvd, Winsted, CT 06098

    Stunning Lakehouse! Victorian charm! One of the earliest Highland Lake homes with extensive custom upgrades and quality renovation. A true lakefront sanctuary offering spacious living areas, extensive outdoor living areas and wide open lake views offering South and West exposure for incredible sunsets. Lakefront dock system with hydraulic boat lift, Recently renovated kitchen /dining with newer

    KAREN NEWTON William Pitt Sotheby's Int'l

    424 E Wakefield Blvd, Winsted, CT 06098
  • 115 Laurel Way, Winsted, CT 06098

    $261,000

    Sold Oct 17, 2025

    115 Laurel Way, Winsted, CT 06098

    • 1 Bed
    • 1 Bath
    • 604 Sq Ft
    • Built 1940

    Last Sold Summary

    • 4% Above List Price
    • $432/SF
    • 9 Days On Market

    Current Estimated Value $250,503

    Last Listing Agent Jill Menard Realty One Group Cutting Edge

    115 Laurel Way, Winsted, CT 06098
    • 3 Brookside Ave, Winsted, CT 06098

      Est $226,352

      Not Listed For Sale

      3 Brookside Ave, Winsted, CT 06098

      • 6 Beds
      • 2,421 Sq Ft
      • Built 1900
      3 Brookside Ave, Winsted, CT 06098

      Last Sold Summary

      • 33% Above List Price
      • $70/SF
      • 78 Days On Market
      • Last Sold Price $170,000
      • Jul 03, 2023

      Last Listing Agent Jayson Kemp Five Stars Realty

  • 51 Hinsdale Ave, Winsted, CT 06098
    51 Hinsdale Ave, Winsted, CT 06098
    51 Hinsdale Ave, Winsted, CT 06098
    /40

    $475,000

    Under Contract
    • 7 Beds
    • 5 Baths
    • 3,538 Sq Ft

    51 Hinsdale Ave, Winsted, CT 06098

    Owner Occupants take notice: Rare three family home with market rents (one three-bedroom unit vacant) building is in exceptional condition!! A new roof will be installed in May before closing. One unit, a three-bedroom with a kitchen, living room, dining room, and two full bathrooms, this unit is rented @ $2136. per month ($2221.00 for the June 30, 2026-May 31, 2027 lease).) A one-year lease for

    Suzie Larson Turning Point Realty, LLC

    51 Hinsdale Ave, Winsted, CT 06098
  • 174 Wallens St Unit D3, Winsted, CT 06098

    $260,000

    Sold Sep 05, 2025

    174 Wallens St Unit D3, Winsted, CT 06098

    • 2 Beds
    • 2 Baths
    • 1,352 Sq Ft
    • Built 2005

    Last Sold Summary

    • 6% Above List Price
    • $192/SF
    • 1 Day On Market

    Last Listing Agent Mary New Berkshire Hathaway NE Prop.

    174 Wallens St Unit D3, Winsted, CT 06098
    • 111 Riverton Rd Unit 66, Winsted, CT 06098

      Est $196,141

      Not Listed For Sale

      111 Riverton Rd Unit 66, Winsted, CT 06098

      • 2 Beds
      • 1.5 Baths
      • 1,204 Sq Ft
      • Built 1987
      111 Riverton Rd Unit 66, Winsted, CT 06098

      Last Sold Summary

      • 9% Above List Price
      • $149/SF
      • 0 Days On Market
      • Last Sold Price $179,900
      • Apr 15, 2024

      Last Listing Agent Amy Sartirana Northwest CT Realty

  • 111 Torringford St Unit 7, Winsted, CT 06098
    111 Torringford St Unit 7, Winsted, CT 06098
    111 Torringford St Unit 7, Winsted, CT 06098
    /40

    $179,900

    Under Contract
    • 2 Beds
    • 2 Baths
    • 1,156 Sq Ft

    111 Torringford St Unit 7, Winsted, CT 06098

    SELLER REQUESTS ALL OFFERS BY SATURDAY, MAY 9TH @ 5:00 Have I got a home for you! Unpack and relax in this rarely available condo, the perfect spot for you. With easy access to the highway and a quaint downtown area filled with restaurants and shops, this two-bedroom unit offers plenty of room to breathe. The cozy kitchen comes equipped with ample cabinetry and a brand new gas stove. You can

    Janice Madore Country Manor Realty

    111 Torringford St Unit 7, Winsted, CT 06098
  • 111 Riverton Rd Unit 61, Winsted, CT 06098

    $194,900

    Sold Dec 08, 2025

    111 Riverton Rd Unit 61, Winsted, CT 06098

    • 2 Beds
    • 1.5 Baths
    • 1,204 Sq Ft
    • Built 1987

    Last Sold Summary

    • 5% Below List Price
    • $162/SF
    • 61 Days On Market

    Current Estimated Value $198,772

    Last Listing Agent Bethany Lydem Stone Crest Realty LLC

    111 Riverton Rd Unit 61, Winsted, CT 06098
    • 45 Beach St, Winsted, CT 06098

      Est $246,691

      Not Listed For Sale

      45 Beach St, Winsted, CT 06098

      • 4 Beds
      • 2 Baths
      • 2,076 Sq Ft
      • Built 1900
      45 Beach St, Winsted, CT 06098

      Last Sold Summary

      • 53% Above List Price
      • $78/SF
      • 97 Days On Market
      • Last Sold Price $161,500
      • Nov 29, 2023

      Last Listing Agent Michael Barnes Coldwell Banker Realty

  • 111 Riverton Rd Unit 28, Winsted, CT 06098
    111 Riverton Rd Unit 28, Winsted, CT 06098
    111 Riverton Rd Unit 28, Winsted, CT 06098
    /22

    $184,900

    Pending
    • 2 Beds
    • 1.5 Baths
    • 1,204 Sq Ft

    111 Riverton Rd Unit 28, Winsted, CT 06098

    Stop paying rent and get into the housing market with this affordable end-unit townhouse! Two bedrooms, one and a half baths and a two car garage, make this a very livable home. The primary bedroom has a vaulted ceiling and walk-in closet and you'll enjoy the fireplace in the spacious living room. Convenient to routes 8 and 44, close to NWCC, Highland Lake, the Farmington River, hiking and other

    Ellen Sebastian William Pitt Sotheby's Int'l

    111 Riverton Rd Unit 28, Winsted, CT 06098
  • 279 Pratt St, Winsted, CT 06098

    $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 $309,442

    Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

    279 Pratt St, Winsted, CT 06098
    • 193 Spencer Hill Rd, Winsted, CT 06098

      Est $398,928

      Not Listed For Sale

      193 Spencer Hill Rd, Winsted, CT 06098

      • 4 Beds
      • 2.5 Baths
      • 2,313 Sq Ft
      • Built 2012
      193 Spencer Hill Rd, Winsted, CT 06098

      Last Sold Summary

      • 38% Above List Price
      • $125/SF
      • 57 Days On Market
      • Last Sold Price $290,000
      • Apr 03, 2024

      Last Listing Agent Victor Santana Santana Realty Group LLC

  • 393 Winchester Rd, Winsted, CT 06098
    393 Winchester Rd, Winsted, CT 06098
    393 Winchester Rd, Winsted, CT 06098
    /5

    $295,000

    • Land
    • 51 Acres
    • $5,784 per Acre

    393 Winchester Rd, Winsted, CT 06098

    WINCHESTER CREST 51 acres of forested gently rolling land sited upland in Winchester Center. There is a former homesite and multiple choices for additional homesites affording complete privacy. There is abundant wildlife, trails, intermittent streams, dense and sparse forest. Perfect for year round home site, weekend retreat or recreational land.

    Tom McGowan Elyse Harney Real Estate

    393 Winchester Rd, Winsted, CT 06098
  • 102 Hollow Hill Rd, 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 $648,118

    Last Listing Agent Dawn Rousseau Showcase Realty, Inc.

    102 Hollow Hill Rd, Winsted, CT 06098
    • 160 Hinsdale Ave, Winsted, CT 06098

      Est $324,152

      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

      • 7% Below List Price
      • $147/SF
      • 46 Days On Market
      • Last Sold Price $350,000
      • Aug 16, 2024

      Last Listing Agent Laura Krzewski Realtor Bolanos & Associates LLC

Showing Results 81 - 120, Page 3 of 18

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