Winchester, CT Homes

• 

  Est $293,178

  Not Listed For Sale

  58 Cherry St, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,287 Sq Ft
  • Built 1948

  58 Cherry St, Winsted, CT 06098

  Last Sold Summary

  • 7% Above List Price
  • $214/SF
  • 22 Days On Market

  • Last Sold Price $275,000
  • Apr 17, 2025

  Last Listing Agent David Sartirana Northwest CT Realty
• 

  

  

  /35

  $1,495,000

  Pending

  • 3 Beds
  • 3.5 Baths
  • 2,699 Sq Ft

  129 E Lake St, Winsted, CT 06098

  A true vacation retreat on the shore of Highland Lake! Rare offering in exceptional condition ready for summer enjoyment. Central AC/heat with an open floorplan offering spacious family and entertaining opportunity. Folding glass doors to large lakefront deck with panoramic views of the water. Original house completely renovated inside and out in 2016, with recent stone patio and fire pit added

  KAREN NEWTON William Pitt Sotheby's Int'l

  129 E Lake St, 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
• 

  Est $272,446

  Not Listed For Sale

  39 Rockwell St, Winsted, CT 06098

  • 5 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • Built 1900

  39 Rockwell St, Winsted, CT 06098

  Last Sold Summary

  • 27% Above List Price
  • $86/SF
  • 19 Days On Market

  • Last Sold Price $215,000
  • May 25, 2023

  Last Listing Agent Andrew Vincent Santa Realty
• 

  

  

  /22

  $335,000

  $15K PRICE DROP Under Contract

  • 3 Beds
  • 1 Bath
  • 1,282 Sq Ft

  90 Colony Dr, Winsted, CT 06098

  Turnkey Winsted gem completely renovated inside & out! Get ready to just move and and not worry. Here is a beautifully reimagined 3-bedroom, 1-bathroom property in Winsted, offering the perfect blend of modern luxury and ultimate peace of mind. Every detail has been thoughtfully updated to create a true turnkey experience. Step inside to a bright, inviting space where the wall between the

  Michelle Grant Coldwell Banker Premier Real Estate

  90 Colony Dr, Winsted, CT 06098
• 

  $320,000

  Sold Sep 03, 2025

  107 Old Rd N, Winchester, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,616 Sq Ft
  • Built 1973

  Last Sold Summary

  • 2% Above List Price
  • $198/SF
  • 24 Days On Market

  Last Listing Agent Jill Rubino Century 21 AllPoints Realty

  107 Old Rd N, Winchester, CT 06098
• 

  Est $274,115

  Not Listed For Sale

  160 Glendale Ave, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,114 Sq Ft
  • Built 1957

  160 Glendale Ave, Winsted, CT 06098

  Last Sold Summary

  • 10% Above List Price
  • $224/SF
  • 85 Days On Market

  • Last Sold Price $250,000
  • Nov 01, 2024

  Last Listing Agent Cathy Macias Northwest CT Realty
• 

  

  /24

  $189,900

  Under Contract

  • 2 Beds
  • 2 Baths
  • 1,102 Sq Ft

  111 Torringford St Unit 33, Winsted, CT 06098

  Tucked within the desirable Green Ridge community, this inviting townhouse-style condo offers comfortable living with thoughtful updates and flexible space throughout. Featuring 2 bedrooms and 2 bathrooms, this home blends functionality, warmth, and opportunity for a new owner to make it their own. The updated kitchen serves as the centerpiece of the home, offering modern finishes, ample cabinet

  Ryan Horvay Smith & DeGroat Real Estate

  111 Torringford St Unit 33, 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
• 

  Est $324,745

  Not Listed For Sale

  153 Mathew Rd, Winsted, CT 06098

  • 2 Beds
  • 1.5 Baths
  • 1,544 Sq Ft
  • Built 1800

  153 Mathew Rd, Winsted, CT 06098

  Last Sold Summary

  • 12% Above List Price
  • $188/SF
  • 141 Days On Market

  • Last Sold Price $290,000
  • Nov 21, 2024

  Last Listing Agent Liz Zakrzewski Coldwell Banker
• 

  

  /8

  $389,000

  • Land
  • 20.87 Acres
  • $18,639 per Acre

  7 Stadler Heights, Winsted, CT 06098

  Welcome, You be the first, to come and conquer this land here in Winchester, Connecticut. There are 20.87 acres of virgin land. Come and build, do what you do best, you can have Peace and Privacy!!! There are no sidewalks, no streets that drive through. You are 40 minutes from multiple private schools. 16 minutes from Charlotte Hungerford Hospital. 1 hour from Tweed Airport New Haven. 39 minutes

  Hector Ortiz KW Legacy Partners

  7 Stadler Heights, 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
• 

  Est $197,816

  Not Listed For Sale

  111 Torringford St Unit 19, Winsted, CT 06098

  • 2 Beds
  • 2 Baths
  • 1,626 Sq Ft
  • Built 1987

  111 Torringford St Unit 19, Winsted, CT 06098

  Last Sold Summary

  • $121/SF
  • 14 Days On Market

  • Last Sold Price $197,000
  • Dec 04, 2024

  Last Listing Agent David Sartirana Northwest CT Realty
• 

  

  /15

  $859,000

  • Land
  • 65.29 Acres
  • $13,157 per Acre

  257-259 Torringford St, Winchester, CT 06098

  Uncover this hidden gem - 65.29 pristine acres of raw land, with natural beauty and endless potential. This picturesque parcel features serene ponds and mature trees. Distant views and incredible sunsets can be enjoyed from the property. Much site work has been done to date. A driveway with a binder course is already in place offering easy access into and throughout the property. Many acres have

  Lisa Toczko Home Valley Realty, LLC

  257-259 Torringford St, Winchester, 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
• 

  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
• 

  

  /5

  $158,000

  $3K PRICE INCREASE

  • Land
  • 1.18 Acres
  • $133,898 per Acre

  843-845 (lots - 10A, E Wakefield Blvd, Winchester, CT 06098

  1.18 Acre ,Approximately 201 Ft Road fro . ntage )Lightly wooded E. Wakefield Blvd. lot located at the end of 3rd Bay . Panoramic view overlooking the length or lake. Survey , Zoning HL regulations and Deed are available , and Access is also available off E. Mtn Road . Survey shows Town of Winchester parcel with warterfront access Rare opportunity to build your dream home . , SELLER WILL CONSIDER

  David D'Amore Northwest CT Realty

  843-845 (lots - 10A, E Wakefield Blvd, Winchester, CT 06098
• 

  $320,000

  Sold Feb 17, 2026

  148 Danbury Quarter Rd, Winchester, CT 06098

  • 4 Beds
  • 2 Baths
  • 1,999 Sq Ft
  • Built 1800

  Last Sold Summary

  • 6% Below List Price
  • $160/SF
  • 86 Days On Market

  Current Estimated Value $323,625

  Last Listing Agent Susan MCGHEE The Washington Agency

  148 Danbury Quarter Rd, Winchester, 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
• 

  

  /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
• 

  $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
• 

  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
• 

  

  /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
• 

  $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
• 

  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
• 

  

  /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
• 

  $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
• 

  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
• 

  

  /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
• 

  $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
• 

  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
• 

  

  /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
• 

  $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
• 

  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
• 

  

  /31

  $990,000

  Pending

  • 3 Beds
  • 3 Baths
  • 2,097 Sq Ft

  674 E Wakefield Blvd, Winsted, CT 06098

  Experience the best of year-round waterfront living on Highland Lake in this beautifully maintained 3-bedroom, 3-bath home with stunning panoramic views and direct water access. Ideally located in the sought-after 3rd Bay, this property features a private dock-perfect for boating, swimming, kayaking, and enjoying everything lake life has to offer. Inside, an open and inviting layout connects the

  Patrick Smith Smith & DeGroat Real Estate

  674 E Wakefield Blvd, 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
• 

  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
• 

  

  /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
• 

  $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
• 

  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

Showing Results 81 - 120, Page 3 of 18