Winchester, CT Homes

• 

  $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 $328,363

  Last Listing Agent Christine Hunter Hunter Real Estate, LLC

  409 N Main St, Winsted, CT 06098
• 

  Est $341,826

  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

  Last Listing Agent Don Sciarretto Berkshire Hathaway NE Prop.
• 

  

  

  /17

  $365,000

  $35K PRICE DROP

  • 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 lake living come together. Set back from the road on a private lot in the desirable First Bay area, this well-maintained lake-style home offers a quiet setting with seasonal lake views and refreshing breezes throughout. Offering 1,820 square feet, the home is listed as a 3-bedroom with a first-floor finished 4th room for

  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 $298,589

  Last Listing Agent Amanda Balaski Northwest CT Realty

  15 John St, Winsted, CT 06098
• 

  Est $249,863

  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

  Last Listing Agent Jonathan Gineo Silver and Oak Realty
• 

  

  /40

  $495,000

  Under Contract

  • 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 $253,553

  Last Listing Agent Patrick Precourt Century 21 Clemens Group

  30 Rock St, Winsted, CT 06098
• 

  Est $310,195

  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

  Last Listing Agent Tammy Schaller William Raveis Real Estate
• 

  

  /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 $365,239

  Last Listing Agent Amanda Balaski Northwest CT Realty

  102 Wallens St, Winsted, CT 06098
• 

  Est $275,606

  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

  Last Listing Agent Sarah Isabella Glenstone Real Estate LLC
• 

  

  /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
• 

  $483,000

  Sold Jul 30, 2026

  71-73 Wheeler St, Winchester, CT 06098

  • 8 Beds
  • 4 Baths
  • 2,000 Sq Ft
  • Built 1900

  Last Sold Summary

  • 7% Above List Price
  • $242/SF
  • 63 Days On Market

  Last Listing Agent Ida Chaplinski The DIY Listing

  71-73 Wheeler St, Winchester, CT 06098
• 

  Est $209,577

  Not Listed For Sale

  111 Riverton Rd Unit 83, Winsted, CT 06098

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

  111 Riverton Rd Unit 83, Winsted, CT 06098

  Last Sold Summary

  • 65 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty
• 

  

  /9

  $850,000

  $149K PRICE DROP

  • Land
  • 116.5 Acres
  • $7,296 per Acre

  82 Riverton Rd, Colebrook, CT 06021

  Escape to Your Own 116 acres of Paradise in Colebrook, CT! Discover 116 +/- acres of picturesque land nestled along Riverton Road in the heart of scenic Colebrook, Connecticut. This extraordinary property offers a rare opportunity to own a vast expanse of rural beauty, complete with two serene ponds, winding old logging roads, and a mix of standing hardwoods and softwoods that create a lush,

  Suzie Larson Turning Point Realty, LLC

  82 Riverton Rd, Colebrook, CT 06021
• 

  $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 $160,086

  Last Listing Agent Joanne Donne The Washington Agency

  35 Riveredge Dr Unit 35, Winsted, CT 06098
• 

  Est $530,626

  Not Listed For Sale

  16 Alexandria Dr, Winsted, CT 06063

  • 4 Beds
  • 2.5 Baths
  • 2,364 Sq Ft
  • Built 1989

  16 Alexandria Dr, Winsted, CT 06063

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Gina Beiser Better Homes and Gardens Real Estate Executive Real Estate
• 

  

  /27

  $179,990

  Pending

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

  111 Riverton Rd Unit 57, Winsted, CT 06098

  Move right into this well-maintained townhouse offering 2 bedrooms, 1.5 baths, and an attached garage in the desirable Riverwalk community. The spacious living room features a vaulted ceiling, fireplace, and abundant natural light, while the kitchen offers ample cabinet and counter space with sliding door access to a private deck overlooking a wooded backdrop. Upstairs you'll find two generously

  Joseph Caslin Sailpoint Property Group

  111 Riverton Rd Unit 57, 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 $340,181

  Last Listing Agent Kim Trumbull William Raveis Real Estate

  128 Danbury Quarter Rd, Winsted, CT 06098
• 

  Est $348,533

  Not Listed For Sale

  5 Hillside Ave, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 2,664 Sq Ft
  • Built 1900

  5 Hillside Ave, Winsted, CT 06098

  Last Sold Summary

  • 52 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty
• 

  

  /38

  $679,000

  $90K PRICE DROP Pending

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

  121 W Wakefield Blvd, Winsted, CT 06098

  PRICE REDUCTION !! 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

  Elizabeth Stockwell Coldwell Banker Realty

  121 W Wakefield Blvd, Winsted, CT 06098
• 

  $167,900

  Sold Nov 14, 2025

  14 Pratt St, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,340 Sq Ft
  • Built 1900

  Last Sold Summary

  • 16% Below List Price
  • $125/SF
  • 24 Days On Market

  Last Listing Agent Amy Sartirana Northwest CT Realty

  14 Pratt St, Winsted, CT 06098
• 

  Est $234,305

  Not Listed For Sale

  36 S Main St, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,380 Sq Ft
  • Built 1920

  36 S Main St, Winsted, CT 06098

  Last Sold Summary

  • 73 Days On Market

  Last Listing Agent DeVante Roman eXp Realty
• 

  $340,000

  Sold Jun 02, 2026

  1 Hamill Dr, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,600 Sq Ft
  • Built 1973

  Last Sold Summary

  • 6% Below List Price
  • $212/SF
  • 50 Days On Market

  Current Estimated Value $333,363

  Last Listing Agent Paul Duh Realty ONE Group Connect

  1 Hamill Dr, Winsted, CT 06098
• 

  Est $205,710

  Not Listed For Sale

  111 Riverton Rd Unit 55, Winsted, CT 06098

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

  111 Riverton Rd Unit 55, Winsted, CT 06098

  Last Sold Summary

  • 87 Days On Market

  Last Listing Agent Suzie Larson Turning Point Realty, LLC
• 

  $350,000

  Sold May 22, 2026

  9 Colony Dr, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft
  • Built 1966

  Last Sold Summary

  • 6% Above List Price
  • $221/SF
  • 27 Days On Market

  Current Estimated Value $345,690

  Last Listing Agent David Sartirana Northwest CT Realty

  9 Colony Dr, Winsted, CT 06098
• 

  Est $214,015

  Not Listed For Sale

  111 Riverton Rd Unit 45, Winsted, CT 06098

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

  111 Riverton Rd Unit 45, Winsted, CT 06098

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent ROBERT SZABO Szabo Realty
• 

  $33,500

  Sold Mar 20, 2026

  256 Colebrook Rd, Winchester Center, CT 06098

  • Land
  • 40,075 Sq Ft
  • $36,413 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 226 Days On Market

  Current Estimated Value $33,739

  Last Listing Agent Austin Brochu Sullivan Real Estate Inc

  256 Colebrook Rd, Winchester Center, CT 06098
• 

  Est $356,973

  Not Listed For Sale

  202 Old New Hartford Rd, Winsted, CT 06098

  • 4 Beds
  • 1.5 Baths
  • 1,560 Sq Ft
  • Built 1900

  202 Old New Hartford Rd, Winsted, CT 06098

  Last Sold Summary

  • 168 Days On Market

  Last Listing Agent Barry Mackiewicz A-Gold Action Realty
• 

  $274,900

  Sold Jun 29, 2026

  69 Prospect St, Winsted, CT 06098

  • 7 Beds
  • 3 Baths
  • 2,204 Sq Ft
  • Built 1900

  Last Sold Summary

  • $125/SF
  • 5 Days On Market

  Current Estimated Value $269,428

  Last Listing Agent Adam Cannon Coldwell Banker Realty

  69 Prospect St, Winsted, CT 06098
• 

  Est $425,637

  Not Listed For Sale

  173 Smith Hill Rd, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 1,702 Sq Ft
  • Built 1950

  173 Smith Hill Rd, Winsted, CT 06098

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Kim Trumbull William Raveis Real Estate
• 

  $439,900

  Sold Dec 04, 2025

  819 E Wakefield Blvd, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,892 Sq Ft
  • Built 1920

  Last Sold Summary

  • 12% Below List Price
  • $233/SF
  • 72 Days On Market

  Current Estimated Value $496,906

  Last Listing Agent David Sartirana Northwest CT Realty

  819 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $458,629

  Not Listed For Sale

  123 Skinner Rd, Winsted, CT 06098

  • 3 Beds
  • 3 Baths
  • 2,184 Sq Ft
  • Built 2005

  123 Skinner Rd, Winsted, CT 06098

  Last Sold Summary

  • 82 Days On Market

  Last Listing Agent Jacqueline Gardner Coldwell Banker Realty
• 

  $190,000

  Sold Oct 20, 2025

  111 Torringford St Unit 25, Winsted, CT 06098

  • 2 Beds
  • 2 Baths
  • 1,156 Sq Ft
  • Built 1987

  Last Sold Summary

  • 6% Above List Price
  • $164/SF
  • 2 Days On Market

  Current Estimated Value $205,268

  Last Listing Agent Ron Rudek Connecticut Realty, LLC

  111 Torringford St Unit 25, Winsted, CT 06098
• 

  Est $386,533

  Not Listed For Sale

  19 Cottage St, Winsted, CT 06098

  • 4 Beds
  • 4 Baths
  • 2,674 Sq Ft
  • Built 1890

  19 Cottage St, Winsted, CT 06098

  Last Sold Summary

  • 100 Days On Market

  Last Listing Agent Michael Bianca Showcase Realty, Inc.
• 

  $240,000

  Sold Oct 22, 2025

  210 Walnut St, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,056 Sq Ft
  • Built 1988

  Last Sold Summary

  • 7% Above List Price
  • $227/SF
  • 46 Days On Market

  Current Estimated Value $267,931

  Last Listing Agent Nicole Araujo Trend 2000 Real Estate

  210 Walnut St, Winsted, CT 06098
• 

  Est $344,927

  Not Listed For Sale

  161 Spencer St, Winsted, CT 06098

  • 5 Beds
  • 2 Baths
  • 2,615 Sq Ft
  • Built 1895

  161 Spencer St, Winsted, CT 06098

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty
• 

  $180,000

  Sold Dec 19, 2025

  99 Norfolk Rd, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 980 Sq Ft
  • Built 1948

  Last Sold Summary

  • 23% Below List Price
  • $184/SF
  • 156 Days On Market

  Current Estimated Value $208,662

  Last Listing Agent Lisa McCarthy Coldwell Banker Realty

  99 Norfolk Rd, Winsted, CT 06098
• 

  Est $931,092

  Not Listed For Sale

  112 Shore Dr, Winsted, CT 06098

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

  112 Shore Dr, Winsted, CT 06098

  Last Sold Summary

  • 61 Days On Market

  Last Listing Agent Nancy Reardon Berkshire Hathaway NE Prop.
• 

  $410,000

  Sold Apr 13, 2026

  35 Glendale Ave, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 2,196 Sq Ft
  • Built 1955

  Last Sold Summary

  • 3% Above List Price
  • $187/SF
  • 35 Days On Market

  Current Estimated Value $405,615

  Last Listing Agent David Sartirana Northwest CT Realty

  35 Glendale Ave, Winsted, CT 06098

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