Winchester, CT Homes

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  /38

  $395,000

  • 3 Beds
  • 1.5 Baths
  • 1,909 Sq Ft

  720 Main St, Winsted, CT 06098

  Prime Mixed-Use Opportunity in Downtown Winsted! High-visibility two-story building located on bustling Main Street, most recently home to "JT's Cafe," and previously known as "The Winning Ticket Cafe." The first-floor commercial space includes features such as an existing kitchen area with oven range vents, fridge, bathroom, and open seating area. Great potential for a new restaurant, cafe,

  Ryan Marconi The Washington Agency

  720 Main St, Winsted, CT 06098
• 

  $45,000 Sold May 09, 2025

  269 Walnut St, Winsted, CT 06098

  • Land
  • 0.5 Acre
  • $90,000 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 72 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty

  269 Walnut St, Winsted, CT 06098
• 

  Est $239,965 Not Listed For Sale

  17 Front St, Winsted, CT 06098

  • 4 Beds
  • 1.5 Baths
  • 1,600 Sq Ft
  • Built 1915

  17 Front St, Winsted, CT 06098

  Last Sold Summary

  • 158% Above List Price
  • $58/SF
  • 20 Days On Market

  Last Sold Price $93,000

  Last Listing Agent David Sartirana Northwest CT Realty
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  /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
• 

  $1,575,000 Sold Jun 30, 2025

  508 W Wakefield Blvd, Winsted, CT 06098

  • 7 Beds
  • 4 Baths
  • 2,687 Sq Ft
  • Built 1890

  Last Sold Summary

  • 5% Below List Price
  • $586/SF
  • 316 Days On Market

  Current Estimated Value $1,622,303

  Last Listing Agent Pierre Moran William Pitt Sotheby's Int'l

  508 W Wakefield Blvd, Winsted, CT 06098
• 

  Not Listed For Sale

  319 Taylor Brook Rd, Winsted, CT 06098

  • 4 Beds
  • 2.5 Baths
  • 2,969 Sq Ft
  • Built 1990

  319 Taylor Brook Rd, Winsted, CT 06098

  Last Sold Summary

  • 6% Below List Price
  • $158/SF
  • 4 Days On Market

  Last Sold Price $470,000

  Last Listing Agent Heidi Picard-Ramsay Berkshire Hathaway Home Services
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  /5

  $240,000 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
• 

  $360,000 Sold Feb 25, 2026

  187 Torringford St, Winsted, CT 06098

  • 4 Beds
  • 1.5 Baths
  • 2,365 Sq Ft
  • Built 1800

  Last Sold Summary

  • 16% Below List Price
  • $152/SF
  • 109 Days On Market

  Current Estimated Value $396,977

  Last Listing Agent Jessica Washington William Raveis Real Estate

  187 Torringford St, Winsted, CT 06098
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  Est $258,712 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

  • 20% Above List Price
  • $86/SF
  • 19 Days On Market

  Last Sold Price $215,000

  Last Listing Agent Andrew Vincent Santa Realty
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  /21

  $879,990

  • Land
  • 131.5 Acres
  • $6,692 per Acre

  000000 Norfolk Rd, Winchester, CT 06098

  Rare Multi-Parcel Land Opportunity - 5 Parcels, Endless Possibilities Discover this exceptional assemblage of five contiguous parcels spanning the scenic towns of Winchester and Colebrook in Connecticut's pristine Litchfield County. This remarkable offering combines the best of both worlds with a captivating mixture of open fields and mature forest, creating a diverse landscape that's as

  John Harney William Pitt Sotheby's Int'l

  000000 Norfolk Rd, Winchester, CT 06098
• 

  $151,000 Sold Feb 20, 2026

  155 Rockwell St, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,317 Sq Ft
  • Built 1953

  Last Sold Summary

  • 5% Below List Price
  • $115/SF
  • 11 Days On Market

  Current Estimated Value $251,338

  Last Listing Agent Joseph Caslin Sailpoint Property Group

  155 Rockwell St, Winsted, CT 06098
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  Est $267,558 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

  • 7% Above List Price
  • $224/SF
  • 85 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Cathy Macias Northwest CT Realty
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  /2

  $59,900

  • Land
  • 0.41 Acre
  • $146,098 per Acre

  105,107 E Mountain Rd, Winchester, CT 06098

  105 & 107 Mountain Road parcels are contiguous and located on a dirt road . . Deed indicates right of way to Highland lake water frontage within walking distance. See documents attached for Deed , Site plan, Peculation tests , Survey and Septic testing available . Possible city sewer access at buyers expense . Seller will consider financing with a minimum of 15% DOWN PAYMENT FOR A 2 YEAR BALLOON

  David D'Amore Northwest CT Realty

  105,107 E Mountain Rd, Winchester, 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 $287,615

  Last Listing Agent Alison Behlman Tier 1 Real Estate

  39 Colony Dr, Winsted, CT 06098
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  Est $309,691 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

  • 7% Above List Price
  • $188/SF
  • 141 Days On Market

  Last Sold Price $290,000

  Last Listing Agent Liz Zakrzewski Coldwell Banker
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  /5

  $295,000 Under Contract

  • 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
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  $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
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  Est $203,495 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

  • 3% Above List Price
  • $121/SF
  • 14 Days On Market

  Last Sold Price $197,000

  Last Listing Agent David Sartirana Northwest CT Realty
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  /39

  $920,000

  • 4 Beds
  • 2 Baths
  • 3,088 Sq Ft

  469 Platt Hill Rd, Winsted, CT 06098

  HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Customer, whether You're an ANTIQUARIAN, HORSE & ANIMAL LOVER, or just seeking for a PEACEFUL & TRANQUIL LOCATION, this LITCHFIELD COUNTY HOME could possibly fit your Criteria. Stately 1789 11 Room 3,088 Sq. Ft. Colonial expresses Love, Warmth & Care. From the Solid Beams, Chestnut Wide-Board Floors,

  Marshall Cohen Cohen Agency

  469 Platt Hill Rd, Winsted, CT 06098
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  $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 $242,938

  Last Listing Agent Tony Goia The Washington Agency

  56 Lakeview Rd, Winsted, CT 06098
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  Est $198,876 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

  • 14% Above List Price
  • $145/SF
  • 0 Days On Market

  Last Sold Price $175,000

  Last Listing Agent Patricia Scarpa Marino Realty LLC
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  /38

  $289,000 Under Contract

  • 2 Beds
  • 2.5 Baths
  • 1,946 Sq Ft

  174 Wallens St Unit A5, Winsted, CT 06098

  Welcome to Clockmakers Hill, a desirable and active 55+ community offering comfort, convenience, and vibrant living. This immaculately maintained 2 bedroom, 2.5 bath condo blends thoughtful updates with everyday functionality. Warm wood flooring enhances the main living areas, while the kitchen features tile flooring, granite countertops, stainless steel appliances, and a pantry customized with

  Lauren Iraeta KW Legacy Partners

  174 Wallens St Unit A5, Winsted, CT 06098
• 

  $679,000 Sold Apr 30, 2025

  110 South Rd, Winsted, CT 06098

  • 4 Beds
  • 3 Baths
  • 3,870 Sq Ft
  • Built 1984

  Last Sold Summary

  • $175/SF
  • 5 Days On Market

  Current Estimated Value $719,621

  Last Listing Agent Matthew Egan Regency Real Estate, LLC

  110 South Rd, Winsted, CT 06098
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  Est $298,313 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

  • 2% Above List Price
  • $148/SF
  • 40 Days On Market

  Last Sold Price $293,000

  Last Listing Agent Heidi Picard-Ramsay Berkshire Hathaway Home Services
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  /12

  $750,000

  • 4 Beds
  • 2 Baths
  • 5,389 Sq Ft

  436 Main St, Winsted, CT 06098

  One-of-a-Kind opportunity with 4 apartments plus a turnkey, award-winning restaurant in the heart of Litchfield County, perfectly situated in a high-traffic location. The well-established business offers 2,177 sq. ft. of warm, inviting atmosphere with 65 indoor seats and 35 outdoor seats-ideal for both casual dining and special occasions. Has a cafe license (liquor) but no bar. With a 10-year

  Tony Goia The Washington Agency

  436 Main St, Winsted, CT 06098
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  $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 $304,666

  Last Listing Agent Antonio De La Cruz Eagle Eye Realty PLLC

  62 Fruit St Unit 64, Winsted, CT 06098
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  Est $260,972 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

  • 9% Above List Price
  • $203/SF
  • 5 Days On Market

  Last Sold Price $240,000

  Last Listing Agent Judy Guarco Berkshire Hathaway Home Services
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  /26

  $230,000 Under Contract

  • 2 Beds
  • 1.5 Baths
  • 1,172 Sq Ft

  9 John St, Winsted, CT 06098

  Fully renovated 1870 Colonial offering 1,172 sq. ft. of thoughtfully updated living space that blends historic character with modern comfort. Hardwood floors run through the living room and both bedrooms, creating a warm and inviting feel. The flexible layout includes a convenient first-floor bedroom and a spacious primary bedroom on the second level. The bright, refreshed kitchen features new

  Michael Grady William Raveis Real Estate

  9 John St, Winsted, CT 06098
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  $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 $382,100

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

  226 E Wakefield Blvd, Winsted, CT 06098
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  Est $363,900 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

  • 17% Above List Price
  • $194/SF
  • 26 Days On Market

  Last Sold Price $310,000

  Last Listing Agent David Sartirana Northwest CT Realty
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  /6

  $12,500 Pending

  • Land
  • 0.23 Acre
  • $54,348 per Acre

  605 E Wakefield Blvd, Winchester, CT 06098

  Across from the lake. Lot does not meet the set backs & is unbuildable.

  Diane Gombieski Carl Guild & Associates

  605 E Wakefield Blvd, Winchester, CT 06098
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  $135,000 Sold Mar 27, 2025

  13 Riveredge Dr Unit 13, Winsted, CT 06098

  • 1 Bed
  • 1 Bath
  • 643 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $210/SF
  • 72 Days On Market

  Current Estimated Value $140,795

  Last Listing Agent James Bradshaw Berkshire Hathaway NE Prop.

  13 Riveredge Dr Unit 13, Winsted, CT 06098
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  Est $275,216 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

  • 11% Above List Price
  • $167/SF
  • 21 Days On Market

  Last Sold Price $249,000

  Last Listing Agent Meagan Albert Tier 1 Real Estate
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  /29

  $285,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,008 Sq Ft

  95 Colony Dr, Winsted, CT 06098

  Enjoy easy one-level living in this charming 3-bedroom, 2-bath home offering an eat-in kitchen, hardwood floors throughout, a full basement, garage, and a primary bedroom with its own bath. The yard provides great outdoor space for relaxing or entertaining, all just minutes from Winsted Center, Route 8, and Route 44. View the property during open houses only Saturday 2/2/26 and Sunday 2/8/26 from

  Raelyn Lawrence Coldwell Banker Realty

  95 Colony Dr, Winsted, CT 06098
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  $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 $315,698

  Last Listing Agent Susan MCGHEE The Washington Agency

  148 Danbury Quarter Rd, Winchester, CT 06098
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  Est $301,015 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

  • 9% Above List Price
  • $98/SF
  • 10 Days On Market

  Last Sold Price $275,000

  Last Listing Agent Austin Brochu Sullivan Real Estate Inc
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  /5

  $300,000

  • Land
  • 15.9 Acres
  • $18,868 per Acre

  00 Chapel Rd, Winchester, CT 06098

  Look no further for A Very Private location to build your Dream Home?? On this Lot there is the Hilltop which can provide peace and solitude for your home or vacation retreat . Historical Winchester Center is deep with rich heritage and History of Winchester may be the place for you. The access to the Rear lot is though 151 Chapel Rd. property.

  Linda Ganem Borla & Associates Real Estate

  00 Chapel Rd, Winchester, CT 06098
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  $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 $261,927

  Last Listing Agent Patrick Precourt Meridian Realty Group LLC

  343 W Wakefield Blvd, Winsted, CT 06098
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  Est $203,313 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

  • 2% Above List Price
  • $165/SF
  • 12 Days On Market

  Last Sold Price $199,000

  Last Listing Agent Samantha Behm William Pitt
• 

  /2

  $299,900 Under Contract

  • Land
  • 63 Acres
  • $4,760 per Acre

  32 Norfolk Rd, Winchester, CT 06098

  63-Acre Rural Retreat Abutting Algonquin State Forest - A Nature Lover's Dream! Discover the perfect blend of seclusion and accessibility with this 63-acre wooded paradise, directly abutting Algonquin State Forest. Located on a state highway and directly across from a scenic dry dam, this unique parcel provides endless possibilities-whether you're looking to build your dream home, start a hunting

  David D'Amore Northwest CT Realty

  32 Norfolk Rd, Winchester, CT 06098

Showing Results 81 - 120, Page 3 of 18