Winchester, CT Homes

• 

  Est $211,639 Not Listed For Sale

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

  111 Riverton Rd Unit 53, Winsted, CT 06098

  111 Riverton Rd Unit 53, Winsted, CT 06098
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  /32

  $225,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,051 Sq Ft

  817 E Wakefield Blvd, Winsted, CT 06098

  Perched atop a scenic hill overlooking picturesque Highland Lake, this charming ranch offers 1,051+/- square feet of inviting living space with two bedrooms and two full bathrooms. The galley-style kitchen features Thomasville cabinetry and Corian countertops, opening to an intimate dining room with tranquil lake views. Take your pick of relaxing spaces-whether it's the cozy living room with an

  George Sznaj DB Associates of CT, LLC

  817 E Wakefield Blvd, 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

  Last Listing Agent Bethany Lydem Stone Crest Realty LLC

  111 Riverton Rd Unit 61, Winsted, CT 06098
• 

  Est $245,189 Not Listed For Sale

  • 6 Beds
  • 2,421 Sq Ft

  3 Brookside Ave, Winsted, CT 06098

  3 Brookside Ave, Winsted, CT 06098
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  /11

  $159,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 832 Sq Ft

  8 Oak St, Winsted, CT 06098

  Discover a low maintenance and hassle-free alternative to condo living with this easy-to-maintain, single-family home , perfect for investors, first-time buyers, or anyone seeking simplified living without the burden of HOA fees. Step inside to an efficient layout featuring brand-new WREN kitchen cabinets, granite countertops, a new gas stove, and a new refrigerator, offering a fresh and modern

  Austin Brochu Sullivan Real Estate Inc

  8 Oak 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 $302,605

  Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  279 Pratt St, Winsted, CT 06098
• 

  Est $212,432 Not Listed For Sale

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

  111 Riverton Rd Unit 66, Winsted, CT 06098

  111 Riverton Rd Unit 66, Winsted, CT 06098
• 

  

  /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
• 

  $275,000 Sold Apr 16, 2025

  493 N Main St, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,277 Sq Ft
  • Built 1940

  Last Sold Summary

  • 6% Above List Price
  • $215/SF
  • 114 Days On Market

  Current Estimated Value $282,183

  Last Listing Agent Jessica Sperry Maverick Realty

  493 N Main St, Winsted, CT 06098
• 

  Est $256,551 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,076 Sq Ft

  45 Beach St, Winsted, CT 06098

  45 Beach St, Winsted, CT 06098
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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
• 

  $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 $631,240

  Last Listing Agent Dawn Rousseau Showcase Realty, Inc.

  102 Hollow Hill Rd, Winsted, CT 06098
• 

  Est $415,704 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,313 Sq Ft

  193 Spencer Hill Rd, Winsted, CT 06098

  193 Spencer Hill Rd, Winsted, CT 06098
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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
• 

  $8,000 Sold May 16, 2025

  104 Norfolk Rd, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 980 Sq Ft
  • Built 1930

  Last Sold Summary

  • 79% Below List Price
  • $8/SF
  • 44 Days On Market

  Current Estimated Value $141,000

  Last Listing Agent David Sartirana Northwest CT Realty

  104 Norfolk Rd, Winsted, CT 06098
• 

  Est $344,204 Not Listed For Sale

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

  160 Hinsdale Ave, Winsted, CT 06098

  160 Hinsdale Ave, Winsted, CT 06098
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  /6

  $12,500 Under Contract

  • 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
• 

  $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 $372,027

  Last Listing Agent Mary Mary LeBlanc Realty

  41 Lovely St, Winsted, CT 06098
• 

  Est $250,119 Not Listed For Sale

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

  234 Oak St, Winsted, CT 06098

  234 Oak St, Winsted, CT 06098
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  /28

  $275,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,971 Sq Ft

  43 Wallens St, Winsted, CT 06098

  Highest and best 1/4/26 by 5pm Welcome to 43 Wallens Street in the heart of Winsted - a versatile two-family property ideal for owner-occupants, investors or an in law. The first-floor unit offers a one-bedroom layout with recessed lighting, while the spacious second unit features three bedrooms, including one on the main level and two on the upper floor, plus an additional room on the main level

  Kristen Duchene Litchfield County Real Estate

  43 Wallens St, 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

  Last Listing Agent Lana Van Valkenburgh Vision Real Estate

  166 Torringford St, Winsted, CT 06098
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  Est $196,452 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 734 Sq Ft

  110 E Mountain Ave, Winsted, CT 06098

  110 E Mountain Ave, Winsted, CT 06098
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  /17

  $285,000

  • 2 Beds
  • 1 Bath
  • 1,218 Sq Ft

  343 E Wakefield Blvd, Winsted, CT 06098

  Cape-style home with 2 bedrooms and 1 bath, offering 1,218 sq ft on a 0.13-acre lot in desirable Litchfield County. The home has been completely gutted and is ready for a full renovation. Great opportunity to create your ideal living space.

  Thomas Mele Dorrance Realty

  343 E Wakefield Blvd, 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 $304,117 Not Listed For Sale

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

  24 Union St, Winsted, CT 06098

  24 Union St, Winsted, CT 06098
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  /29

  $285,000 Open Sat 12PM - 2PM

  • 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.

  Raelyn Lawrence Coldwell Banker Realty

  95 Colony Dr, 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 $393,117

  Last Listing Agent Christine Hunter Hunter Real Estate, LLC

  409 N Main St, Winsted, CT 06098
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  Est $235,284 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft

  174 Wallens St Unit C7, Winsted, CT 06098

  174 Wallens St Unit C7, Winsted, CT 06098
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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
• 

  $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 $279,447

  Last Listing Agent Amanda Balaski Northwest CT Realty

  15 John St, Winsted, CT 06098
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  Est $234,500 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,236 Sq Ft

  42 Upland Rd, Winsted, CT 06098

  42 Upland Rd, Winsted, CT 06098
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  /17

  $269,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,736 Sq Ft

  38 Upland Rd, Winsted, CT 06098

  TO SETTLE ESTATE: Available for Immediate Occupancy is this Immaculate 3 to 4 Bedroom Colonial tucked away on a quiet street. Features Hardwood Floors throughout the house, 24' x 14' Family Room with Propane Gas Stove, Country Kitchen. Primary Bedroom with it's own office area. Oversized Full Bath. 3-Season 21' x 8' Enclosed Porch. 26' x 10' Concrete Patio. Detached One Car Garage. Attractive

  Marshall Cohen Cohen Agency

  38 Upland Rd, 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

  Last Listing Agent Patrick Precourt Meridian Realty Group LLC

  30 Rock St, Winsted, CT 06098
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  Est $303,879 Not Listed For Sale

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

  125 E Mountain Ave, Winsted, CT 06098

  125 E Mountain Ave, Winsted, CT 06098
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  /2

  $299,900

  • 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

  David D'Amore Northwest CT Realty

  32 Norfolk Rd, Winchester, CT 06098
• 

  $314,000 Sold May 30, 2025

  155 Mathew Rd, Winsted, CT 06098

  • 2 Beds
  • 1.5 Baths
  • 1,536 Sq Ft
  • Built 1979

  Last Sold Summary

  • 3% Below List Price
  • $204/SF
  • 56 Days On Market

  Current Estimated Value $308,353

  Last Listing Agent Austin Brochu Sullivan Real Estate Inc

  155 Mathew Rd, Winsted, CT 06098
• 

  Est $282,857 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,304 Sq Ft

  103 E Mountain Ave, Winsted, CT 06098

  103 E Mountain Ave, Winsted, CT 06098
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  /27

  $375,000

  • 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
• 

  $375,000 Sold Feb 19, 2025

  220 Gilbert Ave, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 2,176 Sq Ft
  • Built 1900

  Last Sold Summary

  • 6% Below List Price
  • $172/SF
  • 77 Days On Market

  Current Estimated Value $397,667

  Last Listing Agent Linda Muraski Century 21 Classic Homes

  220 Gilbert Ave, Winsted, CT 06098
• 

  Est $655,663 Not Listed For Sale

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

  129 Forest Ave, Winsted, CT 06098

  129 Forest Ave, Winsted, CT 06098

Showing Results 121 - 160, Page 4 of 18