Winchester, CT Homes

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  $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
• 

  $135,000 Sold Feb 28, 2025

  234 E Wakefield Blvd, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft
  • Built 1939

  Last Sold Summary

  • 17% Above List Price
  • $165/SF
  • 3 Days On Market

  Current Estimated Value $153,449

  Last Listing Agent Jeffrey Liskin Northwest CT Realty

  234 E Wakefield Blvd, Winsted, CT 06098
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  Est $308,332 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,982 Sq Ft

  182 Florence St, Winsted, CT 06098

  182 Florence St, Winsted, CT 06098
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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
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  $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
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  Est $273,643 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,180 Sq Ft

  36 Charles St, Winsted, CT 06098

  36 Charles St, Winsted, CT 06098
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  $225,000 Under Contract

  • 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
• 

  $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 $298,708

  Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  279 Pratt St, Winsted, CT 06098
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  Est $206,741 Not Listed For Sale

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

  111 Riverton Rd Unit 88, Winsted, CT 06098

  111 Riverton Rd Unit 88, Winsted, CT 06098
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  $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
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  $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 $280,046

  Last Listing Agent Jessica Sperry Maverick Realty

  493 N Main St, Winsted, CT 06098
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  Est $350,002 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,608 Sq Ft

  155 West Rd, Winsted, CT 06098

  155 West Rd, Winsted, CT 06098
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  /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
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  $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 $643,734

  Last Listing Agent Dawn Rousseau Showcase Realty, Inc.

  102 Hollow Hill Rd, Winsted, CT 06098
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  Est $417,148 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,594 Sq Ft

  133 E Wakefield Blvd, Winsted, CT 06098

  133 E Wakefield Blvd, Winsted, CT 06098
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  $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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  $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
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  Est $295,680 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,490 Sq Ft

  257 Walnut St, Winsted, CT 06098

  257 Walnut St, Winsted, CT 06098
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  $419,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 2,747 Sq Ft

  117 South Rd, Winsted, CT 06098

  Nestled in a peaceful rural setting of Winchester Center, this charming home offers a perfect blend of rustic character and modern convenience. The property is located on over 3.3 acres of land and is adjacent to a scenic pond. Inside you will find a three bedroom two bath home with an additional in law apartment with one full bath and one bedroom and its own private entrance. The home also

  Christina Niziolek William Raveis Real Estate

  117 South Rd, Winsted, CT 06098
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  $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 $375,277

  Last Listing Agent Mary Mary LeBlanc Realty

  41 Lovely St, Winsted, CT 06098
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  Est $348,715 Not Listed For Sale

  • 5 Beds
  • 2,820 Sq Ft

  204 Gilbert Ave, Winsted, CT 06098

  204 Gilbert Ave, Winsted, CT 06098
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  $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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  $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 $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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  $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
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  $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
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  Est $211,833 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
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  /40

  $549,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,745 Sq Ft

  106A Pinney St, Colebrook, CT 06021

  Nature Lover's Retreat on 26 Acres!!! Tucked away on 26.12 private acres, this contemporary Cape offers peace, privacy, and a deep connection to nature. A long, winding driveway leads to this stunning home featuring soaring ceilings and dramatic two-story windows that fill the living room with natural light. The open layout includes a warm wood stove, first-floor laundry, and two comfortable

  Kelly Sullivan Sullivan Real Estate Inc

  106A Pinney St, Colebrook, CT 06021
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  $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 $392,117

  Last Listing Agent Christine Hunter Hunter Real Estate, LLC

  409 N Main St, Winsted, CT 06098
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  Est $258,618 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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  /35

  $849,900

  • 4 Beds
  • 2 Baths
  • 1,781 Sq Ft

  119 W Wakefield Blvd, Winsted, CT 06098

  Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay, this beautifully renovated two-family home can be enjoyed as a single-family retreat or an income-generating

  Mela Veltri Case KW Legacy Partners

  119 W Wakefield Blvd, Winsted, CT 06098
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  $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

  Last Listing Agent Amanda Balaski Northwest CT Realty

  15 John St, Winsted, CT 06098
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  Est $445,180 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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  /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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  $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 Dorrance Realty

  30 Rock St, Winsted, CT 06098
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  Est $347,139 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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  /17

  $269,000

  • 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
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  $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 $320,919

  Last Listing Agent Austin Brochu Sullivan Real Estate Inc

  155 Mathew Rd, Winsted, CT 06098
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  Est $248,180 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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  /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

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