Winchester, CT Homes

• 

  $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 $207,268

  Not Listed For Sale

  3 Brookside Ave, Winsted, CT 06098

  • 6 Beds
  • 2,421 Sq Ft
  • Built 1900

  3 Brookside Ave, Winsted, CT 06098

  Last Sold Summary

  • 78 Days On Market
• 

  

  

  /21

  $879,990

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

  000000 Norfolk Rd, Winchester, CT 06098

  Rare Multi-Parcel Land Opportunity 5 Contiguous Parcels | Colebrook & Winchester, CT Discover an exceptional land offering spanning five contiguous parcels across two of Litchfield County's most desirable rural towns. This unique property features a strong presence in highly sought-after Colebrook, known for its scenic beauty, low-density living, and unspoiled New England charm-paired with the

  John Harney William Pitt Sotheby's Int'l

  000000 Norfolk Rd, Winchester, 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 $194,633

  Last Listing Agent Bethany Lydem Stone Crest Realty LLC

  111 Riverton Rd Unit 61, Winsted, CT 06098
• 

  Est $193,167

  Not Listed For Sale

  111 Riverton Rd Unit 66, Winsted, CT 06098

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

  111 Riverton Rd Unit 66, Winsted, CT 06098

  Last Sold Summary

  • 0 Days On Market
• 

  /2

  $59,900

  $9K PRICE DROP

  • Land
  • 17,859 Sq Ft
  • $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
• 

  $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 $305,571

  Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  279 Pratt St, Winsted, CT 06098
• 

  Est $222,383

  Not Listed For Sale

  45 Beach St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 2,076 Sq Ft
  • Built 1900

  45 Beach St, Winsted, CT 06098

  Last Sold Summary

  • 97 Days On Market
• 

  

  /26

  $250,000

  Pending

  • 3 Beds
  • 1 Bath
  • 1,392 Sq Ft

  111 Moore Ave, Winsted, CT 06098

  *Deadline set of Tuesday 6/30 at Noon. Seller reserves the right to take an offer at anytime.* Nestled on a well maintained lot, this charming Cape offers the perfect balance of privacy and convenience. Set just off the beaten path, the property enjoys a peaceful, rural feel while remaining close to shopping, dining, and everyday amenities. Thoughtfully updated over the years, improvements

  Melanie LeRoy William Raveis Real Estate

  111 Moore Ave, 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 $645,800

  Last Listing Agent Dawn Rousseau Showcase Realty, Inc.

  102 Hollow Hill Rd, Winsted, CT 06098
• 

  Est $425,251

  Not Listed For Sale

  193 Spencer Hill Rd, Winsted, CT 06098

  • 4 Beds
  • 2.5 Baths
  • 2,313 Sq Ft
  • Built 2012

  193 Spencer Hill Rd, Winsted, CT 06098

  Last Sold Summary

  • 57 Days On Market
• 

  

  /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
• 

  $255,000

  Sold May 08, 2026

  94 Holabird Ave, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,422 Sq Ft
  • Built 1942

  Last Sold Summary

  • 2% Above List Price
  • $179/SF
  • 47 Days On Market

  Current Estimated Value $248,612

  Last Listing Agent Rob Rosa Berkshire Hathaway NE Prop.

  94 Holabird Ave, Winsted, CT 06098
• 

  Est $314,272

  Not Listed For Sale

  160 Hinsdale Ave, Winsted, CT 06098

  • 4 Beds
  • 1.5 Baths
  • 2,379 Sq Ft
  • Built 1930

  160 Hinsdale Ave, Winsted, CT 06098

  Last Sold Summary

  • 46 Days On Market
• 

  

  /28

  $749,999

  Pending

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft

  660 E Wakefield Blvd, Winsted, CT 06098

  Nestled along the coveted east side of Highland Lake, 660 East Wakefield Blvd offers a rare opportunity to create the waterfront retreat you've always imagined. Bursting with classic lake charm and timeless character, this home is ready for a new owner to make it their own and bring fresh vision to an unforgettable setting. Enjoy excellent water access for swimming, boating, kayaking, and

  Patrick Smith Smith & DeGroat Real Estate

  660 E Wakefield Blvd, Winsted, 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 $381,098

  Last Listing Agent Mary Mary LeBlanc Realty

  41 Lovely St, Winsted, CT 06098
• 

  Est $273,887

  Not Listed For Sale

  234 Oak St, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft
  • Built 1890

  234 Oak St, Winsted, CT 06098

  Last Sold Summary

  • 29 Days On Market
• 

  

  /3

  $79,900

  • Land
  • 1.32 Acres
  • $60,530 per Acre

  -00 Colebrook Rd, Colebrook, CT 06021

  Set in the quiet beauty of Colebrook, this 1.32-acre approved building lot offers an excellent opportunity to bring your new home plans to life. Much of the early groundwork has already been completed, including a perc test, survey, driveway plan, septic design, and approvals for up to a 4-bedroom home, helping streamline the path from concept to construction. The lot has been cleared, offering a

  Steve Howey Coldwell Banker Realty

  -00 Colebrook Rd, Colebrook, CT 06021
• 

  $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

  Current Estimated Value $371,453

  Last Listing Agent Lana Van Valkenburgh Vision Real Estate

  166 Torringford St, Winsted, CT 06098
• 

  Est $283,052

  Not Listed For Sale

  24 Union St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 2,582 Sq Ft
  • Built 1895

  24 Union St, Winsted, CT 06098

  Last Sold Summary

  • 47 Days On Market
• 

  

  /40

  $895,000

  • 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
• 

  $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 $398,090

  Not Listed For Sale

  323 E Wakefield Blvd, Winsted, CT 06098

  • 3 Beds
  • 2.5 Baths
  • 1,426 Sq Ft
  • Built 1989

  323 E Wakefield Blvd, Winsted, CT 06098

  Last Sold Summary

  • 4 Days On Market
• 

  

  /39

  $339,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 2,040 Sq Ft

  93 Eno Hill Rd, Colebrook, CT 06021

  ***HIGHEST & BEST OFFERS DUE BY SUNDAY MAY 17 BY MIDNIGHT*** In the magical woods of Colebrook lies an animal lovers paradise! Great for homesteading, this property has: 2 chicken coops, 1 double wide dog house, 1 goat shed, a 12x24 shed for storage or convert to a small barn, fenced in garden, large animal pen with shelter off back side of shed, fenced in yard with electric fence strands on

  Tracy Wagner Rockoff Realty

  93 Eno Hill Rd, Colebrook, CT 06021
• 

  $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 $357,534

  Last Listing Agent Christine Hunter Hunter Real Estate, LLC

  409 N Main St, Winsted, CT 06098
• 

  Not Listed For Sale

  174 Wallens St Unit C7, Winsted, CT 06098

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft
  • Built 2005

  174 Wallens St Unit C7, Winsted, CT 06098

  Last Sold Summary

  • 36 Days On Market
• 

  

  /24

  $174,900

  $25K PRICE DROP

  • Land
  • 5,227 Sq Ft
  • $1,457,500 per Acre

  624 Wynne Rd, Winsted, CT 06098

  Exceptional opportunity to build near one of Northwest Connecticut's most desirable lake communities. Just steps from beautiful Highland Lake, this water-view parcel offers the chance to create your dream home in a setting that combines lake lifestyle, natural beauty, and convenient access to some of Litchfield County's most sought-after destinations. Highland Lake is a true Connecticut gem-a

  AJ Davis Better Homes and Gardens Real Estate Executive Real Estate

  624 Wynne Rd, 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 $280,094

  Last Listing Agent Amanda Balaski Northwest CT Realty

  15 John St, Winsted, CT 06098
• 

  Est $254,943

  Not Listed For Sale

  42 Upland Rd, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 1,236 Sq Ft
  • Built 1891

  42 Upland Rd, Winsted, CT 06098

  Last Sold Summary

  • 71 Days On Market
• 

  

  /6

  $12,500

  Pending

  • Land
  • 10,018 Sq Ft
  • $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
• 

  $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 $230,695

  Last Listing Agent Patrick Precourt Meridian Realty Group LLC

  30 Rock St, Winsted, CT 06098
• 

  Est $294,848

  Not Listed For Sale

  125 E Mountain Ave, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,622 Sq Ft
  • Built 1953

  125 E Mountain Ave, Winsted, CT 06098

  Last Sold Summary

  • 39 Days On Market
• 

  

  /40

  $735,000

  • 4 Beds
  • 2.5 Baths
  • 3,158 Sq Ft

  44 Pine Rd, Colebrook, CT 06021

  Enjoy exceptional privacy and peaceful country living in this spacious 4 bedroom, 2.5 bath contemporary Cape set atop a long winding driveway surrounded by natural beauty. The open floor plan on the main level offers comfortable living and entertaining spaces, including an updated eat in kitchen with stainless steel appliances, a dining room with a cozy wood burning fireplace, a generous living

  Mike Gregor Cohen Agency SiM, LLC

  44 Pine Rd, Colebrook, CT 06021
• 

  $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 $351,142

  Last Listing Agent Amanda Balaski Northwest CT Realty

  102 Wallens St, Winsted, CT 06098
• 

  Est $270,468

  Not Listed For Sale

  103 E Mountain Ave, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,304 Sq Ft
  • Built 1955

  103 E Mountain Ave, Winsted, CT 06098

  Last Sold Summary

  • 29 Days On Market
• 

  

  /39

  $679,900

  • 3 Beds
  • 2.5 Baths
  • 2,806 Sq Ft

  426 Platt Hill Rd, Winsted, CT 06098

  Custom built log Home!This home sits on a 3 acre, private landscaped lot with mountains laurel and a park nearby. This sprawling home with a covered front porch(28x 8)is perfect for relaxing and features over 1100 sq of decking which wraps around the house for entertaining. The Home features a stunning living room with interior balcony, chandeliers, field stone wood fireplace, cathedral ceiling,

  Mary Mary LeBlanc Realty

  426 Platt Hill Rd, Winsted, CT 06098
• 

  $862,500

  Sold Jul 23, 2025

  112 Shore Dr, Winsted, CT 06098

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

  Last Sold Summary

  • 11% Below List Price
  • $408/SF
  • 61 Days On Market

  Current Estimated Value $861,005

  Last Listing Agent Nancy Reardon Berkshire Hathaway NE Prop.

  112 Shore Dr, Winsted, CT 06098
• 

  Est $610,665

  Not Listed For Sale

  129 Forest Ave, Winsted, CT 06098

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • Built 2007

  129 Forest Ave, Winsted, CT 06098

  Last Sold Summary

  • 195 Days On Market
• 

  /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
• 

  $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 $161,284

  Last Listing Agent Joanne Donne The Washington Agency

  35 Riveredge Dr Unit 35, Winsted, CT 06098

Showing Results 121 - 160, Page 4 of 18