Winchester, CT Homes

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  /16

  $85,000

  • 3 Beds
  • 1 Bath
  • 1,435 Sq Ft

  34 Hannifin Rd, Winsted, CT 06098

  Set on 1.8 private acres amid the scenic rolling hills of Winsted, this circa-1850 home offers a rare opportunity to restore and reimagine a property rich with character. A compelling value with exceptional upside, this property invites buyers, investors, or renovators to unlock its full potential. Inside, you'll find timeless details including wide plank flooring and a fireplaced living room,

  Michael Barnes Coldwell Banker Realty

  34 Hannifin Rd, 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 $309,442

  Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  279 Pratt St, Winsted, CT 06098
• 

  Est $226,352

  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

  • 33% Above List Price
  • $70/SF
  • 78 Days On Market

  • Last Sold Price $170,000
  • Jul 03, 2023

  Last Listing Agent Jayson Kemp Five Stars Realty
• 

  

  

  /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
• 

  $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 $648,118

  Last Listing Agent Dawn Rousseau Showcase Realty, Inc.

  102 Hollow Hill Rd, Winsted, CT 06098
• 

  Est $196,141

  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

  • 9% Above List Price
  • $149/SF
  • 0 Days On Market

  • Last Sold Price $179,900
  • Apr 15, 2024

  Last Listing Agent Amy Sartirana Northwest CT Realty
• 

  /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
• 

  $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 $249,521

  Last Listing Agent Rob Rosa Berkshire Hathaway NE Prop.

  94 Holabird Ave, Winsted, CT 06098
• 

  Est $246,691

  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

  • 53% Above List Price
  • $78/SF
  • 97 Days On Market

  • Last Sold Price $161,500
  • Nov 29, 2023

  Last Listing Agent Michael Barnes Coldwell Banker Realty
• 

  

  /40

  $1,595,000

  Open Sun 12PM - 2PM

  • 5 Beds
  • 2 Baths
  • 3,693 Sq Ft

  424 E Wakefield Blvd, Winsted, CT 06098

  Stunning Lakehouse! Victorian charm! One of the earliest Highland Lake homes with extensive custom upgrades and quality renovation. A true lakefront sanctuary offering spacious living areas, extensive outdoor living areas and wide open lake views offering South and West exposure for incredible sunsets. Lakefront dock system with hydraulic boat lift, Recently renovated kitchen /dining with newer

  KAREN NEWTON William Pitt Sotheby's Int'l

  424 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 $383,550

  Last Listing Agent Mary Mary LeBlanc Realty

  41 Lovely St, Winsted, CT 06098
• 

  Est $398,928

  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

  • 38% Above List Price
  • $125/SF
  • 57 Days On Market

  • Last Sold Price $290,000
  • Apr 03, 2024

  Last Listing Agent Victor Santana Santana Realty Group LLC
• 

  

  /40

  $475,000

  Under Contract

  • 7 Beds
  • 5 Baths
  • 3,538 Sq Ft

  51 Hinsdale Ave, Winsted, CT 06098

  Owner Occupants take notice: Rare three family home with market rents (one three-bedroom unit vacant) building is in exceptional condition!! A new roof will be installed in May before closing. One unit, a three-bedroom with a kitchen, living room, dining room, and two full bathrooms, this unit is rented @ $2136. per month ($2221.00 for the June 30, 2026-May 31, 2027 lease).) A one-year lease for

  Suzie Larson Turning Point Realty, LLC

  51 Hinsdale Ave, 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

  Current Estimated Value $374,467

  Last Listing Agent Lana Van Valkenburgh Vision Real Estate

  166 Torringford St, Winsted, CT 06098
• 

  Est $324,152

  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

  • 7% Below List Price
  • $147/SF
  • 46 Days On Market

  • Last Sold Price $350,000
  • Aug 16, 2024

  Last Listing Agent Laura Krzewski Realtor Bolanos & Associates LLC
• 

  

  /40

  $179,900

  Under Contract

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

  111 Torringford St Unit 7, Winsted, CT 06098

  SELLER REQUESTS ALL OFFERS BY SATURDAY, MAY 9TH @ 5:00 Have I got a home for you! Unpack and relax in this rarely available condo, the perfect spot for you. With easy access to the highway and a quaint downtown area filled with restaurants and shops, this two-bedroom unit offers plenty of room to breathe. The cozy kitchen comes equipped with ample cabinetry and a brand new gas stove. You can

  Janice Madore Country Manor Realty

  111 Torringford St Unit 7, 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 $259,500

  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

  • 10% Above List Price
  • $180/SF
  • 29 Days On Market

  • Last Sold Price $235,000
  • Dec 27, 2023

  Last Listing Agent Timothy McGrane Berkshire Hathaway Home Services
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  /22

  $184,900

  Pending

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

  111 Riverton Rd Unit 28, Winsted, CT 06098

  Stop paying rent and get into the housing market with this affordable end-unit townhouse! Two bedrooms, one and a half baths and a two car garage, make this a very livable home. The primary bedroom has a vaulted ceiling and walk-in closet and you'll enjoy the fireplace in the spacious living room. Convenient to routes 8 and 44, close to NWCC, Highland Lake, the Farmington River, hiking and other

  Ellen Sebastian William Pitt Sotheby's Int'l

  111 Riverton Rd Unit 28, 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 $361,760

  Last Listing Agent Christine Hunter Hunter Real Estate, LLC

  409 N Main St, Winsted, CT 06098
• 

  Est $291,372

  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

  • 17% Above List Price
  • $97/SF
  • 47 Days On Market

  • Last Sold Price $250,000
  • Apr 25, 2024

  Last Listing Agent Farzaneh RE/MAX
• 

  

  /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
• 

  $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 $279,905

  Last Listing Agent Amanda Balaski Northwest CT Realty

  15 John St, Winsted, CT 06098
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  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

  • 7% Above List Price
  • $165/SF
  • 36 Days On Market

  • Last Sold Price $220,000
  • Dec 07, 2023

  Last Listing Agent Kirk Coates Luxe Estates, Inc
• 

  

  /39

  $339,000

  • 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
• 

  $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 $236,943

  Last Listing Agent Patrick Precourt Meridian Realty Group LLC

  30 Rock St, Winsted, CT 06098
• 

  Est $249,975

  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

  • 20% Above List Price
  • $169/SF
  • 71 Days On Market

  • Last Sold Price $209,000
  • Jul 11, 2024

  Last Listing Agent Glenn Kohrs Coldwell Banker Realty
• 

  

  /24

  $199,900

  • Land
  • 5,227 Sq Ft
  • $1,665,833 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
• 

  $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 $311,106

  Last Listing Agent Austin Brochu Sullivan Real Estate Inc

  155 Mathew Rd, Winsted, CT 06098
• 

  Est $311,320

  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

  • 11% Above List Price
  • $173/SF
  • 39 Days On Market

  • Last Sold Price $280,000
  • Mar 18, 2024

  Last Listing Agent David Sartirana Northwest CT Realty
• 

  

  /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
• 

  $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 $869,159

  Last Listing Agent Nancy Reardon Berkshire Hathaway NE Prop.

  112 Shore Dr, Winsted, CT 06098
• 

  Est $257,413

  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

  • 6% Below List Price
  • $211/SF
  • 29 Days On Market

  • Last Sold Price $275,000
  • Aug 01, 2024

  Last Listing Agent David Merrigan Merrigan & Lefebvre Realty
• 

  

  /25

  $285,000

  $5K PRICE INCREASE Pending

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft

  350 Walnut St, Winsted, CT 06098

  Fully remodeled from top to bottom, 350 Walnut St offers the perfect blend of modern updates, efficient living, and outdoor space. This move-in-ready 2-bedroom, 1-bath ranch has been beautifully reimagined with a fresh, stylish feel and all the major improvements already done for you. Inside, you will find a brand-new kitchen with quartz countertops and stainless-steel appliances, a fully updated

  Vincent Miller Hudson Home Services LLC

  350 Walnut St, 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 $320,797

  Last Listing Agent Kim Trumbull William Raveis Real Estate

  128 Danbury Quarter Rd, Winsted, CT 06098
• 

  Est $596,419

  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

  • 11% Below List Price
  • $279/SF
  • 195 Days On Market

  • Last Sold Price $670,000
  • Nov 22, 2024

  Last Listing Agent Daniel Burgio William Raveis Real Estate
• 

  

  /38

  $274,900

  Pending

  • 2 Beds
  • 1 Bath
  • 993 Sq Ft

  149 E Mountain Ave, Winsted, CT 06098

  Welcome to this beautifully updated single-level home offering the ease of one-floor living. This charming property features two spacious bedrooms and an updated full bathroom, along with a generously sized living room perfect for relaxing or entertaining. The renovated kitchen boasts modern finishes and stainless steel appliances, providing both style and functionality. A heated sunroom adds

  Kevin Eagan Berkshire Hathaway NE Prop.

  149 E Mountain Ave, 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 $318,098

  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

  • 14% Above List Price
  • $223/SF
  • 92 Days On Market

  • Last Sold Price $279,000
  • Jan 16, 2024

  Last Listing Agent Don Sciarretto Berkshire Hathaway Home Services
• 

  /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 121 - 160, Page 4 of 18