Winchester, CT Homes

• 

  $800,000 Sold Aug 04, 2025

  266 Perch Rock Trail, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 1928

  Last Sold Summary

  • 7% Above List Price
  • $538/SF
  • 0 Days On Market

  Current Estimated Value $810,383

  Last Listing Agent Laurie Murray KW Legacy Partners

  266 Perch Rock Trail, Winsted, CT 06098
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• 

  Est $207,285 Not Listed For Sale

  • 4 Beds

  14 Pine Rd, Colebrook, CT 06021

  14 Pine Rd, Colebrook, CT 06021
• 

  

  

  /40

  $399,000 Under Contract

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

  187 Torringford St, Winsted, CT 06098

  Welcome to 187 Torringford Rd! Set on a beautiful 4-acre lot, this spacious 4-bedroom home offers the perfect blend of natural light, character, and country living. Step inside through the mudroom, also serving as a convenient laundry area, and head up to a charming loft that overlooks the bright, window filled kitchen. The kitchen features an abundance of natural light and provides a warm,

  Jessica Washington William Raveis Real Estate

  187 Torringford St, Winsted, CT 06098
• 

  $269,000 Sold May 05, 2025

  39 Finn St, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,175 Sq Ft
  • Built 1880

  Last Sold Summary

  • $229/SF
  • 35 Days On Market

  Current Estimated Value $262,695

  Last Listing Agent Christine Hunter Hunter Real Estate, LLC

  39 Finn St, Winsted, CT 06098
• 

  Est $358,709 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,635 Sq Ft

  268 Smith Hill Rd, Colebrook, CT 06021

  268 Smith Hill Rd, Colebrook, CT 06021
• 

  

  /35

  $329,900 Pending

  • 4 Beds
  • 2 Baths
  • 1,999 Sq Ft

  148 Danbury Quarter Rd, Winchester, CT 06098

  Welcome to this Wonderful Historic Colonial Farmhouse.. This home has been lovingly remodeled with many of the original features still intact. This home offers a large kitchen with newer counters open to the dining area and is complete with a fireplace. Living room is generous sized, it's filled with light, exposed beams and hardwood floor. On this level you'll also find 2 bedrooms and a fully

  Susan MCGHEE The Washington Agency

  148 Danbury Quarter Rd, Winchester, CT 06098
• 

  $220,000 Sold Apr 24, 2025

  830 Main St, Winsted, CT 06098

  • 5 Beds
  • 4 Baths
  • 3,115 Sq Ft
  • Built 1900

  Last Sold Summary

  • 2% Below List Price
  • $71/SF
  • 14 Days On Market

  Current Estimated Value $222,364

  Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  830 Main St, Winsted, CT 06098
• 

  Est $118,878 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft

  11 Gibbs St Unit 6, Winsted, CT 06098

  11 Gibbs St Unit 6, Winsted, CT 06098
• 

  

  /39

  $339,900 Under Contract

  • 4 Beds
  • 2 Baths
  • 2,345 Sq Ft

  123 Wetmore Ave, Winsted, CT 06098

  What a wonderful Home! Walk in and be Wowed! This 4 bedroom home built in 1900 has been meticulously redone inside and out in 2020. Featuring gleaming hardwood floors on all 3 floors. Thermal paned windows through out. Spacious 12x10 foyer makes a great sitting room or office. First floor has the open floor plan with formal dining, living room and kitchen all in one. Comes with a full bath and

  Christine Hunter Hunter Real Estate, LLC

  123 Wetmore Ave, Winsted, CT 06098
• 

  $227,500 Sold Nov 20, 2025

  174 Wallens St Unit H1, Winsted, CT 06098

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft
  • Built 2007

  Last Sold Summary

  • 3% Below List Price
  • $171/SF
  • 91 Days On Market

  Last Listing Agent Kim D'Andrea William Pitt Sotheby's Int'l

  174 Wallens St Unit H1, Winsted, CT 06098
• 

  Est $125,542 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft

  11 Gibbs St Unit 4, Winsted, CT 06098

  11 Gibbs St Unit 4, Winsted, CT 06098
• 

  

  /22

  $499,000

  • 3 Beds
  • 2 Baths
  • 2,354 Sq Ft

  11 Old Creamery Rd, Colebrook, CT 06021

  FULLY RENOVATED! In addition this home is fully insulated, energy-efficient, and enhanced with solar panels for low utility costs. The open floor plan and cozy fireplace create the perfect space for gatherings, while multiple decks, an above-ground pool, and serene natural surroundings provide a tranquil retreat-ideal for year-round living or a weekend getaway. Located perfectly on a beautiful

  Rodrigo Aguiar Real Broker CT, LLC

  11 Old Creamery Rd, Colebrook, CT 06021
• 

  $190,000 Sold May 15, 2025

  154 Wallens St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1905

  Last Sold Summary

  • 13% Below List Price
  • $103/SF
  • 20 Days On Market

  Current Estimated Value $196,724

  Last Listing Agent Adam Devine Dorrance Realty

  154 Wallens St, Winsted, CT 06098
• 

  Est $395,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft

  111 Mundry Rd, Torrington, CT 06790

  111 Mundry Rd, Torrington, CT 06790
• 

  

  /35

  $419,000 Pending

  • 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
• 

  $277,000 Sold Oct 09, 2025

  12 Cherry St, Winsted, CT 06098

  • 4 Beds
  • 1 Bath
  • 1,492 Sq Ft
  • Built 1800

  Last Sold Summary

  • 4% Below List Price
  • $186/SF
  • 54 Days On Market

  Current Estimated Value $283,346

  Last Listing Agent Susan MCGHEE The Washington Agency

  12 Cherry St, Winsted, CT 06098
• 

  Est $297,276 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft

  28 Maloney Ct, Winsted, CT 06098

  28 Maloney Ct, Winsted, CT 06098
• 

  

  /40

  $549,000 Open Sun 1PM - 3PM

  • 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
• 

  $160,000 Sold Apr 29, 2025

  14 Riveredge Dr Unit 14, Winsted, CT 06098

  • 2 Beds
  • 1.5 Baths
  • 992 Sq Ft
  • Built 1986

  Last Sold Summary

  • $161/SF
  • 0 Days On Market

  Current Estimated Value $160,959

  Last Listing Agent Maria Smith KW Legacy Partners

  14 Riveredge Dr Unit 14, Winsted, CT 06098
• 

  Est $351,856 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 920 Sq Ft

  103 Shore Dr, Winsted, CT 06098

  103 Shore Dr, Winsted, CT 06098
• 

  

  /37

  $500,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,416 Sq Ft

  440 Platt Hill Rd, Winsted, CT 06098

  Distinctive Country Estate with Two Homes on 9.6 Rolling Acres Set amid 9.6 picturesque country acres, this unique property offers two homes and endless potential. The stone and stucco main residence features eight spacious rooms, including four bedrooms and four fireplaces, blending classic character with old-world charm. Rolling open land and mature trees surround the home, providing an ideal

  David D'Amore Northwest CT Realty

  440 Platt Hill Rd, Winsted, CT 06098
• 

  $225,000 Sold Jul 03, 2025

  39 Baker St, Winsted, CT 06098

  • 5 Beds
  • 2 Baths
  • 1,612 Sq Ft
  • Built 1900

  Last Sold Summary

  • $140/SF
  • 166 Days On Market

  Current Estimated Value $231,661

  Last Listing Agent Christine Hunter Hunter Real Estate, LLC

  39 Baker St, Winsted, CT 06098
• 

  Est $305,230 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,104 Sq Ft

  139 Boyd St, Winsted, CT 06098

  139 Boyd St, Winsted, CT 06098
• 

  

  /12

  $319,000

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  230 E Wakefield Blvd, Winsted, CT 06098

  This Highland Lake house is in great condition, remodeled 4 years ago. Lower level has a separate entrance and was revamped with large living room and full bathroom. Walk to the Association beach in 5 mins.

  Peter D'Addeo Commercial Services Realty

  230 E Wakefield Blvd, 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

  Current Estimated Value $157,000

  Last Listing Agent David Sartirana Northwest CT Realty

  269 Walnut St, Winsted, CT 06098
• 

  Est $238,522 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft

  174 Wallens St Unit D2, Winsted, CT 06098

  174 Wallens St Unit D2, Winsted, CT 06098
• 

  

  /40

  $749,999 Pending

  • 5 Beds
  • 2.5 Baths
  • 2,950 Sq Ft

  151 Losaw Rd, Winsted, CT 06098

  This property is your personal sanctuary, complete with private trails for hiking your own land. Feel worlds away while being less than 2 miles to town amenities in this like-new retreat nestled on an expansive 11.59-acre lot. The eat-in-kitchen is well-equipped with ample cooking space, seamlessly connected to the formal dining room and open to living space, and leads out to the large deck with

  Breanna Goebel Compass Connecticut, LLC

  151 Losaw 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 $1,607,252

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

  508 W Wakefield Blvd, Winsted, CT 06098
• 

  Est $240,771 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft

  174 Wallens St Unit D1, Winsted, CT 06098

  174 Wallens St Unit D1, Winsted, CT 06098
• 

  

  /40

  $299,900 Pending

  • 6 Beds
  • 3 Baths
  • 1,874 Sq Ft

  106 Rockwell St, Winsted, CT 06098

  Looking to expand your investment portfolio-or live nearly rent-free while building one? This rare 3-family opportunity checks all the boxes! Hard to come by, this multi-family property features long-term, reliable tenants plus a vacant unit ready for an owner-occupant or a new rental. The lower level offers a comfortable 1-bedroom unit with walk-out patio. The main (2nd) level features 2

  Dawn Rousseau Showcase Realty, Inc.

  106 Rockwell St, Winsted, CT 06098
• 

  $400,000 Sold Mar 03, 2025

  296 Colebrook Rd, Winsted, CT 06098

  • 7 Beds
  • 3.5 Baths
  • 4,253 Sq Ft
  • Built 1958

  Last Sold Summary

  • 24% Below List Price
  • $94/SF
  • 132 Days On Market

  Last Listing Agent David D'Amore Northwest CT Realty

  296 Colebrook Rd, Winsted, CT 06098
• 

  Est $284,322 Not Listed For Sale

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

  174 Wallens St Unit C3, Winsted, CT 06098

  174 Wallens St Unit C3, Winsted, CT 06098
• 

  

  /17

  $319,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,754 Sq Ft

  25 Center St, Winsted, CT 06098

  Don't miss this unique opportunity to own a multi family residential property and an office space! (Owner currently has permission from the town to create a 2nd residential unit on the first floor) - will have 2.5 baths when completed. Great central location close to all amenities that Winsted has to offer including restaurants, parks, college, public transportation and shopping. First floor

  Tony Goia The Washington Agency

  25 Center St, Winsted, 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 $282,597

  Last Listing Agent Alison Behlman Tier 1 Real Estate

  39 Colony Dr, Winsted, CT 06098
• 

  Est $278,324 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,040 Sq Ft

  17 Colony Dr, Winsted, CT 06098

  17 Colony Dr, Winsted, CT 06098
• 

  

  /31

  $159,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,317 Sq Ft

  155 Rockwell St, Winsted, CT 06098

  Value-add opportunity in Winsted, CT. Property is currently occupied by a tenant on a month-to-month basis. Sight unseen; sold as-is. Ideal opportunity for investors seeking upside potential.

  Joseph Caslin Sailpoint Property Group

  155 Rockwell St, Winsted, CT 06098
• 

  $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
• 

  Est $260,742 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  159 Pratt St, Winsted, CT 06098

  159 Pratt St, Winsted, CT 06098
• 

  

  /8

  $389,000

  • Land
  • 20.87 Acres
  • $18,639 per Acre

  7 Stadler Heights, Winsted, CT 06098

  Welcome, You be the first, to come and conquer this land here in Winchester, Connecticut. There are 20.87 acres of virgin land. Come and build, do what you do best, you can have Peace and Privacy!!! There are no sidewalks, no streets that drive through. You are 40 minutes from multiple private schools. 16 minutes from Charlotte Hungerford Hospital. 1 hour from Tweed Airport New Haven. 39

  Hector Ortiz KW Legacy Partners

  7 Stadler Heights, Winsted, CT 06098
• 

  $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 $257,427

  Last Listing Agent Tony Goia The Washington Agency

  56 Lakeview Rd, Winsted, CT 06098

Showing Results 41 - 80, Page 2 of 18