Winchester, CT Homes

• 

  $33,500

  Sold Mar 20, 2026

  256 Colebrook Rd, Winchester Center, CT 06098

  • Land
  • 40,075 Sq Ft
  • $36,413 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 226 Days On Market

  Current Estimated Value $44,000

  Last Listing Agent Austin Brochu Sullivan Real Estate Inc

  256 Colebrook Rd, Winchester Center, CT 06098
• 

  Est $211,656

  Not Listed For Sale

  11 Orchard St, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,759 Sq Ft
  • Built 1900

  11 Orchard St, Winsted, CT 06098

  Last Sold Summary

  • 29% Above List Price
  • $93/SF
  • 19 Days On Market

  • Last Sold Price $164,000
  • Apr 29, 2024

  Last Listing Agent Jonathan Gineo Silver and Oak Realty
• 

  

  /2

  $299,900

  • Land
  • 34 Acres
  • $8,821 per Acre

  00 Ramsgate Ln, Barkhamsted, CT 06063

  30 +/- acres in ideal location in Barkhamsted bordering American Legion State Forest in the rear. Minutes from historic Riverton Center and world-renowned fly fishing. Many outdoor activities close by including hiking, biking, tubing, skiing, boating and many more. Land is ideal for almost any application, subdividing, recreation, horses, etc. Land will be subdivided upon contract and prior to

  Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

  00 Ramsgate Ln, Barkhamsted, CT 06063
• 

  $439,900

  Sold Dec 04, 2025

  819 E Wakefield Blvd, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,892 Sq Ft
  • Built 1920

  Last Sold Summary

  • 12% Below List Price
  • $233/SF
  • 72 Days On Market

  Current Estimated Value $464,088

  Last Listing Agent David Sartirana Northwest CT Realty

  819 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $274,885

  Not Listed For Sale

  303 E Wakefield Blvd, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1986

  303 E Wakefield Blvd, Winsted, CT 06098

  Last Sold Summary

  • $286/SF
  • 21 Days On Market

  • Last Sold Price $275,000
  • Nov 06, 2024

  Last Listing Agent Tammy Schaller William Raveis Real Estate
• 

  

  /26

  $239,000

  Under Contract

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

  Unlisted Address

  Brand new to the market. Must see large 2 story Colonial featuring 13 rooms, 7 Bedrooms, 3 Bathrooms, Walk up attic and full basement. Includes a 2 story barn. Convenient location in the heart of town lends itself to easy access to many nearby amenities. As an investment this residence also has great potential to convert to a multi family home or could be renovated for commercial office space.

  Frank J. Berg Broker/Owner Town & Country Real Estate

  Unlisted Address
• 

  $190,000

  Sold Oct 20, 2025

  111 Torringford St Unit 25, Winsted, CT 06098

  • 2 Beds
  • 2 Baths
  • 1,156 Sq Ft
  • Built 1987

  Last Sold Summary

  • 6% Above List Price
  • $164/SF
  • 2 Days On Market

  Current Estimated Value $190,623

  Last Listing Agent Ron Rudek Connecticut Realty, LLC

  111 Torringford St Unit 25, Winsted, CT 06098
• 

  Est $262,765

  Not Listed For Sale

  151 Hinsdale Ave, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,634 Sq Ft
  • Built 1948

  151 Hinsdale Ave, Winsted, CT 06098

  Last Sold Summary

  • 19% Above List Price
  • $135/SF
  • 154 Days On Market

  • Last Sold Price $220,000
  • Sep 11, 2023

  Last Listing Agent Sarah Isabella Glenstone Real Estate LLC
• 

  

  /36

  $419,000

  Under Contract

  • 4 Beds
  • 3 Baths
  • 2,240 Sq Ft

  118 South Rd, Winsted, CT 06098

  Tucked away in a peaceful country setting just minutes from Winchester Center, this well-maintained 4-bedroom Colonial offers space, comfort, and timeless charm. Proudly owned by just one owner, this home reflects true pride of ownership throughout, with thoughtfully updated mechanicals and the added peace of mind of a whole-house generator. The inviting main level features a spacious family room

  Becky Grieco Berkshire Hathaway NE Prop.

  118 South Rd, Winsted, CT 06098
• 

  $240,000

  Sold Oct 22, 2025

  210 Walnut St, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,056 Sq Ft
  • Built 1988

  Last Sold Summary

  • 7% Above List Price
  • $227/SF
  • 46 Days On Market

  Current Estimated Value $243,828

  Last Listing Agent Nicole Araujo Trend 2000 Real Estate

  210 Walnut St, Winsted, CT 06098
• 

  Est $197,401

  Not Listed For Sale

  111 Riverton Rd Unit 83, Winsted, CT 06098

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

  111 Riverton Rd Unit 83, Winsted, CT 06098

  Last Sold Summary

  • 1% Below List Price
  • $166/SF
  • 65 Days On Market

  • Last Sold Price $200,000
  • Dec 13, 2024

  Last Listing Agent David Sartirana Northwest CT Realty
• 

  

  /34

  $399,000

  Under Contract

  • 5 Beds
  • 4 Baths
  • 2,779 Sq Ft

  217 Walnut St, Winsted, CT 06098

  In-Town Victorian 2-Family - Exceptional Condition & Versatility Rare opportunity to own a beautifully maintained, vinyl-sided Victorian-style side-by-side two-family home in a prime in-town location! This unique property offers incredible flexibility for investors, owner-occupants, or multi-generational living. Each unit features its own private entrance and spacious layout-one side offering a

  David D'Amore Northwest CT Realty

  217 Walnut St, Winsted, CT 06098
• 

  $950,000

  Sold Jun 27, 2025

  355 W Lake St, Winsted, CT 06098

  • 5 Beds
  • 3.5 Baths
  • 3,216 Sq Ft
  • Built 2008

  Last Sold Summary

  • 3% Below List Price
  • $295/SF
  • 55 Days On Market

  Current Estimated Value $889,489

  Last Listing Agent David Sartirana Northwest CT Realty

  355 W Lake St, Winsted, CT 06098
• 

  Est $523,636

  Not Listed For Sale

  16 Alexandria Dr, Winsted, CT 06063

  • 4 Beds
  • 2.5 Baths
  • 2,364 Sq Ft
  • Built 1989

  16 Alexandria Dr, Winsted, CT 06063

  Last Sold Summary

  • 25% Above List Price
  • $177/SF
  • 17 Days On Market

  • Last Sold Price $418,000
  • Sep 01, 2023

  Last Listing Agent Gina Beiser Executive Real Estate
• 

  

  /27

  $375,000

  Pending

  • 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
• 

  $180,000

  Sold Dec 19, 2025

  99 Norfolk Rd, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 980 Sq Ft
  • Built 1948

  Last Sold Summary

  • 23% Below List Price
  • $184/SF
  • 156 Days On Market

  Current Estimated Value $188,393

  Last Listing Agent Lisa McCarthy Coldwell Banker Realty

  99 Norfolk Rd, Winsted, CT 06098
• 

  Est $332,471

  Not Listed For Sale

  5 Hillside Ave, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 2,664 Sq Ft
  • Built 1900

  5 Hillside Ave, Winsted, CT 06098

  Last Sold Summary

  • 17% Above List Price
  • $106/SF
  • 52 Days On Market

  • Last Sold Price $283,500
  • Nov 03, 2023

  Last Listing Agent David Sartirana Northwest CT Realty
• 

  

  /31

  $269,999

  $20K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,652 Sq Ft

  118 Meadow St, Winsted, CT 06098

  This charming historic home, built in 1860, blends timeless character with thoughtful updates. Featuring 3-4 bedrooms, this property offers flexible living space to meet your needs. The beautifully remodeled upstairs bathroom is a standout feature, offering modern comfort within this classic home. Enjoy your LARGE eat-in kitchen with laundry hook ups and plenty of natural lighting and ample

  Ashley Henry The Washington Agency

  118 Meadow St, Winsted, CT 06098
• 

  $410,000

  Sold Apr 13, 2026

  35 Glendale Ave, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 2,196 Sq Ft
  • Built 1955

  Last Sold Summary

  • 3% Above List Price
  • $187/SF
  • 35 Days On Market

  Current Estimated Value $392,265

  Last Listing Agent David Sartirana Northwest CT Realty

  35 Glendale Ave, Winsted, CT 06098
• 

  Est $227,546

  Not Listed For Sale

  36 S Main St, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,380 Sq Ft
  • Built 1920

  36 S Main St, Winsted, CT 06098

  Last Sold Summary

  • 17% Above List Price
  • $141/SF
  • 73 Days On Market

  • Last Sold Price $194,000
  • Sep 21, 2023

  Last Listing Agent DeVante Roman eXp Realty
• 

  

  /29

  $299,900

  • 2 Beds
  • 1 Bath
  • 702 Sq Ft

  147 E Wakefield Blvd, Winsted, CT 06098

  Come enjoy Highland Lake living just in time for Summer. Relax in this one level living, cozy cottage home with views of the lake from your deck and just a short distance to Resha beach. Enter through a large mudroom to your open living room with large window to let in natural light, updated kitchen, 2 bedrooms, 1 full bath, main level laundry, front and rear deck, large yard & shed. New flooring

  Mary Mary LeBlanc Realty

  147 E Wakefield Blvd, Winsted, CT 06098
• 

  $860,000

  Sold Jun 24, 2025

  399 Colebrook Rd, Colebrook, CT 06021

  • 4 Beds
  • 3 Baths
  • 3,016 Sq Ft
  • Built 1956

  Last Sold Summary

  • 7% Below List Price
  • $285/SF
  • 90 Days On Market

  Current Estimated Value $893,635

  Last Listing Agent David Taylor Elyse Harney Real Estate

  399 Colebrook Rd, Colebrook, CT 06021
• 

  Est $198,448

  Not Listed For Sale

  111 Riverton Rd Unit 55, Winsted, CT 06098

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

  111 Riverton Rd Unit 55, Winsted, CT 06098

  Last Sold Summary

  • 9% Above List Price
  • $151/SF
  • 87 Days On Market

  • Last Sold Price $182,000
  • Apr 26, 2024

  Last Listing Agent Suzie Larson Turning Point Realty, LLC
• 

  

  /37

  $765,000

  • 3 Beds
  • 2.5 Baths
  • 4,387 Sq Ft

  184 Smith Hill Rd, Winsted, CT 06098

  Beautiful Private Brick/Clapboard Tudor set back on 8.46 private acres (which includes an extra 2+ acre abutting lot). New Hand Split Cedar Shingled Roof and new rebuilt brick chimney set off this custom elegant home. All warm cherry wood floors and special custom moldings throughout the home add charm. Classy center island Kit with new subzero, granite counters & bow window-Fireplaced Dining

  Mary New Berkshire Hathaway NE Prop.

  184 Smith Hill Rd, Winsted, CT 06098
• 

  $1,500,000

  Sold Oct 14, 2025

  538 Wheelers Point, Winsted, CT 06098

  • 4 Beds
  • 3 Baths
  • 2,496 Sq Ft
  • Built 1930

  Last Sold Summary

  • 20% Below List Price
  • $601/SF
  • 292 Days On Market

  Current Estimated Value $1,498,289

  Last Listing Agent KAREN NEWTON William Pitt Sotheby's Int'l

  538 Wheelers Point, Winsted, CT 06098
• 

  Est $204,185

  Not Listed For Sale

  111 Riverton Rd Unit 45, Winsted, CT 06098

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

  111 Riverton Rd Unit 45, Winsted, CT 06098

  Last Sold Summary

  • 5% Below List Price
  • $179/SF
  • 4 Days On Market

  • Last Sold Price $215,000
  • Aug 30, 2024

  Last Listing Agent ROBERT SZABO Szabo Realty
• 

  

  /36

  $1,850,000

  • 9 Beds
  • 5.5 Baths
  • 7,000 Sq Ft

  431 W Wakefield Blvd, Winsted, CT 06098

  Live the Highland Lake Dream - 431 W. Wakefield Blvd, Winchester, CT Summer is just around the corner - and in Winsted, resort living never ends. Recently named one of the most desirable towns to live in, with the breathtaking Highland Lake at its heart, Winchester offers the perfect blend of beauty and lifestyle. This waterfront estate at 431 W. Wakefield Blvd isn't just a home - it's your

  Lisa Ogren Berkshire Hathaway NE Prop.

  431 W Wakefield Blvd, Winsted, CT 06098
• 

  $225,000

  Sold Nov 03, 2025

  130 Stanton Ave, Winsted, CT 06098

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Below List Price
  • $293/SF
  • 115 Days On Market

  Current Estimated Value $236,103

  Last Listing Agent David D'Amore Northwest CT Realty

  130 Stanton Ave, Winsted, CT 06098
• 

  Est $248,944

  Not Listed For Sale

  9 Fruit St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 2,472 Sq Ft
  • Built 1900

  9 Fruit St, Winsted, CT 06098

  Last Sold Summary

  • 39% Above List Price
  • $72/SF
  • 35 Days On Market

  • Last Sold Price $178,550
  • Jul 13, 2023

  Last Listing Agent Michael J Flaherty Jr Sullivan Real Estate Inc
• 

  

  /19

  $579,000

  • 11 Beds
  • 5.5 Baths
  • 5,233 Sq Ft

  150 Oak St, Winsted, CT 06098

  150 Oak St. is a fully rented, rare, charming 1920's 5-family apartment home located in a beautiful residential neighborhood in Winsted/Winchester, CT. Old World charm with original woodwork, high ceilings, mostly hardwood floors, and hallways connecting the spacious rooms in 4 of the units -which feature 2 bedrooms and a dining room. The 5th floor is a 3 bedroom, 1 1/2 bath unit with electric

  Pamela Silvestri Turning Point Realty, LLC

  150 Oak St, Winsted, CT 06098
• 

  $292,000

  Sold Jul 25, 2025

  126 Williams Ave, Winsted, CT 06098

  • 6 Beds
  • 2 Baths
  • 2,225 Sq Ft
  • Built 1890

  Last Sold Summary

  • 2% Above List Price
  • $131/SF
  • 42 Days On Market

  Current Estimated Value $289,031

  Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  126 Williams Ave, Winsted, CT 06098
• 

  Est $309,313

  Not Listed For Sale

  202 Old New Hartford Rd, Winsted, CT 06098

  • 4 Beds
  • 1.5 Baths
  • 1,560 Sq Ft
  • Built 1900

  202 Old New Hartford Rd, Winsted, CT 06098

  Last Sold Summary

  • 3% Below List Price
  • $205/SF
  • 168 Days On Market

  • Last Sold Price $320,000
  • May 14, 2024

  Last Listing Agent Barry Mackiewicz A-Gold Action Realty
• 

  

  /9

  $850,000

  $149K PRICE DROP

  • Land
  • 116.5 Acres
  • $7,296 per Acre

  82 Riverton Rd, Colebrook, CT 06021

  Escape to Your Own 116 acres of Paradise in Colebrook, CT! Discover 116 +/- acres of picturesque land nestled along Riverton Road in the heart of scenic Colebrook, Connecticut. This extraordinary property offers a rare opportunity to own a vast expanse of rural beauty, complete with two serene ponds, winding old logging roads, and a mix of standing hardwoods and softwoods that create a lush,

  Suzie Larson Turning Point Realty, LLC

  82 Riverton Rd, Colebrook, CT 06021
• 

  $397,000

  Sold Jun 04, 2025

  323 E Wakefield Blvd, Winsted, CT 06098

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

  Last Sold Summary

  • 6% Above List Price
  • $278/SF
  • 4 Days On Market

  Current Estimated Value $398,303

  Last Listing Agent Heather Crabtree RE/MAX RISE

  323 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $375,833

  Not Listed For Sale

  173 Smith Hill Rd, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 1,702 Sq Ft
  • Built 1950

  173 Smith Hill Rd, Winsted, CT 06098

  Last Sold Summary

  • 5% Below List Price
  • $232/SF
  • 26 Days On Market

  • Last Sold Price $395,000
  • Dec 03, 2024

  Last Listing Agent Kim Trumbull William Raveis Real Estate
• 

  

  /35

  $345,000

  • 5 Beds
  • 3 Baths
  • 2,602 Sq Ft

  63 Meadow St, Winsted, CT 06098

  Discover 63 Meadow, a turnkey 3-unit asset where thoughtful updates, strong rental performance, and a prime location come together to prove a high confidence investment opportunity. The property offers three well-proportioned units, a two-car attached garage, off-street parking spaces, and shared outdoor area that tenants appreciate. The current owner continued to elevate the building's value and

  Lauren Hill Mark Tavares Realty, LLC

  63 Meadow St, Winsted, CT 06098
• 

  $250,000

  Sold May 30, 2025

  150 Meadow St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 2,094 Sq Ft
  • Built 1860

  Last Sold Summary

  • $119/SF
  • 80 Days On Market

  Current Estimated Value $261,598

  Last Listing Agent David Sartirana Northwest CT Realty

  150 Meadow St, Winsted, CT 06098
• 

  Est $428,188

  Not Listed For Sale

  123 Skinner Rd, Winsted, CT 06098

  • 3 Beds
  • 3 Baths
  • 2,184 Sq Ft
  • Built 2005

  123 Skinner Rd, Winsted, CT 06098

  Last Sold Summary

  • 15% Above List Price
  • $170/SF
  • 82 Days On Market

  • Last Sold Price $372,000
  • Feb 21, 2024

  Last Listing Agent Jacqueline Gardner Coldwell Banker Realty
• 

  

  /38

  $749,000

  $20K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,265 Sq Ft

  121 W Wakefield Blvd, Winsted, CT 06098

  Discover unparalleled Highland Lake living with this exceptional 1.00-acre retreat, boasting 50 feet of direct lake frontage and a newly renovated dock/deck. Enjoy breathtaking water views from your sunroom, dining room, and multiple bedrooms within this versatile 4/5 bedroom home. A unique first-floor suite with a separate exterior entrance offers ideal flexibility as a main-floor master or

  Elizabeth Stockwell Coldwell Banker Realty

  121 W Wakefield Blvd, Winsted, CT 06098
• 

  $320,000

  Sold Oct 21, 2025

  160 Walnut St, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,674 Sq Ft
  • Built 1950

  Last Sold Summary

  • 11% Above List Price
  • $191/SF
  • 11 Days On Market

  Current Estimated Value $317,384

  Last Listing Agent Jeremy Beamer William Raveis Real Estate

  160 Walnut St, Winsted, CT 06098

Showing Results 161 - 200, Page 5 of 18