5,132

Winchester, CT Homes

Section Image Section Image
  • 18 Pine Rd, Colebrook, CT 06021
    18 Pine Rd, Colebrook, CT 06021
    /2

    $49,000

    • Land
    • 2 Acres
    • $24,500 per Acre

    18 Pine Rd, Colebrook, CT 06021

    Discover the perfect setting for your dream home on this private 2.0-acre parcel in the scenic hills of Colebrook. Featuring 236 feet of road frontage on quiet Pine Road, this property offers a beautiful building site situated on a gently elevated plateau with desirable southern and western exposures, providing excellent sunlight and the potential for stunning sunset views. Surrounded by nature

    Agent Photo

    David Sartirana

    Northwest CT Realty

    18 Pine Rd, Colebrook, CT 06021
  • 19 Center St Unit 1, Winsted, CT 06098
    19 Center St Unit 1, Winsted, CT 06098
    19 Center St Unit 1, Winsted, CT 06098
    /8

    $1,695 Per Month

    • 3 Beds
    • 1 Bath
    • 900 Sq Ft
    • House for Rent

    19 Center St Unit 1, Winsted, CT 06098

    Three bedroom apartment on the first floor. Large kitchen, light filled living room and a recently remodeled bath. Washer/dryer can be added for an additional $75 per month. Pets considered. Off-street parking. First month and two months security, if applicable. Credit and background check required.

    Agent Photo

    Amanda Balaski

    Northwest CT Realty

    19 Center St Unit 1, Winsted, CT 06098
  • 147 Smith Hill Rd, Winsted, CT 06098

    $362,000

    Sold Nov 18, 2025

    147 Smith Hill Rd, Winsted, CT 06098

    • 4 Beds
    • 2 Baths
    • 1,910 Sq Ft
    • Built 1949

    Last Sold Summary

    • 6% Below List Price
    • $190/SF
    • 84 Days On Market

    Current Estimated Value $373,238

    Last Listing Agent SHARON GILSON Northwest CT Realty

    147 Smith Hill Rd, Winsted, CT 06098
  • 103 Cordano Rd, Winsted, CT 06098
    103 Cordano Rd, Winsted, CT 06098
    103 Cordano Rd, Winsted, CT 06098
    /35

    $339,900

    • 3 Beds
    • 1.5 Baths
    • 1,442 Sq Ft

    103 Cordano Rd, Winsted, CT 06098

    Well-maintained Cape in a desirable rural setting, yet just minutes from shopping, dining, schools, and other everyday conveniences. This 7-room home offers 3 bedrooms and 1.5 baths with a flexible floor plan designed for comfortable living. The main level features a formal living room, dining room, kitchen, family room, primary bedroom, and a full bath w/laundry, providing the convenience of

    Agent Photo

    David Sartirana

    Northwest CT Realty

    103 Cordano Rd, Winsted, CT 06098
  • 101 Whiting St, Winsted, CT 06098
    101 Whiting St, Winsted, CT 06098
    101 Whiting St, Winsted, CT 06098
    /34

    Starting at $1,500 Plus Fees

    • 1 Bed

    101 Whiting St, Winsted, CT 06098

    By far the best place to live in Winsted, Connecticut. Turn of the century construction, every unit overlooks the beautiful Still River, our 700-1000 square-foot one and two bedroom interiors are bright and charming and feature exposed wood beams, 10-foot ceilings, oversized industrial windows, and exposed brick walls. We deliver nature at your door. Our community amenities include same-floor

    Mill at Still River

    101 Whiting St, Winsted, CT 06098
  • 43 E Lake St, Winsted, CT 06098

    $920,000

    Sold Nov 17, 2025

    43 E Lake St, Winsted, CT 06098

    • 4 Beds
    • 3 Baths
    • 2,131 Sq Ft
    • Built 2002

    Last Sold Summary

    • 3% Below List Price
    • $432/SF
    • 56 Days On Market

    Current Estimated Value $930,148

    Last Listing Agent Keith Meyer Northwest CT Realty

    43 E Lake St, Winsted, CT 06098
  • 99 Hubbard St, Winsted, CT 06098
    99 Hubbard St, Winsted, CT 06098
    /2

    $49,000

    Pending
    • Land
    • 16,117 Sq Ft
    • $132,432 per Acre

    99 Hubbard St, Winsted, CT 06098

    99 Hubbard St. - Private Lot Near Downtown & Highland Lake. Tucked away at the end of a quiet dead-end street, this .37-acre lot offers both privacy and convenience. While enjoying a peaceful setting, you're still just minutes from downtown with easy access to shopping, dining, and entertainment. Plus, Highland Lake is just a short distance away, providing endless opportunities for boating,

    Agent Photo

    David Sartirana

    Northwest CT Realty

    99 Hubbard St, Winsted, CT 06098
  • 88 Spencer St Unit 2, Winsted, CT 06098
    88 Spencer St Unit 2, Winsted, CT 06098
    88 Spencer St Unit 2, Winsted, CT 06098
    /3

    $1,495 Per Month

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • House for Rent

    88 Spencer St Unit 2, Winsted, CT 06098

    Two bedroom, 1st flr apartment close to town. Private front porch. A washer-dryer can be provided for an extra $75 per month. Pets considered, and a background and credit check are required. Minimum credit score required. Showings only in the evening or on Sundays.

    Agent Photo

    Amanda Balaski

    Northwest CT Realty

    88 Spencer St Unit 2, Winsted, CT 06098
  • 262 Holabird Ave, Winsted, CT 06098

    $365,000

    Sold May 15, 2026

    262 Holabird Ave, Winsted, CT 06098

    • 3 Beds
    • 1.5 Baths
    • 1,312 Sq Ft
    • Built 1973

    Last Sold Summary

    • 1% Above List Price
    • $278/SF
    • 11 Days On Market

    Current Estimated Value $358,535

    Last Listing Agent Mary Anne Casey D. Beckley Realty

    262 Holabird Ave, Winsted, CT 06098
    • 355 W Lake St, Winsted, CT 06098

      Est $902,093

      Not Listed For Sale

      355 W Lake St, Winsted, CT 06098

      • 5 Beds
      • 3.5 Baths
      • 3,216 Sq Ft
      • Built 2008
      355 W Lake St, Winsted, CT 06098

      Last Sold Summary

      • 55 Days On Market

  • 752 Lake Dr, Winsted, CT 06098
    752 Lake Dr, Winsted, CT 06098
    /2

    $1,600,000

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 2,129 Sq Ft

    752 Lake Dr, Winsted, CT 06098

    We apologize we have to cancel the open house. Will reschedule for next weekend. Experience the best of lakefront living with breathtaking views, spectacular sunsets, and exceptional outdoor spaces. This amazing waterfront home features a brand-new 100' x 14' Brazilian hardwood deck, a 35' x 6' stationary Trex and steel dock, and a private cabana-perfect for relaxing, boating, swimming, and

    Agent Photo

    Pam Famiglietti

    William Raveis Real Estate

    752 Lake Dr, Winsted, CT 06098
  • 13 Wallens St, Winsted, CT 06098
    13 Wallens St, Winsted, CT 06098
    13 Wallens St, Winsted, CT 06098
    /20

    Starting at $1,150 Plus Fees

    • Studio - 2 Beds

    13 Wallens St, Winsted, CT 06098

    At Gilbert Clock Apartments , our designer-inspired amenities set us apart from the competition. We pride ourselves on providing top-quality apartments outfitted with the everyday amenities you expect as well as luxury amenities to delight your senses and enhance your modern life. Indulge your culinary instincts in your state-of-the-art kitchen, furnished with Beautiful and energy-efficient

    Gilbert Clock Apartments

    13 Wallens St, Winsted, CT 06098
  • 49 Walnut St, Winsted, CT 06098

    $305,000

    Sold Dec 22, 2025

    49 Walnut St, Winsted, CT 06098

    • 5 Beds
    • 2 Baths
    • 2,344 Sq Ft
    • Built 1824

    Last Sold Summary

    • 2% Above List Price
    • $130/SF
    • 6 Days On Market

    Current Estimated Value $302,384

    Last Listing Agent David Sartirana Northwest CT Realty

    49 Walnut St, Winsted, CT 06098
  • 55 Walnut St, Winsted, CT 06098
    55 Walnut St, Winsted, CT 06098
    55 Walnut St, Winsted, CT 06098
    /37

    $449,000

    $101K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 5,016 Sq Ft

    55 Walnut St, Winsted, CT 06098

    Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family

    Agent Photo

    David Sartirana

    Northwest CT Realty

    55 Walnut St, Winsted, CT 06098
  • 98 Spencer St Unit 4N, Winsted, CT 06098
    98 Spencer St Unit 4N, Winsted, CT 06098
    98 Spencer St Unit 4N, Winsted, CT 06098
    /7

    $1,695 Per Month

    • 4 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    98 Spencer St Unit 4N, Winsted, CT 06098

    Spacious 4 bedroom, 2nd floor apartment. Washer/dryer included. Off street parking. Pets considered. Credit and background check done by listing office. Minimum credit score required.

    Agent Photo

    Amanda Balaski

    Northwest CT Realty

    98 Spencer St Unit 4N, Winsted, CT 06098
  • 171 Wallens St, Winchester, CT 06098

    $370,000

    Sold Mar 25, 2026

    171 Wallens St, Winchester, CT 06098

    • 2 Beds
    • 2 Baths
    • 1,274 Sq Ft
    • Built 1957

    Last Sold Summary

    • 3% Above List Price
    • $290/SF
    • 23 Days On Market

    Current Estimated Value $353,353

    Last Listing Agent Meagan Albert Tier 1 Real Estate

    171 Wallens St, Winchester, CT 06098
    • 39 Baker St, Winsted, CT 06098

      Est $224,911

      Not Listed For Sale

      39 Baker St, Winsted, CT 06098

      • 5 Beds
      • 2 Baths
      • 1,612 Sq Ft
      • Built 1900
      39 Baker St, Winsted, CT 06098

      Last Sold Summary

      • 166 Days On Market

  • 32 Hubbard St, Winsted, CT 06098
    32 Hubbard St, Winsted, CT 06098
    /2

    $45,000

    • Land
    • 17,859 Sq Ft
    • $109,756 per Acre

    32 Hubbard St, Winsted, CT 06098

    Rare opportunity to build in a convenient in-town location! This level 0.41-acre lot is ideally situated close to downtown amenities while offering easy access to Highland Lake's public beach and boat launch. Formerly improved with a three-story Colonial home, the property presents a unique opportunity to redevelop an established homesite. Public water, public sewer, and natural gas are available

    Agent Photo

    David Sartirana

    Northwest CT Realty

    32 Hubbard St, Winsted, CT 06098
  • 111 Rockwell St Unit A, Winsted, CT 06098
    111 Rockwell St Unit A, Winsted, CT 06098
    111 Rockwell St Unit A, Winsted, CT 06098
    /20

    $1,225

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft
    • Condo for Rent

    111 Rockwell St Unit A, Winsted, CT 06098

    Charming 2-bedroom, 1-bath unit located in a quiet Winsted neighborhood on a spacious corner lot. This home features a well-appointed kitchen with ample cabinet space, a cozy island, and appliances. The unit includes beautiful hardwood floors throughout the living spaces and large windows that fill the rooms with natural light. Outside, enjoy a private entrance and a shared green space.

    111 Rockwell St Unit A, Winsted, CT 06098
  • 39 Orchard St, Winsted, CT 06098

    $208,900

    Sold Jul 18, 2025

    39 Orchard St, Winsted, CT 06098

    • 3 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Built 1875

    Last Sold Summary

    • 9% Below List Price
    • $174/SF
    • 131 Days On Market

    Current Estimated Value $284,748

    Last Listing Agent Michael J Flaherty Jr Sullivan Real Estate Inc

    39 Orchard St, Winsted, CT 06098
  • 26 Elm St, Winchester, CT 06098
    26 Elm St, Winchester, CT 06098
    26 Elm St, Winchester, CT 06098
    /13

    $398,000

    Pending
    • 5 Beds
    • 3 Baths
    • 2,496 Sq Ft

    26 Elm St, Winchester, CT 06098

    Welcome to 26 Elm Street, a newly renovated and legally converted three-family property in the heart of Winsted. This is a rare opportunity for investors or owner-occupants seeking a move-in-ready, income-producing asset with strong upside potential. Two of the units have been completely renovated, featuring updated interiors that appeal to today's tenants, while the exterior has also been

    Agent Photo

    Annie Q Simard

    LPT Realty

    26 Elm St, Winchester, CT 06098
  • 440 Main St Unit B, Winchester, CT 06098
    440 Main St Unit B, Winchester, CT 06098
    440 Main St Unit B, Winchester, CT 06098
    /5

    $1,000 Per Month

    • 2 Beds
    • 1 Bath
    • 4,668 Sq Ft
    • Apartment for Rent

    440 Main St Unit B, Winchester, CT 06098

    Second Floor two Bedroom room apartment set in town. Convenient to stores, restaurants and medical facility. Minimum credit score, credit checks are to be done by listing office.

    Linda Ganem Borla & Associates Real Estate

    440 Main St Unit B, Winchester, CT 06098
  • 156 Shore Dr, Winsted, CT 06098

    $691,000

    Sold May 21, 2026

    156 Shore Dr, Winsted, CT 06098

    • 5 Beds
    • 1.5 Baths
    • 1,258 Sq Ft
    • Built 1930

    Last Sold Summary

    • 12% Below List Price
    • $549/SF
    • 31 Days On Market

    Current Estimated Value $779,019

    Last Listing Agent Bryan Palladino Showcase Realty, Inc.

    156 Shore Dr, Winsted, CT 06098
  • 30 Upland Rd, Winsted, CT 06098
    30 Upland Rd, Winsted, CT 06098
    30 Upland Rd, Winsted, CT 06098
    /26

    $220,000

    • 4 Beds
    • 2 Baths
    • 1,844 Sq Ft

    30 Upland Rd, Winsted, CT 06098

    Located in the charming community of Winsted, this 4-bedroom home is tucked away in a quiet, low-traffic neighborhood while still being close to many local amenities. Hardwood floors run throughout the home, adding warmth and character, and the tree-lined backyard offers a private outdoor setting to enjoy year round. This home also features a beautiful enclosed second-floor sun porch, perfect for

    Agent Photo

    Jeffrey Liskin

    Northwest CT Realty

    30 Upland Rd, Winsted, CT 06098
  • I 9 Nanni Dr Unit F-09, Winchester, CT 06098
    I 9 Nanni Dr Unit F-09, Winchester, CT 06098
    I 9 Nanni Dr Unit F-09, Winchester, CT 06098
    /6

    $1,495

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,045 Sq Ft
    • 2 Bedroom Townhouse Apartment

    I 9 Nanni Dr Unit F-09, Winchester, CT 06098

    Discover the charm of Litchfield County living at Litchfield Heights. Our generously sized townhomes — over 1,000 square feet — have been thoughtfully upgraded with brand new white shaker cabinets, granite countertops, stainless steel appliances, and new vinyl plank flooring. Spacious bedrooms, remodeled bathrooms, private entrances, and backyard sliders round out everything you need to feel

    I 9 Nanni Dr Unit F-09, Winchester, CT 06098
  • 32 Charles St, Winsted, CT 06098

    $225,000

    Sold Dec 10, 2025

    32 Charles St, Winsted, CT 06098

    • 3 Beds
    • 1 Bath
    • 1,044 Sq Ft
    • Built 1953

    Last Sold Summary

    • 2% Below List Price
    • $216/SF
    • 41 Days On Market

    Current Estimated Value $233,674

    Last Listing Agent David Sartirana Northwest CT Realty

    32 Charles St, Winsted, CT 06098
  • 77 Hubbard St, Winsted, CT 06098
    77 Hubbard St, Winsted, CT 06098
    77 Hubbard St, Winsted, CT 06098
    /8

    $299,900

    Pending
    • 6 Beds
    • 2 Baths
    • 2,699 Sq Ft

    77 Hubbard St, Winsted, CT 06098

    Discover this versatile two-family residence offering a blend of modern updates and timeless charm. Each unit boasts three bedrooms and a full bath, providing ample space and comfort for tenants or multi-generational living. The first-floor unit has been beautifully renovated, featuring a brand-new kitchen with stylish finishes, updated bath, gleaming hardwood floors, and plush new carpet in the

    Agent Photo

    Amy Rio

    Better Homes and Gardens Real Estate Executive Real Estate

    77 Hubbard St, Winsted, CT 06098
  • 936 Main St Unit 14, Winchester, CT 06098
    936 Main St Unit 14, Winchester, CT 06098
    936 Main St Unit 14, Winchester, CT 06098
    /9

    $1,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • Property for Rent

    936 Main St Unit 14, Winchester, CT 06098

    Recently purchased and re-built manufactured home community in Winsted in final stages of being completed. The entrance to the property is being worked on now with 3 new homes to be put in front. The property will look much nicer when completed. This is the final phase. Beautiful free standing ranch style homes, 2 bedroom, 2 baths with attached closed porch available. There are 2 houses available

    Michael Block Building Blocks LLC

    936 Main St Unit 14, Winchester, CT 06098
  • 331 Colebrook Rd, Winsted, CT 06098

    $300,000

    Sold Nov 07, 2025

    331 Colebrook Rd, Winsted, CT 06098

    • 2 Beds
    • 1.5 Baths
    • 1,323 Sq Ft
    • Built 1940

    Last Sold Summary

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

    Current Estimated Value $298,968

    Last Listing Agent Alison Malkin Essentia Realty

    331 Colebrook Rd, Winsted, CT 06098
  • 5 Stadler Heights, Winsted, CT 06098
    5 Stadler Heights, Winsted, CT 06098
    5 Stadler Heights, Winsted, CT 06098
    /15

    $499,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 3,556 Sq Ft

    5 Stadler Heights, Winsted, CT 06098

    Spacious and full of potential, this 10-room home offers 4 bedrooms and 2.5 baths with plenty of room for everyone. Priced below current market value, this property presents a fantastic opportunity for buyers willing to make some cosmetic updates and build instant equity. Set in a quiet country location within a private development known for its large lots and peaceful surroundings, the home

    Agent Photo

    David Sartirana

    Northwest CT Realty

    5 Stadler Heights, Winsted, CT 06098
  • 277 N Main St Unit 3, Winsted, CT 06098
    277 N Main St Unit 3, Winsted, CT 06098
    277 N Main St Unit 3, Winsted, CT 06098
    /14

    $900 Per Month

    • 1 Bed
    • 1 Bath
    • 650 Sq Ft
    • Apartment for Rent

    277 N Main St Unit 3, Winsted, CT 06098

    Second-floor apartment available in a convenient Winsted location, close to local shops, dining, and everyday amenities. This freshly painted unit offers a bright, open living space with an efficient layout, along with an in-wall A/C unit for added comfort. The kitchen provides ample cabinet storage, and the unit is complemented by a clean, well-maintained bath. Enjoy the convenience of on-site

    Ryan Marconi The Washington Agency

    277 N Main St Unit 3, Winsted, CT 06098
  • 230 E Wakefield Blvd, Winsted, CT 06098

    $300,000

    Sold May 11, 2026

    230 E Wakefield Blvd, Winsted, CT 06098

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • Built 1978

    Last Sold Summary

    • 6% Below List Price
    • $195/SF
    • 109 Days On Market

    Current Estimated Value $310,531

    Last Listing Agent Peter D'Addeo Commercial Services Realty

    230 E Wakefield Blvd, Winsted, CT 06098

Showing Results 1 - 40, Page 1 of 18

Connecticut Litchfield County Winchester

Real Estate & Homes

Home Prices in Winchester, CT

The median home sale price in Winchester, CT is $345,000, down 10% year-over-year. Homes in Winchester sell in 50 days on average, compared to the national average of 57 days.

Home Price Trends

Median Sale Price
$345,000
Median Single Family Sale Price
$345,000
Median 2 Bedroom Sale Price
$370,000
Average Price Per Sq Ft
$248
Number of Homes for Sale
0
Last 12 months Home Sales
4
Months of Supply
0.00
Median List Price
$349,900
Median Change From 1st List Price
-2%
Median Home Sale Price YoY Change
-10%
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