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Newest Homes for Sale in Winsted, CT

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  • /14

    $398,000 Coming Soon

    • 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

    (860) 407-3930

    26 Elm St, Winchester, CT 06098
  • /29

    $359,900

    • 3 Beds
    • 1.5 Baths
    • 1,600 Sq Ft

    1 Hamill Dr, Winsted, CT 06098

    Step into luxury in this nicely updated 3-bedroom raised ranch, perfectly positioned on a quiet cul-de-sac. The interior shines with hardwood floors and a designer kitchen boasting new custom cabinetry, quartz countertops and stainless-steel appliances. Lower level is completely finished featuring a large family room with natural gas stove. Enjoy maintenance-free living with a newer roof (less

    Paul Duh Realty ONE Group Connect

    1 Hamill Dr, Winsted, CT 06098
  • /22

    $335,000

    • 3 Beds
    • 1 Bath
    • 1,282 Sq Ft

    90 Colony Dr, Winsted, CT 06098

    Turnkey Winsted gem completely renovated inside & out! Get ready to just move and and not worry. Here is a beautifully reimagined 3-bedroom, 1-bathroom property in Winsted, offering the perfect blend of modern luxury and ultimate peace of mind. Every detail has been thoughtfully updated to create a true turnkey experience. Step inside to a bright, inviting space where the wall between the

    Michelle Grant Coldwell Banker Premier Real Estate

    90 Colony Dr, Winsted, CT 06098
  • /38

    $769,000

    • 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
  • /37

    $779,900

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

    156 Shore Dr, Winsted, CT 06098

    Summer is just around the corner, and this is your opportunity to own a highly sought-after waterfront property on the beautiful Highland Lake! Located on Shore Drive in the 1st Bay, this private 5-bedroom home offers breathtaking western exposure, giving you the perfect view of every sunset. Enjoy direct waterfront access and make the most of the flat, easy-to-maintain lot - ideal for outdoor

    Bryan Palladino Showcase Realty, Inc.

    156 Shore Dr, Winsted, CT 06098
  • /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
  • /30

    $159,500

    • 2 Beds
    • 1.5 Baths
    • 992 Sq Ft

    35 Riveredge Dr Unit 35, Winsted, CT 06098

    Charming Riverview Townhouse with Patio Enjoy easy living in this well-located two-bedroom townhouse set on a slab and overlooking the river. The main level features a living room, dining room, and functional kitchen, perfect for everyday comfort and entertaining. Sliding glass doors lead to a private patio where you can relax and enjoy the peaceful water views. Upstairs offers two comfortable

    Joanne Donne The Washington Agency

    35 Riveredge Dr Unit 35, Winsted, CT 06098
  • /38

    $395,000

    • 3 Beds
    • 1.5 Baths
    • 1,909 Sq Ft

    720 Main St, Winsted, CT 06098

    Prime Mixed-Use Opportunity in Downtown Winsted! High-visibility two-story building located on bustling Main Street, most recently home to "JT's Cafe," and previously known as "The Winning Ticket Cafe." The first-floor commercial space includes features such as an existing kitchen area with oven range vents, fridge, bathroom, and open seating area. Great potential for a new restaurant, cafe,

    Ryan Marconi The Washington Agency

    720 Main St, Winsted, CT 06098
  • /11

    $750,000

    • 4 Beds
    • 2 Baths
    • 5,389 Sq Ft

    436 Main St, Winsted, CT 06098

    One-of-a-Kind opportunity with 4 apartments plus a turnkey, award-winning restaurant in the heart of Litchfield County, perfectly situated in a high-traffic location. The well-established business offers 2,177 sq. ft. of warm, inviting atmosphere with 65 indoor seats and 35 outdoor seats-ideal for both casual dining and special occasions. Has a cafe license (liquor) but no bar. With a 10-year

    Tony Goia The Washington Agency

    436 Main 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 minutes

    Hector Ortiz KW Legacy Partners

    7 Stadler Heights, Winsted, CT 06098
  • /2

    $24,900

    • Land
    • 0.44 Acre
    • $56,591 per Acre

    124 Rockwell St, Winsted, CT 06098

    124 Rockwell St. - Versatile .44-Acre Lot Near Downtown This .44-acre lot offers a prime location close to downtown with city water and sewer available in the street. The previous home sat at street level, while the majority of the lot slopes below, creating a unique landscape with plenty of potential. With a little imagination and the right site contractor, this property presents endless

    Agent Photo

    David Sartirana

    Northwest CT Realty

    (860) 891-6121

    124 Rockwell St, Winsted, CT 06098
  • /2

    $49,000

    • Land
    • 0.37 Acre
    • $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

    (860) 946-4468

    99 Hubbard St, Winsted, CT 06098
  • /37

    $469,000

    • 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

    (860) 390-5071

    55 Walnut St, Winsted, CT 06098

Frequently Asked Questions

What is the average home price in Winsted, CT?
Homes for sale in Winsted, CT have an average home price of $383,978.
How many homes have sold over the last 12 months in Winsted, CT?
112 homes have sold in Winsted, CT over the last 12 months.
What are the most popular zip codes in Winsted, CT?
The most popular zip codes in Winsted, CT include 06098, 06063, 06790, 06021 and 06057.
How much do you need to make to afford a house in Winsted?
The median home price in Winsted is $288,375. If you put a 20% down payment of $57,700 and had a 30-year fixed mortgage with an interest rate of 6.37%, your estimated principal and interest payment would be $1,440 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $62K a year to afford the median home price in Winsted. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Winsted, CT?
Winsted, CT has highly rated public and private schools. Some of the best schools in Winsted based on Niche Grades are Northwestern Regional High School, Barkhamsted Elementary School and Northwestern Regional Middle School. Browse all the schools in Winsted, CT to learn more.

Home Trends in Winsted, CT

Housing Trends

Median Sale Price
$287,278
Median Single Family Sale Price
$314,500
Median Townhouse Sale Price
$160,000
Median 2 Bedroom Sale Price
$224,000
Median 1 Bedroom Sale Price
$127,900
Average Price Per Sq Ft
$242
Number of Homes for Sale
8
Last 12 months Home Sales
112
Months of Supply
0.90
Median List Price
$288,375
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
0%
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