Winsted, CT Homes for Sale

Q: What are the most popular zip codes in Winsted, CT?

The most popular zip codes in Winsted, CT include 06098 , 06063 , 06021 , 06057 and 06790 .

/15
$499,000
- 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

David Sartirana

Northwest CT Realty

(860) 467-0358

5 Stadler Heights, Winsted, CT 06098
Explore Winsted
/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

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,

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

David Sartirana

Northwest CT Realty

(860) 390-5071

55 Walnut St, Winsted, CT 06098
/35
$339,900 Coming Soon
- 2 Beds
- 1 Bath
- 975 Sq Ft
621 Wynne Rd, Winsted, CT 06098

Tucked away on a private road in the sought-after Highland Lake district, this impeccably maintained Ranch offers the perfect blend of privacy, simplicity, and natural beauty. Built in 1995 and set on a .59-acre lot, the home is surrounded by over 500 acres of preserved land, creating a peaceful, nature-filled setting that is increasingly hard to find. Inside, the home features 975 square feet of

David Sartirana

Northwest CT Realty

(860) 385-6622

621 Wynne Rd, Winsted, CT 06098
/21
$360,000
- 3 Beds
- 1.5 Baths
- 1,312 Sq Ft
262 Holabird Ave, Winsted, CT 06098

Discover the perfect blend of small time charm with many conveniences close at hand! This well maintained, warm and inviting, 1 owner home offers it all! Having beautiful Highland Lake in this community is certainly one of many pluses! The renovated eat in kitchen offers granite counter tops, stainless steel appliances and access to a beautiful new Trex deck! Along with new decking, new windows

Mary Anne Casey D. Beckley Realty

262 Holabird Ave, 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
/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
/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
/39
$920,000
- 4 Beds
- 2 Baths
- 3,088 Sq Ft
469 Platt Hill Rd, Winsted, CT 06098

HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Customer, whether You're an ANTIQUARIAN, HORSE & ANIMAL LOVER, or just seeking for a PEACEFUL & TRANQUIL LOCATION, this LITCHFIELD COUNTY HOME could possibly fit your Criteria. Stately 1789 11 Room 3,088 Sq. Ft. Colonial expresses Love, Warmth & Care. From the Solid Beams, Chestnut Wide-Board Floors,

Marshall Cohen Cohen Agency

469 Platt Hill Rd, Winsted, CT 06098
/12
$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
/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

Connecticut Litchfield County Winsted

Why Live in Winsted

Winsted, Connecticut, situated at the edge of the Berkshire Mountains, is part of the town of Winchester and home to about 7,200 residents. Winsted features a revitalized downtown with a 2-mile commercial corridor offering diverse shops, eateries and entertainment venues in historic buildings. Residents enjoy activities like antique shopping, duckpin bowling and Go-Kart racing. Highland Lake, one of Connecticut’s largest waterways, is popular for fishing, swimming and boating, while East End Park provides a walking path, memorials and a bandstand. The Winsted Senior Center has services and activities for those aged 55 and over.

The city hosts the American Mural Project, a large collaborative indoor work of art, and the Soldier’s Monument and Memorial Park, a Civil War memorial. The Winchester Historical Society, in an 1813 Colonial Revival mansion, showcases Civil War memorabilia and Victorian artifacts. Housing options include detached single-family homes, apartments and townhouses, with many properties predating 1970. The Winchester Public Schools system has a reputation for well-run science and engineering programs.

Commuting is common, with residents traveling to nearby towns like Hartford and Waterbury for work. Although flooding is possible due to the community's proximity to lakes and rivers, the town has implemented measures like retaining walls and dams to mitigate risks.

Learn more about living in Winsted

Frequently Asked Questions

What is the average home price in Winsted, CT?

Homes for sale in Winsted, CT have an average home price of $393,562.

How many homes have sold over the last 12 months in Winsted, CT?

110 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, 06021, 06057 and 06790.

How much do you need to make to afford a house in Winsted?

The median home price in Winsted is $295,000. If you put a 20% down payment of $59,000 and had a 30-year fixed mortgage with an interest rate of 6.38%, your estimated principal and interest payment would be $1,470 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $63K 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

On average, homes in Winsted, CT sell after 58 days on the market compared to the national average of 55 days. The median sale price for homes in Winsted, CT over the last 12 months is $287,278, down 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$287,278

Median Single Family Sale Price

$317,450

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

$241

Number of Homes for Sale

Last 12 months Home Sales

110

Months of Supply

0.80

Median List Price

$295,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

-1%

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