Winsted, CT Homes for Sale

/16
$399,900
- 4 Beds
- 1.5 Baths
- 1,944 Sq Ft
122 Standard Ave, Winsted, CT 06098

Well-maintained 4-bedroom Colonial tucked away on a quiet dead-end street. This inviting home features a newly renovated eat-in kitchen with updated cabinetry, countertops, and finishes, perfect for everyday living and gathering. The comfortable layout includes a spacious living room and dining area, while four bedrooms offer flexibility for family, guests, or a home office. Enjoy the large yard,

Amanda Balaski

Northwest CT Realty

122 Standard Ave, Winsted, CT 06098
Explore Winsted
/28
$349,900

$20K PRICE DROP
- 4 Beds
- 1.5 Baths
- 2,722 Sq Ft
70 Walnut St, Winsted, CT 06098

Step back in time and experience the timeless elegance of this spacious 2,722 sq. ft. Victorian offering 10 rooms, 5 bedrooms, and 1.5 baths. Rich in original character and architectural detail, this classic home showcases beautiful hardwood floors, impressive natural woodwork, pocket doors, built-ins, decorative moldings, and stunning stained-glass accents that capture the craftsmanship of a

David Sartirana

Northwest CT Realty

70 Walnut St, Winsted, CT 06098
/35
$305,000

$35K PRICE DROP
- 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

David Sartirana

Northwest CT Realty

103 Cordano Rd, Winsted, CT 06098
/37
$429,000

$121K 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

David Sartirana

Northwest CT Realty

55 Walnut 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

David Sartirana

Northwest CT Realty

32 Hubbard St, Winsted, CT 06098
/5
$42,900

$27K PRICE DROP
- Land
- 5,227 Sq Ft
- $357,500 per Acre
319 White Oak Trail, Winchester, CT 06098

Wooded interior lot located at the end of a dead-end street, offering a private setting. The parcel is slightly sloped and accessed from the end of the road. Clients, do your homework , including but not limited to surveys, zoning, and building approvals. Convenient location with approximately a 15-minute walk to Resha Beach on Highland Lake for recreational enjoyment. Lake rights are granted to

Matt Tearman Coldwell Banker Realty

319 White Oak Trail, Winchester, CT 06098
/7
$499,900
- 6 Beds
- 5 Baths
- 2,864 Sq Ft
205 Old New Hartford Rd, Winchester, CT 06098

Charming Multi-Family Property with steady income potential! Welcome to your next lucrative investment venture! Nestled on an expansive 1-acre lot, this multi-family property features 5 distinct living spaces, making it an ideal addition to your real estate portfolio. This property comprises 4 studio apartments and a spacious 2-bedroom apartment, catering to a variety of tenants and maximizing

TK Krumm Berkshire Hathaway NE Prop.

205 Old New Hartford Rd, Winchester, CT 06098
/38
$649,900
- 2 Beds
- 1 Bath
- 1,361 Sq Ft
600 E Wakefield Blvd, Winsted, CT 06098

Set along the highly desirable east side of Highland Lake, 600 East Wakefield Boulevard offers a unique opportunity to create a waterfront retreat tailored to your lifestyle. Brimming with charm and character, this home is ready for its next chapter and the fresh vision. Spend your days swimming, boating, and kayaking with easy access to the lake and the added benefit of a semi-private boat

Stacy Anselmo Coldwell Banker Realty

600 E Wakefield Blvd, 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
/23
$199,900
- 4 Beds
- 2 Baths
- 1,376 Sq Ft
46 Cherry St, Winsted, CT 06098

A wonderful opportunity to own a spacious antique Colonial with endless potential! This 4-bedroom, 2-full-bath home features a living room, dining room, and an eat-in kitchen, providing a solid foundation for your vision. While the home would benefit from updates, it offers an excellent opportunity for buyers to add their personal style and transform it into a truly standout property. Ideally

Debra Jablonski Berkshire Hathaway NE Prop.

46 Cherry St, Winsted, CT 06098
/6
$386,000
- Land
- 1.91 Acres
- $202,094 per Acre
00 Main St, Winsted, CT 06098

Exceptional 2+ Acre Development Opportunity - Route 44, Winsted, CT** Rare opportunity to acquire approximately 2+- acres with nearly 700 feet of frontage on Main Street (Route 44), one of Winsted's primary commercial corridors. Located within the Town Gateway Zone, this highly visible parcel offers outstanding flexibility for a variety of development opportunities, including commercial,

Dan Merrigan Merrigan & Lefebvre Realty

00 Main St, Winsted, CT 06098
/5
$295,000
- Land
- 51 Acres
- $5,784 per Acre
393 Winchester Rd, Winsted, CT 06098

WINCHESTER CREST 51 acres of forested gently rolling land sited upland in Winchester Center. There is a former homesite and multiple choices for additional homesites affording complete privacy. There is abundant wildlife, trails, intermittent streams, dense and sparse forest. Perfect for year round home site, weekend retreat or recreational land.

Tom McGowan Elyse Harney Real Estate

393 Winchester Rd, Winsted, CT 06098
/40
$895,000
- 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
/26
$239,000
- 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
/35
$849,900
- 4 Beds
- 2 Baths
- 1,781 Sq Ft
119 W Wakefield Blvd, Winsted, CT 06098

Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay, this beautifully renovated two-family home can be enjoyed as a single-family retreat or an income-generating

Mela Veltri Case KW Legacy Partners

119 W Wakefield Blvd, Winsted, CT 06098
/24
$395,000
- 3 Beds
- 2 Baths
- 1,909 Sq Ft
720 Main St, Winsted, CT 06098

Where Opportunity Meets Lifestyle! Unlock the potential of this exceptional mixed-use property located in the heart of downtown Winsted. Positioned on a bustling Main Street with excellent exposure and constant pedestrian traffic, this property is an outstanding opportunity for entrepreneurs, investors, or anyone looking to combine business ownership with residential living. The street-level

Arlene Gonzalez The Gonzalez Property Group

720 Main St, Winsted, CT 06098
/17
$365,000

$35K PRICE DROP
- 3 Beds
- 2 Baths
- 1,820 Sq Ft
132 E Lake St, Winsted, CT 06098

Welcome to East Lake Street at Highland Lake, where privacy, comfort, and lake living come together. Set back from the road on a private lot in the desirable First Bay area, this well-maintained lake-style home offers a quiet setting with seasonal lake views and refreshing breezes throughout. Offering 1,820 square feet, the home is listed as a 3-bedroom with a first-floor finished 4th room for

Bryan Palladino Showcase Realty, Inc.

132 E Lake St, Winsted, CT 06098
/19
$549,000

$30K PRICE DROP
- 11 Beds
- 5.5 Baths
- 5,233 Sq Ft
150 Oak St, Winsted, CT 06098

*PRICE REDUCTION* 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 3-4 bedroom, 1 1/2 bath

Pamela Silvestri Turning Point Realty, LLC

150 Oak St, Winsted, CT 06098
/19
$469,900
- 3 Beds
- 2 Baths
- 1,768 Sq Ft
9 Loomis St, Winsted, CT 06098

Spacious 3 to 4 Bedroom Colonial Style Home on a 0.35 Acre Lot, plus located on a No Through Street. OPEN FLOOR PLAN. Beautifully Remodeled from "TOP TO BOTTOM" for Energy Efficient Living. Redesigned Country Style Kitchen offers Ample Cabinetry and includes New Oven/Range, Microwave, Refrigerator & Dishwasher.. 27' x 12' Living/Dining Combo with Bay/Bow Window that takes in Natural Light on

Marshall Cohen Cohen Agency

9 Loomis St, Winsted, CT 06098

Connecticut Litchfield County

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 $412,655.

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

113 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, 06790, 06063, 06021 and 06057.

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

The median home price in Winsted is $304,999. If you put a 20% down payment of $61,000 and had a 30-year fixed mortgage with an interest rate of 6.69%, your estimated principal and interest payment would be $1,570 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $67K 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 Prices in Winsted, CT

The median home sale price in Winsted, CT is $310,000, up 7% year-over-year. Homes in Winsted sell in 55 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price $310,000	Median Single Family Sale Price $327,500
Median Townhouse Sale Price $160,000	Median 2 Bedroom Sale Price $233,717
Median 1 Bedroom Sale Price $250,000	Average Price Per Sq Ft $261
Number of Homes for Sale 11	Last 12 months Home Sales 113
Months of Supply 1.20	Median List Price $304,999
Median Change From 1st List Price 0%	Median Home Sale Price YoY Change 7%

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