Winsted, CT Homes for Sale

/38
$1,600,000
- 4 Beds
- 2.5 Baths
- 2,129 Sq Ft
752 Lake Dr, Winsted, CT 06098

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 entertaining. Soak in panoramic water views from multiple vantage points, including

Pam Famiglietti

William Raveis Real Estate

752 Lake Dr, Winsted, CT 06098
Explore Winsted
/40
$579,900

$19K PRICE DROP
- 4 Beds
- 2.5 Baths
- 2,628 Sq Ft
237 Wallens Hill Rd, Winsted, CT 06098

Welcome to 237 Wallens Hill Road, where comfort, quality, and exceptional entertaining spaces come together in a beautiful rural setting. This 9-room Colonial with a farmhouse front porch is set on .80 acres and offers 4 bedrooms and 2.5 baths. The main level features a formal dining room, large family room, mudroom, and an impressive eat-in kitchen with quartz countertops, stainless steel

David Sartirana

Northwest CT Realty

237 Wallens Hill Rd, Winsted, CT 06098
/35
$324,900

$15K 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
$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

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
/28
$369,900
- 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
/40
$959,900

Coming Soon
- 2 Beds
- 1.5 Baths
- 1,472 Sq Ft
204 E Wakefield Blvd, Winsted, CT 06098

Exceptional Highland Lake waterfront Colonial rebuilt in 1996 to modern standards and codes, offering quality construction and timeless appeal. Perfectly positioned with 58 feet of direct northwest-facing waterfront, this home is designed to capture breathtaking lake views from nearly every angle. The spacious living/great room features a dramatic fieldstone fireplace and walls of glass with

David Sartirana

Northwest CT Realty

204 E Wakefield Blvd, Winsted, CT 06098
/14
$299,000
- 4 Beds
- 2 Baths
- 2,270 Sq Ft
64 Wheeler St, Winsted, CT 06098

Excellent opportunity for investors! This well-maintained Victorian-style two-family home offers the perfect blend of character, functionality, and income potential. Each spacious unit features 5 rooms, 2 bedrooms, and 1 full bath, with beautiful hardwood flooring throughout and separate, efficient natural gas heating systems. The upper-level apartment also includes a charming enclosed porch,

David Sartirana

Northwest CT Realty

64 Wheeler St, Winsted, CT 06098
/5
$49,999

$20K PRICE DROP
- Land
- 5,227 Sq Ft
- $416,658 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
/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
/39
$749,900
- 2 Beds
- 1 Bath
- 760 Sq Ft
812 W Wakefield Blvd, Winsted, CT 06098

Year-round waterfront retreat with breathtaking sunrise views from one of the widest sections of the lake! This well-maintained 2-bedroom, 1 bath home offers comfortable living with a flexible loft area for additional sleeping space and a convenient half bath on the lake level. The updated kitchen and new windows provide modern comfort while showcasing expansive water views throughout the home.

Ryan Horvay Smith & DeGroat Real Estate

812 W Wakefield Blvd, 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
/14
$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
/29
$269,900

$30K PRICE DROP
- 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
/37
$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
/17
$389,900

$10K 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
/27
$179,990
- 2 Beds
- 1.5 Baths
- 1,204 Sq Ft
111 Riverton Rd Unit 57, Winsted, CT 06098

Move right into this well-maintained townhouse offering 2 bedrooms, 1.5 baths, and an attached garage in the desirable Riverwalk community. The spacious living room features a vaulted ceiling, fireplace, and abundant natural light, while the kitchen offers ample cabinet and counter space with sliding door access to a private deck overlooking a wooded backdrop. Upstairs you'll find two generously

Joseph Caslin Sailpoint Property Group

111 Riverton Rd Unit 57, 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 $438,711.

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

114 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 $317,000. If you put a 20% down payment of $63,400 and had a 30-year fixed mortgage with an interest rate of 6.58%, your estimated principal and interest payment would be $1,620 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $69K 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 $315,500, up 10% year-over-year. Homes in Winsted sell in 56 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price $315,500	Median Single Family Sale Price $330,000
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 $276
Number of Homes for Sale 14	Last 12 months Home Sales 114
Months of Supply 1.50	Median List Price $317,000
Median Change From 1st List Price 0%	Median Home Sale Price YoY Change 10%

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