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 , 06790 , 06063 , 06065 and 06057 .

/2
$29,900
- Land
- 5,662 Sq Ft
- $230,000 per Acre
17 Birdsall St, Winsted, CT 06098

Rare opportunity to build in a convenient in-town location! This level 0.13-acre vacant lot is within walking distance of downtown shopping, dining, and services, while also offering easy access to Highland Lake's public beach, boat launch, and recreational opportunities. This property offers an excellent combination of location and potential. Public water and public sewer are available in the

David Sartirana

Northwest CT Realty

(860) 295-4250

17 Birdsall St, Winsted, CT 06098
Explore Winsted
/2
$29,000
- Land
- 5,227 Sq Ft
- $241,667 per Acre
82-84 Rockwell St, Winchester, CT 06098

Rare opportunity to build in a convenient in-town location! This level 0.12-acre vacant lot is within walking distance of downtown shopping, dining, and services, while also offering easy access to Highland Lake's public beach, boat launch, and recreational opportunities. This property offers an excellent combination of location and potential. Public water and public sewer are available in the

David Sartirana

Northwest CT Realty

(860) 419-2496

82-84 Rockwell St, Winchester, CT 06098
/2
$45,000
- Land
- 1.07 Acres
- $42,056 per Acre
132 Florence St, Winsted, CT 06098

Rare opportunity to build your dream home on this 1.07-acre vacant lot conveniently located close to downtown shopping, dining, and everyday amenities. Situated in an established neighborhood, this property offers season-long westerly views and spectacular sunset vistas, creating the perfect backdrop for your future home. Public water and public sewer are available in the street (buyer to verify

David Sartirana

Northwest CT Realty

(860) 217-5758

132 Florence 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

David Sartirana

Northwest CT Realty

(860) 390-5071

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

(860) 217-3265

32 Hubbard St, 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

Jeffrey Liskin

Northwest CT Realty

(860) 854-8201

30 Upland Rd, Winsted, CT 06098
/5
$65,000

$5K PRICE DROP
- Land
- 5,227 Sq Ft
- $541,667 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
/26
$284,000

$5K PRICE DROP
- 3 Beds
- 1 Bath
- 1,008 Sq Ft
104 Maloney Ct, Winsted, CT 06098

Perched on desirable Wallens Hill with beautiful western sunset views, this lovingly maintained 3 bed 1957 ranch is full of warmth, charm, and pride of ownership. Bright and sunny throughout, the home offers 1,008 square feet of comfortable living space with hardwood floors, central air conditioning, and an easy-flow layout designed for everyday living. The spacious eat-in kitchen features oak

Lisa Garten Johnson Turning Point Realty, LLC

104 Maloney Ct, Winsted, CT 06098
/25
$474,900

$25K PRICE DROP
- 5 Beds
- 3 Baths
- 3,404 Sq Ft
441 Platt Hill Rd, Winsted, CT 06098

Tucked away on 2.09 private acres in the desirable Platt Hill area of Winchester, this custom-built contemporary offers the perfect blend of architectural character, space, and recent updates. With over 3,400 square feet, 5 bedrooms, 3 full baths, and a 2-car garage, this home provides flexibility for everyday living, entertaining, or multi-generational needs. Inside, you'll find a thoughtfully

Meagan Albert Tier 1 Real Estate

441 Platt Hill Rd, Winsted, CT 06098
/28
$349,999
- 6 Beds
- 2.5 Baths
- 2,555 Sq Ft
68 Wetmore Ave, Winsted, CT 06098

Extremely well-cared-for two-family home located on a desirable street! This property offers plenty of off-street parking, a rear lot, a 3-car garage with basement adds potential for additional income. Large back yard with gazebo.The first floor is unoccupied, while the second floor is tenant-occupied, making this a great opportunity for an owner-occupant or investor. Come take a look while it

Alex King Lock and Key Realty, Inc

68 Wetmore Ave, 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
/24
$544,000
- 1 Bed
- 1.5 Baths
- 1,308 Sq Ft
736 W Wakefield Blvd, Winsted, CT 06098

Welcome to "WatersEdge" a Seasonal Cottage perched on a landscaped hillside overlooking Third Bay of beautiful Highland Lake. Views Views Views! Highland is a fully recreational lake. On the main floor of the cottage you will find one bedroom, a bath with shower, a spacious family room with a stone fireplace, and an efficient kitchen with storage. The lower walk-out level can be accessed by the

Ed Richman Lakefront Living Realty, LLC

736 W Wakefield Blvd, Winsted, CT 06098
/17
$450,000
- 8 Beds
- 4 Baths
- 2,000 Sq Ft
71-73 Wheeler St, Winchester, CT 06098

A positive income even if you live in one of the units. Two 2 family homes(4 units total) on one parcel. Good parking. Large lot. Residential setting. Second floor of back house has a private deck, back yard and woods, yet is convenient to downtown.

Ida Chaplinski The DIY Listing

71-73 Wheeler St, Winchester, 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
/24
$174,900

$25K PRICE DROP
- Land
- 5,227 Sq Ft
- $1,457,500 per Acre
624 Wynne Rd, Winsted, CT 06098

Exceptional opportunity to build near one of Northwest Connecticut's most desirable lake communities. Just steps from beautiful Highland Lake, this water-view parcel offers the chance to create your dream home in a setting that combines lake lifestyle, natural beauty, and convenient access to some of Litchfield County's most sought-after destinations. Highland Lake is a true Connecticut gem-a

AJ Davis Better Homes and Gardens Real Estate Executive Real Estate

624 Wynne 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
/29
$299,900
- 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
/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
/19
$579,000
- 11 Beds
- 5.5 Baths
- 5,233 Sq Ft
150 Oak St, Winsted, CT 06098

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 unit with electric

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
/38
$749,000

$20K PRICE DROP
- 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

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 $406,689.

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

109 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, 06065 and 06057.

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

The median home price in Winsted is $299,000. If you put a 20% down payment of $59,800 and had a 30-year fixed mortgage with an interest rate of 6.48%, your estimated principal and interest payment would be $1,510 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $65K 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 $300,000, up 4% year-over-year. Homes in Winsted sell in 58 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price $300,000	Median Single Family Sale Price $320,000
Median Townhouse Sale Price $172,500	Median 2 Bedroom Sale Price $231,000
Median 1 Bedroom Sale Price $227,500	Average Price Per Sq Ft $260
Number of Homes for Sale 14	Last 12 months Home Sales 109
Months of Supply 1.50	Median List Price $299,000
Median Change From 1st List Price 1%	Median Home Sale Price YoY Change 4%

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