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Newest Homes for Sale in Winsted, CT

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  • /19

    $349,000

    • 3 Beds
    • 1.5 Baths
    • 1,888 Sq Ft

    107 Roberts Ave, Winsted, CT 06098

    Peaceful country living with unlimited potential! Nestled on a quiet Winsted street, this three bedroom, two bathroom ranch sits on nearly 2 acres of private, setback land. It offers excellant structural bones and a functonal layout, making it an ideal candidate for a rewarding renovation project. The large living and dining space features high cathedral ceilings and exposed wood beams with the

    Mary Anne Casey D. Beckley Realty

    107 Roberts Ave, Winsted, CT 06098
  • /38

    $539,900

    Open Sun 1PM - 3PM Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,011 Sq Ft

    257 Wallens Hill Rd, Winsted, CT 06098

    Set on 6 beautiful acres of open meadows with extensive road frontage and picturesque views, this exceptional Cape offers privacy, efficiency, and convenience...... Thoughtfully updated throughout, the home features 3 spacious bedrooms, 2.5 baths, a dedicated office, and a functional floor plan designed for comfortable living. Energy-conscious buyers will appreciate the solar system with backup

    Kelly Sullivan Sullivan Real Estate Inc

    257 Wallens Hill Rd, Winsted, CT 06098
  • /26

    $998,000

    Open Sat 11AM - 1PM
    • 4 Beds
    • 3 Baths
    • 3,330 Sq Ft

    878 W Wakefield Blvd, Winsted, CT 06098

    WATERFRONT AND PRIVACY-WIN, WIN! PACK YOUR CLOTHES AND TOOTHBRUSH, THIS GEM IS TURN KEY AND WAITING FOR YOU! FULLY REMODELED INSIDE AND OUT! Nestled along the shores of HIGHLAND LAKE, this stunning waterfront retreat offers the perfect blend of year-round living and vacation-style comfort. Featuring 4 bedrooms and 3 bathrooms, this spacious home is designed to capture breathtaking lake views

    Agent Photo

    Annie Q Simard

    LPT Realty

    (860) 891-6304

    878 W Wakefield Blvd, Winsted, CT 06098
  • /25

    $499,900

    • 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
  • /5

    $70,000

    • Land
    • 5,227 Sq Ft
    • $583,333 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.

    Matt Tearman Coldwell Banker Realty

    319 White Oak Trail, Winchester, 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
  • /7

    $499,900

    Coming Soon
    • 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
  • /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
  • /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
  • /19

    $469,900

    Open Sun 1PM - 3PM
    • 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
  • /24

    $199,900

    • Land
    • 5,227 Sq Ft
    • $1,665,833 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

    $289,000

    • 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
  • /28

    $749,999

    • 2 Beds
    • 2 Baths
    • 1,320 Sq Ft

    660 E Wakefield Blvd, Winsted, CT 06098

    Nestled along the coveted east side of Highland Lake, 660 East Wakefield Blvd offers a rare opportunity to create the waterfront retreat you've always imagined. Bursting with classic lake charm and timeless character, this home is ready for a new owner to make it their own and bring fresh vision to an unforgettable setting. Enjoy excellent water access for swimming, boating, kayaking, and

    Patrick Smith Smith & DeGroat Real Estate

    660 E Wakefield Blvd, 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
  • /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 bedroom, 1 1/2 bath unit with electric

    Pamela Silvestri Turning Point Realty, LLC

    150 Oak 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
  • /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
  • /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
  • /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

    Agent Photo

    David Sartirana

    Northwest CT Realty

    (860) 390-5071

    55 Walnut 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

Frequently Asked Questions

What is the average home price in Winsted, CT?
Homes for sale in Winsted, CT have an average home price of $407,382.
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, 06790, 06063, 06057 and 06021.
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 6.53%, your estimated principal and interest payment would be $1,520 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 Trends in Winsted, CT

Housing Trends

Median Sale Price
$300,000
Median Single Family Sale Price
$317,950
Median Townhouse Sale Price
$172,500
Median 2 Bedroom Sale Price
$250,000
Median 1 Bedroom Sale Price
$127,900
Average Price Per Sq Ft
$259
Number of Homes for Sale
15
Last 12 months Home Sales
110
Months of Supply
1.60
Median List Price
$299,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
4%
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